Easy Agile Podcast Ep.25 The Agile Manifesto with Jon Kern

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.

"I really enjoyed speaking with Melissa Reeve, VP of Marketing at Scaled Agile about how non-software teams are adopting a new way of working."

It's more important than ever to be customer-focused.

We talk about the danger of 'walk-up-work' and how to avoid this through proper sprint planning.

Melissa also gives an update on how agile is spreading to non-technical teams.

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Transcript

Sean Blake:

Hello everyone. And welcome to the Easy Agile Podcast. We have a really interesting guest with us today. It's Melissa Reeve, the Vice President of Marketing at Scaled Agile. We're really excited to have her on today. Melissa Reeve is the Vice President of Marketing at Scaled Agile, Inc. In this role Melissa guides the marketing team, helping people better understand Scaled Agile, the Scaled Agile Framework. In other words, SAFe and its mission. She also serves as the practice lead for integrating SAFe practices into marketing environments. Melissa received her Bachelor of Arts degree from Washington University in St. Louis, and she currently resides in Boulder, Colorado with her husband, chickens, and dogs. Melissa, thanks so much for joining us on the podcast today.

Melissa Reeve:

It's such a pleasure to be here. I really appreciate it.

Sean Blake:

Great. That's great. I really like your enthusiasm straight off the bat. So what I'm really interested in hearing about, Melissa is a little bit about how you got to where you are today. What have been the highlights of your career so far and how as a marketer, did you find yourself in the Agile space?

Melissa Reeve:

Well, thanks for asking. And I have to tell you, but just before the podcast my husband knocked on the door and he was all proud because we just got a new set of chickens and one of the chickens had laid its first egg. So that's been the highlight of my day so far, not necessarily the highlight of my career.

Sean Blake:

So you'll be having scrambled eggs and eggs on toast probably for the next few weeks now.

Melissa Reeve:

I think so. So back to the career, I really fell into marketing. My background was in Japanese literature and language. And I had anticipated this great career and international business in Asia. And then I moved out to the Navajo Indian Reservation and just pivoted. Found my way into marketing and found my way into Agile right around 2013 when I discovered that there was an Agile marketing manifesto. And that really was a changing point in terms of how I thought about marketing. Because up until that point, it really considered marketing in what's termed waterfall. Of course, marketers generally don't use the term waterfall.

Melissa Reeve:

But then I started to think about marketing in a different way. And when I came across Scaled Agile, it brought together so many elements of my career. The lean thinking that I'd studied when I studied in Japan and the lean manufacturing, it was Agile marketing that I'd discovered in 2013 and just education and technology have always been part of my career. So I really consider myself fortunate to have found Scaled Agile and found myself in the midst of scaling Agile into both enterprises, as well as marketing parts of the enterprise.

Sean Blake:

Oh wow, okay. And I noticed from your LinkedIn profile, you worked at some universities and colleges in the past. And I assume some of the teams, the marketing teams you've worked in, in the past have been quite large. What were some of those structures that you used to work in, in those marketing teams? And what were some of the challenges you faced?

Melissa Reeve:

Yes, well, the largest company was Motorola. And that was pretty early on in my career. So I don't think I can recall exactly what that team structure is. But I think in terms of the impediments with marketing, approvals has always been an issue. No matter if you're talking about a smaller organization or a larger organization, it seems like things have to go up the chain, get signed off, and then they come back down for execution. And inherent in that are delays and wait states and basically waste in the system.

Sean Blake:

Right. So, what is Agile marketing then and how does it seek to try and solve some of those problems?

Melissa Reeve:

Well, I'm glad you asked because there's a lot of confusion in the market around Agile marketing. And I can't tell you how many news articles I've read that say marketing should be Agile. And they're really talking about lowercase Agile, meaning marketing should be more nimble or be more responsive. But they're not really talking about capital-A Agile marketing, which is a way of working that has principles and practices behind it. And so that's one aspect where there's confusion around Agile marketing.

Melissa Reeve:

And then another aspect is really how big of a circle you're talking about. In the software side when someone mentions Agile, they're really talking about a smaller team and depending on who you talk to, it could be anywhere from five to 11 people in that Agile team. And you're talking about a series of teams of that size. So when you're talking about Agile marketing, you could be talking about an individual team.

Melissa Reeve:

But some people, when they're talking about Agile marketing, they're talking about a transformation and transforming that entire marketing organization into an Agile way of working. And of course, in the SAFe world, we're really talking about those marketing teams that might be adjacent to a SAFe implementation. So, I think it's a good question to ask and a good question to ask up front when you're having a conversation about Agile marketing.

Sean Blake:

Okay. Okay. And for those people that don't know much about SAFe, can you just explain, what's the difference between just having a marketing team now working in a capital-A Agile way, and what's the difference between an organization that is starting to adopt Scaled Agile? What's the difference-

Melissa Reeve:

Sure.

Sean Blake:

...between those?

Melissa Reeve:

Yeah. So what software organizations found is that Agile teams, so those groups of five to 11 people, that way of working works really well when you have a limited number of software developers when you started to get into the world's largest organizations. So I think of anybody on the Global 2000, they might have tens of thousands of software developers in their organization. And in order to leverage the benefits of Agile, you needed to have cadence and synchronization, not only within a team, but across multiple teams up into the program level and even the portfolio level.

Melissa Reeve:

And the same holds true with large marketing organizations. Imagine you're a CMO and you have 6,000 marketers underneath you. How are you supposed to get alignment to your vision, to your strategies that you're setting if you don't have a way of connecting strategy to execution. And so the Scaled Agile Framework is a way of taking those Agile practices across multiple teams and up into the highest levels of the organization so that we're all moving in a similar direction.

