How I Survived the Past 3 Years in Product Leadership

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Hannah Clark: Here’s a crazy exercise for you. Try to picture a day in your own life three years ago. In 2022, the big topics of the day were things like product-led growth versus sales-led growth, and the debate around return-to-office versus remote-first. AI felt like an optional side quest, and the employment landscape felt like a buyer’s market for job seekers. Oh, how things have changed in such a short period of time.

But another difference was that this show had a different host—and that former host is my guest today. Michael Luchen has spent the past three years shifting his focus into product leadership, and as a Product Transformation Architect, he’s been in the weeds through a pivotal time when the only constant has been changed, both outside and within product teams.

In today’s episode, we’ll be reflecting on the strategic and tactical bets he’s made over the past several years, the ones that worked, the ones that didn’t, and where the wind is blowing for product management as we move into the second half of 2025. Let’s jump in.

Oh, by the way, we hold conversations like this every week. So if this sounds interesting to you, why not subscribe? Okay, now let’s jump in. Welcome back to the Product Manager podcast. I’m here today with Michael Luchen, who some of you might remember.

Michael, thank you for joining us today.

Michael Luchen: Thanks, Hannah. Great to be here again.

Hannah Clark: Yeah. First of all, can you tell us a little bit about your background and how you got to where you are today?

Michael Luchen: Yes, so hey everyone. I’m Michael, former host of this podcast, but more lately, I refer to myself as a product transformation architect. And my focus has been helping on growth stage companies build product orgs that ship like startups. Scale like enterprises. So personally, I’ve had 12 plus years of experience working on over 50 products from 10 person startups to global brands like Adidas.

And through this time I’ve learned that companies that win aren’t just ideal rich, but they’re systems driven. And so from my experience, great product systems turn vision into repeatable execution. And this insight comes from leading products across every imaginable context in org structure. Each one teaching me new patterns about what actually works.

Most recently, I was the director of product at Float, where I transformed a product org from irregular releases to continuous cadences of delivery across all the teams helping achieve significant ARR growth and the G2 number one position. For that, I spent nine years at Crema, fantastic leading digital product agency, leading their product management practice for the agency and for clients from elite consulting firms to early stage startups.

And then on a personal level, I’m a systems thinker at heart. Whether I’m architecting product ops, framing a shot with my Fuji, or building Lego with my kids, always exploring how pieces fit together. It creates something greater than the sum other parts.

Hannah Clark: Very cool. And we’ve been talking a lot about systems thinking on the show recently this is slots are right into our thematic little situation here.

So we were the founding host, actually, of the product manager podcast. So thanks for laying the groundwork here for the show. That was, I wanna say, 2022. Not really a long time ago, but in product land that’s like decades now. The discipline looked completely different. So what have you found to be the biggest shifts from then to now?

Rewind and compare what the discipline looked like then and what are you seeing out in the field?

Michael Luchen: Yeah, it’s a really good question because I think in our industry we feel like this constant wave of change that we have to ride. There’s no like ever one fixed process or structure or way that we collaborate as product managers and with product teams to get great work done and out to our customers.

And so it’s really hard to answer this question because honestly, I’ve been thinking about what’s next right now as I answer the shift that I’ve seen. So what is that shift like? When I first started hosting this podcast that time, there was two worlds of thinking that we’re competing.

There was either the feature factory type, we’ve got a really defined process for better and for worse. But then there was also like the pure agile scrum almost warship to an extent. Teams, pick your poison or if you’re at the enterprise scale, it was safe. And now I’m seeing that really having like taken a backseat.

Like those processes are still there. Waterfall’s still there, scrum is still there. Safe is still there for better and worse. But what I see that the teams that are succeeding, are doing is they’re really looking at their own product culture, their own ways of thinking, the people on the team, and they’re picking and choosing pieces from each of those processes without naming it as process.

Really creating a systematic way of how they approach building great product and having fun doing it in a way that leads to that continuous discovery and delivery.

Hannah Clark: Okay. So I wanna pivot a little bit and talk about something that we don’t usually talk about on the show, but I think is so compelling, which is a failure story.

