Easy Agile Podcast Ep.8 Gerald Cadden Strategic Advisor & SAFe Program Consultant at Scaled Agile Inc.

"Having gone through a cloud migration at Splunk, Greg share's some insightful key learnings, challenges and opportunities" - Chloe Hall

Greg Warner has been involved with the Atlassian ecosystem since 2006 and is a frequent speaker at Atlassian events. Greg has worked as a senior consultant for a solution partner, supported Jira and Confluence at Amazon, and in his current role at Splunk, executed a cloud migration to Atlassian Enterprise Cloud for over 10,000 of his colleagues.

In this episode, Greg and Chloe discuss the cloud migration journey:

📌 The mental shift to cloud migration and how to think beyond the technical side

📌 How to navigate the journey without a roadmap to follow

📌 The four pillars to success for your cloud migration journey

📌 Finding the right time to migrate & thinking about future opportunities    beyond your migration

📌 The unexpected value that can come from a cloud migration

+ more!

📲 Subscribe/Listen on your favourite podcasting app.

Thanks, Greg and Chloe!

Transcript

Chloe Hall:

Hey everyone and welcome back to the Easy Agile Podcast. So I'm Chloe, Marketing Coordinator at Easy Agile, and I'll be your host for today's episode. So before we begin, we'd like to acknowledge the traditional custodians of the land from which I am recording today, the Wodiwodi people of the Dharawal-speaking nation and pay our respects to elders past, present, and emerging. We extend that same respect to all Aboriginal and to Australia Islander peoples who are tuning in today.

Chloe Hall:

So we have a very exciting guest on the podcast today. This guest has been involved with the Atlassian ecosystem since 2006 and is a frequent speaker at Atlassian events. He has worked as a senior consultant for a solution partner, supported Jira and Confluence at Amazon and at his current role at Splunk, executed a cloud migration to Atlassian Enterprise Cloud for over 10,000 colleagues. So welcome to the Easy Agile podcast, Greg Warner.

Chloe Hall:

How are you?

Greg Warner:

Good, and thank you for having me.

Chloe Hall:

No worries. It's great to have you here today.

Greg Warner:

This is one of my favorite topics. We talk about cloud migration and yeah, I hope I can explain why.

Chloe Hall:

Yes, that's exactly what we want for you because I remember when we met at Team 22, you were just so passionate about cloud migration and had so many insights to share and I was very intrigued as well.

Greg Warner:

To give it a bit background about myself.

Chloe Hall:

Yeah.

Greg Warner:

I haven't always been a cloud person. So you mentioned before about being involved since 2006. I was involved early days with when Jira had the several different flavors of standard and professional, when you'd order an enterprise license for Atlassian and they'd send you a shirt. That was one of the difference between one of the licenses. So based a lot in the server versions, over many years. I looked at the cloud as being the poorer cousin, if you like.

Greg Warner:

I'd been to several Atlassian summits and later Team events where there was always things of what was happening in cloud but not necessarily server. I participated in writing exam questions for Atlassian certification program for both server and DC. For me, in the last 18 months, two years now, to make this fundamental shift from being certainly a proponent of what we do doing on server in DC to now absolutely cloud first and that is the definite direction that we as a company have chosen and certainly why I'm so passionate about speaking to other enterprise customers about their cloud migration journey.

Chloe Hall:

Wow. So what do you think it was that you were like, okay, let's migrate to the cloud, as you were so involved in the server DC part of it? What was it that grabbed your attention?

Greg Warner:

I joined Splunk in 2019 and it wasn't all roses in regards to how we maintained Jira and Confluence. It wasn't uncommon to have outages that would last hours. For two systems that were just so critical to our business operations to have that, I was kind of dumbfounded but I thought, hey, I've been here before. I have seen this. And so it was a slow methodical approach to root cause our problems, get us to a version that was in long-term support, and then take a breather.

Greg Warner:

Once we got to that point where we didn't have outages, we kind of think of what the future would be. And for me, that future was exactly what I'd done before, what I'd done at Amazon, which is where we would move all of our on-prem infrastructure, Jira, Confluence, and Crowd to public cloud, whether it would be a AWS or GCP, something of that flavor. I'd done that before. I knew how we were going to do that to the extent that I'd even held meetings in my team about how we were going to stand up the infrastructure, what the design was going to be.

Greg Warner:

But there was probably one pivotal conversation that was with our CIO and it was in one of those, just passing by, and he's like, "Greg, I've seen the plans and the funding requests." He's like, "But have you considered Atlassian Cloud?" Now, the immediate personal reaction to me was like, we are not going to do that because I'd seen the iterations. I'd seen it over time. I'd worked for a solution partner. I'd worked with customers in cloud, never really thought we could be enterprise-ready. So my immediate reaction was not going to do that. I said, "I'm not going to answer that question right now." I said, "I don't know enough to give you an answer."

Greg Warner:

And I'm absolutely glad I did that because I would've put a foot in mu mouth had I given the immediate response that was... So yeah, I took that question, went and did some analysis, spoke to our technical account manager at the time, and really looked at what had been going on and where was cloud today? Where was it in its maturity? And the actual monumental thing for me was that I think it's actually ready. People make excuses for why they can't do it, but there are a bunch of reasons why you should. And if we look at us as a company, with our own products that we are moving our own customers to cloud, and we are using cloud services, like Google Workspace and Zoom and a variety of SaaS applications. What was so different about what we did in engineering that couldn't go to cloud? And that was like, okay, I think the CIO was actually asking me a much bigger question here.

Greg Warner:

So the result of that was yes, we decided that it was the right time for Splunk to move. And that is a monumental shift. And I know there's a lot of Jira admins out there that are like, if you do this, you're putting your own jobs at risk. The answer is no, you're not. And even within my team, when we had we'd discussed this, there was emotional connection to maintaining on-premise infrastructure and were we giving our own jobs away if we do this? There's all those... No.

Greg Warner:

And there have actually been two people in my team that got actually promoted through the work of our cloud migration that otherwise wouldn't have because they could demonstrate the skills. But that's kind of like the backstory about how we decided to go to cloud. And I think as we are thinking about it, there is a mental shift first. Before you even go down the technical path about how you would do it, change your own mind so that it's open so that you're ready for it as well.

Chloe Hall:

Yeah, I love that. It's so good. And I think just the fact that you didn't respond to your CIO, did you say that?

Greg Warner:

Yep.

Chloe Hall:

That you didn't respond to your CIO straight away and you weren't like, "No, I don't want to do that." You actually stepped away, took that time to do your research, and think maybe cloud is the better option for Splunk, which is just so great and really created that mental shift in yourself. So when you say that your employees, like everyone kind of has that beef that, oh, we're going to lose our job if we move from on-prem to cloud and those employees ended up getting promoted. How did their roles change?

Greg Warner:

When we moved from on-prem to cloud, you no longer have to maintain the plumbing, right?

Chloe Hall:

Yeah.

Greg Warner:

You no longer have to maintain all the plumbing that's supporting Jira, Confluence, BitBucket, whatever is going to move. Now we thought that was the piece that's actually providing value to the organization. And it wasn't until we went to cloud, we actually realized it wasn't. Like what we can do now is different. And that's what my team has done. They've up-leveled.

Greg Warner:

So in the times since we moved from Jira, Confluence on-prem to cloud, we now get involved a lot more with the business analysis and understanding what our project teams want. So when someone from engineering is requesting something that has an integration or a workflow, we've got more time to spend on that than are we going to upgrade? Are we on the current feature release? Is there a bug we have to close? Log for J as a prime example where the extent of where we covered was logging a call with the Atlassian enterprise support and then telling us, "Yep, it's done."

Greg Warner:

Whereas other colleagues within the ecosystem that I spoke to spent a week dealing with that, right? Dealing with patching and upgrades. So the value for our team in the work we do has shifted up. We've also done Jira advanced roadmaps in that time. So we've been able to provide things we would've never got to because we're too busy to the plumbing, to the extent now that we have a very small footprint of on-prem that remains and that's primarily FedRAMP and IO5. It's not quite certified yet. It's going to get there. So we have a very small footprint and I'm the one who has to do the upgrades and now you look at it like, oh my god, that's going to be this couple-week tasks we going to do where I could do all this other better work that's waiting for us in cloud. You don't realize it until you have it removed how much you used to do.

Greg Warner:

And so we used to do two upgrades of Jira year and two upgrades of Confluence a year. We put that down to about a month's work of each. By the time you do all of your testing and you're staging and then do that. So you're really looking at four months of the year you were spending doing upgrades. We don't have that anymore. It's completely gone. And so now we make sure that we do things cloud first. We don't bring across behaviors that we were doing on-prem into cloud. So that's probably one thing we learned was that don't implement server DC in cloud.

Chloe Hall:

Yeah, that's so great. It seems like it's opened up a lot more opportunity for you as well. So I think something that I kind of want to look into and understand a bit more is that people focus a lot on the technical aspect of the cloud migration. What other aspects do you think need to be considered?

Greg Warner:

Certainly people. I mentioned at the very front here the mental mindset and that really started with my team, to get their mind around how we're going to do this cloud migration. There isn't necessarily yet a roadmap that says these are all the steps need to take to get ready for your cloud migration. So we had to invent some of those and one of those two was, what did we want to get out of the cloud migration?

Greg Warner:

I speak to other Atlassian customers. You talk about they're running a project, the project is the cloud migration, the start and the end is the cloud migration day. No, completely wrong. The cloud migration actually has a beginning, a middle, and an end. What you're talking about here, about this first changes is in the beginning, and that should be we're moving to cloud because it should be fundamentally better than what we have today.

Greg Warner:

If it's not better, there's no value in doing the activity. So we started with a vision and that vision was that all of the core things had to work from day one and they had to work better. So create issue, edit issue, up to issue, that just needs to work. There should be no argument whether it does or does not. That needs to work and work better. Create a page, edit a page, share a page. That stuff needs to work in Confluence without any problems. We also need to make sure that there are people in the organization who this could be a fundamental change of how they work, depending on how much they work with Jira and Confluence. So appreciating that there is some change management and some communications that needs to be ready as you do your cloud migration to ensure that your vision is going to work, but also acknowledging you will break some things. You're not going to be able to do a cloud migration and shift you from A to B without nothing.

Greg Warner:

It will go wrong. So we were aware of that and for that, what I would always tell people was that we're really fixed on the vision of making it sure it's better than it was today, but flexible on the details, how we get there. We will probably find different ways as we go along because things will change. Cloud changes itself. You'll discover things you didn't know before. There was a Jira admin that made a decision 10 years ago, you now found that. So yeah, very, very fixed on that vision that day one that we had to have this unboxing experience that when people got to use Jira and Conference Cloud for the first time, they could see why we'd spent so much effort to make sure it was polished and things just worked. And as you went a bit further out, there might be things to do with apps that might not be quite the same.

Greg Warner:

That's okay. And then further out, things you just ultimately can't control. And for that, we had 76 integrations of teams that had written automations from all over the company. We're never going to get to find out what they do, but we knew that some of those would probably break. And so just dealing with some change control and allowing those people to know this is coming, what the rest endpoints will be, how to set up their API keys. We did a lot of that, but we did have one integration that broke and that integration broke because the entire team was on PTO or leave that week. We can't avoid that one. But it was good to see other teams actually jumped in because they'd been involved in updating theirs to go help fix that. So that was okay. We had one integration that we really gave the white glove support to and that was for... We have a Salesforce to Jira integration that's a revenue-generating integration.

Greg Warner:

We gave that a lot of attention to make sure that just worked. But the 76 others, we provided a runbook. The runbook was essentially teams, you do things like this. So they knew how to change and update to the new system. But yeah, certainly the beginning, middle and end. The beginning is all those shifts that you're going to have to change and probably some history about design decisions. The middle is in fact your cloud migration and the end, middle to the end is everything you do with it afterwards. So that's where the real value comes from in your cloud migration. It's once you're in, what can we do with it?

