Easy Agile Podcast Ep.30 Aligned and thriving: The power of team alignment

In this insightful episode, we dive deep into one of the most common frustrations in engineering and dev teams: retrospectives that fail to drive meaningful change. Join Jaclyn Smith, Senior Product Manager at Easy Agile, and Shane Raubenheimer, Agile Technical Consultant at Adaptavist, as they unpack why retrospectives often become checkbox exercises and share practical strategies for transforming them into powerful engines of continuous improvement.

Want to put these insights into practice? We hosted a live, hands-on retro action workshop to show you exactly how to transform your retrospectives with practical tools and techniques you can implement immediately.

Key topics covered:

• Common retrospective anti-patterns and why teams become disengaged
• The critical importance of treating action items as "first-class citizens"
• How to surface recurring themes and environmental issues beyond team control
• Practical strategies for breaking down overwhelming improvement initiatives
• The need for leadership buy-in and organizational support for retrospective outcomes
• Moving from "doing agile" to "being agile" through effective reflection and action

This conversation is packed with insights for making your retrospectives more impactful and driving real organizational change.

About our guests

Jaclyn Smith is a Senior Product Manager at Easy Agile, where she leads the Easy Agile TeamRhythm product that helps teams realize the full benefits of their practices. With over five years of experience as both an in-house and consulting agile coach, Jaclyn has worked across diverse industries helping teams improve their ways of working. At Easy Agile, she focuses on empowering teams to break down work effectively, estimate accurately, and most importantly, take meaningful action to continuously improve their delivery and collaboration.

Shane Raubenheimer is an Agile Technical Consultant at Adaptavist, a global family of companies that combines teamwork, technology, and processes to help businesses excel. Adaptavist specializes in agile consulting, helping organizations deliver customer value through agile health checks, coaching, assessments, and implementing agile at scale. Shane brings extensive experience working across multiple industries—from petrochemical to IT, digital television, and food industries—applying agile philosophy to solve complex organizational challenges. His expertise spans both the technical and cultural aspects of agile transformation.

Transcript

This transcript has been lightly edited for clarity and readability while maintaining the authentic conversation flow.

Opening and introductions

Jaclyn Smith: Hi everyone, and welcome back to the Easy Agile Podcast. Today I'm talking to Shane Raubenheimer, who's with us from Adaptavist. Today we're talking about why your retrospectives keep failing and how to finally fix them. Shane, you and I have spent a fair amount of time together exploring the topic of retros, haven't we? Do you want to tell us a little bit about yourself first?

Shane Raubenheimer: Yeah, hello everyone. I'm Shane Raubenheimer from Adaptavist. I am an agile coach and technical consultant, and along with Jaclyn, we've had loads of conversations around why retros don't work and how they just become tick-box exercises. Hopefully we're going to demystify some of that today.

Jaclyn Smith: Excellent. What's your background, Shane? What kind of companies have you worked with?

Shane Raubenheimer: I've been privileged enough to work across multiple industries—everything from petrochemical to IT, to digital television, food industry. All different types of applied work, but with the agile philosophy.

Jaclyn Smith: Excellent, a big broad range. I should introduce myself as well. My name is Jaclyn. I am a Senior Product Manager here at Easy Agile, and I look after our Team Rhythm product, which helps teams realize the benefits of being agile. I stumbled there because our whole purpose at Easy Agile is to enable our customers to realize the benefits of being agile.

My product focuses on team and teamwork, and teamwork happens at every level as we know. So helping our customers break down work and estimate work, reflect—which is what we're talking about today—and most importantly, take action to improve their ways of working. I am an agile coach by trade as well as a product manager, and spent about five years in a heap of different industries, both as a consultant like you Shane, and as an in-house coach as well.

The core problem: When retrospectives become checkbox exercises

Jaclyn Smith: All right, let's jump in. My first question for you Shane—I hear a lot that teams get a bit bored with retros, or they face recurring issues in their retrospectives. Is that your experience? Tell me about what you've seen.

Shane Raubenheimer: Absolutely. I think often what should be a positive rollup and action of a sequence of work turns out to normally become a checkbox exercise. There's a lot of latency in the things that get uncovered and discussed, and they just tend to perpetually roll over. It almost becomes a checkbox exercise from what I've seen, rather than the mechanism to actively change what is happening within the team—but more importantly, from influences outside the team.

I think that's where retros fail, because often the team does not have the capability to do any kind of upward or downstream problem solving. They tend to just mull about different ways to ease the issues within the team by pivoting the issues rather than solving them.

I think that's where retros fail, because often the team does not have the capability to do any kind of upward or downstream problem solving. They tend to just mull about different ways to ease the issues within the team by pivoting the issues rather than solving them.

Jaclyn Smith: Yeah, I would agree. Something that I see regularly too is because they become that checkbox, teams get really bored of them. They do them because they're part of their sprint, part of their work, but they're not engaged in them anymore. It's just this thing that they have to do.

It also can promote a tendency to just look at what's recently happened and within their sphere of influence to solve. Whereas I think a lot of the issues that sometimes pop up are things that leadership need to help teams resolve, or they need help to solve. It can end up with them really focusing on "Oh well, there's this one bit in how we do our code reviews, we've got control over that, we'll try to fix that." Or as you say, the same recurring issues come up and they don't seem to get fixed—they're just the same complaints every time.

Shane Raubenheimer: Absolutely. You find ways that you put a band-aid on them just so you can get through to the next phase. I think the problem with that is the impact that broader issues have on teams is never completely solvable within that space, and it's no one else's mandate necessarily to do it. When an issue is relatable to a team, exposing why it's not a team-specific issue and it's more environmental or potentially process-driven—that's the bit that I feel keeps getting missed.

When an issue is relatable to a team, exposing why it's not a team-specific issue and it's more environmental or potentially process-driven—that's the bit that I feel keeps getting missed.

The pressure problem and overwhelming solutions

Jaclyn Smith: Yeah, I think so too. The other thing you just sparked for me—the recurring issue—I think that also happens when the team are under pressure and they don't feel like they have the time to solve the problems. They just need to get into the next sprint, they need to get the next bit of work done. Or maybe that thing that they need to solve is actually a larger thing—it's not something small that they can just change.

They need to rethink things like testing strategies. If that's not working for you, and it's not just about fixing a few flaky tests, but you need to re-look at how you're approaching testing—it seems overwhelming and a bit too big.

Shane Raubenheimer: Absolutely. Often environmental issues are ignored in favor of what you've been mandated to do. You almost retrofit the thing as best you can because it's an environmental issue. But finding ways to expose that as a broader-based issue—I think that should be the only output, especially if it's environmental and not team-based.

The problem of forgotten action items

Jaclyn Smith: Something I've also seen recently is that teams will come up with great ideas of things that they could do. As I said before, sometimes they're under pressure and they don't feel they have the capacity to make those changes. Sometimes those actions get talked about, everyone thinks it's a wonderful idea, and then they just get forgotten about. Teams end up with this big long backlog of wonderful experiments and things that they could have tried that have just been out of sight, out of mind. Have you seen much of that yourself?

Shane Raubenheimer: Plenty. Yes, and often teams err on the side of what's expected of them rather than innovate or optimize. I think that's really where explaining the retrospective concept to people outside fully-stacked or insular teams is the point here. You need, very much like in change management, somebody outside the constructs of teams to almost champion that directive—the same way as you would do lobbying for money or transformation. It needs to be taken more seriously and incorporated into not just teams being mini-factories supporting a whole.

You transform at a company level, you change-manage at a company level. So you should action retrospective influences in the same way. Naturally you get team-level ones, and that's normally where retrospectives do go well because it's the art of the possible and what you're mandated to do. I think bridging the gap between what we can fix ourselves and who can help us expose it is a big thing.

I see so much great work going to waste because it simply isn't part of the day job, or should be but isn't.

You transform at a company level, you change-manage at a company level. So you should action retrospective influences in the same way.

