Shaping Customer Discovery During Active Vs Passive Looking Phases

Ryan Singer




Felt Presence
Ryan Singer
Ryan Singer

Episode Summary

Today on the show we have Ryan Singer, the founder of Felt Presence and former head of strategy at Basecamp.

In this episode, Ryan shares his experience in evolving the Shape Up framework to better fit diverse team structures and needs.

We then discussed his insights on navigating customer engagement through the concepts of active vs. passive looking.

We wrapped up by discussing how these strategies are applied in real-world scenarios to enhance customer discovery and engagement processes.

Mentioned Resources



Introduction: Ryan Singer’s Journey Post-Basecamp00:01:14
Adapting the Shape Up Framework to New Team Dynamics00:02:45
Unpacking Active vs. Passive Customer Looking Phases00:07:24
Marketing Insights: Transitioning from Product Strategy to Sales00:14:53
Aligning Product and Engineering with Shape Up During Build Cycles00:21:01
Evolving Market Demands and the Role of AI in Product Management00:27:10
Career Paths in Product Management: Technical vs. Strategic Focus00:34:20
Looking Ahead: Ryan’s Plans and Predictions for 202400:38:09


[00:00:00] Ryan Singer: And I've got kind of a good sense of, kind of, the three main jobs that lead people to buy something like the Shaping in Real Life course. And that's a big part of understanding now how to market and how to improve the course. And it's like I have a little bit of a framework around me for how value is getting created in this kind of new universe that I'm in.

[00:00:33] Andrew Michael: This is Churn.FM, the podcast for subscription economy pros. Each week we hear how the world's fastest growing companies are tackling churn and using retention to fuel their growth.

[00:00:45] VO: How do you build a habit-forming product? We crossed over that magic threshold to negative churn. You need to invest in customer success. It always comes down to retention and engagement. Completely bootstrapped, profitable and growing.

[00:00:58] Andrew Michael: Strategies, tactics and ideas brought together to help your business thrive in the subscription economy. I'm your host, Andrew Michael, and here's today's episode.

[00:01:10] Andrew Michael: Hey Ryan, welcome to the show.

[00:01:12] Ryan Singer: Hey, Andrew. Good to be back.

[00:01:14] Andrew Michael: It's great to have you. For the listeners, Ryan is the author of Shape Up, founder of Felt Presence and the previous head of strategy at Basecamp. He's also a previous guest of Churn FM and his episode is still to this day one of the most listened to episodes of the show. And I highly recommend you to do so if you haven't already. So my first question for you today, Ryan, is what has the journey been like since leaving Basecamp and founding Felt Presence for you?

[00:01:38] Ryan Singer: It's been fascinating. I think probably one of the biggest things is I didn't know what I didn't know about how many different ways there are to run a team, about how many different ways teams are structured and stuff like that. There were a lot of things that kind of worked just organically inside a Basecamp. There were things that were just kind of understood between people that happened naturally. And then when I started to work with different teams, I started to kind of get all this new contrast, you know, and I was like, Oh, wow, actually, this is a different step than that, or this is a different problem solving area than this.

[00:02:18] Ryan Singer: And all kinds of new material. I mean, it was like a party for a framework designer, you know, somebody who likes to extract lessons out of how people work, you know, to see so many more examples and so many different ways of doing things and then to try and adapt the principles of Shape Up to all those different situations. It's been amazing. It's been a big learning experience for me. And it's also been a lot of fun because I've gotten, I've been able to extend the framework in a lot of ways.

[00:02:45] Andrew Michael: Yeah. I can imagine that being something probably not even that surprising, if you think, like, Basecamp is one of the more successful, most successful companies in its space and does really hold, like the super high bar in terms of the way the team works and operates. And I can definitely see like a lot of times we take for granted and assume other companies are in similar ways.

[00:03:05] Andrew Michael: But really like you said, across the board with all different aspects. I know, like for myself, like coming from more of a product analytics background and [hitting BI] at Hotjar, like just going into other startups later on and just seeing, like how much of a mess things are. Like I would have assumed that you're at this stage and at this level of growth that you'd have the perfect set up and you have a full understanding of how things operate in your business, but it's just never the case.

[00:03:27] Ryan Singer: Yeah. And a big part of it is there are a lot of teams I've worked with who are just as good in terms of their bar, but the structure is just different. They have a totally different ratio of designers to engineers, or they're working in a different stack, or they're under different timeline pressures, or they have different stakeholders. So in some cases, in a lot of cases, the quality is there, the teams are fantastic, but they're just in a different situation where they need different tools and they need to solve things in a different way.