Greg Warner:

And we are towards the end of that now. There have been things that I couldn't have planned for that people have done. So we did your advanced roadmaps, saving the forest there, but also we're encouraging our staff to extend the platform. That used to be really difficult and we've worked with Atlassian to understand what should that look like? And we've settled on using it Atlassian Forge. And so now we have our first app this week, in UAT, in Atlassian Cloud to solve business problems that we have. That's a custom Atlassian Forge app. And we're encouraging our engineers to build those and so they can extend and get that real value through the cloud migration.

Chloe Hall:

Yeah, wow. You've come so far and it's nice to hear that you're towards the end of it and all the opportunities are coming with it and you're seeing all the value. It's all paying off as well. I think I just want to go back to that moment where you talk about there isn't essentially a roadmap outlay. There isn't someone or something to follow where it says this is where you need to start. These are the steps to cloud migration. And I think a lot of people, that's what they fear. They're like, we're not sure exactly where to start. We're not sure what roadmap we'll follow. How do you navigate that in a way?

Greg Warner:

So I get back to that when I talked about the vision. We said we're fixing the vision flexible details. Early on when we signed for cloud migration, it was in the first week after we'd signed for it, that same CIO asked me, "Greg, what's our date? When are we moving? Because you've sold me that this is so much better. Where's the action? When are we get this?" And we took a good six weeks after we signed to actually understand the tooling that's available. So for Jira, there's really two options. There's the Jira site import and the Jira cloud migration assistant. And on Confluence side, there's one that's called the Confluence cloud migration assistant. Better kind of understand how those technologies work. And for a couple weeks there, my team actually considered if we did the migration ourself, we could probably save the company a bunch of money and we would own it.

Greg Warner:

We would know how this thing worked. We got about four weeks in and decided that was a terrible idea. Do not do that. Any enterprise customers I talk about that say we're going to do it ourselves, do not do that. Do not do that. And part of the reason is that there's really four pillars to success for your cloud migration. Jira migration, Confluence migration, apps, and users. And we did not know how to do apps and users and we probably could have gotten away with Confluence and Jira. But we said, look, this is something that we actually need to have a partner involved. And so we did ask for partners to provide their way of doing it, knowing what they knew about us. And we did provide as much detail as we can. We had two partners actually provided completely different methodologies how to get there.

Greg Warner:

So this is that flexible on the details, but we really had to make a decision on what worked for us. So when it really came down to Jira, would we do a big bang approach and just switch it over in the course of a weekend or did we want to do cohort by cohort over time? And we decided for us, because we are a 24/7 organization that's supporting our customers, doing the big bang switchover, that was the best way to do it. So that's one of the reasons we chose the partner we did. But that partner didn't necessarily have a roadmap of where they want to go. But we did then explain what we want to get out of this. That was the first thing, was about it needs to happen on a weekend. So that then filters down what your choices are. The ecosystem apps part is really important to make sure that one, there may have been apps installed in your system that have been there for 10 years and you're not sure why they're there anymore because it was four Jira admins ago.

Greg Warner:

Nobody knows what's there. But if they don't have a cloud migration pathway, you really should consider they're probably going to hit their end because there is no equivalent. So you can rule them out. Identify the ones that do have a business process with them. And for that, Salesforce for us, we had to find a cloud-first connect that would work. So that meant that we knew that was going forward. But really, I think the key thing that we invented that we didn't know about was that we created this thing called an App Burn Down. And that's where we looked at all the apps we had. We had about 40 apps. We said, okay, which ones are not going to go to cloud? Which ones don't have a migration pathway? Which ones are going to replace something else? And so we started to remove apps over the course of about three months.

Greg Warner:

So people would see that we're starting to get away from on-prem design decisions and old ways of doing things. But we also said, but once we get to cloud, this is the pathway out of it. So that we said, look, we're going to turn this app off but you're going to get this one instead, which is the cloud-first app. So people could see how we're going to make the jump over the river to get there. But it meant that we would, over time, identify apps that weren't used. If we turned them off and nothing happened, it's fine. But also we did come across some where they were critical to a business use. And so if we didn't have an answer for those yet, it gave us time to find one. And with your user base, typically it's your colleagues, that's going to be your most critical customers. They're going to ask, okay, you're turning it off. When do I get the functionality back?

Greg Warner:

And by doing that App Burn Down over time, that does buy you time to then have that answer. So it's a much easier conversation than I'm simply turning off functionality, I don't have an answer for you yet. There are things like that. It wasn't necessarily a roadmap, but working with a solution partner is absolutely the right way to go. Don't try and do it yourself. They also work with Atlassian and they have far better reach into getting some of these answers than you can possibly ever have. And I have on at least three different occasions where our solution partner did go and speak directly with an ecosystem partner to find out what's the path forward. How can we make this work? So it is good. The migration is really a three-way collaboration between yourself, your solution partner, and Atlassian. And you all have the same goals. You want to get to cloud and it does work really well.

Chloe Hall:

Wow. Yeah. So sounds like hope everyone got that advice. Definitely don't take this on your own. Reach out to solution partner. And I really like how you said you went to two different solution partners and you found out what their ideas were, which ways they wanted to take you, so you could kind of explore your options, work out what was the best route for Splunk. And it's worked very well for you as well. Having that support I think as well. Yeah. Sorry, you go.

Greg Warner:

The choice of the partner is really important and it's probably one of the earliest decisions that we made to get that one right. And I remember several times thinking about, have we got the right people on board? Did we speak to... And it was an interview process to the extent that when we had our final day after we'd been working with Atlassian and with our partner for six months, one month after our migration was completed and we're all done, we had one final Zoom call with all of us and took a photo and did that. But it kind of felt like a breakup, to be honest, because we'd been in each other's faces for six months and working. We're now all saying goodbye. We might not see each other. It was like the weirdest feeling. But it did work. And so yeah, it is a real fundamental choice.

Greg Warner:

Just take the time, make sure they understand what we want to do, make sure you understand how they're going to do it. But yeah, if we have done it ourselves, we would've got ourselves all caught up in knots, wouldn't have been a successful migration or so. I'm a technical guy. I want to solve it. I want to be like... But I think the actual right answer was no, you don't need to know how this works 100% because you're going to do this hopefully just once. And so focus on the real business value things about dealing with stakeholders and the change and making design decisions that are really important for you because you're going to own those probably the next decade rather than worrying about how do I get my data from A to Z?

Chloe Hall:

Yeah. It definitely would've felt like a breakup for you because you would've been working side by side for so long, dealing with so much. Are you still in contact with them or...

Greg Warner:

Yeah, we had this fundamental thing we always said is we're always, if there's a problem, we're always cautiously optimistic, we're going to solve it. We did engineering challenges that we went through, but I did say right early on is, the ecosystem is only big and we're all going to bump into each other at some point. So yeah, let's make sure that we're still friends at the end of this. And I didn't realize how important that was until later when I was in New York for Christmas and I arranged to meet the project manager that worked for us. She lives in New York, so how about I meet you so... So we met each other at the hotel and she's like, "I have never met a customer outside of work to do this." Yeah, I gave the story about it felt like a breakup, but she did say that at the beginning you said we'll be friends after.

Greg Warner:

Yeah it is because it can be really hard. I've been on the consultant side where you kind of have to have some hard conversations and sometimes... You want to make sure that everyone understands the problem. You're trying to make it better so that at the end of it, you can still be friends like that. That is the thing. There probably will be engagements later on that you might need them again. So you want to make sure that you have your choice of best in breed partner to choose from. You have those relationships. They understand what you want to choose. So yeah, it is really important to choose the right partner. Don't necessarily based on price but choose the partner that's going to work for you, understands what you're trying to get out of your cloud migration and they'll be there in the future when you need them for another cloud migration or a much more gnarly project. Try and be friends at the end of it.

Chloe Hall:

And definitely it's good that you have that friendship now because they have that understanding about your business and what you want and the value of it. So if you do need help again, it's a lot easier to bring them on board straight away. So now that you've performed a cloud migration and you're coming towards the end of it, do you look at the process any differently to when you were at the very beginning?

Greg Warner:

Yeah, I thought we were just executing a data migration just yeah, on-prem to cloud.

Chloe Hall:

Yeah.

Greg Warner:

Pretty straightforward, nothing big. I was pleasantly surprised as we're making some of these decisions as we went along, that it was more than that. There were business processes that we could improve. There was the beginning, the middle, and end. I didn't realize that until actually after the end. So when we did our cloud migration, it was actually the week before Thanksgiving in the US. It was November 19. And even that decision was made in just going for a walk at lunchtime. When should we really do this? And I kind of came down again, spoke to my project manager and said, "How about we do this in the cloud migration the week before Thanksgiving?" Because 50% of our workforce is located in the US and a large proportion of that will be on leave or PTO before.

Greg Warner:

So by doing it over a weekend before then we're ensuring that... Like when you open a new restaurant. You don't want to have all of your tables full on the first night. We knew that we were going to have everybody using Jira and Confluence day one after a migration because we're going to break some stuff. They actually turned out to be really exceptionally good idea. And I encouraged people to find... Look at your data and work out when is low time to do this? I've been involved in Jira and Confluence for a long time and just thought it's task tracker and it's a wiki. There's nothing there that I don't really know about. But one of the decisions we made was actually that when we completed the data migration and it was ready to go, I always said if we waited, do we get a better result? And the answer was no.

Greg Warner:

We should make this available to people now. And so we opened it up on a Sunday morning in the US, which was starting to be business hours in Australia. We started making teams aware that they can now go ahead and use Jira and Confluence. And it was the feedback that we immediately got from those teams that were starting to use Jira service management in cloud for the first time, about, "Wow, this is so much better than it was on-prem." And people said, "I can actually see the attention to detail you've made on fields and descriptions and the changes you've made." And it started to impact people's workday that this was better than it was. I didn't expect that to come back. And so I have a montage that we share with the team of all these Slack messages from people saying, "This is really good. This is much better than we had before."

Greg Warner:

What I didn't also realize is that when we moved from on-prem to cloud is the data that we had became more usable and accessible. Hadn't planned that. It seems obvious now, but when we put it in cloud and it has all the security controls around it and now no longer has the requirements of things like VPN to get access to it, people could build new things to use it to be able to interact with your issues, to interact with pages. And so we started with 76 integrations and over space of three months now we had this big jump in the first three months up to about a hundred something and now we're going to Forge And what it means is people who have had this need to be able to get to the data can now get to it. I didn't see that coming. I just thought we were just server cloud. But yeah, having a more accessible has led to improvements in the way that our teams are working but also how they use it in other applications that just simply wasn't available before.

Chloe Hall:

Yeah. Wow. That's great. And it's good that you were able to receive that feedback straight away from the teams that you had in Australia. I think that's really good and it sounds like it's created such a good opportunity for you at Splunk as well now that you're on cloud.

Greg Warner:

Yeah, it's certainly a business leader that can propel you forward and I eagerly come in now and look at what are other teams going to do with it. And so when we had the first team that said they want to build a Forge app, I'm like, Sure. We should not discourage that at all. Extend the platform. That's why we spent the money and time to do it. What can you do with it now? And we did certainly make Atlassian aware on the product side, like how we're using it and where we'd like to see improvements. If you look at the server DC comparison, I used to be that person that would look at the new features in cloud and ask that question about, when is that new feature coming to on-prem? To going to being that customer who's now, I have that feature today, right? And I'm using it because we don't wait for it.

Greg Warner:

So you mentioned about things you didn't plan from the roadmap. There are design decisions that I talk to enterprise customers that I need to make aware of about. One of them is to do with release tracks. In enterprise cloud, you can choose to bunch up the change to cloud and then they get released periodically every two weeks, every month. When I looked at that, came back to one of our principles about don't implement server in cloud, why would we do that? Atlassian has far more data points on whether this works for customers at scale than we do. So why would we hold back functionality? So as a result we don't do release tracks. We let all of the new functionality get delivered to us as Atlassian sees fit. And the result of that is our own engineering staff, our own support staff who use Jira, get the notifications about new products and features and this is fantastic.