Making action items first-class citizens

Jaclyn Smith: Yeah, absolutely. I know particularly in the pre-Covid times when we were doing a lot of retros in person, or mostly in person with stickies on walls, I also found even if we took a snapshot of the action column, it would still end up on a Confluence board or something somewhere and get forgotten about. Then the next retro comes around and you sort of feel like you're starting fresh and just looking at the last sprint again. You're like, "Oh yeah, someone raised that last retro, but we still didn't do anything about that."

Shane Raubenheimer: I think Product Owners, Scrum Masters, or any versions of those kinds of roles need to treat environmental change or anti-pattern change as seriously as they treat grooming work—the actual work itself. Because it doesn't matter how good you are if the impediments that are outside of your control are not managed or treated with the same kind of importance as the actual work you're doing. That'll never change, it'll just perpetuate. Sooner or later you hit critical mass. There's no scenario where your predictability or velocity gets better if these things are inherent to an environment you can't control.

Product Owners, Scrum Masters, or any versions of those kinds of roles need to treat environmental change or anti-pattern change as seriously as they treat grooming work—the actual work itself.

Jaclyn Smith: Yeah, that's true. We've talked about action items being first-class citizens and how we help teams do that for that exact reason. Because a retro is helpful to build relationships and empathy amongst the team for what's happening for each of them and feel a sense of community within their team. But the real change comes from these incremental changes that are made—the conversations that spark the important things to do to make those changes to improve how the team works.

That action component is really the critical part, or maybe one of two critical parts of a retro. I feel like sometimes it's the forgotten child of the retro. Everyone focuses a lot on engaging people in getting their ideas out, and there's not as much time spent on the action items and what's going to be done or changed as a result.

Beyond team-level retrospectives

Shane Raubenheimer: Absolutely, consistently. I think it's symptomatic potentially of how retros are perceived. They're perceived as an inward-facing, insular reevaluation of what a team is doing. But I've always thought, in the same way you have the concept of team of teams, or if you're in a scaled environment like PI planning, I feel retrospectives need the same treatment or need to be invited to the VIP section to become part of that.

Because retrospectives—yes, they're insular or introspective—but they need to be exposed at the same kind of level as things like managing your releases or training or QA, and they're not.

Jaclyn Smith: Yeah, I think like a lot of things, they've fallen foul of the sometimes contentious "agile" word. People tend to think, "Oh retros, it's just one of those agile ceremonies or agile things that you do." The purpose of them can get really lost in that, and how useful they can be in creating change. At the end of the day, it's about improving the business outcomes. That's why all of these things are in place—you want to improve how well you work together so that you can get to the outcome quicker.

At the end of the day, it's about improving the business outcomes. That's why all of these things are in place—you want to improve how well you work together so that you can get to the outcome quicker.

Shane Raubenheimer: Absolutely. Outcome being the operative word, not successfully deploying code or...

Jaclyn Smith: Or ticking the retro box, successfully having a retro.

Shane Raubenheimer: Yeah, exactly. Being doing agile instead of being agile, right?

Expanding the scope of retrospectives

Jaclyn Smith: One hundred percent. It also strikes me that there is still a tendency for retros to be only at a team level and only a reflection of the most recent period of time. So particularly if a team are doing Scrum or some version of Scrum with sprints, to look back over just the most recent period. I think sometimes the two things—the intent of a retro but also the prime directive of the retro—gets lost.

In terms of intent, you can run a retro about anything. Think about a post-mortem when you have an incident and everyone gets together to discuss what happened and how we prevent that in the future. I think people forget that you can have a retro and look at your system of work, and even hone in on something like "How are we estimating? Are we doing that well? Do we need to improve how we're doing that?" Take one portion of what you're working on and interrogate it.

You can run a retro about anything. I think people forget that you can have a retro and look at your system of work, and even hone in on something like "How are we estimating? Are we doing that well? Do we need to improve how we're doing that?" Take one portion of what you're working on and interrogate it.

Understanding anti-patterns

Shane Raubenheimer: Absolutely. You just default to "what looks good, what can we change, what did we do, what should we stop or start doing?" That's great and all, but without some kind of trended analysis over a period of time, you might just be resurfacing issues that have been there all along. I think that's where the concept or the lack of understanding of anti-patterns comes in, because you're measuring something that's happened again rather than measuring or quantifying why is it happening at all.

I think that's the big mistake of retros—it's almost like an iterative band-aid.

I think that's the big mistake of retros—it's almost like an iterative band-aid.

Jaclyn Smith: Yeah. Tell me a little bit more about some of the anti-patterns that you have seen or how they come into play.

Shane Raubenheimer: One of them we've just touched on—I think the buzzword for it is the cargo cult culture for agile. That's just cookie-cutting agile, doing agile because you have to instead of being agile. Literally making things like your stand-up or your review or even planning just becomes "okay, well we've got to do this, so we've ticked the box and we're following through."

Not understanding the boundaries of what your method is—whether you like playing "wagile" or whether you're waterfall sometimes, agile at other times, and you mistake that variability as your agility. But instead, you don't actually have an identity. You're course-correcting blindly based on what's proportionate to what kind of fire you've got in your way.

Another big anti-pattern is not understanding the concept of what a team culture means and why it's important to have a team goal or a working agreement for your team. Almost your internal contracting. We do it as employees, right?

I think a lot of other anti-patterns come in where something's exposed within a team process, and because it's not interrogated or cross-referenced across your broader base of teams, it's not even recognized as a symptom. It is just a static issue. For me, that's a real anti-pattern in a lot of ways—lack of directive around what to do with retrospectives externally as well as internally. That's simply not a thing.

A lot of other anti-patterns come in where something's exposed within a team process, and because it's not interrogated or cross-referenced across your broader base of teams, it's not even recognized as a symptom. It is just a static issue. For me, that's a real anti-pattern in a lot of ways—lack of directive around what to do with retrospectives externally as well as internally.

Jaclyn Smith: Yeah, I think that's a good call-out for anyone watching or listening. If you're not familiar with anti-patterns, they're common but ineffective responses to recurring problems. They may seem helpful initially to solve an immediate problem, but they ultimately lead to negative outcomes.

Shane, what you just spoke about there with retrospectives—an example of that is that the team feel disengaged with retrospectives and they're not getting anything useful out of it, or change isn't resulting from the retrospectives. So the solution is to not hold them as frequently, or to stop doing them, or not do them at different levels or at different times. That's a really good example of an anti-pattern. It does appear to fix the problem, but longer term it causes more problems than it solves.

Another one that I see is with breaking down work. The idea that spending time together to understand and gain a shared understanding of the work and the outcome that you need takes a lot of time, and breaking down that work and getting aligned on how that work is going to break down on paper can look like quite an investment. But it's also saving time at the other end, reducing risk, reducing duplication and rework to get a better outcome quicker. You shift the time spent—development contracts because you've spent a little bit more time discovering and understanding what you're doing.

A common anti-pattern that I see there is "we spent way too long looking at this, so we're going to not do discovery in the same way anymore," or "one person's going to look at that and break it down."

The budget analogy

Shane Raubenheimer: I always liken it to your budget. The retrospective is always the nice shiny holiday—it's always the first to go.

I always liken it to your budget. The retrospective is always the nice shiny holiday—it's always the first to go.

Jaclyn Smith: It's the contractor.

Shane Raubenheimer: Yeah. It's almost like exposing stuff that everybody allegedly knows to each other is almost seen as counterintuitive because "we're just talking about stuff we all know." It often gets conflated into "okay, we'll just do that in planning." But the reality is the concept of planning and how you amend what you've done in the retrospective—that's a huge anti-pattern because flattening those structures from a ceremonies perspective is what teams tend to do because of your point of "well, we're running out of daylight for doing actual development."