[00:03:55] Andrew Michael: Nice. Maybe we can get a little bit meta then today just thinking about it.

[00:04:00] Ryan Singer: Okay.

[00:04:00] Andrew Michael: Thinking a little bit about how you're applying the process of Shape Up to your offering as you're going through and as you're learning now with these different setups and companies and what does that look like as you're evolving it now?

[00:04:12] Ryan Singer: So there's kind of, two big aspects of this kind of work. I've learned to think about it in terms of shaping and framing. And shaping is more like when there's something that I think I want to do, so I want to give a talk at a conference. Like we were at How to Web together earlier this year, right? And I need to actually figure out, like what's gonna go into the talk, right? Like how do I actually structure the talk and how do I design the talk? Or if I'm building out, if I'm prototyping a little piece of tool and software, or if we are putting the new course together, we have the Shaping in Real Life course, those are all things that have to get built, they have to get made.

[00:04:51] Ryan Singer: And then in order for me to actually finish those things on time and have them be successful, they have to be shaped. But the shaping is more the technical piece of what are the moving parts and how does this thing actually work so that I can build it? And then the framing aspect of this is a step before that, which is like, what is the actual problem I'm trying to solve? What is this actually about, right? And why am I doing this instead of something else? So this is kind of more on the product strategy side. And I've had to do a lot of both of that kind of on this meta level, like you said.

[00:05:24] Ryan Singer: So one of the things that was really important for me when I started to be independent for the, kind of, for the first time. I mean, I had been working with the team at Basecamp for 17 years, and then here I am on my own. I'm like, okay, I kind of feel like I know how to do things and I have experience. But I have to connect that to what, are people actually trying to solve, right? And how is what I know actually relevant to people? So in order to start to do that framing work, I actually did a lot of customer interviews. I did a lot of talking to people. And I went through a lot of learning process to see, what is, the actual struggles? What are those struggling moments that are happening for people?

[00:06:08] Ryan Singer: And today, I mean, for example, we did… When we did the first cohort of the Shaping in Real Life course, I didn't just open it up for sale. There was an application process. People had to answer long essay questions. I selected a variety of very different people to go through the first cohort and then afterwards did interviews on the people who participated. I've got a good sense of the three main jobs that lead people to buy something like the Shaping in Real Life course. That's a big part of understanding now how to market and how to improve the course. I have a little bit of a framework around me for how value is getting created in this kind of new universe that I'm in.

[00:06:54] Andrew Michael: Nice. So maybe let's double click into that as well, because I think there's a lot of interesting areas there that you've mentioned is one sort of, you're focusing really on the problem space and trying to understand, like what are the challenges people are having in these moments. It's interesting, like that can really inform them, like the go-to market and how to reach them at those points in time as well. What are some of the questions you're going into these interviews? Like what are some of your go-to questions that you always find to pull out interesting information from users?

[00:07:24] Ryan Singer: So, you know, the way that I learned to do interviews is according to, kind of, Bob Moesta's Method, the Demand Side interview. And in that case, there isn't a predefined list of questions, but there is a kind of mission in the interview. It's like, I'm the detective who is trying to figure out why out of everything that they could have done, you know, on this particular day, they bought this course, you know, especially with something like an online course, if they actually go through it, if they actually make that time commitment, you know, it's one thing to buy a course and it's another thing to actually do it, you know?

[00:08:05] Ryan Singer: So if they did the time commitment, it's like, why did they do that? What was happening that made this relevant, you know, and why do it now instead of putting it off for later, right? So it's trying to answer that, kind of solve that mystery and to figure out the dominoes that had to fall, the cause and effect that had to tip over one after the other, for them to realize that they needed some help to identify that this thing might actually be the thing that helps them and then to figure out like, from their point of view, what was this actually doing, you know?

[00:08:39] Ryan Singer: And I knew when I put the course out, I had already done a couple consulting projects with teams and I knew that there was a big gap between what's in the book and what you need to know in order to do it for real. So what I kind of imagined when we were doing the first cut of the course was that this is going to help people to do it, you know, you're going to go from the theory in the book to like doing it for real. And one of the things that I learned when I was doing the interviews is that a giant part of the course, it's not necessarily that people expect the course to teach them how to do all the different steps of framing and shaping and spiking and handing off responsibility and all that stuff.