Greg Warner:

Again, why would we implement server, which is where you would bunch up all your changes and then go forward? The other thing too about our cloud migration journey is don't be blinked that you're just doing a cloud migration today and then the project ends. There are things you need to be thinking about as you go along, but what's the impact in the future? So for us, we have multiple sites. Enterprise customer have multiple sites. So there are design decisions that we've made so that we can, in the future, do cloud to cloud migration. You will move sites. Your organization could be bought or could be buying companies. So you do mergers and acquisitions. And so as part of that, we have some runbooks now that talk about using the cloud-to-cloud tooling so we can move a Jira project from a site here to a site there, how we'd move users here and users there.

Greg Warner:

And that actually came about through the assistance with our TAM, not focusing just always on the cloud migration date but also what's that look like six months later? What's it look 12 months later? So that you don't perform your cloud migration and then lock yourself in a corner that later on now I have to unwind something. I had the opportunity to fix it. So yeah, I do encourage migration customers to also think six months, 12 months beyond their cloud migration. But what could also happen and then speak to your solution partner about design decisions today that could affect you in the future.

Chloe Hall:

Yeah. So you definitely need to be thinking future-focus when you're doing this cloud migration. I know you've addressed a lot of the opportunities that came out of the cloud migration. Was there anything else that was an unexpected value that came from it that you wanted to share?

Greg Warner:

The other value is make it more accessible. We have seen people use it in different places that we hadn't thought about. So some of the things that we were doing before, we had to have a company-owned asset to get on the VPN and just things like that. That actually restricted people in where they could do work. Whereas now we've, as long as you've got a computer or mobile device connected to the Internet, absolutely you can use a mobile device support, you can get access to it. Approvals that used to be done on a computer are now done on a mobile device. Those things. But I think the integrations has been probably been the one thing I'm most... We're not the catalyst. We kind of pushed it along but seeing people get real use out of it and using the data for other purposes. We have seen people build some microservices that use the data from Jira that we couldn't do before. Again, you're just unlocking that potential by making it more usable and accessible.

Chloe Hall:

After going through the whole migration journey and, like you said, you're coming towards the end of it, what were the things that stood out to you that you're like, okay, they didn't go so well? Maybe if I was to do this again, how would I do this better next time?

Greg Warner:

So I get back to that day one unboxing experience. You know you want to give it that best experience. And we delivered that for people in Australia and APAC as we opened it and they got to use Jira for the first time and it worked fine. And that is mainly the result of a lot of emphasis on the Jira piece because we said, we know this is going to be hard. It's got workflows, issue schemes, notifications schemes. This is going to be hard.

Greg Warner:

So we started that one really early and then probably about 60% down through our migration journey, we started on Confluence. We thought how hard can Confluence be. It's a bunch of spaces and pages. It can't be that hard. We actually hit some migration challenges with the engineering tooling with Confluence, which meant that the Confluence UAT was delayed. The Jira UAT was fantastic. Ran for a month. We found some problems, got fixed, got answers. We were really confident that was going to be fine.

Greg Warner:

And then we hit this Confluence piece. We're like, wow, this is going to be a challenge. And there was at least one time I could think of. It was a Saturday morning at breakfast where our solution partner sent me a Slack message about, I think we've got a problem here with some tooling. What are we going to do? Towards the middle of the day, I was kind of scratching my head. This could be a real blocker. We actually worked with Atlassian, came up with the engineering solution, cleared that out. That was good to see, like in the space of 12 to 24 hours, there was a solution. But what it meant was that it delayed the Confluence UAT and it made a week. And there was something we found to do with the new Confluence editor and third-party apps right at the end of that week. And we had to really negotiate with our stakeholders to make this go ahead.

Greg Warner:

Because again, if we'd waited, we'd get a better result. No, we really should go. We know that there's this problem. It's not system-wide but it affects a small group people. So we did it. But for about a hundred people they have this really bad Confluence experience because of this thing. And so for me, I couldn't deliver on that thing I promised, which was a day one experience that was going to be better than what it had before.

Greg Warner:

Now we did work with Atlassian and app vendors to get some mitigation so it wasn't as bad on day five. It wasn't day one but it wasn't perfect. But I would certainly encourage people to make sure that you do treat Jira and Confluence with as much importance as each other. They do go together. When I did our cloud migration, we did it on a weekend and I remember coming back after dropping my kids at school on Tuesday and sitting in the car park. I was like, wow, we actually pulled that off.

Greg Warner:

If we'd propose to the company to move your company email system and your finance system on a weekend, the answer would be no because it's too big a hat. But what we'd said is we're going to move all of our Atlassian stack in a weekend, which really is two big systems, Jira and Confluence. So if I had the time again, we would've started Confluence much, much earlier and then we wouldn't have the need to rush it at the end. And that really did result in a bad day one experience for those people. We have worked with Atlassian since then. We're getting that resolved. We know other Atlassian guys have the same problem. I would start early and don't underestimate the complexity that could happen. There will be some things outside of your control.

Greg Warner:

I talk about this Confluence problem and the migration tooling, which is actually do at scale. Not every customer will see it. We saw it, I conducted customer interviews when we were doing our solution partner decision and the customer actually told me this. Like I should have started Confluence because we had this problem, we wasted some time, and we did it. I even have my notes. But it wasn't until later, same problem, you even had the answer and they told you and you still waited. So I'm spending a few minutes on this podcast talking about it because it happened to me. It's probably going to happen to the next person. So if I could do one thing and that is just encourage you to start it earlier. You're going to end up with a much, much better migration and hopefully can deliver on that day one experience that I couldn't do.

Chloe Hall:

Yeah, no I'm so glad that you've shared that with the Easy Agile audience as well because now they know and hopefully the same mistake won't keep getting repeated. Well, Greg, my final question for you today, and I don't know if you want that to be your answer, but I think it's really good just for the audience, if there's one key takeaway that they can go away with them today from the podcast, what would be that one piece of advice for everyone listening to start their migration journey?

Greg Warner:

The first thing to do is to prioritize it. So if you're an Atlassian customer that's using on-prem Jira or Confluence and you don't have a timeline and you don't have a priority to your cloud migration, start there. Open up the task, which is start to investigate Atlassian Cloud and choose a date. Because yeah, there will come a situation down the track where you might be asked by your CIO and so it's better to have an answer prepared already. I would encourage people to start to look at it because it is the future. If you look across the industry, people are moving to SaaS. It's really a question. Do you want to maintain and be that customer wondering when that feature's coming to cloud or do you want to be that customer in cloud who has it today? We have seen a monumental shift to when we moved to cloud in functionality, availability, all the good things that cloud delivers. And it's one of the biggest promoter... The person that used to write exam questions for servers now saying go to cloud.

Greg Warner:

Absolutely. So when I've spoken to other enterprise customers, particularly at Team, I said like, when do you plan your cloud migration? I was like, wow, we're going to start it in three years. I'm like, three years? You need to go back to the office next week and start like 12 months because yeah you will... There is absolutely a competitive advantage to doing it. And it's not just me being now as biggest cloud opponents. We see it, we see it every day and for me, this is one of the most influential projects I've been involved in with Atlassian since 2006. This one here is going to have a long-lasting effect at Splunk for a long time and I'm happy to speak to yourself at Easy Agile and others about it and here at their cloud journey because I want to go to Team next year. I want to make sure we have these conversations in the whole way about, I got that one thing. It's either I started my Confluence migration earlier or I actually put in a timeline of when we should start our cloud migrations.

Chloe Hall:

Yeah, beautiful. That is some great advice to take away, Greg. And so honestly, thank you so much for coming on the podcast today. You have provided some brilliant insights, takeaways, and also because there is no roadmap, I feel like your guidance is so good for those who are looking to start their cloud migration. Yeah. We really appreciate you sharing your knowledge.

Greg Warner:

All right. Thanks for having me on. Thank you for listening.

Chloe Hall:

No worries.

What a great conversation this was with Chris Stone, The Virtual Agile Coach!

Chris shared some insights into the importance of sharing and de-stigmatising failures, looking after your own mental health, and why work shouldn't be stale.

Some other areas we discussed were, why you should spend time in self reflection - consider a solospective? and asking "how did that feel?" when working as a team.

"I really enjoyed our chat. Plenty to ponder over the silly season, and set yourself up with a fresh perspective for 2021. Enjoy and Merry Christmas!"

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Transcript

Sean Blake:

Hello, and welcome to another episode of the Easy Agile Podcast. It's Sean Blake here, your host today, and we're joined by Chris stone. Chris is going to be a really interesting guest. I really enjoyed recording this episode. Chris is the Virtual Agile Coach. He's an agility lead. People First champion blogger, speaker and trainer, who always seeks to gamify content and create immersive Agile experiences. An Agile convert all the way from back in 2012, Chris has since sought to broaden his experiences, escape his echo chamber and to fearlessly challenge dysfunction and ask the difficult questions. My key takeaways from this episode were; it's okay to share your failures, the importance of recognizing our mental health, why it's important that work doesn't become stale, how to de-stigmatize failure, the importance of selfreflection and holding many self retrospectives, and the origins of the word deadline. You'll be really interested to find out where that word came from and why it's a little bit troubling. So here we go. We're about to jump in. Here's the episode with Chris stone on the Easy Agile Podcast. Chris, thanks so much for joining us and spending some time with us.

Chris Stone:

Hey there Sean, thank you for having me. It's a pleasure.

Sean Blake:

I have to mention you've got a really funky Christmas sweater on today. And for those people listening on the audio, they might have to jump over to YouTube just for a section to check out this sweater. Can you tell us a bit about where that came from?

Chris Stone:

So this sweater was a gift. It's a Green Bay Packers, Chris, Ugly Christmas Jumpers, what they call it. And I'm a fan of the Green Bay Packers, I've been out there a few times to Wisconsin, Green Bay, Wisconsin. It's so cold out there in fact. When you're holding a beer and minus 13 degrees, the beer starts turning to slush just from being outside in the cold air. It's a great place, very friendly, and the jumper was just a gift one Christmas from someone.

Sean Blake:

Love it. There's nothing better than warm beer is there? Okay. So Chris, I first came across you because of the content that you put out on LinkedIn. And the way that you go about it, it's so much fun and so different to really anything else I've seen in the corporate space, in the enterprise space, in the Agile space even, why have you decided to go down this track of calling yourself the virtual Agile coach, building a personal brand and really putting yourself out there?

Chris Stone:

Well, for me, it was an interesting one because COVID, this year has forced a lot of people to convert to being virtual workers, remote workers, virtual coaches themselves. Now, what I realized this year is that, the aspiration for many is those co-located teams, it's always what people desired. They say, "Oh, you have to work harder, Katie, that's the best way." And I realized that in my whole Agile working life, I'd never really had that co-located team. There was always some element of distributed working and the past two years prior to where I'm currently, my current company, I was doing distributed scaled Agile with time zones, including Trinidad and Tobago, Alaska, Houston, the UK, India, and it was all remote.

Chris Stone:

And I thought, all right, this is an opportunity to recognize the fact that I was a virtual Agile coach already, but to share with others, my learnings, my experiences, the challenges I've faced, the failures I've had with the wider community so they can benefit from it because obviously, everyone, or more many have had to make that transition very quickly. And there's lots of learnings there that I'm sure people would benefit from. And this year in particular, I guess the honest answer, the reason for me being, I guess out there and working more on that side of things, being creative is because it's an outlet for my mental health.

Chris Stone:

I suffer from depression and one of my ways of coping with that is being creative and creating new content and sharing it. So I guess it's a reason of... it's linked to that also, but also the stories that people tell me afterwards, they motivate me to keep doing it. So when someone comes to me and says, "Hey, I did the Queen retrospective, the Queen Rock Band retrospective, and this program manager who never smiles connected to the content and admitted he liked Queen and smiled." And this was a first and when people come to me and say, "Hey, we did the Home Alone retrospective, the one of your Christmas themed ones and people loved it. It was great." It was the most engaging retrospective we've had so far because the problem is work can become stale if you let it be so.