Sean Blake:

Okay. Okay, I think that makes sense. And from a software team's point of view, one of the benefits of Agile is that it helps teams become more customer focused. And many would argue, well, marketing has always been customer focused. But have you found in your experience that maybe that's not so true? And when marketing teams start to adopt Agile, they realize what it really means to become customer focused.

Melissa Reeve:

Yeah. I mean, you raised another great point because I think most marketers think that they're customer focused. Like many things in the world, the world is a relative place. So you can, in your mind, in theory, be thinking about the customer or you can be actually talking to the customer. So I just finished what I call the listening session. And it was during our hackathon, which is our version of an innovation, couple of days worth of innovation. So it was eight hours on a Zoom call with somebody South Africa. Just listening to her experience and listening to her go through one of our courses, slide by slide, by slide, explaining what her experience was at each step of the way.

Melissa Reeve:

So if you think about somebody who is sitting in a large enterprise, maybe has never met the customer, only knows the customer in theory, on one end of the spectrum. And you think about this listening session on the other end of the spectrum, you start to get an understanding of what we're talking about. Now, your question really pointed to the fact that in Agile practices, you're thinking about the customer every time. In theory, every time you write a story. So when you write a story, you write the story from the perspective of the customer. And I would just encourage all the marketers out there to know the customer personally. And I know that's not easy in these large organizations. It's sometimes hard to get face time with the customer, but if you aren't speaking directly to a customer, chances are you don't actually know the customer.

Melissa Reeve:

So find a way, talk to the sales folks, get on the phone with some of your customer service representatives. Go to a trade show, find a way to talk directly to the customer because you're going to uncover some nuances that'll pay dividends in your ability to satisfy the customer. And when you go to write that story again, it will be even more rich.

Sean Blake:

Oh, that's really good advice, Melissa. I remember from personal experience, some of these large companies that I've worked in, we would say, "Oh, this is what the customer wants." But we actually didn't know any customers by name. Some of us personally were customers, but it's not really the same thing as going out and listening to people and what did they find challenging about using that app or what do they actually want out of this product? So there's a huge difference, isn't there, between guessing what a customer might want or should want? And then what their day to day actually looks like, and what are the things that they struggle with? That's hugely important.

Sean Blake:

For someone who's in one of these big companies, they're in a marketing team, perhaps they don't have the power or the influence to say, "Okay, now we're going to do Agile marketing." What would your advice be for someone like that, who can see the upside of moving their teams in that direction, but they don't necessarily know where to start?

Melissa Reeve:

Well, there's a philosophy out there that says take what you can get. So if you are just one person who is advocating for Agile marketing, maybe that's what you can do is you can advocate. Maybe you can start building alliances within the organization, chatting casually to your coworkers, finding out if you have allies in other parts of the organization and start to build a groundswell type movement.

Melissa Reeve:

Maybe you can build your own personal Kanban board and start tracking your work through your own Kanban board. And through visualizing your work in that way, it's a little bit harder now that we're all remote, but should we get back into offices somebody could in theory, walk by your cubicle, see your Kanban board and ask about it. And now you might have two people using a Kanban board, three people. And really start to set the example through your mindset, through your behaviors, through your conversations in order to start getting some support.

Sean Blake:

Oh, that's really good. So be the change that you want to see in the organization.

Melissa Reeve:

Exactly.

Sean Blake:

Okay. Okay, that's really good. And when these companies are moving towards this way of working, and then they're looking to take the next level, let's say it starts in the software development teams and then say marketing is the next team to come on board. How does it then spread throughout the whole organization? Because I know from personal experience, if there's still that part of the organization that's working anti-Agile it actually still makes it really difficult for the Agile teams to get anything done. Because there's still the blockers and the processes and the approvals that you need to go through with those other teams. And I guess SAFe is the answer, right? But how do you start to scale up Agile throughout the whole organization?

Melissa Reeve:

Sure. And what you're talking about is really business agility, is taking the whole business and making the business Agile. And you pointed out something that's key to that, which is once you solve the bottleneck and the impediments in one area of the business, then it'll shift to another area of the business. So the advantage of business agility is that you're trying to keep those bottlenecks from forming or shifting. But what a bottleneck essentially does is it creates what we call a burning platform. So it creates a need for change. And that's actually what we're seeing in the marketing side is we've got these IT organizations, they're operating much more efficiently with the use of Agile and with the use of SAFe. And what's happening is the software teams are able to release things more quickly than the teams that are surrounding them, one of which could be marketing.

Melissa Reeve:

And so now marketing is incentivized to look at ways of changing. They're incentivized to take a look and say, "Well, maybe Agile is the answer for us." So let's just say that marketing jumps on board and all of a sudden they're cranking along, and except for that everything's getting stuck in legal. And so now legal has a case for change and the pressures on legal to adopt it. So there is a way to let it spread organically. Most transformation coaches will understand this phenomenon and probably encourage the organization to just go Agile all in, obviously not in a big bang kind of way, but gradually move in that direction so that we're not just constantly shifting bottlenecks.

Sean Blake:

Okay. Okay, that makes sense. And when these companies are trying to build business agility across the different functions, are there some mistakes that you see say pop up over and over again? And how can we avoid those when we are on this journey of business agility?