[00:09:22] Ryan Singer: Actually, what they expect the course to do is to give them this clarity of like, oh, that's what it really looks like to do it when you're in a real world team that's not Basecamp. So they know that there's still gonna be a lot of trial and error and that they're gonna have to pilot it and figure out kind of the hands-on skill part, that's gonna take time. But that clarity of like, okay, now I can really see who to involve in which step and I can understand where this step stops and this step starts. And I can more clearly understand, like which parts I should actually do with my team that are gonna work for my team versus the things that are in the book that actually don't even apply to my team. Right?

[00:10:05] Ryan Singer: That it's that clarity that kind of like lifting the fog is really what they needed. You know, so that was a big takeaway. And then also kind of the triggers that led people to have the first thought and to start to think that they actually need something like this were really different. So there's one group where it's more about we're literally like at a place where we're not able to complete the big things. You know, it's like we can get tickets done, we can fix bugs, we can fix minor things, we can do incremental changes. But for some reason, it's like we've gotten slower and we can't seem to get those really important strategic projects done anymore. The way that we, you know, we can't deliver them on time and get them out the door. So that's a push for some folks.

[00:10:51] Ryan Singer: But then there's other folks where they're like, you know what, actually we can deliver okay, but the problem is that we have a small team of senior people. And we don't have any process for how we do it. We just do it naturally. And now we're growing and they need to onboard new people. And I have to give them, like a way of working, you know, now that we're getting bigger and I don't want to tell them to do scrum, right? And this is something that's closer to the way that we're working organically that we think we can actually kind of create a structure out of. So it becomes more repeatable. So there's very kind of, different reasons that lead people down the road, to taking the course and to learning more.

[00:11:26] Andrew Michael: Nice. So these are things that you've pulled out then obviously from the interviews and figuring out, and I think like two of those are triggers and reasons for people to come to you sort of like, they, as you mentioned, are finding it difficult to ship the big things and having blockers or now they've hit a point in scale where they need to systemize things and have a repeatable approach to product. You mentioned, like using that in the context of marketing and stuff. How are you thinking about applying those two notions? Because it's not probably the easiest thing to determine at which point in time people are hitting these moments in time. So how do you think about that in terms of like your go-to markets?

[00:12:02] Ryan Singer: You know, I really feel like a newbie when it comes to marketing, because I never had to market for myself before. I was always, you know, attached to Basecamp and you have folks like Jason there who are like just kind of natural marketers, Jason and David are both totally natural marketers. And to have to figure out how to do this on my own has been like, Whoa, it's like, it's another, like new world of stuff to learn. And I don't feel like I'm the guy who really has figured out marketing, you know, so I reach for the things that I know to try and make sense out of like, what should I do next? And since the job, to be, that be done, stuff is kind of, it's like one of the main things in my toolbox, aside from the Shape Up stuff, it's like, this is what I reached for.

[00:12:47] Ryan Singer: And when you look into, for example, the way that Bob teaches it in Demand Side Sales 101, that’s his kind of book about applying jobs in the sales and marketing space. One of the key things is this idea that people go through these phases in their buying journey from having the first thought that what they're doing isn't working to passive looking, to active looking, to deciding. And this passive looking is like, it's not really like this full-time project of like, so for example, you know, like you start to think that like, maybe you need to buy a new car. And you're not really like, Hey, we need to decide on the car yet. You're not like visiting the dealers, but you're kind of starting to watch more YouTube videos and you're, you know, you're noticing cars on the street. It's that passive looking phase.

[00:13:36] Ryan Singer: And a big part, what he explains in the book is that, what people need when they're in passive looking is very different from what they need in active looking. So in passive looking, it's more about like, we need to hear the story of what the problem is and how somebody else got through the problem. And in active looking, it's more like, well, I could do this or I could do that, or I could do this to solve the problem. So it's a little bit more like features and benefits and trade-offs and stuff like that, but it's like you already have understood that you have a problem, that there's a way to do things differently.

[00:14:12] Ryan Singer: So what I learned was that the passive looking part is really, I think, critical to helping teams make progress with being stuck with Scrum and having disconnects between product and engineering and projects not shipping. Because a lot of teams don't even know that there's another way. It just kind of feels like it's normal and having these kinds of inefficiencies and delays and getting a Figma File and then having to throw a bunch of it away, like having a meeting where you have to go backwards to all the stuff that you thought you already solved before. Like a lot of teams just think that this is just how it is.