You had mentioned before in a previous conversation that you had a transformation initiative at Float, which failed the first time around what happened. What’s the postmortem on this and what have you learned in the wake of that?

Michael Luchen: Yeah, so I started at Float after my, nine years in agency space, like having the privilege of being able to work with so many different orgs.

And so I had seen it all in terms of the patterns of, small orgs, large orgs, orgs that were getting over a growth stage hump. And so I came in the Float and I saw some of these patterns. I had been talking to everyone up and down and across the org. Everybody was aligned on these patterns of the pain points around the process.

And what was slowing down our ability to ship great work. So I came in there, I got trusted by the CEO and the two, basically two co-founders to give a presentation in person at the first all company offsite. A few months into the role I was like, we’re moving to squads. This is gonna be great.

And the presentation was great. Everyone loved it, including the two co-founders. Everyone throughout that meetup was saying, this really resonates. This is gonna solve all our pain points. And then over the next few months, it dissipated and we started to go back to our old ways of working. And so what I realized in retrospect was even though I came in and I was like, here’s the problem, and everybody agreed with that problem and everybody agreed with the way to fix that problem, the reality is that it wasn’t the right time to make such a big move to process improvement.

Part of this was just due to how we had grown the org we were hiring for. And we had specialized roles in engineering, for example. And so if something happened or somebody was building a feature that needed a very specific skillset, there was only one person that could do that, and that would of course throw a wrench in any sort of kind of sustainable squads.

The other aspect I learned from this is that culture change. It takes time. It’s not just one presentation, even if everybody’s bought into it. It is that series of ongoing conversations, very much nuanced, things that you’re working through on a one-to-one level or in a team setting. And yeah, I’ll never forget that.

And it’s funny because if chatting with the CEO later about this, we laugh about it today, about coming in, guns a blazing, we’re gonna change and then that happened.

Hannah Clark: I guess this is like the systems thinking kinda thing, is that you kinda have to take into account all the reasons why something might not work and and then also evaluate things from the same perspective of oh, what were the other context pieces that kinda inform how we might wanna re-approach this in the future.

So I wanna talk about the practical sign of transformation. You developed a framework for mapping org-wide pain points using Miro tool that most of us are familiar with. So how did you identify, what was the process for identifying the friction points beyond just product and what did the process actually look like from day to day?

Michael Luchen: Yeah. I think even before you get into the tools, just having curiosity and empathy. So I remember when I started at Float and these same lessons apply to some of the clients that I worked with in my time at Crema. You hear a lot of pain and like challenges of oh it takes. And these are just broad examples over my career, but it like, it takes this long for, designs to be ready so I can build them.

Or maybe they’re, not aligned with what we wanna build or, there’s no clear scope, alignment or definition of done. All the things that we all feel in our practice, the pain points every day, and the things that we hear from our team. And I think what’s really easy to do is to have a kneejerk reaction where.

You take that and you weaponize that to try to force a solve for that one specific pain point if you’re the leader of that person’s team. And so for me, like at Float, I was director of product overseeing the product manager’s data UX research, and for a time design before it grew onto into its own department.

And so naturally, like my instinct is to protect my team, but I had to set that aside in order to go about this exercise and not only meet one-on-one with people across my team. A cross section of the org from engineers to marketing to even customer success and sales. What’s working well? What are you not getting?

Like what are the pain points that you’re feeling and how we shift great product and talk about that product to our customers. And it’s just a conversation. You don’t go into it judging. You don’t go into it trying to point blame or fingers at one another. And if you set that up and you just have that honest.

Curious conversation. You get so much great insight that you can then map to sticky notes on a mirror board and start to identify what those themes are once you do that, and once I have that, then I go and I map like alongside that. It doesn’t matter when before or after those conversations, what is the process that the company has agreed upon, and you can pretty easily see like what are those discrepancies?

Then from there I take those discrepancies and those themes that have those pain points across the org and basically map it to a new visual process. And from there, that’s what I use as the foundation to seek alignment with the folks I talked with, but also across the entire org up and down the entire org on these are the things we want to try, these are the process change experiments we wanna make.