Melissa Reeve:

Yeah. So I feel like the most common mistake, at least the one that I see the most often in marketing, although I've seen it in software as well, is people thinking that the transformation is about processes or tools. So for example, in marketing, they might adopt a tool to "become more Agile." Maybe it's a Kanban visualization tool, or maybe they're being suggested to adopt another common ALM type tool. And so they adopt this tool and they learn how to use it, and they wonder why they're not seeing big improvements.

Melissa Reeve:

And it's because Agile at its heart is a human transformation. So we're really taking a look at in trying to change the way people think. One of the topics I speak on is the history of management theory. And while it sounds pretty dry, in reality, it's eye opening. Because you realize that a lot of the habits that we have today are rooted back in the 20th and 19th centuries. So they're rooted in assembly lines. They're rooted in French management theory, which advocated command and control.

Melissa Reeve:

They're rooted in classism. There was a management class and a laboring, and the management class knew the one best way of doing things. So more than a process, more than a tool, we're talking about transforming this legacy of management thinking into a way that's appropriate for today's workers. And I feel like that's the number one mistake that I see organizations making as they're moving into transforming to Agile, an Agile way of working.

Sean Blake:

Mm-hmm (affirmative). Okay. Yeah, that's really interesting. And it really is eye opening, is it? When you look at how the nine to five workday came about, because that's the time when the factories were open and all the history around how organizations are structured. And it's really important, I think, to challenge some of those things that we've done in the past that worked back in the industrial age. But now we're moving into the information age and into these times of digital transformation. It probably doesn't work for us anymore, does it, some of those things? Or do you think some of those things are still valuable now that we have distributed teams, a lot of people are working remotely? Are there any things that come to mind that you think actually we shouldn't get rid of that just yet?

Melissa Reeve:

Oh, I'm sure there are. John Kotter has presented in his book, Accelerate, this notion of a dual operating system. So that you have the network part of the organization, which moves fast and nimble like a startup and then you have the hierarchical part of the organization. And the hierarchy is very, very good at scaling things. It's a well oiled machine. You do need somebody to approve your expense report. You do need some policies and some guidelines, some guard rails. And so we're not actually saying abolish the hierarchy. And I do feel like that's part of this legacy system. But what we are saying is abolish some of the command and control, this notion that the management knows the one best way, because the knowledge worker oftentimes knows more than his or her manager.

Melissa Reeve:

It's just too hard for a manager to keep up with everything that is in the heads of the people who report to him or her. So that's a really big change and it was a change for me. And I think why I got so fascinated in this history of management theory is because I came across some notes from my college days. And I realized that I had been taught these historic management theories. I'd been taught Taylorism, which stems from 1911. And I realized, wow, there's a lot of undoing that I've had to do in order to adopt this Agile way of working.

Sean Blake:

Well, that's great. Yeah, that's really important, isn't it? I've heard you speak before about this concept of walk-up work, especially in the realm of marketing. But I suppose, well, firstly, I'd like to know what is walk-up work. Why is it so dangerous, not just for marketers, but for all teams? And how do we start to fight back against walk-up work?

Melissa Reeve:

Yeah. So, marketers in particular get bombarded with what I like to call walk-up work. And that's when an executive or even a peer literally walks up, so think again about the cubicle farm, and makes a request. So how that looks in the virtual world is the slack or the instant message, "Hey, would you mind?" One is that it results in a lot of context switching and there's time lost in that context switching. And then the other part is rarely do these requests come in well-defined or even with any sort of deadline detach. In marketing, it might look like, "Hey, can you create this graphic for this email I'm sending out?" So now you've left your poor graphic designer with this knowledge that here she has to make a graphic, but they don't really have any of the specs.

Melissa Reeve:

So it's very, very helpful to put these things into stories, to follow the Agile process, where you're taking that walk-up work to the product owner, where the product owner can work with you to define that story, keep the person who's doing the work on task, not making them context switch or do that. Get that story in that acceptance criteria very well defined and prioritized before that work then comes into the queue for the graphic designer. And this is an anti-pattern, whether you're talking about an organization of 50 or 5,000.

Melissa Reeve:

And what I've found is the hardest behavior to change is that of the executives. Because not only do they have walk-up work, but they have positional authority too. And it's implied that, that person will stop working on whatever they're working on and immediately jump to the walk-up work being defined by the executive. So I feel like it's really dangerous to the whole Agile ecosystem because it's context switching, it interrupts flow and introduces waste into the system. And your highest priority items might not being worked on.

Sean Blake:

Okay. So how many people do you have on your marketing team at Scaled Agile?

Melissa Reeve:

We're pretty small, still. We've got about somewhere in the 20s, 23, 25, give or take or few.

Sean Blake:

So how do you-

Melissa Reeve:

I think right now we're three Agile teams.

Sean Blake:

Three. Okay. So those 20 something is split into three Agile teams. And do they each have a product owner or how does the prioritization of marketing work in your teams?

Melissa Reeve:

Yeah, it's a good question. So we do have individual product owners for those three product teams. And what's fascinating is the product owners then also have to meet very regularly to make sure that the priorities stay aligned. Because like many marketing teams, we don't have specialized skill sets on each of those teams. So for the group of 23, we only have one copywriter. For the group of 23, we have two graphic designers. So it's not like each team has its own graphic designer or its own copywriter.

Sean Blake:

Yes.

Melissa Reeve:

So that means the three POs have to get together and decide the priorities, the joint priorities for the copywriter, the joint priorities for those graphic designers. And I think it's working. I mean, it's not without its hiccups, but I think it's the role of the PO and it's an important role.