[00:14:53] Ryan Singer: And so this really informed, kind of, how I structured the talks that I gave on this little sort of speaking tour that I gave this summer. When we were together at How To Web, I think the first third of my talk was just describing the ways that things are going wrong for teams. I didn't even talk about Shape Up, I didn't talk about, you know, tools or frameworks, it was just like, Hey, have you seen this happening in your team? And that kind of trying to help people connect the dots to say, Oh, this is a problem. That's very much like the passive looking thing.

[00:15:29] Ryan Singer: And this was actually super fun this summer, because when I put those slides up, you know, with the cartoons of the designers and the engineers and stuff like that, you could see people, people who came to the conference together. There'd be like two people from the same company and they would be looking at each other like, oh my, that's us, like, oh, you know, that's totally us, right? And I would hear that afterward too, right?

[00:15:52] Andrew Michael: It's amazing that you've applied it this way though, cause I was literally thinking in my mind, I was like, oh, this must be the speaking tour that Ryan was on, this was the purpose. And you explained the thought process behind it. Yeah.

[00:16:02] Ryan Singer: Yeah. I mean, I wouldn't say that I had some master plan. It was more like I was very pleasantly surprised to get a lot of invitations in Europe this year. And then when I got the invitations, then I'm thinking like, well, what am I gonna do? What am I gonna talk about, right? And then I actually, I mean, I went back to Demand Side Sales and I went back to everything that I had learned so far to just think through like, okay, I don't think that if I talk about a lot of nitty gritty details about how to do Shape Up better, that this is gonna be the thing that helps.

[00:16:33] Ryan Singer: I don't think it's going to help them and it's also not going to generate business for me because what's needed is not this, like kind of tips and tricks in the implementation side. It's much more, what is the problem and is there another way and what does it look like to kind of be on the other side of the problem, you know, to get through and what does it look like to actually feel like I'm in the after of that problem and now things are better, right? And so a lot, a big part of what I tried to do this year was to learn and how to talk about that, you know, and how to describe that and not just be totally…

[00:17:08] Ryan Singer: You know, we were talking before we started recording about how when you're working on your own things, you have all your biases about all these little things that are so important, you know, cause it's my product or it's my framework or my book or my course or whatever. And to step out of that and try and just think about, oh, what's the progress people are trying to make and what are the things that they're struggling with so that we're at least talking about the same thing that's interesting to both of us. And then we can kind of figure out from there how much detail is really useful to people, at what phase in their process.

[00:17:39] Andrew Michael: Yeah, no, definitely. I think like, from my perspective, as you mentioned, like I'm busy exploring now what's next and I'm doing a whole bunch of research, really trying to invalidate what I'm doing, but it's so so difficult like when you deepen it and you sort of, thinking. So what I said this time around was like, I want to focus on the problem space first. Like, let me just focus on like, be like, diligent about this. But no matter how hard you try to convince yourself, you always just end up gravitating towards that idea that you have for that product that you want to build.

[00:18:04] Andrew Michael: And I'm trying to fight the urge all the time, but in terms of, like listening and active listening, I think, like there's been some really great quotes that I found to help me describe the problem better. And actually one of the quotes like I loved a lot was like somebody said to me, he's like, really like what your product or service is going to help people with is the way he framed it was something along the line, like, Currently today, people are held hostage by the decisions they've made in the past. And they're too scared to make those changes now in the future because of the thing.

[00:18:32] Andrew Michael: And I… was just like a really powerful, little quotes. And then like now, every time I've mentioned that in interviews and follow on people like, yeah, I feel that, like they sort of like, so you get these really interesting nuggets out of these interviews that I think can be so powerful for the way you can position the problem to users.

[00:18:48] Ryan Singer: That's been a big thing for me too. Yeah. When I do the interviews, I'm really trying to get their words. And more and more try and speak the language that's natural to the people who are going through the process of buying, you know, buying the course or understanding that the course is something that's going to help them because my words are just my words and I have my own weird way of understanding all this stuff, you know, and I need to figure out kind of how do they actually describe it and what does it look like from their perspective? So that's huge.

[00:19:16] Andrew Michael: Yeah, absolutely. So in terms of, and let's continue on this path. Cause it's interesting, like just to hear how you've approached this. You focus on, like the meetings, sorry, the conferences side of things. It wasn't really intentional, but then afterwards you decide, okay, like let's make use of this time and really focus on communicating the problem to get people aware of it to begin with. How are you thinking about, like the next phase then for your, on the user journey in terms of like now they're problem aware, there, were passively, like looking now they may be actively actively seeking a solution, like what is the gameplay there, like how are you approaching it?