But it's hitting your head against the wall repeatedly and hoping for a different outcome without actually implying a different outcome. Use a different wall even. I think it's because people are so disillusioned with retrospectives. I firmly believe it's not an internal issue. I believe if the voices are being heard at a budgeting level or at a management level, it will change the whole concept of the retrospective.

Solution 1: Getting leadership buy-in

Jaclyn Smith: I like it, and that's a good thread to move on to. So what do we do about it? How do we help change this? What are some of the practical tips that people can deploy?

Shane Raubenheimer: A big practical tip—and this is going to sound like an obvious one—is actual and sincere buy-in. What I mean by that is, as a shareholder, if I am basing your performance and your effectiveness on the quality and output of the work that you're promising me, then I should be taking the issues that you're having that are repeating more seriously.

Because if you're course-correcting for five, six, or seven sprints and you're still not getting this increasing, predictable velocity, and if it's not your team size or your attitude, it's got to be something else. I often relate that to it being environmental.

Buying into the outputs for change the same way as you would into keeping everyone honest, managing budgets, and chasing deadlines—it should all be part of the same thing. They should all be sitting at the VIP table, and I think that's a big one.

Buying into the outputs for change the same way as you would into keeping everyone honest, managing budgets, and chasing deadlines—it should all be part of the same thing. They should all be sitting at the VIP table.

Solution 2: Making patterns visible

Jaclyn Smith: I think so too. Something that occurs to me, and it goes back to what we were talking about right at the beginning, is sometimes identifying that there's a pattern there and that the same thing keeps coming up isn't actually visible, and that's part of the problem, right?

I know some things we've been doing in Easy Agile TeamRhythm around that recently, attempting to help teams with this. We've recently started surfacing all incomplete action items in retrospectives so people can see that big long list. Because they can convert their action items to Jira items or work items, they can also see where they've just been sitting and languishing in the backlog forever and a day and never been planned for anything to be done about them.

We've recently started surfacing all incomplete action items in retrospectives so people can see that big long list. Because they can convert their action items to Jira items or work items, they can also see where they've just been sitting and languishing in the backlog forever and a day and never been planned for anything to be done about them.

We've added a few features to sort and that kind of thing. Coming in the future—and we've been asked about this a lot—is "what about themes? What about things that are bubbling up?" So that's definitely on our radar that will be helpful.

I think that understanding that something has been raised—a problem getting support from another team, or with a broken tool or an outdated tool that needs to be replaced in the dev tooling or something like that—if that's been popping up time and time again and you don't know about it, then even as the leader of that team, you don't have the ammunition to then say "Look, this is how much it's slowed us down."

I think we live in such a data world now. If those actions are also where the evidence is that this is what needs to change and this is where the barriers are...

Solution 3: The power of trend analysis

Shane Raubenheimer: Certainly. I agree. Touching on the trend analytics approach—we do trend analysis on everything except what isn't happening or what is actually going wrong, because we just track the fallout of said lack of application. We don't actually trend or theme, to your point.

We do trend analysis on everything except what isn't happening or what is actually going wrong, because we just track the fallout of said lack of application.

We theme everything when we plan, yet somehow we don't categorize performance issues as an example. If everybody's having a performance issue, that's the theme. We almost need to categorize or expose themes that are outward-facing, not just inward-facing. Because it's well and good saying "well, our automated testing system doesn't work"—what does that mean? Why doesn't it work?

I think it should inspire external investigation. When you do a master data cleanup, you don't just say "well, most of it looks good, let's just put it all in the new space." You literally interrogate it at its most definitive and lowest level. So why not do the same with theming and trending environmental issues that you could actually investigate, and that could become a new initiative that would be driven by a new team that didn't even know it was a thing?

Jaclyn Smith: Yeah, and you're also gathering data at that point to evidence the problem rather than "oh, it's a pain point that keeps coming up." It is, but it gives you the opportunity to quantify that pain point a little bit as well. I think that is sometimes really hard to do when you're talking about developer experience or team member experience. Even outside of product engineering teams, there are things in the employee experience that affect the ability for that delivery—whatever you're delivering—to run smoothly. You want to make that as slick as possible, and that's how you get the faster outcomes.

Solution 4: The human factor

Shane Raubenheimer: Absolutely. You can never underestimate the human factor as well. If everything I'm doing and every member of my team is doing is to the best of not just their capability, but to the best of the ability in what they have available to them, you become jaded, you become frustrated. Because if you're hitting your head against the same issue regardless of how often you're pivoting, that can be very disillusioning, especially if it's not been taken as seriously as your work output.

If everything I'm doing and every member of my team is doing is to the best of not just their capability, but to the best of the ability in what they have available to them, you become jaded, you become frustrated.

We run a week late for a customer delivery or a customer project, and we start complaining about things like money, budget overspend, over-utilization. But identifying systematic or environmental issues that you can actually quantify should be treated in exactly the same way. I feel very strongly about this.

Solution 5: Breaking down overwhelming action items

Jaclyn Smith: We tend to nerd out about this stuff, Shane, and you're in good company. You've also reminded me—we've put together a bit of a workshop to help teams and people understand how to get the most out of their retrospectives, not just in terms of making them engaging, but fundamentally how to leverage actions to make them meaningful and impactful.

We've spoken a lot about the incremental change that is the critical factor when it is something that's within the team's control or closely to the team's control. That's how you get that expansion of impact—the slow incremental change. We've talked about sometimes those action items seem overwhelming and too big. What's your advice if that's the scenario for a team? What do you see happen and what can they do?

Shane Raubenheimer: I would suggest following the mantra of "if a story is too big, you don't understand enough about it yet, or it's not broken down far enough." Incremental change should be treated in exactly the same way. The "eat the elephant one bite at a time" analogy. If it's insurmountable, identify a portion of it that will make it a degree less insurmountable next time, and so on and so forth.

If we're iterating work delivery, problem-solving should be done in rapid iteration as well. That's my view.

Jaclyn Smith: I like it.

The "eat the elephant one bite at a time" analogy. If it's insurmountable, identify a portion of it that will make it a degree less insurmountable next time, and so on and so forth. If we're iterating work delivery, problem-solving should be done in rapid iteration as well.

Wrapping up: What's next?

Jaclyn Smith: I think we're almost wrapping up in terms of time. What can people expect from us if they join our webinar on July 10th, I believe it is, where we dive and nerd out even more about this topic, Shane?

Shane Raubenheimer: I think the benefit of the webinar is going to be a practical showing of what we're waxing lyrical about. It's easy to speak and evangelize, but I think from the webinar we'll show turning our concepts into actual actions that you can eyeball and see the results of.

With our approach that we took to our workshop, I think people will very quickly get the feeling of "this is dealing with cause and effect in a cause and effect way." So practical—to put that in one sentence, an active showing or demonstration of how to quantify and actually do what we've been waxing lyrical about.

the benefit of the webinar is going to be a practical showing of what we're waxing lyrical about. It's easy to speak and evangelize, but I think from the webinar we'll show turning our concepts into actual actions that you can eyeball and see the results of.

‍Jaclyn Smith: Excellent. That was a lovely summation, Shane. If anyone is interested in joining, we urge you to do so. You can hear us talking more about that but get some practical help as well. There is a link to the registration page in the description below.

I think that's about all we have time for today. But Shane, as always, it's been amazing and lovely to chat to you and hear your thoughts on a pocket of the agile world and helping teams.

Shane Raubenheimer: Yeah, it's always great engaging with you. I always enjoy our times together, and it's been my pleasure. I live for this kind of thing.

Jaclyn Smith: It's wonderful! Excellent. Well, I will see you on the 10th, and hopefully we'll see everyone else as well.

Shane Raubenheimer: Perfect. Yeah, looking forward to it.

Jaclyn Smith: Thanks.

Ready to end the frustration of ineffective retrospectives?

Jaclyn Smith and Shane Raubenheimer also hosted a live, hands-on webinar designed to turn retrospectives into powerful engines for continuous improvement.