Sean Blake:

So how do you avoid the temptation to come to these teams and say, "Drop what you're doing, there's something new that we all need to work on?" Do you find that challenging as an executive yourself to really let the teams be autonomous and self-organizing?

Melissa Reeve:

Yeah, I think the biggest favor we've done to the teams is really, I don't want to say banned walk-up work, but the first thing we did is we defined it. And we said, "Walk-up work is anything that's going to take you more than two hours and that was not part of iteration planning." And iteration is only two weeks. And so, in theory, you've done it within the past 10 days. So if it wasn't part of that and you can't push it off to the next iteration planning, and there's a sense of urgency, then it's walk-up work.

Melissa Reeve:

And we've got the teams to a point where they are in the habit of then calling in the PO and saying, "Hey, would you mind going talking to so and so, and getting this defined and helping me understand where this fits in the priority order." And really that was the biggest hurdle because as marketers, I think a lot of us want to say yes if somebody approaches us with work. But what's happened is people have, myself included, stopped approaching the copywriters, stopped approaching the graphic designer with work. I just know, go to the PO.

Sean Blake:

That's good. So it's an extra line of defense for the team so they can continue to focus on their priorities and what they were already working on without being distracted by these new ideas and new priorities.

Melissa Reeve:

Yes. And in fact, I think we, in this last PI reduced walk-up work from 23% down to 11%. So we're not a 100%. And I don't know if we'll ever get to be a 100%, but we're certainly seeing progress in that direction.

Sean Blake:

Oh, that's really good. Really good. And so your marketing teams are working in an Agile way. Do you feel that across the board, not only within your organization, but also just more generally, are you seeing that Agile is being adopted by non-technical teams, so marketing, legal, finance? Are these sort of non-technical teams adopting Agile at a faster rate, or do you feel like it's still going to take some years to get the message out there?

Melissa Reeve:

Yeah. And I guess my question to you would be, a faster rate than what?

Sean Blake:

Good question. I suppose what I'm asking is, do you feel like this is a trend that non-technical teams are adopting Agile or is it something that really is in its infancy and hasn't really caught on yet, especially amongst Scaled Agile customers or people that you're connected to in the Agile industry?

Melissa Reeve:

I would say yes. Yes, it's a trend. And yes, people are doing it. And yes, it's in its infancy.

Sean Blake:

So, yes?

Melissa Reeve:

Yeah. So all of those combined, and I'm not going to kid you, I mean, this is new stuff. In fact, as part of that listening session I mentioned and we were talking about all these different parts of the business. And there was mentioned that the Scaled Agile Framework is the guidance to these teams, to HR, to legal, to marketing could be more robust. And the answer is absolutely. And the reason is because we're still learning ourselves. This is brand new territory that we're cutting our teeth on. My guess is that it'll take us several years, I don't know how many several is, to start learning, figuring out how this looks and really implementing it.

Melissa Reeve:

Now, my hope is that we'll get to a point where Agile is across the organization, that it's been adapted to the different environments. When I've seen it and when I've thought through things like Agile HR, Agile Legal, Agile procurement, the underpinnings seem to be solid. We can even things like the continuous delivery pipeline of DevOps. When I think about marketing and I think about automation. And I think about artificial intelligence, yeah, I can see that in marketing and I can see the need for this to unfold, but will it take us a while to figure out that nuance? Absolutely.

Sean Blake:

Okay. And can you see any other trends more broadly happening in the Agile space? You know, if we're to look forward, say 10 years, a decade into the future, what does the way of working look like? Are we all still remote or how are team's going to approach digital transformations in 10 years time? What's your perspective on the future?

Melissa Reeve:

Yeah, I mean, sometimes to look to the future I like to look to the past. And in this case I might look 10 or 12 years to the past. And 12 years ago, I was getting my very first iPhone. I remember that it was 2007, 2008. And you think about what a seismic shift that was in terms of our behavior and social media and connecting and having this computer in our hand. So I ask myself, what seismic shift lies ahead? And certainly COVID has been an accelerant to some of these shifts. I ask myself, will I be on airplanes as frequently as I was in the past? Or have we all become so accustomed to Zoom meetings that we realized there's power there. And we don't necessarily need to get on an airplane to get the value.

Melissa Reeve:

Now, as it pertains to Agile, I feel like in 10 years we won't be calling it Agile. I feel like it will look something more like a continuous learning organization or responsive organization. Agile refers to a very specific set of practices. And as that new mindset, well, the practices and the principles and the mindset, and as that new mindset takes hold and becomes the norm, then will we be calling it Agile? Or will it just be the way that people are working? My guess is it'll start to be moving toward the latter.

Sean Blake:

Well, let's hope that it becomes the normal, right? I mean that it would be great to have more transparency, more cross functional work, less walk-up work and more business agility across the board, wouldn't it? I think it would be great if that becomes the new normal.

Melissa Reeve:

Yeah, me too. Yeah. And I think, we don't call the way we manage people. We don't say, "Oh, that's Taylorism. Are you going to be practicing Taylorism? It's just the way we've either learned through school or learned from our bosses how to manage people. And that's my hope for Agile, is that we won't be calling it this thing. It's just the way we do things around here.

Sean Blake:

Great. Well, Melissa, I think we'll leave it there. I really enjoyed our conversation, especially as a marketer myself. It's great to hear your insight into the industry. And everything we've discussed today has been really, really eyeopening for me. So thank you so much for sharing that with me and with our audience. And we hope to have you on the podcast again, in the future.