[00:19:48] Ryan Singer: Yeah, that's, it's really interesting question. I’m taking the baby steps to try and put things into place that are somehow, you know, there's theory, and then there's like what can I actually execute? And especially like, what can I execute with the time and resource and skills that I have, you know? So I think of the conference talks as very much being passive, looking. What I want people to get out of the conference talks is so far, you know, for this year at least it was, I want people to really see those moments where they're struggling and be like, oh man, I hate it when the designer just brings the Figma File and then we have, like engineering just crushes their dreams.

[00:20:27] Ryan Singer: And it's like we're not moving forward, but we're moving backward. You know, those different moments, or work product, like, has all of these explanations about why we need to do this and why this is valuable for the customer. And there's all this data behind it, but none of it tells us what to go build, right? There's all of these like struggling moments. And you're like, Oh, I've been there. But then to also show, here's what it looks like to do the shaping. Here's what it looks like when we talk about framing. Here's how the team operates differently when they're all aligned on what it is that they're doing and they don't have to have as many meetings and stuff like that.

[00:21:01] Ryan Singer: So people see a little bit of the before and after and they get a sense that like, okay, there's a better way and if I need that better way, maybe I go look at that Shape Up stuff or I go Google Ryan Singer and I go look at that stuff. And then here's the place where the buying timeline is really important because everybody is in their own life. And you know, there's going to be people, who kind of sense that there's something wrong and they recognize the problems that were described in the talk, but it's not really the big problem for them in their work right now. You know what I mean? Like it's not like the thing they have to solve today.

[00:21:42] Ryan Singer: Or maybe they're not even in the role where they feel like they can do something about it right now versus there's going to be other folks who are, there's going to be a CTO in the audience who is like, man, I need to like, I need to be doing this tomorrow, right? Because I have these problems and I can see how they're seriously holding me back. And I'm under pressure to deliver like, I've got to do this. So there's going to be people in different stages. And then for the folks who aren't immediately ready to move forward to the next stage. Other things are going to have to happen to them for those pushes, for those struggles to start to kind of become the higher priority thing that they have to solve in their day, you know?

[00:22:19] Ryan Singer: And what I want to do is I want there to be kind of these next steps of, if you've heard about me or you've heard about my work, you've heard about the book, and some time has gone by and now you're struggling with that stuff, what's the thing that you can do that that helps you to go a little bit deeper? And I think actually that the book itself is part of active looking. So if you kind of have a sense of problem solution and you think that there's a better way, you're not ready to actually commit to like, our team is going to work differently, or we're going to go hire Ryan to help us, or we're going to go buy a course or something like that. I've seen a lot of folks who will, they will go and they'll read the book.

[00:23:03] Ryan Singer: And what they're trying to do is kind of get a clearer picture for themselves of, like what they could actually do differently, what the change looks like and reading the book is a little bit like going to the car dealer. You know, it's like, it's a little bit like taking the test drive or like really starting to compare and like look seriously at like, what are my possibilities here? What could I do? I think another thing that you see a lot is there's folks, who they want to dig a little bit deeper, but the book isn't the right format or it's not the right time commitment. And then I'll see folks who are looking for, you know, what's the podcast I can listen to that's going to tell me more? What's the YouTube video I can watch that's going to give me more?

[00:23:43] Ryan Singer: And so that's also where that transition into active looking is starting to happen. And so, for example, I have a video out called Shaping in a Nutshell. And the idea of Shaping in a Nutshell is to be one of those bridges from passive to active looking. It's like, maybe you're not ready to read a book, but you do feel like there might be something here for you. So here's something that you can watch in 17 minutes that's gonna give you kind of an end to end, slightly clearer idea than what I could present on a conference talk, maybe. And then there comes a point where maybe somebody thinks that they actually want to do something, they actually wanna make a change and it's coming closer to deciding. So that's where I'm trying to help people to actually make trade-offs.

[00:24:29] Ryan Singer: So a big part of, so passive looking is more about understanding, problem. Active looking is more about understanding the solution and how the solution works. And then deciding, like pulling the trigger on the change, like we're going to adopt this, or we're going to take the course or whatever. A big part of it, Bob describes it in terms of making trade-offs. You know, like we bought a car recently and, you know, we moved to Portugal, didn't have a car and wanted to have a car here. And there's, you know, you want the car with everything you want, like that, it's gotta be fun to drive with, like tons of power, but it also has to have enough space. And it needs to be, like, big and spacious so we can put our luggage in it.