Once you have that buy-in because you’re actually building it on top of the real life pain points that everybody is feeling across the org, like you rarely get any pushback from that.

Hannah Clark: That’s awesome. And I was just gonna push on that point because I think the buy-in is often the hardest part.

Even if the proposed solution on the surface is gonna create that source of relief for those pain points, change is difficult. It’s really difficult to change people’s habits and workflows. And for example, like you’d mentioned. Before that Float had a pretty specialized engineering culture, and so moving towards more of a cross-functional product squad wasn’t quite as well received, or there was a little bit of tension there.

So how do you manage situations like that and ease transitions when you’re trying to transform things and make life easier? Like how do you acquire that buy-in with more. When there’s tension to balance?

Michael Luchen: Yeah, it’s a good question. And it comes down to, no pun intended, the actual intent of Float as a product, which is resource management.

And having those discussions that lead to that, because it was really about clarity and respect. Without having those clear lines of communication with partners across the org or respect in doing so, then what happens is like that’s where you can have friction, but if you really focus on collaborating on, okay, let’s say there’s this really specialized.

Individual that we wanna have dedicated to a squad, for example, but they have to support like this really key piece of infrastructure. It’s, you can’t answer that black and white. So usually the options are we can hire, but hiring and onboarding that the quality that Float does, it takes some time.

So then what’s the plan B in the interim? That’s where capacity planning and resource management comes into play and aligning on those trade-offs. And so this gets to two angles. One, it’s the person and the individual themselves. Are they approaching this in a healthy way? If, are they being allocated to a squad like halftime or full-time or whatever that looks like?

How are they serving kind of those specialized needs of support or mentoring across the org that they have? And are we okay with that trade off? Usually the answer is we don’t wanna like split that focus. And so then it gets back into the product roadmap, and this is where I really see the value of ops and product coming together because you can’t answer like how do we actually allocate this person effectively without the context of what are the.

That’s, that we’re making or deferring based on our staffing approach to setting up these squads for success.

Hannah Clark: That’s a really good point. Okay. Tell me how the role of practical rituals fits into that scenario. ’cause you’d come up with something called One Team, One Roadmap, and you’d set up some async design sprints to facilitate some of this.

So how did that evolve and what did you find were like some of the most helpful takeaways from that time?

Michael Luchen: Yeah. One team, one roadmap was really the culmination of all of my product transformation work at Float. From coming in with that failed squad implementation that later did transform into a successful lasting implementation.

Once you, we did make that investment and the cultural investment, the hiring investments, but one team, one roadmap really came up about as Float was scaling. Now it’s okay, there’s all these product squads. There’s also platform squads. There’s like marketing focused work going on over here. Now product marketing is asking questions like, what’s coming up?

Sales is asking questions like, how can I tell the narrative authentically of what’s coming down the pipe or not? How can I authentically involve product managers as spokespeople when we have like really key new client opportunities? And then of course, the two co-founders are asking questions as well, like, how do we make sure we’re budgeting right and investing in the right way?

So one team, one roadmap was really about today. Each squad has their roadmap. Each platform team has a roadmap. These are all like managed time separately and linear. Let’s bring this together in a really systematic way that is as lean as possible, but provides as much up-to-date context as possible without taking as much time as possible from the people that are involved in that.

And so there was really the systems piece of it first, which using some of the newer linear roadmap features were able to create some great save roadmap views of all the, basically all the product and platform, et cetera, streams that were ongoing at a time. This was really great because it meant that the product teams actually doing this really only just how to provide a status update and linear.

A very lean one. Every now and then, those status updates will go out to a channel that I set up in Slack. So anyone across the org, regardless of how close they were to any sort of this product work, could subscribe to that channel if they just wanted to be aware of what was happening. And usually that channel would include like a Loom demo or even a link to a test environment if they wanted to play around with it.

Then I also paired that with. A ongoing monthly product huddle. These were 60 minute sessions that were focused on demos. Only product managers across the product teams would share and celebrate their team and what they’ve been working on. And then platform leads across the platform. Teams would be doing the similar work as well.