Melissa Reeve:

Sean, it's been such a pleasure and I'd be happy to come back anytime.

Sean Blake:

Great. Thanks so much.

Melissa Reeve:

Thank you.

In this episode, we dive deep into the challenges of aligning teams with strategic goals across organisations of all sizes. From fast-growing startups to large enterprises, teams everywhere struggle with the same fundamental issue: translating high-level objectives into actionable work that drives real value.

Our guest Andreas Wengenmayer, Practice Lead for Enterprise Strategy and Planning at catworkx (the #2 Atlassian partner worldwide and #1 in EMEA), shares his 11 years of experience helping organisations bridge the gap between strategic vision and team execution.

Want to see these concepts in action? Andreas and Hayley hosted an interactive webinar where they demonstrated practical techniques for strategic goal alignment using Easy Agile Programs. Watch the recording here→

About Our Guest

Andreas Wengenmayer is the Practice Lead for Enterprise Strategy and Planning at catworkx, one of the leading Atlassian Platinum Solution Partners globally and the #1 in EMEA. With over a decade of hands-on experience helping enterprise teams scale agile effectively, Andreas specialises in bridging the gap between strategy and execution. His work focuses on guiding organisations through complex transformation programs, optimising portfolio planning practices, and helping teams adopt frameworks like SAFe with clarity and purpose. Known for blending pragmatic insight with systems thinking, Andreas brings stories from the field - ranging from fast-moving startups to complex, multinational enterprises.

Transcript

Note: This transcript has been lightly edited for clarity, readability, and flow while preserving the authentic conversation and insights shared.

Recognising the signs - when teams aren't aligned

Hayley Rodd: Awesome to have you here. So I'm going to start with a bit of a reality check. We've worked in organisations across the spectrum from really fast-growing startups to really big enterprises. From your experience, when you walk into a PI planning or quarterly planning session, and I'm sure they're pretty hectic, what are the telltale signs that teams aren't truly aligned on what success looks like?

Andreas Wengenmayer: That's a great question - one I hear frequently. You can imagine, especially post-COVID when teams returned to in-person planning sessions. Back in 2017, we'd have huge arenas with hundreds of people in one place. People are happy to see each other, excited to chat with colleagues from different locations. This became even more pronounced after COVID, when everyone was working from home more frequently. That's a good sign - the mood is positive.

But you also notice some teams under pressure. They'd rather be working on actual deliverables. They know they have to be there, and it takes two full days to complete all the planning. Meanwhile, they're carrying a mental backlog - technical debt, unfinished work from the previous PI, catching up on delayed items.

This is what I often observe: teams get bogged down discussing minor details. People debate specifics, and you can see they're frustrated about something deeper - but they're not addressing the root cause. This creates its own negative momentum and can derail otherwise solid planning sessions.

Teams get bogged down discussing minor details. People debate specifics, and you can see they're frustrated about something deeper - but they're not addressing the root cause. This creates its own negative momentum and can derail otherwise solid planning sessions.

Sometimes you have to step in and ask what's really underneath. What's the actual cause? People say, "Yeah, I have to be here because that's the format, but I'm not engaged." Maybe it didn't work well in the past and there's lingering skepticism.

The prevailing attitude then becomes: "This isn't really collaborative. Leadership plans from the top anyway. The outcomes are predetermined - here's the plan, just make it work and update your boards." When people feel they can't meaningfully contribute or influence direction, they simply go through the motions.

My favourite example happens at the end when teams must formulate their objectives. It becomes a box-checking exercise - create something that satisfies the coach or Release Train Engineer so everyone can "get back to real work."

What good alignment actually looks like

Hayley Rodd: You've touched on so many things there. I can imagine walking into that room and feeling the pressure. People getting caught up in minor details rather than talking about root causes, or not asking the five whys to get to that root cause. You also touched on getting buy-in across the organisation. When people are really nailing it, when alignment is really there, what does that room feel like?

Andreas Wengenmayer: Yes, I've fortunately experienced those environments, and they're actually more common than you might think. When companies genuinely commit to grassroots planning, truly investing the time it requires, and ensure teams aren't overwhelmed from the start with everything marked "priority zero," you create the foundation for successful planning.

When companies genuinely commit to grassroots planning, truly investing the time it requires, and ensure teams aren't overwhelmed from the start with everything marked "priority zero," you create the foundation for successful planning.

You can see it immediately in people's body language and interactions. The energy in the room is palpable. If people appear resigned or intimidated, afraid to speak up, that's typically a red flag. The opposite creates magic.

Think about high-performing teams, like being a Scrum Master with an exceptional group. The best teams aren't just collections of highly skilled individuals in specific roles.

The best teams are those who communicate openly, genuinely enjoy each other's company, maintain positive energy, and actively support one another. This dynamic enables remarkable achievements. Maybe someone knows a contact in another tribe, release train, or department who can provide crucial answers and facilitate communication. Communication is absolutely fundamental.

That collaborative spirit is the hallmark of truly effective teams.

Hayley Rodd: Absolutely. We would know it in our day-to-day work, right? If your teams aren't communicating, if they're too overburdened as you said, it's not a good place to start. But if you can get that starting point right, if you can get that communication right, so many things will flow after that.

Andreas Wengenmayer: Absolutely. Looking back at any planning cycle, the real test is: did you plan the right things? You only know at the quarter's end whether you estimated capacity accurately.

Here's the crucial question: How does your organisation respond when goals aren't met? Do stakeholders focus on finding solutions? Do team members feel safe asking probing questions and seeking answers? Or does the blame game begin, searching for scapegoats?