[00:25:10] Ryan Singer: We can, like, go with friends on trips, but the roads are really small here. So it needs to fit on tiny roads. You know what I mean? And it's like, you can't have it all, right? And that's like the really, like hard part about making a big decision is that you reach this point where you have to give up certain things that you want to get the other things that you want. And you really have to start to clarify yourself, like what's actually important to me? And you know, and like, what is this really about in order to get through that, to break through that wall of like, I can't have it all. So that's kind of where I feel like the Shaping in Real Life course page, the webpage for that, and also the way that the course is sold is designed to help people kind of through that moment.

[00:25:56] Ryan Singer: So for example, you can't just buy the course whenever you feel like it. We intentionally limit the availability of the course. We do it not more than four times a year. We do only groups of 20 people in a cohort. We don't announce the dates far in advance. So when the course, when you hear that another cohort of the course is coming, it creates a kind of urgency where, like if in the next quarter, basically, in terms of what's going on around you in your business or in your team, this kind of thing needs to be solved. It's kind of like, oh, I actually kind of need to act on this now. This is my chance, you know.

[00:26:39] Ryan Singer: If I'm going to make progress on this in the next quarter, and the book hasn't done it for me, and the YouTube videos and podcasts haven't given me enough answers to my questions to be able to see it clearly enough to actually lead the change, then like I think I'm going to have to put something else aside and make the time to do this course. Right.

[00:26:56] Andrew Michael: Make it a–

[00:26:56] Ryan Singer: So really, so the design of the offering, kind of the productization or the sort of go-to-market of the course itself, you know, that is very much designed around that kind of active looking into deciding phase, you know?

[00:27:10] Andrew Michael: Yeah.

[00:27:11] Ryan Singer: And whereas the other things are further upstream. So that's kind of a sketch of, like how I'm trying to think about this sort of whole system right now. You know, and every piece of it is, like super rough because I'm not a marketer and I don't, you know what I mean? So there's pieces in place, but they're all very, it's all very iterative.

[00:27:28] Andrew Michael: So, I mean, like I, I'm listening to you talking, like playing through all the different steps in the process that I'm taking as well at the moment now. And it's very, very aligned. And like I spend most of my time in marketing in my career. So like, I think what I've been using lately is I didn't, if you're familiar with Brian Balfour's Four Fits to build a $100 Million company.

[00:27:45] Ryan Singer: No, I don't know that one.

[00:27:47] Andrew Michael: It's an interesting framework, basically just extending, on the product market fit where you need products and markets to fit, but you need, what is it? Like the market and the product to fit the price, the model to the–

[00:28:00] Ryan Singer: Ah, all these different aspects of–

[00:28:02] Andrew Michael: Four different fits basically, needs to fit. So like, it's not necessarily to say that I want to build a hundred million dollar company, but it's more just, I want to make sure that what I'm building, that these fits all fit together quite nicely and that there's the opportunity to do it further down the line, but one of the challenges I think definitely for me is like the go-to-market side of things is like, how will I reach these people? And it's a similar process to you in the sense that it's not very easy to determine and understand at which point in time they're going to be having this challenge.

[00:28:30] Andrew Michael: I'd say I have like one extra additional challenge too, is that for me, trying to produce content in my space will be incredibly difficult just because the market leader in this space, like, dominates content, like is the go-to people for this? Like it's almost going to be impossible for me to like, I'll just be creating noise if I had to do that approach. So I've also been thinking through some of the lens of, like, okay, at which moment in time can I reach these people? And so for the thing I've uncovered, I think it's really interesting is sort of, partnerships at this point in time.

[00:28:59] Andrew Michael: So the people that deliver services that are ancillary that work around the problem space that I'm in and they, some of the results that they end up delivering to their customers are like, this is the problem that you have. And then it's like at that moment in time, the partner can say, Hey, like, well, we partner with Andrew, you should go and check it out. They'll be able to help you with this component of it. So I think this is the one thing I uncovered through, but it's also just working through all those different steps, trying to figure out, okay, when they're like, they have this problem, they become problem aware, like what can I do to meet them at that point in time? What can I do to meet them in time?