These were actually biweekly, I say monthly because that’s how often people would have to attend these, but I intentionally set them up as biweekly because we had async team members across 15 plus time zones. And so to be respectful of time zones, we wanted to alternate ultimately how we presented this to make the best respect of everyone’s time.

And so this radical transparency ultimately that was being shared through these focus product huddles through the completely automated linear roadmap updates, and then the, so every so often project status updates that would get piped into Slack with live demos, it created this transparency that built trust, that created a culture of shared understanding so that we can make the decisions on how we move forward across, all teams effectively.

Hannah Clark: Yeah, and I’m also really getting like this, it’s a huge amount of empathy for people’s different learning styles and ability to integrate themselves into the strategy at their own pace and be able to there’s the multiple levels of being able to get buy-in from different stakeholders. So I really appreciate this layered approach.

Michael Luchen: That also like segues into what you mentioned around design sprints as well. So at Crema, like I had spent years leading design sprints with clients and new teams and I think that today I don’t believe you have to necessarily follow the, buy the book async design or design sprint process, but I do believe it’s kinda pick your own kind of tools that you cultivate what your own design sprint looks like for that alignment.

And so at Flow to align on that strategic piece, I shifted that into async design sprints. And so it was essentially like a fig jam board at the time of, how do you take a five day sprint of exercises and then move it into an async format? You gotta have more time because people on one hemisphere are going to sleep after contributing to that board.

And then the other hemisphere is waking up, reviewing, and then sharing back what they thought asynchronously on that board. So extended it to two weeks. And what this leads to is actually you get like more participation because people have the time and the context of their own environments to safely share what’s on their mind and add comments to that discussion.

And then you can always elevate it to a one-off sync discussion if you want to talk about anything that is a hot button topic that usually comes up in these strategy debates.

Hannah Clark: Yeah, it sounds to me almost like a pen pal versus classroom dynamic. There’s there a little bit more, some degree of safety and being able to put out thoughts without the sense of immediate judgment or immediate, like overthinking what other people are gonna think in the moment.

Michael Luchen: Exactly, yeah. And being able to shift back and forth between the two. Again, ultimately outta respect of what’s best for the team.

Hannah Clark: Yeah. Yeah. That’s really cool. I’m gonna change gears a little bit because we can’t get through this conversation without mentioning everyone’s favorite two letter word, which should be AI of course. So when you would’ve been hosting this show. I don’t think anyone was really talking about AI in any certain terms, and now it’s all anyone wants to talk about.

At the time that you would’ve gone been here, we would’ve been talking about AI as really Actually I even remember I was coming onto the team right around that time and I remember the conversations around AI were very loose. It didn’t really seem that the technology was ready yet to be useful, and now everyone is in a rush to adopt AI in every workflow and in and their products. So at Float, what was the approach to AI integration? And obviously that’s a huge thing. You were navigating this, you’ve been really close to that project in the last little while. How did you navigate that?

Michael Luchen: It’s really interesting ’cause I think in the early days when ChatGPT first came out, I was in awe and enamored by the product, much like everyone was.

And so I started experimenting with it and I started. Researching some of the capabilities and the opportunities that we had from a product perspective with it just outta personal interest. And then I started to bring it back into how do I apply this to the product at Float? So I started like mapping out some ideas and ultimately that just led into a side passion project of mine where I remember I put together this like big notion doc white paper that had some of my own kind of beliefs of it was the early days at the time, but where is this modern LLM tech going?

Where is it gonna be in three months, six months, one year, three years? And how’s that gonna impact SaaS, particularly B2B SaaS that Float serves. So then bringing in some industry references, I was like actually, how do you make bets that we need to invest in from a product perspective today? And make sure that we’re timing those bets appropriately, but also not, like throwing everything away and just focusing solely on AI as was so the temptation at the time.

And then also a few sketches too, like mapping some of our data points in the API to if we had this available to LLM. What are some of the things we could do with this? And so it was really just from a place of curiosity that led to this doc that I then created and shared with the rest of the leadership team and got a lot of really great excitement and buy-in from that.