Chris Stone:

Retrospectives can become this, what did we do last time? What are we going to do next time? What actions can we do? Et cetera, et cetera. And unless you refresh it and try new things, people will get bored and they'll disconnect and they'll disengage, and you're less likely to get a good outcome that way. So for me, there's no reason you can't make work a little bit fun, with a little bit of creativity and a little bit of energy and passionate about it.

Sean Blake:

I love that. And do you think a lot of people come to work even when they're working in Agile co-located teams and it's just not fun, I mean what do you think the key reasons are that work isn't fun?

Chris Stone:

I think because it can become stale. All right. So let's reflect on where we are today. Today, we're in a situation where we're not face-to-face with one another. We don't have time for those water cooler chats. We don't connect over a coffee or a lunch. We don't have a chat about idle banter and things of that on the way to a meeting room, we didn't have any of that. And that forces people to look at each other and see themselves as an avatar behind a screen, just a name. Often in particular, people aren't even on video camera.

Chris Stone:

It forces them to think of people as a name on a screen, rather than a beating heart on a laptop. And it can abstract people into just these entities, these names you talk to each day and day out, and that can force it to be this professional non-personal interaction. And I'm a firm believer that we need to change that. We need to make things more fun because it can, and in my experience, does result in much better outcomes. I'm very, very people first. We need to focus on people being people. People aren't resources. This is a common phrase I like to refer to you.

Sean Blake:

I love that, people aren't resources. You spoke a little bit about mental health and your struggle with depression. Something that I hear come up time and time again, is people that talk about imposter syndrome. And I wonder, firstly, if you think that might be exasperated through working remotely now. People are not so sure how they fit in, where their role is still the same role that it was 12 months ago. And do you have any tips for people when they're dealing with imposter syndrome, especially in a virtual environment?

Chris Stone:

Well, yeah I think this current environment, this virtual environment, the pandemic in particular, has led to a number of unhelpful behaviors. That there's a lot more challenges with people's mental health and negativity, and that can only lead to, I guess, less desire, less confidence in doing things, maybe doubting yourself. There's some great visuals I've shared on this recently, and it's all about reframing those imposter thoughts you have, the unhelpful thinking, that thing that goes through your mind that says, Oh, they're all going to think I'm a total fraud because maybe I don't have enough years of experience, or I should already know this. I must get more training. There's lots of “shoulding” and “musting” in that. There's lots of jumping to conclusions in this.

Chris Stone:

And a couple of ways of getting around that is, so if you're thinking of the scenario where I'm a fraud think, "Oh, well I'm doing my best, but I can't predict what they might think." When you're trying to think about the scenario of do I need to get more training? Well, understand and acknowledge the reality that you can't possibly know everything. You continue to learn every single day and that's great, but it's unrealistic to know it all. There's a great quote I often refer to and it's, true knowledge is knowing that you know nothing. I believe it's a quote from Socrates.

Chris Stone:

And it's something that very much resonates with me. Over the years I've gone through this learning journey where, when I first finished university, for example, I thought I knew everything. I thought I've got it all. And I'd go out to clients and speak and I'm like, "Oh yeah, I know this. I've got this guys." And then the more involved I've become and the more deeper I've gone into the topic, the more I realized, actually there's so much that I don't know. And to me, true knowledge is knowing that you know nothing tells me there's so much out there that I must continuously learn, I must continuously seek to challenge myself each and every day.

Chris Stone:

Other people who approach me and say, "How do you, or you produce a lot of content. How would you put yourself out there?" And I say, "Well, I just do it." Let's de-stigmatize failure. If you put a post out there and it bombs, it doesn't matter, put another one out there. It's as simple as that, learn from failure, Chuck something out there, try it, if it doesn't work, try something else. We coach Agile teams to do this all the time, to experiment. Have a hypothesis to test against that. Verify the outcomes and do retrospectives. I do weekly solospectives. I reflect on my week, what works, what hasn't worked, what I'm going to try differently. And there's no reason you can't do that also.

Sean Blake:

Okay. So weekly solospectives. What does that look like? And how do you be honest with yourself about what's working, what's not working and areas for yourself to improve? How do you actually start to have that time for self-reflection?

Chris Stone:

Unfortunately you got to make time for some reflection. One thing I've learned with mental health is you have to make time for your health before you have to make time for your illness or before you're forced to make time for your illness. And it can become all too easy in this busy working world to not make time for your health, to not make time and focus on you. So you do just have to carve out that time, whether that's blocking some time in the diary on a Friday afternoon, just to sit down and reflect, whether that's making time to go out for a walk, setting up a time on your Alexa to have a five minute stretching break, whatever it is, there's things you can do, and you have things you have to do to make time for yourself.

Chris Stone:

With regards to a solospective, the way I tend to do things is I tend to journal on a daily basis. That's almost like my own daily standard with myself, it's like, what have I observed? What have I... what challenges do I face in the past day? And then that sums up in the weekly solospective, which is basically a retro for one, where I reflect on, what did I try it? What do I want to achieve this week? What's gone well? What hasn't gone well. It's the same as a retrospective just one and allows me to aggregate my thoughts across the week, rather than them being single events. So that I'm focusing more on the trajectory as opposed to any single outlier. Does that make sense?

Sean Blake:

It does. It does. So you've got this trajectory with your career. You're checking in each week to see whether you're heading in the right direction. I assume that you set personal goals as well along the way. I also noticed that you have personal values that you've published and you've actually published those publicly for other people to look at and to see. How important are those personal values in informing your life and personal and career goals?

Chris Stone:

So I'd say that are hugely important, for me, what I thought was we see companies sharing their values all the time. You look on company websites and you can see their values quite prominently. And you could probably think do they often live up to their values? You have so many companies have customer centricity as their value, but how many of them actually focus on engaging with their customers regularly? How many have a metric where they track, how often they engage with customers? Most of them are focusing on velocity and lead time. So I always challenge, are you really customer centric or is that lip service? But moving aside, I digress. I thought companies have values, and obviously we do as well, but why don't we share them? So I created this visual, showing what mine were and challenged a few others to share it also. And I had some good feedback from others which was great.

Chris Stone:

But they hugely influence who I am and how I interact on a day-to-day basis. And I'll give you an example, one of my values is being open source always. And what that means is nothing I create, no content I create, nothing I produce would ever be behind a payroll. And that's me being community driven. That's me sharing what I've learned with others. And how that's come to fruition, how I've lived that is I've had lots of people come to me say, "Hey, we love the things you do. You gave me flying things. Would you mind, or would you like to collaborate and create this course that people would pay for?" So often I've said, "If it's free, yes. But if it's going to be monetized, then no."

Chris Stone:

And I've had multiple people reach out to me for that purpose. And I've had to decline respectfully and say, "Look, I think what you're doing is great. You've got a great app and I can see how having this Agile coaching gamification course on that would be of great value. But if it's behind the payroll, then I'm not interested because it's in direct conflict with my own values, and therefore, I wouldn't be interested in proceeding with it. But keep doing what you're doing, being people first, #people first." This is about me embodying the focus on people being beating hearts behind a laptop, rather than just this avatar on a screen. And I have this little... the audio listeners, won't be able to see this, but I'm holding up a baby Groot here. And he's like my people first totem.

Chris Stone:

And the reason for that is I have a group called the Guardians of Agility, and we are people first. That's our emblem. And these are my transformation champions in my current company. I like to have Guardians of Agility, and I've got this totem reminding me to be people first in every interaction I have. So when, for example, I hear the term resources and I'm saying, well... As soon as I hear it, it almost triggers me. I almost hear like, "Oh, what do they mean by that?" And I'll wait a little moment and I'll say, "Hey, can you tell me what you mean by that?" And you tease it out a little bit. And often they meant, "Oh, it's people, isn't it?" If you're talking about people, can we refer to them as people?

Chris Stone:

Because people aren't resources. They're not objects or things you mine out the ground. They're not pens, paper or desks. They're not chairs in an office. They are people. And every time you refer to them as a resource, you abstract them. You make it easier to dehumanize them and think of them as lesser, you make it easier to make those decisions like, oh, we can just get rid of those resources or we can just move that resource from here to there and to this team and that team, whether they want to or not. So I don't personally like the language.

Chris Stone:

And the problem is it goes all the way back to how it's trained. You go to university and you take a business degree and you learn about human resources. You take a course, Agile HR, Agile human resources, right, and it's so prevalent out there. And unless we challenge it, it won't change. So I will happily sit there and a meeting with a CTO and he'll start talking about resource and I'll say, "Hey, what do you mean by that?" And I'll challenge it and he'll go, "Yeah, I've done it again, have I not?" "Yes. Yes, you have." And it's gotten to the point now where I'll be on this big group call for example, and someone will say it, and I'll just start doing this on a screen waving, and they'll go, "Did it again, didn't I?" "Yes, you did."

Sean Blake:

So some of these habits are so ingrained from our past experiences our education, and when you're working with teams for the first time, who's never worked in Agile before, they're using phrases like resources, they're doing things that sometimes we call anti-patents, how do you start to even have that conversation and introduce them to some of these concepts that are totally foreign to people who've never thought the way that you or I might think about our teams and our work?

Chris Stone:

Sure. So I guess that the first response to that is with empathy. I'm not going to blame someone or make out that they're a bad person for using words that are ingrained, that are normal. And this is part of the problem that that term, resource is so ingrained in that working language nowadays, same as deadlines. Deadlines is so ingrained, even though deadlines came from a civil war scenario where it referred to, if you went past the line, you were shot. How did that land in the business language? I don't know. But resources, it's so ingrained, it's so entrenched into this language, so people do it without intending to. They often do it without meaning it in a negative way. And to be honest, the word itself isn't the issue, it's how people actually behave and how they treat people.

Chris Stone:

I said my first approach is empathy. Let's talk about this. Let's understand, "Hey, why did you use term?" "Oh, I use it to mean this." "Okay. Well." Yeah, and not to do it or call them out publicly or things like that. It's doing things with empathy. Now, I also often use obviously gamification and training approaches, and Agile games to introduce concepts. If someone's unfamiliar to a certain way of working, I'll often gamify. I'll create something, a virtual Agile game to demonstrate. The way I do say, is I'm always looking to help people understand how it feels, not just to talk theory. And I'll give you an example. I'm a big fan of a game called the Virtual Name Game. It's a game about multitasking and context switching.

Chris Stone:

And I always begin, I'll ask group of people, "Hey guys, can you multitask?" And often they go, "Yeah, we can do that." And there'll be those stereotypical things like, "Oh yeah, I'm a woman. I can do that." It happens. Trust me. But one of the first things I do, if I'm face-to-face with them, I'll say, "Hey, hold your hands out like this. And in your left hand..." And people on the audio can't see me, I'm holding out like my hands in front of me. In my left hand, we're going to play an endless game of rock, paper, scissors. And in my right hand, we're going to play a game of, we have a thumb war with each other. And you can try, you can challenge them, can they do those concurrently? No, they can't. They will fail because you just can't focus on both at the same time.

Chris Stone:

Now the Virtual Name Game, the way it works is you divide a group of people up into primarily customers and one developer. And I love to make the most senior person in the room, that developer. I want them to see how it feels to be constantly context switching. So if you were the developer, you're the senior person to review the hippo in this scenario, the highest paid person. I would say Sean, in this game, these customers, they are trying to get their name written first on this virtual whiteboard. And we're going to time how long it takes for you to write everyone's name in totality. The problem is that they're all going to shouting at you continuously, endlessly trying to get your attention. So it's going to be Sean, Sean, write my name, write my...

Chris Stone:

And it's just going to be wow, wow, wow, who do I focus on? You won't know. And this replicates a scenario that I'm sure many people have experienced. He who shouts loudest gets what they want. Prioritization is often done by he who's... or the person who shouts loudest not necessarily he. We then go into another rounds where you say, I'm this round, Sean, people are to be shouting their name at you. But in this round, you're going to pay a little bit attention to everyone. So the way you're going to do that is you're going to read the first letter of one person's name, then you move on to the first letter of the next person's name, and you're going to keep going around. The consequence of that is everyone gets a little bit of attention, but the result is it's really slow.