[00:29:31] Andrew Michael: But I think the acting thing that I liked here is you went is putting that a little bit of urgency. Because that's what I find as well is like the biggest problem can be the biggest struggle for me is like, it's an important thing. It has a huge, big impact on the business when you end up going around doing it. But it's like, it's one of those things that always gets shifted in priority and trying to get to that point in time when it becomes like a big priority. So I think selfishly thing is like I'm gonna use something. Like what can I do to create a little bit more of that urgency? And like, this is the time to act now. I think that's something that hasn't been sold through the interviews that I've been doing and figuring out some, very interesting. Nice.

[00:30:07] Andrew Michael: So you started now, evolving the book as well. You mentioned some changes that you've been seeing and I'm keen as well to sort of see, Shape Up was written in the context of Basecamp and then now you started to evolve that and to see how different teams are working. I'm keen to hear how you think things will be evolving over the next few years now with all the advancements in AI and the ability for like traditionally somebody who was a product manager, not being so technical, now having sort of the abilities to become a lot more technical and to be able to deliver product. Do you see any evolution in the way that we build products, changing? And are you seeing some of that now with the teams that you work with?

[00:30:43] Ryan Singer: I think the biggest shift that's been evident in the last couple of years, I think we haven't seen any effects of AI yet. And the, I mean, the one thing that we see with AI that is like hitting us over the head is that, you know, lots and lots and lots of programmers are using it to help them just as the expert that sits next to them while they're solving their coding problems. It used to be that you would Google and look at Stack Overflow all day if you were a programmer. And today, the GPT-4 or the different kinds of GitHub co-pilot and stuff, that is clearly a real thing that is happening big time. But I don't see that.  I haven't seen that bubbling up as a kind of change that affects the way that the different parts of the product team work together. You know what I mean?

[00:31:36] Ryan Singer: It doesn't change the way product and engineering work together. It's more of a productivity thing on the level of the individual engineers. I am sure that there will be a million things that come with AI that we can't foresee and I think it's gonna be amazing, but we haven't seen them yet, right? We're not seeing effects yet. The one thing that I think we really are seeing, is over the last few years with everything that's happened on the, kind of macroeconomic level is a return to focusing on cost and efficiency, the idea that people should be performing in order to earn those high salaries.

[00:32:12] Ryan Singer: This has put some pressure on folks in product management because there are a lot of folks who came into product management in the last few years when there were way more people inside these big tech companies before the wave of layoffs happened. There was, a lot more people, so there was, just simply a lot more cats to herd. You needed to have more people to hold it all together. And now that there's been a lot of cuts and there's been a lot of fat trimming and stuff like that, there's more of this sense like how, I think for all of us who are in these different roles, like whether we are a product manager or we are doing product strategy or whatever, we're kind of…

[00:32:52] Ryan Singer: There's more pressure than before to say, like, what am I doing that is really valuable? And how can I be more sure that the business needs me and wants me to be here? And I'm going to be the one who can stay if we come under pressure again. I think that's something that everyone is asking themselves more. And one of the things I'm seeing is that when it comes to the delivery management side of things, to making sure that projects move forward according to the way that they were defined, that program management, project management, delivery management, that the folks who are more successful there are actually more technical.

[00:33:33] Ryan Singer: So we're seeing much more emphasis on product engineers. Sometimes it's called technical product manager. Because when you're on a clock and you have a limited amount of time and something turns out to be harder or more complicated than you thought, to fix that, you have to really understand the wiring and what you can do technically to get through that challenge. It's not enough just to remind everyone of the reason, of why we're doing this, we actually have to get our hands dirty in the technical options to get through that difficulty. I think we're seeing that on the delivery side that the more technical we are, the better we can do. But that doesn't mean that the product management function is going away or anything like that.

[00:34:20] Ryan Singer: The other side of the coin is that this framing work of defining the opportunity, understanding the problem, figuring out, like what is a bigger thing to work on today? Why work on this thing instead of that other thing? Kind of really figuring out, like what matters to the business and what matters to the customer. We need that more than ever. And that thing is the furthest away from, I mean, the idea that AI is gonna help us with that is I think not the close thing on the horizon at least. I don't think anybody can see that actually happening because you really have to understand the struggling moments of the customer, how the business makes money, and how to bring all that stuff together.

[00:35:00] Ryan Singer: So I think there's a ton of opportunity for basically for folks who are in the product management role today to kind of make a choice, I would even say about where they want their career to point into the future and say either I want to go more in the technical side, you know, or I'm going to go more in the strategy side, you know. And those are both really good options, but kind of just being there in the middle as the person who makes sure that everybody is coordinating and having meetings and stuff, I think there's less value today than there was before.