We actually ended up consulting with a generative AI consultancy out of Melbourne. A couple great guys moved 37, and they really guided us on. Not just how to approach AI, but making sure that we approach it in a way that aligns with what we wanna provide from a user facing value perspective. And so the earliest kind of separation they provided was the difference between structured data and unstructured data.

At the time, we were also looking at, improvements to make to the reporting product that Float has. But a lot of those improvements you could make just with structured data and some improvements to the database that we started working on later. The unstructured data is really where generative AI, that ambiguous stuff that we use every day with ChatGPT or Claude comes from, and that’s where able to separate the experiments.

The core thing that came from that was focusing on the agent workflows. They helped us create an agent playground that allowed us to play with some of the data to get some varying results so that we could see and figure out how might we implement this in the product? And so for me what that meant is as a product person moving forward, I’m looking at not just user flows.

But I’m also looking at agent flows. So I started designing things where we would have yeah, the user flow, the user does X, so they can do get y result. But then like almost under, like quite actually literally from a visual underneath that here’s what the agent is doing in the background to help support the user in that result.

This was different from a lot of the implementations that you see in the industry where it’s a chat box, a glorified chat box, and those are fine. They’re great quick ways to interact with data as quickly as possible, but it’s also not the idea that user experience, I think of where AI has the capability of going in terms of product integration.

That gets better with use over time, but you don’t necessarily have to use or know as a user that you’re actually interacting with AI.

Hannah Clark: Okay. I’m gonna change gears on you one more time. Let’s talk a little bit about the differences in how PMs need to operate now, because we’re looking at transformation on all levels, culturally as an industry and in the actual role of product managers as well, who are now moving from a very execution focused role to one that’s very much more strategic.

So in your experience, leading transformation, how do you advise product leaders to guide their PMs into adjusting their approach and adopting some of these more kind of radical shifts in focus and skillset.

Michael Luchen: So it’s an interesting one ’cause I’m actually gonna leave with a hot take that I’ve held true to throughout my career and I continue to even more a great product manager or product person, if you’re wearing that hat, is holding both execution and strategy together at the same time. And typically, I know that’s a hot take because the way I’ve seen it is, and I think what your question alludes to is there are people that say if you’re just doing execution, you’re just a glorified project manager.

Or if you are just doing strategy, you’re a mini CEO, I think both takes are toxic and I think what is ultimately good is, and where the PM has an increasingly unique ability to guide an org forward in is balancing both how do we execute this in a way that brings together the expertise of everybody across the product team from development to design QA and more in a way that strategically serves the needs of the business and the opportunities of the market and the customer and more.

And that’s easier said than done because during this, and I think where some of these arguments that are more black and white thinking have had merit in the past is that they’ll say these two are just at odds with one another. Like you can’t be strategic if you’re thinking about how you’re gonna efficiently get this done.

I disagree with that because I think when you, as I’ve shared through some of these other kind of stories, like when you lead with empathy and you lead with curiosity, it gets you to a place where you have all the context in front of you. If you’re using a Miro board or a fig jam board, you got sticky notes with your team.

It’s almost like a messy architectural desk, and you can move all the pieces around to see like what’s the best, most effective way that we can strategically execute this. It’s gonna guarantee us results. But it’s also making an efficient use and a respectful use of the team’s time, and everybody’s coming together for that.

What this means for those who are more execution focused today is to like actually lead with curiosity and think about from a strategic perspective, what are the things that you’re hearing from your engineering counterparts in terms of, tech debt concerns or new technical opportunities on the horizon, or things that they’re exploring?

What are you seeing from design in terms of. New design stacks or ways of approaching how you do that, and then of course, what are you as a product manager seeing in terms of what you’re hearing from customers in the business. You bring all that together and I think you can have like just a really great approach to execution and strategic, moving the strategy forward at the same time.

Hannah Clark: I don’t even think that’s a very hot take. I think that’s a very good take, firstly. Okay, let’s end it off on something a little lighter, a little bit more personal. ‘Cause you had mentioned to me that you’ve been doing some AI building projects with your son on the side, which I think is very cool.