Chris Stone:

You're starting lots of things but not finishing them. And again, in each round, we're exploring how it feels. How did it feel to be in that round? Sean, you were being shouted at, how did that feel? Everyone else, you were shouting to get your attention. You had to shout louder than other people, how did that feel? And it's frustrating, it's demotivating, it's not enjoyable. In the final around, I would say, "Hey, Sean, in this round, I'm going to empower you to decide whose name you write first. And you can write the whole thing in order. And the guys actually they're going to help you this time, there are no shouts over each other, they are going to help you." And in this scenario, as I'm sure you can imagine, it feels far better. The result is people finish things, and you can measure the output, the number of brand names written on a timeframe.

Chris Stone:

It's a very quick and easy way of demonstrating how it feels to be constantly context switching and the damage you can have, if, for example, you've prioritized things into a sprint and you got lots of trying to reorder things and so on and so forth, and lots of pressure from external people that ideally should be shielded from influencing this and that, and how that feels and what the result is, because you may start something, get changed into something else. You got to take your mindset of this, back into something else, and then the person who picks up the original thing might not have even been the same person, they've got to learn that over again. There's just lots of waste and efficiency costs through that. And that's just an example of a game I use, to bring that sort of things to life.

Sean Blake:

That's great. That's fantastic. I love that. And I think we need to, at Easy Agile, start playing some of those games because there's a lot of lessons to be learned from going through those exercises. And then when you see it play out in real life, in the work that you're doing, it's easier to recognize it then. If you've done the training, you've done the exercise, that all seems like fun and games at the time, but when it actually rears its head in the work that you're doing, it's much easier to call it out and say, "Oh wait, we're doing that thing that we had fun playing, but now we realize it's occurring in real life and let's go a different direction." So I can see how that would be really powerful for teams to go through that so Chris [crosstalk 00:22:26].

Chris Stone:

I'd also add that every game that I do, I construct it using the four Cs approach. So I'm looking to connect people... firstly, connect people to each other, and then to the subject matter. So in this game is about multitasking. To contextualize why that matters, why does context switching and multitasking matter in the world of work? Because it causes inefficiencies, because it causes frustration, de-motivation, et cetera. Then we do some concrete practice. We play a game that emphasizes how it feels. And at the end we draw conclusions, and the idea is that with the conclusion side of things, it's almost like a retrospective on the game. We say, "Hey, what did we learn? What challenges we face? And what can we do differently in our working world?" And that hopefully leaves people with actionable takeaways. A lot of the content I share is aiming to leave it with actionable takeaways, not just talking about something, but reflecting on what you could do differently, what you could try, what experiment you might like to employ with your working life, your team that might help improve a situation you're facing.

Sean Blake:

Okay. Yeah, that's really helpful. And you've spoken about this concept of Agile sins, and we know that a lot of companies have these values, they might've committed to an Agile transformation. They might've even gone and trained hundreds or thousands of people at accompany using similar tactics and coaching and educational experiences that you provide. But we still see sometimes things go terribly wrong. And I wonder, what's this concept of Agile sins that you talk about and how can we start to identify some of these sins that pop up in our day-to-day work with each other?

Chris Stone:

I guess, so the first thing I would emphasize about this is that using sin, it's a very dogmatic religious language and it's more being used satirically than with any real intent. So I just like to get that across. I'm not a dogmatic person, I don't believe there is any utopian solution. I certainly don't believe there's any one size fit to all situation for anyone. So the idea that there's really any actual sins is... yeah, take that with a pinch of salt. The reason the Agile sins came up is because I was part of... I'd done a podcast recently with a guy called Charles Lindsey, and he does this Agile confessional. And it's about one coach confessing to another, their mistakes, their sins, the things they've done wrong.

Chris Stone:

And I loved it because I'm all about de-stigmatizing failure. I'm all about sharing with one another, these war stories from one coach to another, because I've been a proponent of this in the past. I've shouted, "Hey there, I failed on this. I made this mistake. I learned from it." And I challenge others to do so as well and there's still this reluctance by many to share what went wrong. And it's because failure is this dirty word. It's got this stigma attached to it. No one wants to fail, leaders in particular. So the podcast was a great experience.

Chris Stone:

And it was interesting for me because that was the first time I'd given a confession, because I'll be honest with you, I'm someone who is used to taking confession myself. I go to this hockey festival every year and I got given years ago, this Archbishop outfit, and I kind of made that role my own way. I was drunk, and I said, "You're going to confess your sins to me." And if they haven't sinned enough, I tell them to go and do more. And I give them penicillin with alcohol shots and things like that. And I've actually baptized people in this paddling pool whilst drunk. Anyway, again, I digress, but I wasn't used to confessing myself, usually, I was taking confession, but I did so and it was a good experience to share some of my failures and my patterns was to create... and it was my own idea, to create my videos, seven videos of my seven Agile sins. And again, this was just me sharing my mistakes, what I've learned from that, with the intent of benefiting others to avoid those similar sins.

Sean Blake:

So you've spoken to a lot of other Agile coaches, you've heard about their failures, you confessed your own failures, is it possible for you to summarize down what are those ingredients that make someone a great coach?

Chris Stone: And that is a question, what makes someone a great coach? I think it's going to be entirely subjective, to be honest. And my personal view is that a great coach listens more than they speak. I guess that would be a huge starting point. When they listen more than they speak, because I've... and this is one of the things I've been guilty of in the past, is I've allowed my own biases to influence the team's direction. An approach I'd taken in the past was, "Hey, I'm working with this team and this has worked well in the past. We're going to do that." Rather than, "So guys, what have you done so far? What have you tried? What's worked well? What hasn't worked well? What can we create or what can we try next? That works for you guys. Let's have you make that decision and I'm here to guide you through that process to facilitate it, rather than to direct it myself."

Chris Stone:

Again, I find ... it's an approach that resonates more with people. They like feel that they own that decision as opposed to it being forced upon them. And there's far less, I guess, cognitive dissonance as a consequence. So listening more than speaking is a huge for me, a point an Agile coach should do. Another thing I think for me nowadays, is that there's too much copying and pasting. And what I mean by that is, the Spotify, the Spotify model came out years ago and everyone went, "Oh, this is amazing. We're going to adopt it. We're going to have tribes and chapters and guilds and squads, and it's going to work for us. That's that's our culture now."

Chris Stone:

I was like, "Well, let's just take a moment here. Spotify never intended for that to happen. They don't even follow that model themselves anymore. What you've done there is you've just tried to copy and paste another model." And people do it with SAFe as well. They just say, "Hey, we're going to take the whole SAFe framework and Chuck it into our system in this blueprint style cookie cutter." And the problem is that it doesn't take into account for me, the most important variable in any sort of transformation initiative, the people, what they want, and the culture there. So this is where another one of my values is, innovate, don't replicate. Work with people to experiment and find that Agile, what works for them rather than just copying and pasting things.

Chris Stone:

So tailor it to their needs rather than just coming in with some or seen dancing framework, and then the way I do it is I say, "Hey, well, SAFe is great. Well, it's got lots of values, and lots of great things about it. Lots of benefits to it, but maybe not all of it works for us. Let's borrow a few tenent of that." Same with LeSS, same with Scrum At Scale, same with Scrum, similar to Kanban. There's lots of little things you can borrow from various frameworks, but there's also lots of things you can inject yourself, lot's of things you can try that work for you guys, and ultimately come up with your own tailor-made solutions. So innovate, don't replicate would be another one for me.

Chris Stone:

Learning, learning fast and learning often, and living and breathing that yourself. Another mistake I and other coaches I think have made is not making time for your own personal development to allowing, day in, day out to just be busy, busy, busy, but at the same time you're going out there, coaching teams, "Hey, you've got to learn all the time. You got to try new things." But not making that time for yourself. So I always carve out time to do that, to attend conferences, to read books, to challenge myself and escape my echo chamber. Not just to speak to the same people I do all the time, but perhaps to go on a podcast with people I've never spoken to. To a different audience, maybe to connect with people that actually disagree with me, because I want that.

Chris Stone:

I don't want that homophilous thinking where everyone thinks exactly like I do, because then I don't get exposed to the perspectives that make me think differently. So I'm often doing that. How can I tend to conference that I know nothing about, maybe it's a project management focus one. Project management and waterfall isn't a dirty word either. There is no utopian system, project management and... sure traditional project management and waterfall has its benefits in certain environments. Environments with less footing, less flexible scope or less frequently changing requirements works very well.

Chris Stone:

I always say GDPR, which is an EU legislation around data protection, that was a two year thing in the making and everyone knew exactly what was happening and when they had to do it by. That was a great example of something that can be done very well with a waterfall style, because the requirements weren't changing. But if you are trying to develop something for a customer base that changes all the time, and you've got lots of new things and lots of competitors and things like that, then it varies, and probably the ability to iterate frequently and learn from it is going to be more beneficial and this is where Agile comes in. So I guess to sum up there, there's a few things, learning fast learning often. I can't even remember the ones I've mentioned now, I've gone off on many tangents and this is what I do.

Sean Blake:

I love it. It's great advice, Chris. It's really important and timely. And you mentioned, earlier on that the customer base that's always changing and we know that technology is always changing and things are only going to change more quickly, and disruptions are only going to be more severe going forward. Can you look into the future, or do you ever look into the future and say, what are those trends that are emerging in the Agile space or even in work places that are going to disrupt us in the way that we do our work? What does Agile look like in five or 10 years?

Chris Stone:

Now that again is a very big question. I can sit here and postulate and talk about what it might look like. I'm going to draw upon what I think is a great example of what will shape the next five or 10 years. In February, 2021, there's a festival called Agile 20 Reflect, I'm not sure if you've heard of it, and it's built as a festival, not conference, it's really important. So it's modeled on the Edinburgh festival and what it intends to be is a celebration of the past, the present and the future of Agile. Now what it is, it's a month long series of events on Agile, and anyone can create an event and speak and share, and it will create this huge community driven load of content that will be freely accessible and available.

Chris Stone:

Now, there are three of the original Agile manifestor signatories that are involved in this. Lisa Adkins is involved in this as is lots of big name speakers that are attached to this festival. And I myself, I'm running a series of retrospectives on the Agile manifesto. I've interviewed Arie van Bennekum, one of the original Agile manifesto signatories. They're going to be lots of events out there. And I think that festival will begin to shape in some way, what Agile might look like because there's lots of events, lots of speakers, lots of panel discussions that are coming up, coming together with lots of professionals out there, lots of practitioners out there that will begin to shape what that looks like. So whilst I could sit here and postulate on it, I'm not the expert to be honest, and there are far greater minds than I. And actually I'd rather leverage the power of the wider community and come into that than suggesting mine at this time.

Sean Blake:

Nice. I like it. And what you've done there, you've made it impossible for us to click this video and prove you wrong in the future when you predict something that doesn't end up happening. So that's very wise if you.

Chris Stone: Future proof myself.

Sean Blake: Exactly. Chris, I think we're coming almost to the end now, but I wanted to ask, given the quality of your Christmas sweater, do you have any tips for teams who are working over the holiday period, they're most likely burnt out after a really difficult 2020? What are some of the things you'd say to coaches on Agile teams as they come into this time where hopefully people are able to take some time off, spend some time with their family. Do you have any tips or recommendations for how people can look after their mental health look after their peers and spend that time in self-reflection?

Chris Stone:

Sure. So a number of things that I definitely would recommend. I'm currently producing and sharing this Agile advent calendar. And the idea is that every day you get a new bite-size piece of Agile knowledge or a template or something working in zany or a video, whatever it may be. There's lots of little things getting in there. And there's been retro templates, Christmas and festive themes. So there's a Home Alone one, a Diehard one, an elf movie one, there's all sorts. Perhaps try one of those as a fun immersive way with your team to just reflect on the recent times as a squad and perhaps come up with some things in the next year.