In this highly interactive session, they talked about how teams can:

• Uncover why retrospectives get stuck in repetitive cycles
• Clearly capture and assign actionable insights
• Identify and avoid common retrospective pitfalls and anti-patterns
• Get hands-on experience with Easy Agile TeamRhythm to streamline retrospective actions
• Practical tools, techniques, and clear next steps to immediately enhance retrospectives and drive meaningful team improvements.

👉 Watch the recording here.

On this episode of The Easy Agile Podcast, join Nick Muldoon and Dave Elkan, Co-CEO's and Co Founders of Easy Agile. As they look forward to the next phase of growth for the company, they wanted to take this opportunity to reflect on their journey so far.

Nick and Dave talk growing a start-up in regional Australia, finding the right people, sustaining a positive team culture and the importance of having values driven teams.

"Our purpose is to help teams be agile and in doing that, we're doing that for ourselves, we're constantly trying to learn and adapt and experiment with new things. I hope that was a useful little tidbit and journey from Dave and I on how we got Easy Agile to this point."

- Nick Muldoon, Co-CEO, Easy Agile

"There's these funny little hacks and analogies and I think that's a longterm vision thing. If you are running a business which doesn't have that longterm vision and purpose, then you can go actually in multiple directions at once, and you're not going to make any progress."

- Dave Elkan, Co-CEO, Easy Agile

Be sure to subscribe, enjoy the episode 🎧

Transcript

Nick Muldoon:

Good day, folks. Nick Muldoon with co-founder, co-CEO of Easy Agile, Dave Elkan. Before we kick off, we'd just like to do an acknowledgement to the traditional custodians of the land on which we broadcast and record today, the Wodiwodi people of the Dharawal Nation. We pay our respects to elders, past and present, and extend that same respect to any of our aboriginal folks that are listening today.

Nick Muldoon:

Dave, just a bit of a reflection on five and a half years of business?

Dave Elkan:

Business? Yeah, a rollercoaster. It's been great fun.

Nick Muldoon:

It is a rollercoaster, isn't it? I guess, where's the best place to start? The best place to start is at the start.

Dave Elkan:

Yeah, I mean we can go before the start. There's always a good prequel. We can do a prequel episode later, I guess. But I guess the earliest I remember working with you, Nick, was at Level 15 at Kent Street, at Atlassian. There was this redheaded guy down the one end of the building, working on Atlassian GreenHopper and I was busy working on the Kick-Ass team at the time, building the new issue navigator, which is now the old issue navigator, back in 2011. And then you screwed off to San Francisco and I followed eventually, and then we hung out there for a while, didn't we?

Nick Muldoon:

Yeah, I remember that because we sat down, I was back to get married, and we sat down and had a coffee and a yarn about you and Rin relocating to San Francisco and how it had been for Liz and I, and what the process was like and all that sort of stuff.

Dave Elkan:

That's a great opportunity to acknowledge our lives in this amazing journey as well and if it wasn't for those, we probably wouldn't have gone to San Francisco in the first place, because a large part of the promotion of going overseas and doing that for me anyway, and for yourself, I'm pretty sure.

Nick Muldoon:

Yeah. Well, Liz was this big conversation of go overseas and experience something new and I was quite comfortable in Sydney and enjoying my role with product management at Atlassian, but it was really a push to try and experience and do something a bit different.

Dave Elkan:

Absolutely, same here. And you were there for over four years, in San Francisco, and I was there for three. But you came home, you got married, and I just grabbed you for a coffee and we sat there in Martin Place and had a chat, and you said, "Yeah, it's great. Come over, you can stay with me for two weeks." And I'm like, "Oh, I barely know you."

Nick Muldoon:

Yeah, but it was so much. I mean, even not knowing Liz or I, it was way better than the alternative. So for folks listening in, the Atlassian apartment, at the time, was in a fairly rough part of The Tenderloin in San Francisco, and it probably wasn't the greatest introduction if someone was relocating to San Francisco.

Dave Elkan:

No. But to cut a long story, there's a lot of good stories here I'm sure we can tell one day, but eventually, we both had daughters in San Francisco and we wanted to be home and closer to family. Then we came home to Sydney and found that the traffic is 20% worse or 50% worse than when we left and we were uprooted. So once you've been uprooted, you've got to plant yourself back somewhere and it's quite easy to change at that point, and you've chosen to go outside of Sydney.

Nick Muldoon:

Yeah, this Wollongong regional lifestyle.

Dave Elkan:

Yeah, where you can have a full block of land to yourself without breaking the bank and you can, relatively speaking, like times have changed a bit in that space, but since then, that's what we were chasing, wasn't it? And we looked at Newcastle, and-

Nick Muldoon:

Looked at Newcastle, looked at Brisbane, Adelaide, we even went through Wagga Wagga. We had the most amazing Indian meal in Wagga Wagga, we were almost like, "This is the place. If we can get food like this in Wagga, we're sweet." Bit too cold, but we ended up settling on Wollongong, in large part because of the proximity to the beach and the Early Start Discovery Space for the kids and just a pretty cool, chill place to raise a family. There are aspects of it as well, I think, that really reminded Liz and I of San Francisco. We used to go to the farmers market down at the Ferry Building a lot on a Saturday morning, and we found the farmers market on a Friday in Wollongong on Crown Street North, so there were these similarities to kind of enable us to transfer from one city to the other fairly easily.

Dave Elkan:

Yeah. It's a pretty easy place to live and to be. The way I like turn it, is it's just far enough away from Sydney.

Nick Muldoon:

Yeah, a nice little national park in between.

Dave Elkan:

That's right, it can't really encroach on us, it's not allowed. You can't build there so you're always going to have that buffer. But I do remember going back to Sydney for a niece's birthday and having been charged $9 an hour for parking at the beach, considering you don't even have a parking sticker anymore because I wasn't a resident, and I was like, "Wow, it's really expensive." But for anyone coming to Wollongong or the other way, you can park for free at the beach. That's just kind of like a good litmus test of the difference that we're talking about here.

Nick Muldoon:

Mm-hmm (affirmative). Yeah, I guess this regional life, like we didn't really have a tech industry here. We come from Sydney where, 10 years ago, there was this emerging tech scene and SydJS, SydCSS, other meetups up there, and in San Francisco we were thrust right in the middle of it. I remember, we were chatting the other week about a meetup where we met, the Ruby Creator at a Heroku meetup, I think it was, and a session on [detrace 00:06:17] at that company that's gone bust now, whose name I can't even remember, but we were in the heart of all the meetups in San Francisco. Then in Wollongong, there was none of it, and so it was like a question of what could we do to build a community here as well, try and meet other like minded folks?

Dave Elkan:

Yeah, it was definitely that desire, wasn't there? And we set out to do that, and I think it was Rin who termed it Siligong. I remember we were actually talking about Siligong Valley before we actually left, and we just decided to make that the name of the community. I was actually looking back on my old emails the other day and I was like, "Oh, we actually talked about Siligong before being in Wollongong," so that's pretty cool.

Nick Muldoon:

I remember early days because I think you and Rin returned on flight with [Umi 00:07:08], and Umi was six or eight weeks old.

Dave Elkan:

Yeah, October.

Nick Muldoon:

If I'm not mistaken, I dropped you at your mom's place so that you could catch up with your mom and Ken and that was kind of like home base. And it was a couple of months after that or something, where we finally had you down here. I think you stayed with Liz and I when you came down here-

Dave Elkan:

Yeah, again for two weeks.

Nick Muldoon:

... for another couple of weeks, and we were really talking about the genesis of what was, at the time, what was termed Arijea Products, and a brand that we never ended up sticking with. What do you remember about those early days and trying to get the business off the ground?

Dave Elkan:

Actually, come to think of it, you were staying in, not Coniston, [Carmila 00:07:59], it was actually less than two weeks because we all had little kids and it was just a bit crazy. So I think Rin and I organized... we came down and did inspections and we stayed with you whilst we're doing that, and then we were able to secure a place in Fairy Meadow and we moved down, so we were going back and forth a bit at that point. And then it was this six months of just literally... I didn't have a bike, I just walked to work, which is super new to me. I've always caught the bus or ridden my bike.