Tell me a little bit, ’cause we’ve discussed through our newsletter and the like, which, if you’re listening and you’re not subscribed, why aren’t you subscribe? We did discuss a little bit about how parenting can really inform your approach as a product manager, as a product leader. So how has your life or parenting informed your approach to leadership and transformation?

Michael Luchen: Yeah, I try to let both sides of my life influence one another. I’d like to say my work-life balance is pretty good, but the reality is what I do is also my personal passion. And so I try to bridge those gaps. So recently my son, he’s five and a half, and one day he came home from school and he’s Hey dad, can we build this Ninja video game and put it on the PlayStation vibe?

And I’m like, okay I could either say yeah, let’s think about it, buddy. Or yeah, let’s figure it out. At the time I haven’t really done any game development, but in my mind I was like, you know what? I’m actually gonna take this as an opportunity to bridge some of that experimentation that I’m doing for work with him.

And I was like, let’s figure it out. We’ll use this new technology called AI on dad’s computer and we’ll do that. So what was interesting is then I started just bringing in like the product development approach that I use without telling him that. And so I was like, Hey, why don’t you start sketching out your ideas of who the character’s gonna be and like how the gameplay’s gonna be and all that.

Ideation and discovery, right? And so he starts like massing, like literally this pile of construction paper over a week or so with that. And then we finally get time to sit down and I say, why don’t you sit down here? And we talk about what is the approach to the game? And I was basically recording this using a transcription tool on my Mac.

Took this interview, dropped it at ChatGPT, asked it to create a game development doc, and then asked it to bring that into something that an AI tool could handle. And so from at the time, what I had heard is that, it’s like you wanna tailor it for the mindset of a junior developer. And so that’s what I used to create kinda this level one concept of this ninja game.

This is requirements gathering. And so then I take it and I drop this into, I was using Bolt at the time as and clean it up the prompt up a little bit. It created it, and now we’re play testing. Now we’re doing QA on production, and he’s saying the sound doesn’t work. The controls are a little iffy.

Okay, cool. We’re providing that feedback, and we’re iterate. Now we got the loop going on, and it eventually gets to the point where he’s excited to share it with family and friends. And then of course, later. Now we’re iterating with other ideas. How do we turn it into a 3D movie? Cool, let’s pull up Google’s VO model and it just goes on and on.

So I was bringing that product thinking. Which, if you think about product thinking at its core, it’s really based on like the scientific hypothesis and kind of the scientific methodology and the way of approaching that. And so yeah, I try to just bridge those two worlds in my day-to-day.

Hannah Clark: I think that is a much more thorough example of bridging. I think most people we’ve talked to are. Yeah. Sometimes they have to convince him to eat their broccoli. Yes. In your case, your kid literally has a product development resume before he’s able to read. That’s very impressive.

Michael Luchen: I guess so I re, I remember when I was his age, it’s it was like, I was like, I would be so cool to like work for a Nintendo or something, I was like reading Nintendo Power back in the day to just date my age. Now you don’t need to do that. Like he can just get on and start saying what he wants and go from there. It’s pretty cool.

Hannah Clark: Oh, cool. Thank you. That’s an absolutely incredible example and also a humbling example from parent to parent. I’m gonna have to update my list of rainy day activities.

Michael Luchen: Yes, yes. It’s a good one.

Hannah Clark: Thank you so much for making time to come back, check in with us, and yeah, it’s been so great to, to talk about what you’ve been up to. Where can people follow you online?

Michael Luchen: Yes, you can go to michaelluchen.com and there’s links to all the various platforms I’m on, so yeah, I’d love to connect. Don’t hesitate to reach out.

Hannah Clark: Thank you so much, Michael.

Michael Luchen: Awesome. Thanks Hannah. Great to be back.

Hannah Clark: Thanks for listening in. For more great insights, how-to guides and tool reviews, subscribe to our newsletter at theproductmanager.com/subscribe. You can hear more conversations like this by subscribing to The CPO Club wherever you get your podcasts.