Chris Stone:

And there's for example, the Diehard one, it's based on the quotes from the movie Diehard so it's what you'd be doing in there, celebrate your... to send them to your team. Or there's one in there about, if this is how you celebrate Christmas, I can't wait for new year. And that question was saying, what do we want to try next year? Like this year has been great, what do we want to try differently next year? So there's opportunities through those templates to reflect in a fun way so give one of those a go. I shared some Christmas eve festive Zoom backgrounds, or Team backgrounds, give those a go and make a bit fun, make it a bit immersive. There's Christmas or festive icebreakers that you can use. What I tend to do is any meeting I facilitate, the first five minutes is just unadulterated chat about non-work things, and I often use icebreakers to do so. And whether that's a question, like if you could have the legs of any animal, what would you have and why, Sean, what would that be?

Sean Blake:

Probably a giraffe, because just thought the height advantage, it's got to be something that's useful in everyday life.

Chris Stone: Hard to take you on the ground maybe.

Sean Blake:

Yes. Yes, you would definitely need that. Although, I don't think I would fit in the lift on the way to work, so that would be a problem.

Chris Stone:

Yeah. That's just how I start. But yeah, that's just a question, because it's interesting to see what could people come up with, but there's some festive ones too, what's your favorite Christmas flick? What would put you on the naughty list this year? Yeah, does your family have any weird or quirky Christmas traditions? Because I love hearing about this. Everyone's got their own little thing, whether it's we have one Christmas present on Christmas Eve or every Christmas day we get a pizza together. There's some really random ones that come out. I love hearing about those and making time for that person interaction, but in a festive way can help as well.

Chris Stone:

And then on the mental health side of things, I very much subscribed to the Pomodoro effect from a productivity side of things. So I will use that. I'll set myself a timer, I'll focus without distractions, do something. And then in that five minute break, I'll just get up and move away from my desk and stretch and get a coffee or whatever it may be. But then I'll also block out time, and I know some companies in this remote working world at the moment are saying, "Hey, every one to 2:00 PM is blocked out time for you guys to go and have a walk." Some companies are doing that. I always make time to get out and away from my desk because that... and a little bit more productive and it breaks up my day a little bit. So I definitely recommend that. Getting some fresh air can do wonders for your mental health.

Sean Blake:

Awesome. Well, Chris, I've learnt so much from this episode and I really appreciate you spending some time with us today. We've talked about a lot of things from around the importance of sharing your failures, the importance of looking after your mental health, checking in on yourself and your own development, but also how you tracking, how you feeling. I love that quote that you shared from, we think it Socrates, that true knowledge is knowing that you know nothing. I think that's really important, every day is starting from day one, isn't it? De-stigmatizing failure. The origins of the word deadline. I did not know that. That's really interesting. And just asking that simple question, how did that feel? How did that feel working in this way? People were screaming your name, walk up work, when work's too busy, how does that feel? And is that a healthy feeling that everyone should have? So that's really important questions for me to reflect on and I know our audience will really appreciate those questions as well. So thanks so much Chris, for joining us on the Easy Agile Podcast.

Chris Stone:

Not a problem. Thank you for listening and a Merry Christmas, everyone.

Sean Blake:

Merry Christmas.

TL;DR

Jeff Gothelf, renowned author of "Lean UX" and "Who Does What By How Much," discusses the evolution from output-based work to outcome-focused goal setting with OKRs. Key insights: Teams need to shift from "we're building a thing" to defining success as "who does what by how much" – meaningful changes in human behaviour that drive business results; the biggest barrier to agile ways of working is that people get paid to ship features, not deliver value; leaders should change their questions from "what are you building?" to "what are you learning?"; psychological safety is critical – teams need to feel safe admitting when something isn't working; start small by simply asking "what will people be doing differently when we ship this?"; rename teams around outcomes (mobile revenue team) rather than outputs (iPhone app team); proactive transparency through weekly three-bullet-point updates builds trust with leadership. Bottom line: OKRs, when done right, are the "Trojan horse" that enables all other agile practices to succeed.

Introduction

For years, agile practitioners have championed better ways of working – Lean UX, design thinking, continuous discovery, customer centricity. Yet despite widespread adoption of these practices, many teams still struggle with the same fundamental problem: they're rewarded for shipping features, not delivering value.

In this episode, our CEO Mat Lawrence sits down with Jeff Gothelf to explore how this misalignment of incentives undermines even the best agile practices, and why customer-centric OKRs might be the missing piece that makes everything else click into place.

Jeff Gothelf is a renowned author, speaker, and consultant whose work has shaped how product teams approach collaboration and customer-centricity. Along with co-author Josh Seiden, Jeff wrote "Lean UX," which revolutionised how designers work in agile environments. Their follow-up book, "Sense and Respond," helped leaders understand how to manage in software-based businesses. Their latest book, "Who Does What By How Much," tackles the thorniest problem yet: how to align incentives and goals with customer outcomes.

This conversation traces Jeff's journey from helping designers work better in agile teams, to helping leaders create the conditions for success, to finally addressing the root cause – the goals and incentives that determine what gets celebrated, rewarded, and promoted in organisations. It's a masterclass in shifting from output thinking to outcome thinking, with practical advice for both team members and leaders navigating this transformation.

About Our Guest

Jeff Gothelf is an author, speaker, and organisational consultant who has spent over 15 years helping companies build better products through collaboration, learning, and customer-centricity. His work focuses on the intersection of agile software development, user experience design, and modern management practices.

Jeff is best known as the co-author (with Josh Seiden) of three influential books that have shaped modern product development practices. "Lean UX" (now in its third edition) began as a guide for designers working in agile environments but has evolved into a comprehensive framework for cross-functional collaboration and risk mitigation in product development. The book's core principle – moving from deliverables to outcomes – has influenced how thousands of teams approach their work.

Following "Lean UX," Jeff and Josh wrote "Sense and Respond," a book aimed at leaders and aspiring leaders. It makes the case that the overwhelming majority of businesses today are software businesses, and that managing software-based businesses requires fundamentally different approaches to team structure, management, and leadership. The book provides a roadmap for creating organisations where teams can actually practise the collaborative, customer-centric approaches described in "Lean UX."

Jeff's latest book, "Who Does What By How Much," represents the natural evolution of this work. After years of helping teams work better and leaders manage differently, Jeff and Josh identified that the real barrier to change was incentives and goals. Teams kept saying, "That's great, Jeff, but I get paid to ship features." This book tackles that problem head-on, showing how to use objectives and key results (OKRs) to create customer-centric goals that align with – rather than undermine – modern ways of working.

Beyond his books, Jeff has also authored "Forever Employable" and "Lean vs Agile vs Design Thinking," and he regularly speaks at conferences and consults with organisations on product strategy, team effectiveness, and organisational transformation. His approach is characteristically practical and rooted in real-world experience, making complex concepts accessible through clear frameworks and relatable examples.

Jeff's work continues to evolve as he helps organisations navigate the challenges of building products that customers actually want and need, whilst creating work environments where teams can thrive.

Transcript

Transcript

Note: This transcript has been lightly edited for clarity and readability.

Why Write Another Book? The Journey from Lean UX to OKRs

Mat Lawrence: Well, Jeff, welcome. I'm Mat Lawrence for our audience. I'm COO at Easy Agile, and today I'm talking with Jeff Gothelf, who is the renowned author, speaker, and consultant. You've written a good few books, Jeff. I've been looking through the list – Lean versus Agile versus Design Thinking, Forever Employable, and co-authored a few. The latest one being "Who Does What By How Much," and I was just telling Jeff in the intro here how you've managed to get across a lot of the things that I care about when trying to build teams and get them to understand OKRs. I've already given it to a few people and I'm definitely going to be giving it around. So, Jeff, welcome.

Jeff Gothelf: Thank you so much, Mat. That's very kind of you on all of that stuff. I appreciate it. Thanks for having me.

Mat: I'd love to cover a little bit around the book and the concept you're trying to get across. So I suppose the first question I have is what problem are you hoping to solve with the book? Why did you write it?

Jeff: It's really interesting. I wrote a blog post about this a while back because somebody challenged me on LinkedIn – and I appreciate a good challenge. They said, "How can you write about all this stuff? There's no way you know enough about each one of these topics to write a book. You're spreading yourself way too thin."

I thought that was a really interesting challenge. No one had ever asked that question, and it got me thinking. The answer that I came up with is that this book, "Who Does What By How Much," and it's a conversation about customer-centric objectives and key results, is the natural evolution of the work that Josh Seiden and I have been doing together for more than 15 years.

"We started with Lean UX, and Lean UX was a solution for designers helping them work more effectively in agile software development environments. The response to that book was, 'That's great, Jeff and Josh. We'd love to work this way. My company won't let me work this way.'"

So we wrote "Sense and Respond," which was a book for leaders and aspiring leaders to inspire them to manage differently, to recognise that the overwhelming majority of businesses today are software businesses, and that managing software-based businesses is different.

As we began to work with that material and talk about that, we kept bumping up against the same ceiling, and that ceiling was incentives and goals. No matter how hard we tried to convince people to be customer-centric, to learn continuously, to improve continuously, to work in short cycles, they said, "That's great, Jeff. But I get paid to ship features."

The goal, the measure of success, was shipped – preferably on time and on budget. That's what got celebrated and rewarded, incentivised and promoted. It was in the job descriptions and all that stuff. So it felt like we were really fighting a losing battle.

Objectives and key results has been gaining momentum for the last decade or so. To us, that felt like the perfect Trojan horse – and I know Trojan horse has a negative connotation, but I don't think of it in this case as a negative thing. It was the perfect way to have a conversation about goals in a customer-centric fashion that, if applied in the way that we describe in the book, would enable everything else that we've done to happen more easily.

"What Will People Be Doing Differently?" – The Question That Changes Everything

Mat: I love the evolution of it, Jeff. I've been working in tech now for about 15 years. Prior to that, I used to work in the arts and special effects, which in itself is a very agile industry where you're constantly building prototypes and figuring out what things need to do before they go on stage or be filmed.

When I entered into the tech world as an inexperienced founder and product developer, I was designing to solve problems, and I found the teams I was working with responded really well to that. "What are we trying to do? What are we trying to get here?" They used to give me feedback all the time on whether I was helping them see far enough ahead with the value we're actually trying to deliver.

When I joined Atlassian in 2014, when we were introducing OKRs there, I think we were facing a problem that you described really well in the book, which is around people focusing on shipping their to-do list. They have a backlog that is predefined, full of great ideas, and they really want to get it out the door. Trying to change that conversation to be around "how do we know if this is any good?" – the answer was we just don't know.

I'd love to touch on how have you guided teams to move from that more traditional output-based metrics and shipping into that outcome approach? Maybe you could give an example of where that shift has led to some significant success.

Jeff: Sure. The title of the book is "Who Does What By How Much?" Overwhelmingly, the teams that we've worked on and with over the years have focused on delivering output, making stuff. The question that we tried to get them to understand is: if you do a great job – let's say when – when you do a great job with this feature, how will you know? What will people be doing differently?

That's the question that starts the mindset shift from outputs to outcomes. Outcomes, the way that we describe them, is a meaningful change in human behaviour that drives business results. The human that we're talking about is the human that consumes the thing that you create.

"The question is how will you know you delivered value to that human? Traditionally, it's been like, 'Well, we made the thing for them. There it is.' We made the Sharpie. Terrific. Did anybody need a Sharpie? Anybody looking for a Sharpie? How do we know? What are people doing now that the Sharpie is out there?"

The mindset shift starts with that question. Even in an organisation that just doesn't get this yet, it's a really safe question. I think it's a safe question to say, "Okay, we're gonna build the thing. What do we expect people to be doing differently once we ship this thing?" And when I say people, let's get specific about who. Which people? Who?

This is the evolution of the book title and how we teach this stuff. So what would people be doing differently before we start? Which people? Who? Okay, it's accountants in large accounting firms. Great. When we ship this new system to them, what are they gonna be doing differently than they're doing today? Well, they'll be entering their data more successfully and finishing their work in half the time.

Terrific. What are they doing? Who does what? And how much of that do we need to see to tell us that this was actually valuable? Well, today they're seeing at least a 30% error rate in data entry. Okay, great. What's meaningful? What's a meaningful improvement? If we cut that in half, that's a meaningful improvement. By how much?