Dave Elkan:

Some of you may know I've never commuted to work and I hopefully will never have to do that, and we've engineered our lives around that kind of concept. But I think that it was really great, I was just living within two kilometers' walk of work, and that was for at least the first six months until I moved to Balgownie, but it was great time of my life and we had a brand new baby and just concentrating on the business, trying to [crosstalk 00:09:00]-

Nick Muldoon:

I remember, we really didn't have much of an idea of what we were doing in early days. We chased down one area and we said, "No, that's not appropriate," and then we kind of turned our attention to something else.

Dave Elkan:

Yeah. We were chasing our tails a little bit. We, at one point, had five products with two people.

Nick Muldoon:

That's right.

Dave Elkan:

I think that, that's too much, but with good conversations with the fellows around us at IXI, that we were able to have... like they were asking good questions and I remember Rob and Nathan asking us, "What is it you're good at?" And I think it was Rin, was like, "Okay, you've got this app idea, who're you going to market it to? Look at your networks." And it was, all those arrows started pointing towards Agile.

Nick Muldoon:

Yeah, I think it was this idea that Rin had like, "You can build it and they will come, or you can figure out your go-to market and your distribution piece, and what's the audience that you've already got, and how do you leverage the audience that you've already got in Agile Software Development to kind of seed and build that audience, and get some momentum?" And that's what really kicked us along and got us going. If I'm not mistaken, I think we'd actually... not that we had a lot of outgoings, but I think we were actually break-even by June of 2016, and it was kind of like this, "Hurray," moment because we were not going to have to get on the train and commute to Sydney for working at Atlassian or something like that. We'd found product-market fit and we could kind of pursue and go to the next stage.

Dave Elkan:

That's right, yeah. There's a lot in that story as well, like how we found product-market fit and the steps towards that and lots of learnings from that time as well, which is great to share eventually, I guess, but we might go down a rabbit hole if we jump into that one. But I certainly do remember good considered conversations that were held by lamingtons and tea in the Mike Codd building at the Innovation Campus at University of Wollongong, where we started. And that was really just a time to... it felt different to my prior, at the time 15 years of experience, where you actually, it's okay to stop and talk and think about what you're doing, whereas in the past, it's just been, "Go, go, go, build this thing." And it's like, "Oh, okay," so that was really refreshing for me and I think that, that was a really good step in opening up what became the story map, which was our first really successful product.

Nick Muldoon:

Mm-hmm (affirmative). You mentioned the lamingtons and tea, it was probably at least 50% of our time getting the business off the ground, was lamingtons and tea. It was chatting about stuff, it wasn't writing code, we didn't have customers to speak of. It was really trying to figure out what sort of market did we want to pursue, what solutions did we want to provide and what sort of business did we want to create? That was a large part of our time getting it off the ground.

Dave Elkan:

Absolutely. And for those listeners out there who don't know what a lamington is, it's actually a delicious piece of sponge cake dipped in chocolate sauce and then coconut, shredded coconut, so I know you can buy them in US, we actually did that at Atlassian and they were a huge success, especially because they had cream inside them as well, so real good for a cup of tea or coffee, whatever you take. But the thing is that it's a good idea to sit down with a co-founder and talk a lot more than you type, that's the kind of rule I took out of that.

Nick Muldoon:

It's interesting because it was kind of like that approach to talking instead of typing that was kind of like the genesis of one of our values, this engaged system, too. And I don't think you'd read Kahneman's book at that time, and that was something that came later, but even just this idea of, "Now, let's just take the time to think and process this sort of stuff," and the context [crosstalk 00:13:09]-

Dave Elkan:

No, I do remember. Sorry, yeah. I did a presentation at Lansing Summit in 2017 on Engaged System too.

Nick Muldoon:

16 or 17?

Dave Elkan:

16 or 17, I can't remember which one it is.

Nick Muldoon:

'16 because you went to Barcelona in '16.

Dave Elkan:

Barcelona, and that's what I did there, wasn't it? Yeah, so that was early on that I read Thinking, Fast and Slow, which I highly recommend.

Nick Muldoon:

And the context around this, for folks listening; in mid 2016, Dave had a nine month old daughter. My daughter was two years old and I had a newborn and you were to have... your number two was on the way, right? So we were building a business as we were starting and establishing our families as well, so it was, "Let's do it all," in a new city. Like, "Let's do it all at once."

Dave Elkan:

Yeah, you might as well, right? Just bite it all off and rip the Band-Aid off and get it done. I mean, my daughters were only 18 months apart, so that kind of... just get it over and done with. Get the hard part done and then you can go and enjoy yourself afterwards, just kidding. It's great to have lots of kids at a young age, like I really do miss that time. But yeah, we were pretty crazy, but we got through.

Nick Muldoon:

It gave us a constraint as well, didn't it? Because we couldn't burn the midnight oil, we couldn't flog ourselves from 05:00 AM to midnight because we simply did not have the energy and we had to get kids fed and bathed and off to bed and all that sort of stuff. So it brought a cadence and now that I reflect on that, there was another value that was kind of coming out of that, which was with respect to our balance and establishing balance in our lives.

Dave Elkan:

Yeah I do remember, sorry to interrupt, a tweet idea, I can probably dig it up, which was me hanging out cloth nappies or diapers on... it must've been, it was in Balgownie so that must've been after six months. But I was hanging out nappies and I must've been working from home that day or something like that, but that was just like me balancing life like that, with work. And I think it came back with like work, life, family balance or something like that. We would expand that to work life, family, community balance, is what we try and chase.

Nick Muldoon:

Mm-hmm (affirmative). How did we get on this journey around the values and kind of establishing the values? When was that in the life of the business?

Dave Elkan:

I can remember the place we were in, we were actually in our Crown Street office when we really sat down and really hunkered down into that, so that would've been 2018.

Nick Muldoon:

I think in November 2018, we held our first advanced Easy Agile, and that's where you ran the session, "What got us here won't get us there." And so at that point in time, we had the two products, we had Easy Agile User Story Maps and Easy Agile Roadmaps, and we had changed our brand from Arijea Products to Easy Agile, to kind of focus our energy on the Agile space. We divested the other three products that weren't focused on Agile, so we'd sold those off to another Atlassian Solution marketplace partner. I think that's where we started having these conversations around the next evolution of the growth of the business. Then it was in 2019 where we were back in Crown Street, back in the office, where we were having that conversation about codifying, establishing, writing down our values.

Dave Elkan:

That's right, and it's a highly valuable process to go through and to really just pause on the day to day, and really focus on it. That's something I've always had trouble with, like I've always got things to do, but once you just extract yourself from that process and zoom out and look at the company and what you've come up and what you hold dear, that's when you can really start having those conversations, but making it an actual thing. I think that you can't just do it on the side, you can't just do it as well as other things, it's really got to be like the priority as I like to say. Priority is not a plural, it doesn't make any sense if it's pluralized, but that should be the one thing you do in an ideal circumstance, like you just do it and really focus on it, because it's really hard.

Dave Elkan:

And it shouldn't, I guess not in one sitting, but at least when you do it, make it a serious thing because if they're real values and you live them, like they just are pretty immutable, they just keep moving forward with you. If you found you're not living them, then you should absolutely revisit them, but we've been lucky enough in that the values we put forward have stayed true and I really feel like, of all the companies I've worked at, even Atlassian, like these ones I've lived every day in very distinct ways.

Nick Muldoon:

Mm-hmm (affirmative). So what are the values we've got? We've talked about better with balance, and we talked about that a little bit. We also talked about engaged System 2 like this System 2 thinking. What are our values?