How does your organisation respond when goals aren't met? Do stakeholders focus on finding solutions? Do team members feel safe asking probing questions and seeking answers? Or does the blame game begin, searching for scapegoats?

When you're permitted, encouraged, even, to be genuinely open and honest, you become much better at assessing realistic capacity. What makes stakeholders universally happy is predictability. You want confidence that your plans will actually materialise, that your commitments will be fulfilled.

Success breeds success, creating a positive foundation for the next PI. It's a continuous cycle that can spiral upward toward excellence or downward toward dysfunction.

The startup vs. enterprise spectrum

Hayley Rodd: Let's talk about the two ends of the spectrum. You've got a lot of experience, so I love hearing about this. Small companies will often say, "We're agile, we can pivot quickly, we don't need formal goal setting." Then enterprises are going all out on OKRs, cascading objectives, saying they're aligned because they've got those things in place. Yet both struggle with the same core problem. What's really going on?

Andreas Wengenmayer: You're absolutely right. I've been in agile projects since 2014, 11 years now, and I've seen a lot of companies pre-COVID, post-COVID, different sizes.

Starting with the really small ones, startup companies - what's really astonishing is that some very small startup companies tend to become overly complex, which is amazing. Some want solutions that are way too overblown. Basically, they need a sailing boat, but they're thinking about ordering an aircraft carrier.

Some startups want solutions that are way too overblown. Basically, they need a sailing boat, but they're thinking about ordering an aircraft carrier.

Maybe that's part of startup CEO culture - where everyone's a CEO on LinkedIn, and they think, "We're corporate, we have to be like that." They mostly get to their senses in the end, but small companies tend to be overly complex and overblown when it comes to technology, tooling, and organisation.

On the other end, large corporations sometimes seem to try their best to become truly agile - living the values everywhere. Still, it's a challenge. In most cases, there's some kind of hybrid planning going on. There's still a roadmap, which is good, but at some level, some people still stick to classical approaches, have some waterfall going on in the back.

I personally have never seen, for example, a full SAFe organisation where it's done truly at every level. There's a good balance and it should be healthy, but it all comes down to execution.

I feel like mid-sized companies are often the healthiest when it comes to that.

There's a balance of method and tooling, but you still need a solid understanding of goal setting and tracking. This includes pivoting when goals aren't right and learning from how you did things in the past. The gap between management and teams isn't that huge, and it's easier to bridge.

Avoiding death by KPI

Hayley Rodd: You've touched on so many fundamental things around getting the method and tooling right, but also that cultural aspect. I love the insight around mid-size organisations often striking that balance well. When we're thinking about the enterprise risk - which could be "death by KPI" or OKR, do you agree? Can you paint a picture of what that looks like and how it actually makes teams less focused?

Andreas Wengenmayer: Absolutely. There is such a thing as "death by KPI." KPIs are important to get a clear picture - you do need metrics, and there's merit to it. But as always, it's about choosing the right KPIs, the right metrics.

My favourite example is comparing story points across teams or ARTs. You measure velocity, and I have to repeat again and again: it's only individual to one team. You shouldn't compare it to another team or across tribes or ARTs - that doesn't work because you're creating the wrong incentives.

You see what will happen: "Well, okay, my stakeholders want higher amounts of story points. Let's estimate the stories bigger." Of course, that's a continuous loop, but it doesn't give you anything. Story points as a metric are just guidance for a team to get a better feeling for estimations.

You see what will happen: "Well, okay, my stakeholders want higher amounts of story points. Let's estimate the stories bigger." Of course, that's a continuous loop, but it doesn't give you anything. Story points as a metric are just guidance for a team to get a better feeling for estimations.

You want predictability - you want to meet a certain range. So it's not a great KPI when it comes to monitoring progress across teams. They have better KPIs in place.

Other metrics tend to create what I call bureaucracy. If you spend too much time creating reports, you have less time to create anything of value.

Hayley Rodd: I think there's so much in what you're saying about people being realistic and honest, open to pivoting or changing a goal if it's not the right one. Admitting to that is really difficult because no one wants to admit that what they set out to do is failing. But understanding that failure can sometimes be a benefit - you can learn from that. There's so much in that cultural aspect, right?

Andreas Wengenmayer: Absolutely. Coming back to goals rather than KPIs - KPIs are like being on a boat in your control room. You see what the engine is doing, the temperature - those are KPIs. Goals, on the other hand, are the course that you set.

KPIs are like being on a boat in your control room. You see what the engine is doing, the temperature - those are KPIs. Goals, on the other hand, are the course that you set.

You could be a small company like a startup - you're in a canoe, you're rowing. Or you're a large company - you're like a big freighter. Still, if you don't set the right course, the right goal, you will never reach your destination. Your team can be as proficient and perfectly working as they could be. If the course isn't right, hopefully you have enough provisions on board to survive a long journey.

Where organisations get stuck in goal setting

Hayley Rodd: Where do organisations typically get stuck? Is it defining the goals, communicating the goals, or translating them into action - that execution point you made before?

Andreas Wengenmayer: It could be basically any one of those. If you have a smaller or mid-size company, it's easier to communicate - you don't have to bridge as huge a gap. But still, you have high-level goals that have to be translated into real work. Real value is created in the teams.

If you have a high-level goal that's highly abstract and sounds good on paper - "increase customer satisfaction," "create better products," "make the world a better place" - people still have to understand: What does that mean to my daily work? If I'm a developer, what's my stake in that? How can I contribute?