All of a sudden, we've constructed the success criteria that has moved the team away from "we're building a thing" to "accountants in large accounting firms reduce their data entry errors by 50%." Who does what by how much. That begins the mindset shift in that conversation in a safe way because we're not saying let's set new goals, let's rewrite our incentives. We're just saying, "Look, I'm just asking a question."

Then once we start to build stuff, and especially once we start to ship stuff, you remember that conversation we had three months ago? We talked about who does what by how much. Is it happening? Do we know? Can we find out? And if it isn't, let's figure it out.

The Non-Profit That Changed Their Approach - From One Million Buses to Ten Iterations

Jeff: I'll give you an example. There was an organisation I worked with – I really loved working with them. They were a non-profit organisation that was looking to address major diseases in the developing world. They had three or four very specific diseases that they were targeting in very specific locations around the world, and I was thrilled to be working with them and helping them.

They managed everything with a task list. They were like, "We're gonna create this campaign and we're gonna put it on buses in China." And I was like, "Okay. How do you know that? So what? If the campaign works, what will people be doing differently?"

"Well, they'll scan the QR code that's on the bus."

"Okay, alright. And then what?"

"They'll sign up for an appointment to get a cardiovascular check."

"And then what?"

"For those who need actual care, they'll sign up for care."

"All of a sudden, we've taken 'put an ad campaign on a bus' to 'who does what by how much.' When we started to think about it that way, they fundamentally were rethinking the level of effort."

Because you might imagine, it was going to be one million buses and hope that it works. Instead, they decided, "Hey, we're gonna do 100 of these in one locality, and we're gonna give it a week, and we're gonna not only see what happens, but find out if people saw the ad, if it speaks to them, if they understood what it said. Then based on that learning, we're gonna iterate on the campaign."

So instead of getting one giant shot at this advertising campaign to drive people to take better care of themselves, now they're gonna get ten iterations. I think that was massively impactful in helping that organisation do better work and help more people.

Mat: I love how you're bringing that back to the experimental and iterative approach that people so often want but really struggle to get to. I've seen so many occasions where OKRs end up describing something that takes three, four, five months to build and ship, and they're only trying to measure the big outcome at the end, whereas what you're talking about there is breaking it down, making it far more iterative and experimental.

Jeff: Reducing your risk. Imagine this organisation had, let's say, £100,000 for this campaign. Traditionally, they would spend that whole hundred grand and hope. The reality is there's no need to do that. They could spend 10 and learn and do a better job with the next 10 and a better job with the next 10, and if they've de-risked it enough, take the last 50 and dump it on the thing that you've actually validated.

It's a de-risking strategy as well. You're increasing the value you're delivering and reducing the risk of spending money on stuff that isn't gonna work. Feels like a no-brainer, doesn't it?

The Reverse Five Whys - Asking "So What?" to Find Your Outcome

Mat: You make it sound like everyone should be doing it, which I agree with. There was something that you did in the middle of that conversation which I really like, and it's kind of like the opposite of the five whys. You know, where you see the problem and you ask why, why, why and you go back to the root cause. Whereas you took that in the other direction there.

Jeff: Right. We were moving forward in time for the desired outcome.

Mat: Yeah, exactly. You said, "Okay, you want to put this thing on a bus. So what?" And you took that three or four steps forward to get to that ultimate outcome. I love that, and that's probably a tactical, practical approach that our audience can take.

I think some of the stuff that I've struggled with over the years is getting teams who are new to OKRs to understand how to move from writing their to-do list, writing their backlog, turning that into their key results, and actually getting it into the outcome base. I think that's one of the things that a lot of teams find hardest to grasp.

Jeff: And as I kicked off with, if your entire career you've been rewarded for shipping and producing and ticking off a to-do list, then it's really hard to break away from that without some form of leadership buy-in. That's coming back to that incentives and performance management criteria side of things. That's really hard because that's what people optimise for.

We can preach outcome-based work until we're blue in the face, as they say in America at least. But if you're paid to ship product, you're gonna optimise in most cases for what gets you paid. That's an important component of this that I think gets ignored a lot.

Two Audiences, Two Approaches - What Should Teams and Leaders Do Differently?

Mat: Let's talk practically around this. We're probably going to have different people listening to this. We could probably give two bits of advice. One is somebody who's in a team and they really want to try this, or maybe they've been trying this and struggling because the incentives don't match. The other group may be someone who's in leadership who is trying to change their organisation to move into this more outcome-based approach. What advice would you give to each of those people?

Jeff: Great question. Let's start with the folks trying to make this happen initially. In my opinion, one of the easiest ways to move this conversation forward in your organisation is to ask that question I mentioned: What will people be doing differently when we ship this?

Have that conversation. Position it any way you'd like, word it any way you'd like. But ultimately, you're not challenging the work. You're not saying "I'm not gonna do the work." You're not pushing back yet.

"All you're saying is, 'Look, we're gonna build this thing, and we're gonna do a great job. What do we hope people will do with this once we have it out there? What are we trying to see? Are we trying to see them increase average order value? Do we want them to abandon their shopping carts less? Are we trying to get them to sign up for a medical check-up at least once a year?'"

That starts it. That starts getting people to think about more than just "I am making a thing."

Mat: If you took that to leadership and said, "Yeah, we're gonna get this stuff out the door, but I want to check with you that you're happy that this is the outcome we're trying to get to, that this is the result if we get it right."

Jeff: I think that's great, and I think that you should come back to them after you ship and say, "Look, remember we met three, six, nine months ago and I said we're building this and we're hoping people will do this? Well, we built it as designed, on time, on budget, and so far we're not seeing the results that we anticipated. We talked to some customers, and here's why we think that is. What we'd like to do next..."

To me, that should be a safe conversation inside your organisation.

Mat: I can imagine people listening to this and getting some cold sweats at the concept of going to someone and saying, "I did everything that you expected from me, but it wasn't good enough."

Jeff: It's not that. What tends to happen in these situations is a lot of upfront planning and commitments, and then we execute. Regardless of all the work that people have done to convince people that there are better ways of working, that's generally speaking how people are doing work still. We did the thing, and guess what? It didn't work. It didn't work as we had hoped. It's not because we built it poorly. It works as designed. We did usability testing on it. People can use it, they can get through the workflow.

What we think is it's not solving a meaningful problem, or we decided to put it somewhere in the workflow that didn't make sense, or whatever the case is. I understand it's not a risk-free conversation. I'm not encouraging people to do things that are career-limiting per se, but at some point we've got to talk about this kind of stuff. Otherwise, we're just a factory. I don't think anybody wants to work in a factory.

It's Not About the Quality of Your Code, It's About Learning

Mat: I couldn't agree more, and I think that the heart of what I spend a lot of my time doing is helping people understand how to get the benefits out of being agile, that agility piece. What we've been discussing there is that key part of learning. You can plan and you can build, you can have alignment on those things, you can improve how you're building all the time and reach quality standards and pass usability testing. But ultimately, if you don't learn, you're never gonna get the insight that you need to adapt what you do next.

"Where a lot of people fall down with agility is they go through all of the motions up to that point, and then through fear, self-preservation, or they've just not seen anybody else around them do it before, they hesitate to say, 'This thing that we've all invested all this time and effort into isn't working as expected.' It does take some courage to do that."

Jeff: It does. I agree. But it's an evidence-based conversation. It's not "we did a crap job." We didn't. It's bug-free, it's high performance, it's scalable, it's usable. But you can build products like that – there are infinite stories of products that were amazingly executed that didn't meet a need, didn't solve a problem.

Mat: Yeah, I built one of those and had to close a business for it, so I know that all too well. If there's a lesson I learned through the years of doing that, which you touched on earlier, it's around by focusing on the outcomes that you want to see, those behaviours you want to change, and bringing the work down, de-scoping the work to start to experiment and iterate, you de-risk all of that. You'll learn a lot earlier whether you're on the right track or not rather than getting that big bang at the end.

Jeff: Yeah. Again, you're reducing the risk of building something that people don't want. Let's just use round numbers because they're easy. If you have a million-pound budget to build something – a new product, a new feature, a new service – and you spend 100 of that million and find out that this isn't the right thing to make, it's not a real problem, for whatever reason, you've just saved the company £900,000.

They should hoist you up on their shoulders and sing your praises, parade you around the halls. That's how it should be. You're a hero, and now we can take that £900 and do something that actually will deliver value with it.

If You're a Leader: Stop Asking "When Will It Be Ready?" and Start Asking "What Are You Learning?"

Mat: The second half of that question was around if you're a senior leader in an organisation and you want to move to an outcome-based approach, maybe you start with celebrating the people who are trying to do that and positively reinforcing it in that way. But what advice would you give that person?

Jeff: Absolutely. Celebrate anybody – literally hoist them up on your shoulders and parade them around the halls and say, "Look, this team tried this, figured out it wasn't going to work, and pivoted, and saved the company a million pounds." That should be a regular conversation and a regular thing that the company celebrates.

What's interesting is that you can find yourself on a team with resistant leadership, and you can also find yourself in leadership with resistant teams. And for a variety of reasons, not the least of which is that they've never actually been allowed to work this way and don't believe you that you're gonna let them work this way.

"Without getting caught up in too much process or training or dogma, I think as a leader you start to soften the conversations around this stuff by changing the questions that you ask."

Normally, it's like, "Hey, what are you guys working on? When will it be ready? How much is it gonna cost me? What do you predict the ROI is gonna be?" That's a typical line of questioning for a product team.

Conversely, you can say, "Hey, folks. What are you learning this week? This sprint? This quarter? What did you learn?" You might get a bunch of blank stares initially. They'll say, "What do you mean, what did we learn? We're building what you told us to build."

"Okay, well, cool. Next quarter when we meet, I'd love for you folks – I'm gonna ask you this question again. What did you learn this quarter about the product, about the customer, about the value of the thing that we're delivering? If you don't know how to answer those questions, I can help. I can get training for you. I can get some folks who've done this in other parts of the company to show you how they're doing this work."

To me, you're not enforcing. One of the issues of organisations just mashing process on top of organisations is folks don't understand why. Why are we doing this, and how is this supposed to make anything better? One of the ways to ease folks into a different way of working is to change your expectations of them and make that clear to them.

Instead of saying "What are you building? When will it be ready? What's the ROI?" say "What are you learning? Are we doing the right thing? How will we know?" And then if they don't know how to get the answers to that, don't make them feel stupid. Say, "Look, I'm gonna help you with that. I'll show you how the other teams are doing it. I'll get you some training. We'll work on this."

That's super powerful because you're changing the expectations that you have for your team, and you're making it explicit to them.

Navigating Conflicting Forces - Outcomes vs. Predictability

Mat: I've got this image in my head of people in a large organisation where they're on this journey that you've described with their team. Maybe they're a leader somewhere in the middle of the organisation, working with multiple teams, and they're starting to see some progress. The teams are on board, they trust that the questions you're asking are genuine and authentic, and they really want to understand the outcomes.

They're starting to come back with great questions themselves around who does what, what's the behaviour we're trying to change, how are we trying to change it, are we successfully doing that or not. Whilst that starts to get some traction and momentum, at the same time this leader's got other people in the organisation – maybe some more traditional executives who are getting investors on their boards asking for their KPIs to be met and the efficiency and the predictability they expect so they can forecast.

They have jobs to do themselves, and they seek some predictability. How do you help guide that person to navigate those two conflicting forces?

Jeff: It's hard. I've seen it multiple times. I think there are a couple of ways to navigate those political challenges in an organisation. One is you have to model the behaviour that you want to see both in your teams and in your colleagues as well.

Every interaction that you have with your peers at leadership level should contain these types of conversations around the customer, around learning, around value, around risk mitigation, and continuing to model the behaviour you want to see.

Someone says, "Well, we just have to build the iPhone app."

"Okay, great. But why? Why do we have to build the iPhone app?"

"Because we have to increase mobile revenue."

"Why? What is it today? What are we hoping to get?"