Dave Elkan:

Be the customer, give back, and [crosstalk 00:18:30]-

Nick Muldoon:

[crosstalk 00:18:30] was a big one, and commit to team. So better with balance, give back, be the customer, punch above our weight, Engaged System 2 and commit as a team. Go back to the conversation that we were having in 2017 around give back, that was something that was really System 2. How did we think about giving back to the community and what that meant to us as a company?

Dave Elkan:

I think it goes back to what you said before about the community in San Francisco we experienced and what we did here with Siligon and just making that a focal point for us to give back to the community. It doesn't build itself, like the community has to be actively built by somebody has to put their hand up and start it, and I think we did that. Since then, like we've enabled heaps of other people to be able to give back in a really easy kind of way like, "Let's host a meetup," "That's fine, here's our framework to go build that on." And also just the daily communication we have amongst each other on our Siligon Slack, which is just super valuable.

Nick Muldoon:

Super active, too.

Dave Elkan:

Oh, super active, especially in lockdown, lots of people on there talking about all sorts of things.

Nick Muldoon:

I think maybe one of the other things, so Dave and I experienced this at Atlassian, which was this idea of the Pledge 1%, but in our first or second year of Easy Agile, Atlassian along with Salesforce and a bunch of other companies came together to actually codify and build the foundation around Pledge 1% and ask other companies to commit to that. And we made that commitment in 2017 if I'm not mistaken, to do Pledge 1% donations and now, where I guess we're kind of doing Pledge 2% donations, but what was the drive behind our Pledge 1% to Room to Read?

Dave Elkan:

It's in part laziness, because I really want a system to these kinds of things and unfortunately, when you're starting a business it's hard to dedicate the time and to think about that. So I took the easy System 1 option, which is to go with what we experienced at Atlassian, which was to back Room to Read, which is a great initiative to help ensure that young ladies, specifically in third world countries, get at least a higher education, get out of primary school, get into high school, and once they've gotten to that point, it's far more likely they're going to be independent. And with that kind of thing, like that investment, it's like restarting at the beginning and enabling countries and people to help themselves. If they're educated, that's a huge step in the right direction to both fighting overpopulation, climate change, all these things which benefit from those people doing well in life.

Nick Muldoon:

Mm-hmm (affirmative). Yeah, continually improving their lot in life, right? Like raising standards of living through education.

Dave Elkan:

That's right.

Nick Muldoon:

And if we think about punching above our weight as one of these other things, I mean I remember that was something that we talked about before we wrote down our values, that was something that we really did focus a lot of energy on. You mentioned before, there were two of us and we had five products in the marketplace. I'm not exactly sure that was a great example of punching above our weight, because we might've struggled a bit, but what are some examples of where we've punched above our weight as a small team from regional Australia?

Dave Elkan:

One of our products that we built initially was really a bit of a thorn in my side, it was continually breaking and it wasn't playing to my strengths, which is traditionally front end development. So after that and getting burned by that and having to stay up all night and fix it, I opted towards apps which are more front end focused, and so we've built Easy Agile User Story Maps and Easy Agile programs and Easy Agile Roadmaps primarily as front end apps. As a matter of fact, Easy Agile Roadmaps, for the first two years, didn't even have a server, it was just a static file in a bucket in CloudFront. That's the way Atlassian Connect works, it allows you to host apps that way, and that really can't break, it's just providing a different view on Jira in essence, but architecturally, it's quite simple. So therefore, we could easily... that was a way of punching above our weight, which also allows better rebalance, so they're kind of complimentary in that respect. What other ideas [crosstalk 00:23:24]-

Nick Muldoon:

Yeah, if not much can go wrong, then you don't have to be on call, and you don't have to fix things out of hours, so you don't wake up blurry eyed and fat finger and have a bug the next day that compounds the problem.

Dave Elkan:

And if you take the analogy too far, like you could think punch above your weight is like being able to punch someone really hard and then knock them over, but this is more like just definitely, you're running around the big [fur 00:23:44]. You're not even engaging in babble, you're just sidestepping it. That's why we've run those products, and until recently, we actually do have servers now for them, and once again, it's still very simple, but they're very well monitored so if something does go wrong, that we're on top of that.

Nick Muldoon:

I think one of the other aspects with respect to technology in punch above our weight, is we've quite often... I think maybe you mentioned before, with respect to Room to Read and the give back, the laziness, but we are lazy in certain respects and we just want to automate things. And I remember the XKCD comic that you share, with what is the right time to automate something and when do you automate it to get the return on investment that you want? But I feel like we've made some fairly good decisions around when to automate things and even around how we provide customer support or the old test and deploy, toying around with products, we've done these things at pretty good times so that we can deliver products to a global audience of a couple of thousand customers, from Wollongong out of timezone with those customers.

Dave Elkan:

Yeah. It's also being ahead of the curve as well, so I think Inception Week, which is something we do every fifth week now, we give up one week to provide the team with the space to explore new things. Amazing things have come out of that, which otherwise, if you would just week to week, week to week, you would never actually realize, but when it comes to mind is our dev container, which is a docket container which contains all of the parts which are required to develop our apps. So you just check out this one repository, run a script and it sets up your entire develop environment. It's a great way for the team to share the tools that help them punch above their weight, so it's a huge punch above our weight thing and that came out of Inception Week. So I think Inception Week's a punch above thing, and also the dev container's a huge punch above thing.

Dave Elkan:

We used to have so many problems with individual versions of this or that on everyone's computer, and now that's just all gone, it's never happening again, it's never come back to bite us since, and I think it's an overwhelming success. Sure, it does need an all new RAM and all new CPU, but it does... we'll get there, like it's going to get better.

Nick Muldoon:

RAM and CPU are cheap, it's okay.

Dave Elkan:

You can never get time back, right?

Nick Muldoon:

Yeah, absolutely. So when we think about these things, how intentional do you think we were around the values in our approach to building and scaling a company versus things that just kind of happened?

Dave Elkan:

For a large part of the starting of the business, there was a lot of, "Just get it done," kind of mentality stuff, which has to happen. However, I want to hop back to when we started, everything was chaos. I remember this, early 2018, mid 2018, we'd come in on Monday, go, "What are we doing today? What's this week? Let's look at the backlog and have a look." And there was no forethought whatsoever.

Nick Muldoon:

And we'd kick a couple of things off the backlog and we'd just work through on that weekend. That was it, right?

Dave Elkan:

Yeah, pretty much. And so you proposed the idea, it was at the beginning of the year, it must've been 2018. Was it 2019? Either way, let's just do one week on clarity, which is our internal CI room, essentially, and just knock out a bunch of products and problems. That was the first time we started really focusing, because since we had so many products, I think we actually might've sold them by now at this point. Yeah, I think we definitely had. However [crosstalk 00:27:28]-

Nick Muldoon:

But we still had Roadmaps, Story Maps, Clarity Week, EACS, like we had other internal systems that we used and the team was actually growing beyond Dave and me, and it was growing. There was Jared and Satvik and Rob, and so the team was growing at that point in time as well. So it gave us the opportunity to put a number of people onto one problem for a period of time, like a week.

Dave Elkan:

That's right, and from that came this idea of focus, and we started doing focused sprints, so product focus sprints, which highlighted another terrible problem of run over, if you did run over in your estimates, then you would have to come back like in nine weeks or something and it was just [diabolical 00:28:12].

Nick Muldoon:

That's right.

Dave Elkan:

So we dropped [crosstalk 00:28:14]-

Nick Muldoon:

What did we do? We did two weeks on Story Maps, two weeks on Roadmaps, two weeks on internal systems, two weeks on something and then one week on Inception Week?

Dave Elkan:

Inception Week. Yeah, I think [crosstalk 00:28:26]-

Nick Muldoon:

I can't even remember now, what that other thing was.

Dave Elkan:

It was nine weeks in total, wasn't it?

Nick Muldoon:

Yeah.

Dave Elkan:

[crosstalk 00:28:31] Roadmaps-

Nick Muldoon:

If you missed it and you didn't ship it, then we went onto the next product and moved that forward, and then we'd come back to it.