If you have a high-level goal that's highly abstract and sounds good on paper - "increase customer satisfaction," "create better products," "make the world a better place" - people still have to understand: What does that mean to my daily work? If I'm a developer, what's my stake in that? How can I contribute?

That's when communication and breaking down goals becomes really important. Breaking them down the right way, having them visible and transparent, and creating that feeling of contribution. You make it visible that you're not just working for yourself or your team, but you're really contributing. You understand what you're working on and why you're doing it. Purpose is critical.

Bridging the strategy-to-sprint gap

Hayley Rodd: That's a really good segue into the next question about translating strategic vision into team-level objectives that people can grab onto and execute. Leadership will often say something like "increase customer satisfaction," and teams are left going, "What does that mean for me in my sprint this week?" How does an organisation bridge that gap between the high-level leadership view and what we can do in our sprints as a team?

Andreas Wengenmayer: First of all, you as company management need to take the time. There have been, and still are, a lot of approaches with company values, putting posters on walls, creating marketing. Those are all values - that's what a company is like. Then you link it with your products, services - great services, customer satisfaction. Okay. Then comes the real challenge: we want to succeed and create the next service, software solution, or product.

The goal is clear on a high level, but how do we break it down? That's when the real work comes into play - breaking down the goals into smaller pieces.

It's like building a LEGO space station when I was a kid. You have the picture on the box in the beginning - 'Oh, that's what we're going to build.' Then you have to start putting together all the small pieces. You need a plan, you need the little pictures of the steps. You start with the big picture, then you're breaking it down one piece at a time. You create different parts, and they come together at the end. Same goes for goals.

It's like building a LEGO space station. You have the picture on the box in the beginning - 'Oh, that's what we're going to build.' Then you have to start putting together all the small pieces. You need a plan, you need the little pictures of the steps. You start with the big picture, then you're breaking it down one piece at a time. You create different parts, and they come together at the end. Same goes for goals.

Hayley Rodd: Nice. A colleague of mine often says you eat an elephant one bite at a time - similar thing, right? When you see that big goal, it's really overwhelming. But if you can break it down into those chunks and smaller pieces, it becomes so much more manageable and achievable. People can get behind that vision.

Managing moving targets

Hayley Rodd: In fast-moving environments, goals often shift. We're agile, we're always moving. How do you help teams stay connected to a moving target without either ignoring changes or constantly thrashing around?

Andreas Wengenmayer: Back in the nineties and early 2000s, there was a computer game that wasted a lot of time in offices where you were shooting at geese in Scottish Highlands. It was a big phenomenon because people were trying to get the next high score.

If you think of moving targets, it's a bit like that. Imagine you're doing your work - whether you're a hunter or developer doesn't matter - but you approach, you take aim, and the geese keep flying up. You miss the target. Same thing if you have moving goals.

It's harder to aim and approach them right. What you should avoid as a company or someone in charge is constant interference. Stick to your goals or objectives that were agreed upon during PI planning. Don't change them midterm during a PI.

What you should avoid as a company or someone in charge is constant interference. Stick to your goals or objectives that were agreed upon during PI planning. Don't change them midterm during a PI.

That doesn't mean you can't learn from mistakes or wrong goals. You can adjust them, but you have to adjust them in the right place and time, which is during planning. Of course, if something security-related comes up, you have to act, but it has to be agreed upon, and you still have to communicate it and create understanding.

Keeping goals visible and actionable

Hayley Rodd: Even when goals are well-defined, keeping them visible and actionable throughout a PI is tough. What practices or tools have you found most effective for maintaining connection between daily work and high-level strategic objectives?

Andreas Wengenmayer: Good question. Having the goals present at all times helps a lot. If you just meet for planning, have your goals set, and never look back during the PI, it doesn't do you any good.

That could be a piece of paper on the wall like we had back in the day - and still could be if you're working in the office. Also, choose the right tools to track the goals and create acceptance for tools. Really use them. Look into them - whether it's an OKR tool or some other solution, even PI objectives. Are we still on track?

What really helps is if it's not static but shows progress, and especially shows the link of what you're contributing - like what you achieved in your last sprint and how it plays into the objectives or goals, progress moving ahead. There's always a good feeling - everybody loves a green bar moving ahead or a checklist.

What really helps is if your tool is not static but shows progress, and especially shows the link of what you're contributing - like what you achieved in your last sprint and how it plays into the objectives or goals, progress moving ahead. There's always a good feeling - everybody loves a green bar moving ahead or a checklist.

It helps keep the vision and goals present.

Hayley Rodd: When I was a teenager in my final year of high school here in Australia, I wanted a specific score on my final exams. I had a big poster in front of my desk that I sat at for hours every day studying. Looking back, I didn't know what I was doing - I just wanted to visualise my goal, and I didn't know the psychology behind it. But I'm happy to report I got that mark and above.

I think it was as you were saying - that constant reminder, that piece of paper worked for me. In organisations, we're looking for something a bit more complex sometimes, but I like your "keep it simple" advice. It doesn't always have to be super complex. It can just be a checklist, progress bar, or piece of paper - something that helps you feel connected to the goal and reminds you of it often.

When good work doesn't align with goals

Hayley Rodd: Have you seen situations where teams were delivering lots of work - good work, but it wasn't clearly contributing to company goals? What tends to cause that disconnect?

Andreas Wengenmayer: Yeah, that happens quite a bit. I can think of one example with very technical teams, like in semiconductors. Very smart people - everyone has a PhD in physics, material science. Awesome, smart people who tend to love their job. They're awesome, but they're also perfectionists who can still improve things and want to make them even better.