The Power of Renaming Teams

There's a super simple trick I wrote about probably a decade ago. If you're in a leadership position to get the organisation to start to think differently about how to do work, it's simply changing the names of the teams.

For example, let's say you and I work on the iPhone app team. What's our mission? Build an iPhone app. Exactly. So that's the iPhone app team, and that's the CRM team and that's the Android app team, whatever.

"What if we change the name of that team? Same team, same people. But it's the mobile revenue team. All of a sudden, the purpose of the team has fundamentally changed. It's no longer 'build iPhone app.' It's 'increase revenue through the mobile channel.'"

That might be an iPhone app, might be an Android app, might be a better website, might be a million different things. But from a leadership perspective, one of the things that you can influence is the name of these teams, and how you name them determines what work they do. That's really powerful.

Prove the Model

The other thing that you can do as a leader is prove the model. There's a lot of "my idea is better than your idea" type of conversations at work. Instead of saying, "I think we should work this way," say, "Look, I've got a pilot team in my group that's been doing this for the last three months. Here's what the team looks like. Here's the work that they're doing. Here's how they work. Here's what they're producing. Here's their happiness score. Here's their productivity. Here's their efficiency. Here's the impact of the work that they're doing with the customer."

If you've got one or two of those teams working that way, that's a compelling argument for saying, "Look, let's give it a shot." You've got the evidence that says this is a better way of working. Proving the model is always a good way to go.

Team Autonomy and Empowerment

Mat: One of the things that I'm picking up on in what you're saying leads to an outcome within teams that I've seen – around autonomy and empowerment within teams. Something I'm always trying to do in my role in organisations is make myself redundant. If the team don't need me anymore, I've done my job.

I'm at work where I've been very clear with the rest of the leadership team: I'm getting involved in way too many decisions, and I need to remove myself from those decisions because I'm slowing us down. If I have to have all of the context to be able to get involved with that and help move us forward, then we're gonna go slower than we should.

We're very quickly removing me from decisions, and it's been a great journey. Terrifying for me because I don't know as much about what's going on. But I'm seeing the teams themselves equipped with questions like "who does what by how much?" – that's one tool around the OKRs. Also equipped with other tools and ways of working, and usually it comes down to: are they asking the right questions? Are they applying the level of critical thinking to achieve those outcomes?

"Ultimately, if we can get teams to be more autonomous, leaders have a much better time of scaling themselves without burnout, without having to get really drawn in. When teams make decisions when you're not in the room that are fighting to achieve the outcome that you also want to achieve, that's when you really start to move quicker. That's when you start to really see the benefits of agility."

Have you got any thoughts on that that you'd like to share?

Jeff: It's a really tough sell. I see it all the time because I think that leaders have defined themselves – I don't want to speak in absolutes, so the majority of leaders have defined themselves in a way that says, "I tell people what to do." That's my job.

If you ask any kid – 10 years old, 12 years old, 9 years old – "What's a boss?" they'll say "A boss is someone who tells people what to do." I think we grow up with that, and I think leadership canon for the last hundred years has roughly said that, with the exception of the last 20 to 30 years where we've seen a lot of agile-themed, agility-themed leadership books and materials come out.

Still, I think the overwhelming majority of people believe that it's their job when they're in a leadership role to tell their teams what to do and to be keenly aware of every little detail. Because what if my boss comes to me and says, "Hey, what are your teams doing?" If the answer is "I don't know," that's probably a bad answer.

I agree with you. Day-to-day decision stuff – who better to make that decision than the teams doing the work day to day? They know far more about it than I do. They're with the work every day, they're with the customer every day, they're getting the feedback.

There's no reason for you to run these tiny things past the leader every day. It's exhausting for the leader, as you said, and the team knows more about it. Big strategic shifts, invalidated hypotheses, radical shifts in the market, new competitive threats – absolutely, let's talk about that.

The Two-Way Solution

I think there's a two-way solution here. Number one, leaders need to let go a little bit and understand that the most qualified people to make decisions about the day-to-day trivial stuff are the team doing the work.

David Marquet said this in "Turn the Ship Around." He ran the worst-performing nuclear submarine crew in the American Navy and turned it around to the best-performing crew. Basically, what he said was he pushed decision-making down as close to the work as possible. The only decision he kept for himself was whether or not to launch a nuclear missile, because people are gonna die and he didn't want that on anybody. That's his job as the leader.

Same thing here. You're gonna push decisions all the way down, and we've got to get folks to think about that.

Demand Proactive Transparency

To make that easier for people to swallow, people who are not used to this way of working, I think we have to demand greater proactive transparency from the teams.

Teams love to play the victim. "They don't let me work this way. My boss won't let me work this way. My boss doesn't get agility, doesn't get customer-centricity. She just comes down here and yells at us."

"What if on a weekly basis, without being asked for it, you sent your leader three bullet points in an email every week? Here's what we did this week. Here's what we learned. Here's what we're planning on doing next week."

If there's anything significant, you're gonna put that in there as well. But otherwise, just those three things. You're not even asking for a response. Weekly update, three bullet points, 15 minutes max of effort on your part.

In my opinion and in my experience, what happens is leaders chill out. Because all of a sudden they know what's going on. They see that you're doing work, that you're making objective decisions, and that you're taking the time to keep them informed. When their boss comes to them and says, "Hey, what are your teams doing?" they can just look at that email and be like, "This is what Mat's team is doing, this is what Jeff's team is doing."

To me, if there's a role here – and it's not an insignificant one – for the teams to play to improve their ways of working or to improve the comfort level that leaders have with new ways of working, this is it.

Mat: I have had the privilege of being someone on the recipient of those equivalent three-bullet-point emails running 12 different product teams, trying to understand what was going on. You're right – the stress levels go down when you understand proactively what's going on. It became the first thing I would do on a Monday morning knowing I had all that information.

It was something that teams were doing as part of their own weekly reviews as a team, and they just captured it and shared it. So there's no extra work for them. But it made this huge difference of suddenly I could understand where did I need to actually spend my time to help, rather than trying to chase and get information or get too close into managing people who didn't need it because they had it in hand.

I was able to prioritise and think, "Oh, that team looks like they're struggling, so we're gonna go and ask them some questions, see how I can remove some blockers for them."

Jeff: And if there is a blocker, add it in there. "We've been trying for three months to get access to customers. The sales team keeps blocking us. Can really use your help here."

The Shift from Being Rewarded for Knowing to Being Rewarded for Learning

Mat: There's a thing I've observed over the years – it takes a while to get there before you actually start getting rewarded for it in most organisations. In forward-thinking, very agile organisations, it starts a lot earlier, and I think that's something I'd like to try and shift left, try and get it earlier in people's careers.

It's this shift between: spend your entire career being rewarded for being knowledgeable, for being the expert, and knowing how to do something. You get promoted for that, you'll get a bonus for that, you'll get rewarded for it time after time. The more you learn, the more capable you become, the more experienced you are, you've got the answers for everything, you get promoted. You work your way up the career ladder.

Then you hit this tipping point where you hit a level where you realise there aren't many people around you at that point who are seeing the problems. Everyone's busy, everyone's focused on their thing. Then you realise that actually it's your job to call out that this thing isn't working. It becomes your responsibility to say, "There's a problem here we need to address as a company, as an organisation."

As an exec – Nick Muldoon is our CEO – we have an exec weekly, and the majority of that conversation is each of us saying what we don't understand, what we don't know, what we haven't figured out yet. We trust each other that all the rest of it's in hand and working beautifully. The things we really want to talk about is what don't we understand and what are we learning or what are we seeing that we need to try and figure out what to do with.

I see people struggle with that transition if they've not started it earlier in their career. Going back to the basics around sharing the learnings and are we actually achieving what we wanted to, are we seeing the behaviour shift, are we seeing it measured – if we're saying no, having the freedom to be able to call that out earlier, I think it makes that transition in life a lot more straightforward.

Jeff: Look, there's a level of seniority, and the subtheme here that we are dancing around but haven't yet named is psychological safety. It's this feeling that I'm comfortable calling things out that are against the grain, that contradict the plan, that are not working, and I keep seeing and nobody's addressing.

"I think there's a level of seniority that brings some psychological safety. But ultimately, organisational culture has to make it safe."

In other words, if leaders like you and your leadership team are consistently curious – "What do we not know? What are we not aware of? What's not working?" – your teams are going to feel comfortable calling those things out to you because you're asking those questions.

When they change the questions that they ask, it models psychological safety. It models the kinds of questions they want their teams to ask, and that's how change starts.

Building Psychological Safety - "If You Don't Know How, I'll Help You"

Mat: I couldn't agree more, Jeff. I think we've covered a lot of ground today, and psychological safety is one of those really hard intangible things for some people, particularly if they've never experienced it. We see it when we get new people joining our team. We're in a privileged environment where we have a lot of psychological safety.

When new people join from organisations that haven't had that, their behaviour is almost fighting against it. They hold on to their protected ways of working where they get a little bit territorial and they don't want to be vulnerable. It can take a good few months for people to settle in and relax into it.

There was a piece that I want to go back to, and maybe we wrap up on this. You talked earlier around a leader talking to their team and asking them questions to help them understand that it's okay to come back and say, "This thing that we've been developing, this product that we've been getting out the door, isn't having the desired impact." To look at it, question it, be curious, and come back to it.

The thing that you touched on there which I really love was that supportive nature of it. It's okay to do this, and if you don't know how to do it, I'll help you. If you were to give one last tip to our audience – how would you encourage people, leaders specifically, to move more into that space?

Jeff: I think it's a question of asking the right questions. I've been married a long time – half my life, it turns out. I did the maths the other day. If I've learned nothing in my 20-plus years of being married, I've learned that you don't start out immediately solving the problem. You listen and you ask questions. I've learned that. It took a long time.

I think that's our nature as leaders as well. The tendency is "let me solve that for you." Well, hang on. Before you jump to solutions, dig into the problem. What's the issue here? What's the problem? How can I best help you?

"Well, listen, we've set these customer-centric goals now. We've got great OKRs. Thanks for teaching us how to do that. Normally though, we're told what to do, and no one's telling us what to do now, and we don't know what to do. We have no idea how to figure that out. In the past, people have told us. Now I don't know what to do. Can you help us? How do we figure that out?"

To me, those are the kinds of answers you want to elicit from your teams. What's actually going on here?

This is where five whys comes in. "Well, you know, we keep hearing that we should be talking to customers. The reality is it's really difficult to get to our customers."

"Why is it difficult?"

"Well, because we're in a B2B space and we sell aeroplane engines."

"Okay, great. And why does that make it difficult to reach customers?"

"Well, because we have a sales team."

"Why does that make it difficult?"

"Well, because they guard their contacts and they don't want us messing with it."

"Okay, now I understand."

"I think if it's about asking the right questions as a leader, and then when you get to the root cause, you say, 'Well, listen, I can try to unblock it in this way. Do you think that would be helpful? Yes or no?' That becomes far more of a partnership than a hierarchical relationship."

Then you trust me to be honest with you about how well things are working and where things need help, and that's tremendous.

I run a very, very tiny business in the sense of number of people – it's three and a half people total. Even in a three-and-a-half-person business, people try to do good work and people don't want to bother you with what's going on. Sometimes people get overwhelmed, whether it's with work or personal stuff or a combination of the two, and then things start to slip.

The more you can foster that kind of transparency and trust, psychological safety, the less you find out that something is broken with the consequences of it being broken. You find out well in advance of anything actually happening.

Mat: I love that, Jeff. I think that's a great place to wrap up. I'm really grateful for your time, really enjoyed the conversation, and thank you for sharing your wisdom.

Jeff: My pleasure, Mat. Thanks so much for having me. This was fun.

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Thank you to Jeff Gothelf for joining us on this episode of the Easy Agile Podcast. To learn more about Jeff's work and get your copy of "Who Does What By How Much," visit jeffgothelf.com. You can also find his other books, including "Lean UX" and "Sense and Respond," which provide the foundation for the customer-centric approach to OKRs discussed in this episode.

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