Dave Elkan:

In ages away. And it was super stressful for the team and we quickly destroyed that, the week we went with a more flexible approach to it, where we dropped the hard mandate of you have to exchange products now, we let them run over a bit and then we'd adjust the story points to the next one, blah, blah, blah. And then eventually, I'm scratching my memory, but essentially, we got to a point where we introduced opportunities, which was based loosely on Shape Up by Basecamp and we took a bunch of things from that, but most things of that didn't really gel with our way of working and our values.

Nick Muldoon:

I mean that whole opportunity cycle, we've evolved three or four times now.

Dave Elkan:

And they were ideally just two or four weeks of work, and then we'd do Inception Week and Tech Debt week, and we have a dedicated Tech Debt week as a mandate. We dropped that since, and we've got to now we have four weeks of work, which includes Tech Debt and then we have Inception Week, and that's kind of cool, right? Like we still have this mandate of Inception week, not Tech Debt week. That's the last thing; I feel like the mandates... because it's like kick starting your motorbike, you've got to really give a good kick and that's essentially what we've been trying to do over the last three years, is like get this thing running. I think we've-

Nick Muldoon:

Built momentum.

Dave Elkan:

The engine is now running... yeah. The engine is now running and we're pulling the clutch out. It's just that the mandates slowly fall away and the team finds their own way, but I still feel that, that cycle is the most important thing, that five weeks where we stop, everyone knows what's happening. Because if it just runs off into the future forever, you can't compute that in your mind, but you can see forward five weeks and go, "I'm going to plan this work, it's not going to be done to a Nth degree because that's kind of a bit weird," it's just like, "Let's try and achieve this and let's bite off one bit at a time." Then we have a break with Inception Week, let our creative juices flow and then we'll come back to it the next round.

Nick Muldoon:

Right, so I have to call timeout here. So this is a sidebar for everyone listening at home; Dave just used this analogy of kick starting the motorcycle and then pulling the clutch out. So one of the things that Dave does tremendously well, is he grabs these analogies and he uses these analogies to simplify what I otherwise feel can be fairly complex kind of concepts, and simplify them and communicate them really nicely. That's not one I've heard before but there's a new one we can add to the repertoire, Dave. I love it.

Dave Elkan:

Thanks, mate.

Nick Muldoon:

What other sorts of things? Because I guess we're charting this journey over five and a half years, where it's gone from Dave and Nick and the addition of Satvik and Teagan and Jared and Rob and Brad, and a few people over time, to the point today where we are 27, 28 people. What are some of the other markers along the way, that we've kind of gone through, that have shifted or evolved how we operate? Like the Easy Agile operating system that we've talked about in the past.

Dave Elkan:

Well, it's something that we've just discussed in the execution kind of level. Obviously, every six months, everything just goes and explodes and you have to fix it, like there's always some major thing that happens every six months, and I feel like that's good and that's healthy, and that continue to run into those things. Either they're internal or external and I feel like we're dealing with an external one right now, which I don't really want to touch in this podcast, but I think that they're healthy for the business to adapt to. But certainly, I think in that time, like really understanding that it's the people that count, right?

Dave Elkan:

The business is in there, like it's a thing, but it's nothing without the people who worked for it, and it's in service of the people who work here, as well as the customers. And so that's something we've come out of it. What do you think, Nick? Like the cultural aspects of what we've built, what do you think stands out to you?

Nick Muldoon:

I certainly think there's these inflection points. I mean, I remember a conversation with Jared when we were in Crown Street Mall, and it was in 2019 and we were talking with the team around the kitchen table there, and we could get eight people around this kitchen table and we were talking about growing the team to take advantage of the opportunity and responding to requests from customers and all that sort of stuff. I think Jared said, "Well, I quite like it the way it is."

Nick Muldoon:

And then I fast forward to an interview with Jared, which went into the five year video that we saw just before Christmas and that was around his trajectory and how he's evolved and adapted professionally and personally along with the company. I think that's the story for all of us as team members, we've all kind of been on a journey together and we're all learning and adapting together. We do live, in many respects, we do live this Agile approach where we do reflect and we take the time and we think and we experiment with new approaches to getting work done.

Nick Muldoon:

Even, I think... and we've been talking about this a bit recently with respect to pace, that first version of our learning and development program, where we wanted to provide funding for people to go and pursue something that they wanted to learn about. But we got that out, "Hey, that was a morning's worth of work," we put out an L&D, people started using the L&D program, and we called it our Version one of our L&D program, and today we're on Version, I don't know, 1.4 or whatever it is, of our L&D program. There's a lot of things that have gone out and we tweak and we improve them over time to make them ever better and better suited, perhaps, to the current state of play within the team. Is that fair?

Dave Elkan:

Yeah, it is. It is, and I think that; A, I've never worked at a business who has anything like that, and where they actively encourage you to use it, spend the money, make yourself better. If you make yourself better, the team will get better, if the team gets better, the customers get better outcomes, and the company continues to improve, and it will be probably a better place for you to work in the future. So it's really a holistic kind of perspective, rather than, not narrow minded, but myopic or focused on just output. It's outcomes of output and I think that could be another value of ours, if we were to have seven, it'd be outcomes over output. So really stopping, having that permission to stop and think, and system to it and think about what it is you're trying to achieve, rather than just blindly doing stuff.

Dave Elkan:

So from a developer's perspective, the fastest code is the code that doesn't exist, and so if you can do something differently, which doesn't require 100 steps or just decide, "Hey, this is really tricky right now, this bit of code we're trying to work on or this feature is really hard. Can we just delete the feature?" And we did it on notice, I know that sounds pretty bold, but quite honestly, that kind of discussion is really healthy to have. I want to encourage the team to think that way and I think that learning development is also something you can do to bring people into it, look at their trajectory as a way of gauging their abilities, and giving them really... throwing fuel on the fire in that respect and seeing them ramp up in their ability, and help those around them.

Nick Muldoon:

Yeah, so take us through that, because that's something that we definitely talked about a few times, like when we've been looking at candidates and in a hiring huddle around candidates, we've talked about those that are on a certain trajectory and that we think that we can accelerate that trajectory. Where did that come from?

Dave Elkan:

Where do thoughts come from? I'm not sure, that's a good question. I couldn't tell you, but I think it's pretty obvious when you look at someone's CV and you see... now, there's nothing wrong with people who have long tenured positions, but if you talk to someone and they can't really say what they've done in the last 10 years and they've donned that one position for 10 years and they haven't really got anything striking they can tell about how they've made that better, that kind of says a lot about that person. Maybe they would come in and they'd just coast... they're a coaster, right? If they're coasting, that's fine, it's their call, but at the same time, we look for people who are actively trying to make their impact bigger through their work, help those around them. And you can see that, you can see, "Oh, look. They've been at the same company, that's fine, but they've gone and done these different roles or they've seen this kind of improvement in their approach."

Nick Muldoon:

This comes back down to that article, that Financial Review article, the mid-career annuity, so this was an article that we must've been kicking around in 2016, 2017, and it was around a Japanese term, mid-career annuity. You could have 20 years of experience in a role or you could have 20 first years of experience, and I think early on, and maybe it still occurs these days, I think it probably does, but it felt like we were getting 20 quarters of experience. Over that five year period, there was always some big, new challenge that we needed to learn and adapt and incorporate into the business over the first five years. So we were always learning and adapting, and we wanted folks that were on a similar journey and they were learning and incorporating and adapting and experimenting themselves.

Dave Elkan:

Yeah, it's something definitely, that can be learned, and I think that if you bring on new stars, they can just get that, this is what they do by default because you've put them into that environment. But some environments, especially older companies, can be fairly stagnant and static, so that just reflects on people's CVs. Either there's some kind of reason why the company won't give them a promotion or give them opportunities to chase, how we have a different approach where we throw too many opportunities at people, I think sometimes, and I've seen people using their L&D so much, it is actually impinging on their better with balance value. I'm like, "Whoa, this is fantastic but don't forget you've got kids and you've got to help look after them," and [crosstalk 00:39:41]-

Nick Muldoon:

Temper your enthusiasm, yeah.