If you're in the business of producing machines used to produce semiconductors, for example, it's a complex task with a complex supply chain or value chain. You're creating lithography machines to create wafers used by other companies, and in the end, you have a customer planning the release of a new phone.

Your customer waits, the end customer waits, and you have to deliver on time. Sometimes this creates a challenge because teams still want to improve and make it even better. That's when economics come into play - the view of the big picture. You still have to communicate it. You shouldn't discourage such a great team, but you need to get the bigger perspective back to the teams and create acceptance instead of saying, "Hey, stop what you're doing, it's good enough." You don't want that. It all comes back to transparency and communication.

On the other spectrum, what you sometimes have is just too much workload on teams. Time for planning gets cut short, and if you don't take enough time to plan well, no wonder the results don't work out. It's just a lot of busy work - a lot of things getting done, but not necessarily the right things at the right time.

On the other spectrum, what you sometimes have is just too much workload on teams. Time for planning gets cut short, and if you don't take enough time to plan well, no wonder the results don't work out. It's just a lot of busy work - a lot of things getting done, but not necessarily the right things at the right time.

Hayley Rodd: If you don't do that planning at the start, you're setting yourself up for misalignments. If you're not communicating that plan regularly, you're setting yourself up for that busy work and people getting distracted. It's just so common. That planning part is so fundamental to getting it right.

One piece of advice for frustrated leaders

Hayley Rodd: We're on the home stretch now. If you could give one piece of advice to an engineering or product leader who's been frustrated because their teams seem to be going through the motions of PI planning or quarterly planning without real buy-in, what would it be?

Andreas Wengenmayer: I can resonate with that so well, and many can. I'd say: take the time to find out what's really going on. Investigate the root cause. It's like if you have a house and you're trying to fix a crack in the wall - you can look at the crack and do some superficial fixing or use a thick layer of paint, but you still have to find out what's causing that issue. Maybe something deeper.

You mentioned the five whys - that can be one way, but you have to have some understanding of the right way to approach people. You don't want to put anyone on the spot. Looking for a scapegoat doesn't help anybody.

We need to look at what's behind it, what's causing it. It all comes back to investing enough time for planning, but doing it with purpose. Not doing the whole planning like theatre, where everybody acts their part - that doesn't do you any good.

It all comes back to investing enough time for planning, but doing it with purpose. Not doing the whole planning like theatre, where everybody acts their part - that doesn't do you any good.

People have to understand why they're doing it. There has to be purpose and understanding - enough time, no distractions, and a positive atmosphere where everybody can contribute and be open.

You don't want people saying nothing because they don't dare to criticise or say no.

The connection between goal clarity and team motivation

Hayley Rodd: What's one thing you wish more organisations understood about the connection between goal clarity and team motivation?

Andreas Wengenmayer: We could get back to the boats we mentioned before. You want to arrive at your destination. If you're not clear about the destination, or maybe some people in your rowing boat don't want to go there, they might not join the rowing. If your crew is not invested, it will take you longer to reach a destination, or you won't get there as well.

It's the same thing. Motivation is key, and I don't talk about superficial motivation that just annoys everybody. Motivation is a positive environment where people rely on each other. They really like spending time with those people.

"Hey, I really like to go to lunch with you and talk to you" - not "I'd rather be home and not talk to anybody." You're not annoyed if your teammate asks you a question; you're happy to help. You're feeling safe that when you have a problem or question, you will get help.

That creates the right kind of motivation - that positive environment, and that can make a lot of things happen. It comes back to openness and transparency, not as buzzwords, but to get the clear picture. As a stakeholder, you get the correct current state because you get true answers.

I've seen strange situations in major corporations where people really didn't report what they were working on or show the right results. I've seen complete shadow Jira environments - one for internal use and one for external use with customers. There can be huge misalignments because people didn't dare to show real progress. In the long term, it will backfire. If you don't have trust in your environment, in your company, you will have a hard time.

I've seen strange situations in major corporations where people really didn't report what they were working on or show the right results. I've seen complete shadow Jira environments - one for internal use and one for external use with customers. There can be huge misalignments because people didn't dare to show real progress. In the long term, it will backfire. If you don't have trust in your environment, in your company, you will have a hard time.

Wrapping up

Hayley Rodd: There are so many key themes coming up throughout our conversation. You've talked about ongoing communication across teams, really planning with purpose, getting that context and buy-in to help with motivation, and allowing for radical candour - being really open if something's not working and being okay to call it out. So many cultural and communication elements are critical to the success of quarterly planning, PI planning, and organisations generally. Great takeaways.

We're going to end it there, but I want to end with a teaser for our interactive webinar that you and I are doing together on September 4th, which dives deeper and shows how to operationalise the ideas we've chatted about here using Easy Agile Programs and linking back to the fundamental services that catworkx provides organisations.

Andreas, it's been super wonderful to chat with you. I look forward to our webinar coming up on September 4th.

Andreas Wengenmayer: Thank you so much for having me. Looking forward to September 4th and seeing you again, talking more about tooling, boats, duck hunt, and anything in between.

Ready to transform your strategic planning?

The conversation doesn't end here. Andreas and Hayley hosted an interactive webinar where they showed how you can put these strategic alignment concepts into practice.

They spoke about:

• Practical techniques for breaking down strategic goals into actionable team objectives
• How to maintain goal visibility throughout your PI cycles
• Real-world examples of successful alignment transformations

Watch the webinar recording here →