Dave Elkan:

Yeah. So that's something to look for.

Nick Muldoon:

Stopping and reflecting on five and a half years, what's the purpose of the business, what's the goal over the next couple of years?

Dave Elkan:

Have fun, learn, what about you?

Nick Muldoon:

Definitely learning.

Dave Elkan:

Stay in business.

Nick Muldoon:

Oh, yeah. Stay in business, sustainable growth is always a good one. I think that's important. Yeah, I don't know, it's interesting. I feel like some days, it can be really fun and other days, it's not fun at all. That's probably due in large part, like when we started this, we were not in service of anyone but ourselves and one another, and now I feel like we are in service of a team of people that are themselves in service of the customer because we've got a couple of thousand of them. So it's the responsibility and the accountability's changed, and the way that fun comes about is, these days... it used to be fun to have lamingtons and chat, and these days, typically, there's someone else in the crew that is organizing the event that often participate in that I find fun and enjoyable with the rest of the team, rather than being able to carve out that time and do that.

Nick Muldoon:

I remember when we roped in a bunch of folks from iAccelerate and we went into town and we'd go into town and we'd go and we'd get a Laksa in town and we'd get a bowl of Laksa. It's been harder to do that in the past 12 months, given the global environment and all that sort of stuff, so hopefully we can find a bit more of that in 2022.

Dave Elkan:

And maybe ramen. There's ramen now.

Nick Muldoon:

Oh, and it's great, you know it.

Dave Elkan:

Yeah. I think refining what we do and continuing to think more about that, so specifically with the engineers, I like to use a goal based... goals are big at Easy Agile, I think you should talk a bit about goals, but we use them to help guide people in chasing down things they want to achieve, and we can align those things with what the business does to an extent. Then, you can actually go and achieve your professional and goals through the business and the business is the vehicle to do that, rather than having to it outside. That's really cool, like find that harmony there so both Easy Agile can succeed and the people who work here can succeed.

Dave Elkan:

I think it actually is quite difficult, like you go, "Hey, take a step back, think about what you want to achieve, give that to me, and then I'll see what I can do to change the course of the business to help you accomplish that. What can we do? Maybe there's a middle ground we can chase down together." And that's something new to me and I'm kind of using that instead of performance reviews so make sure you do your goals, people. [crosstalk 00:42:44]

Dave Elkan:

But yeah, also you've made sure, you want to look back in time and you want to see yourself in the future, reflecting with the team. When they've gone and moved on, [crosstalk 00:42:56]-

Nick Muldoon:

Oh, yeah. Absolutely. I was even chatting with Elizabeth Cranston this week and I was saying, "I can picture in the future, you're living down at Narooma down the coast and I can come down and have a cheese and biccies with the families and you're looking over the bay at Narooma or something, and we're reminiscing on this period of time at Easy Agile." I can totally see that. Yeah, I think it's great and I think just on the goals, the goals are important personally, and we've talked a lot about goals in the past, with respect to tenure vision for the families and that sort of stuff.

Nick Muldoon:

But it's also for the business, I remember we had okay hours in place from getting the business off the ground, we've revised them every year, we've learned and adapted a lot over the last couple of years in how we think about our objectives and our key results. And the fact that we write them on a quarterly basis and we review them on a quarterly basis, but we've got these objectives that align with a business goal that's three years out, and it all kind of flows. I mean, I think we're a lot more mature around that aspect of our... I don't know, would I say strategic planning? Vision goal setting over an extended time period? We're a lot more mature around that today than we were two or three years ago. That's really exciting as well. [crosstalk 00:44:33]

Nick Muldoon:

Come back to what you were saying before about the backlog. We'd come in on a Monday morning, and we go, "What are we going to work on this week?" And we kind of worked over a couple years, we worked it out so that, "Ah, here's the vision for the product." It was a longer term thing, and we've elevated that and it's not like, "Hey, what are we doing for the business this month?" It's now, "Here's our longterm trajectory for the business." We've been elevating that, that's pretty exciting, I think.

Dave Elkan:

And at the same time, trying to get the team to lift their line of sight as well.

Nick Muldoon:

Mm-hmm (affirmative), mm-hmm (affirmative).

Dave Elkan:

And look out further afield, but not too far. You want them to be looking at what's happening next week and next month as well, but also what's the goal, what are we chasing down? What's the bigger picture? And I think that's starting to happen.

Nick Muldoon:

What's the analogy there about golf, Dave?

Dave Elkan:

Oh. No, can you tell me? I can't remember.

Nick Muldoon:

It was this analogy about golf, like you've got to look where you're going to hit the ball and you've got to look up. You don't want to look at the tee, you want to look beyond the tee so that you... not beyond the tee, beyond the hole, sorry. You want to look beyond the hole.

Dave Elkan:

That wasn't my analogy, that's why I don't remember, but I do remember someone telling us that one. But it's a good one, like it wasn't even an analogy, isn't that the literal thing that the golf tutor would do? It's like, "Where are you looking?" And then they go, "Oh, I'm looking at the hole." "No, no, you've got to look further than the hole. Look up where you want the ball to go, and then away it goes."

Nick Muldoon:

Yeah, raise your sights.

Dave Elkan:

Raise your sights, yeah. And if you are looking at your feet, then you're probably not going to go far, but if you do look up and take stock, you can probably... that's actually a soccer analogy I can give you, like from my soccer coach, like you've got to point your toe where you want the ball to go. And that's just the magic thing, it just works. You just put your foot next to the ball with the pointing at the corner of the goal you want it to go in and you kick it, and then it just happens.

Dave Elkan:

There's these funny little hacks like that and I think that's a longterm vision thing. If you are running a business which doesn't have that longterm vision and purpose, then you can go actually in multiple directions at once, and you're not going to make any progress. I think a good analogy I read was like with a team, if you imagine all the team members are tied to a pole with a rubber band and they're all heading in different directions, the pole's not going to move because everyone's just... and the company's going to stay static and still. But if everyone just goes in the same direction, then it's going to move along.

Nick Muldoon:

Shift it, yeah.

Dave Elkan:

Yeah. And that's something that we've bitten off recently, is our purpose.

Nick Muldoon:

Mm-hmm (affirmative), to help teams be agile.

Dave Elkan:

Yeah. It's one of those funny moments when we we're talking about, and we talked about it, we set ourselves a deadline for the sake of a better word, like we had our planning session coming up in a couple of weeks, so we sat down and talked about it. And we went around and around in circles, trying to discover what it is, not to be agile, but just, what is Agile? And we know [inaudible 00:47:45], but we were trying to codify that in words. And when you said that, like it's being agile, it was kind of one of those... the way I like to describe it is, an upside down A-moment, which is our logo as you can see on Nick's jacket there.

Dave Elkan:

So when that was proposed to me, I was like, "No, that's so silly." But I was like, "Oh, but I love it." And I'm not saying that being agile is silly, but the fact that it's so simple, that's what I like about it, it's easy, it's simple, and there's a lot there if you dive into it.

Nick Muldoon:

Mm-hmm (affirmative). Yeah. Well, why don't we wrap it there? I think that's a good place to end.

Dave Elkan:

Yeah.

Nick Muldoon:

Our purpose is to help teams be agile and doing that, we're doing that for ourselves, we're constantly trying to learn and adapt and experiment with new things, being Easy Agile and as our team members here. So I hope that was a useful little tidbit and journey from Dave and I on how we got Easy Agile to this point, and some of the things that have been on our mind.

Dave Elkan:

Yeah.

Nick Muldoon:

Thank you, Dave.

Dave Elkan:

Thank you, Nick. That was fun.

Nick Muldoon:

That was fun. Oh, goody.

‍

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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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