[00:35:33] Andrew Michael: Yeah. And I definitely, I agree with that. I think it's a difficult space to be in. If you're sitting in that point in time. And I think that from a technical aspect, I think the opportunity has opened up much more with the AI and for somebody less technical, they have the ability to come into a more technical role and to learn a lot with the things like you said, like Copilot and GPT-4. I mean, myself, I would not consider myself technical, but like over the last month, I've literally built the product from the ground up and leveraging Copilot and GPT-4 and so forth.

[00:36:04] Andrew Michael: And that's why my line of thinking is like, okay, if I manage to do this, like in the last month, it's only a matter of time before there's others within roles that they start to cannibalize one another within organizations. And as you mentioned, like engineering, yes, like that's become like the Copilot, but it unlocks opportunities for designers, for product managers. So like you might design something in Figma and you actually want to produce the components in React and these, sort of channels, I think are like the lines might get a little bit more blurry in terms of who does what over time.

[00:36:34] Ryan Singer: Interesting. So you, so for the folks who want to aim more in the technical direction, the possibility, like AI is, like helping them to onboard into that because it's easier to learn and easier to start to do stuff. That's awesome.

[00:36:49] Andrew Michael: Yeah. I mean, I literally just like, if something's not working, I say, why is this not working? I get explanation. Okay. How can I implement that? Now that you've got the, giving me an explanation, give me the breakdown of steps one to four and like, just follow it's like paint by numbers, basically. So it's like, I think over time that's going to get better and it's going to become more efficient and then it just becomes up to, like, anyone can essentially within an organization build, product, like become the engineers. And it's a matter of like, I think that can you say like making a decision then.

[00:37:17] Andrew Michael: Do you want to go more towards the technical end or it's more like that strategy piece and what's going to become more critical and viable and less redundant in the future when it comes down. I do agree with you. I think the… figuring out what to build, how to build, who to build it for, their problems, their timing, that sort of stuff feels a lot further in the future in terms of being able to develop, good strategy with AI as it is today.

[00:37:38] Ryan Singer: Yeah, I think the other piece is maybe the architectural piece of kind of making decisions about which technology to use and how to approach building the thing, like in the kind of bigger picture versus at least today, the AI support feels like a little bit more like how to help me with all the glue in between the pieces, you know, to make sure that everything comes together. But man, who knows? Like it's in, it feels like we are so early in this thing. It's going to be incredible to see how it all starts to develop and change.

[00:38:09] Andrew Michael: Absolutely. Talking about development and changes, what's the new year looking like for you? Like what are the big plans for 2024?

[00:38:19] Ryan Singer: 2024, we're going to start off the year with a cohort of the course. We're doing Shaping in Real Life in January, and I'm doing a round of, I'm actually doing a new round of interviews of folks who bought the course in order to dig into some specific things about how we can start to iterate on it. So that's going to be interesting. I have some new stuff I'm working on that I'm not quite ready to talk about yet, but I've been doing some prototyping with teams around, the Shape Up stuff so far is mostly about what happens before you kick off a cycle of work.

[00:38:53] Ryan Singer: It's like, how do we do more of the critical problem solving and remove more big unknowns so that those things don't blow up inside of the time, inside of the time box later. So a lot of shaping has been like, it's all been about before kickoff. And then the framing even more so kind of, more the strategy leading into what is it that we're going to shape and what's important and what are we focusing on. Some of the stuff that I'm working on lead going into next year is how do we actually keep product and engineering aligned during the build cycle? So what are some things that we can do instead of having all those way too many meetings and way too many status meetings and check-ins along the way.

[00:39:34] Ryan Singer: What are the things that we can actually do so that the intent of what we shaped and the way that the builders are actually kind of focusing and aligning together, you know, on, like knocking out milestone after milestone, how to really tie those together. That's something where I have some early tooling and we're doing some projects with a few, kind of pilot teams to really make some improvements there. So I'm really excited to work on that. There's definitely a struggle that I hear a lot about where teams are in like week two or week two and a half of a four week effort.

[00:40:09] Ryan Singer: And this feeling kind of starts to happen of, like, yeah, I kind of feel like everybody isn't all pulling in the same direction and people are all working, but the stuff that they're working on isn't all adding up to us being done on the things that are important about the concept that we shaped. So how to correct that, that's something I'm really excited to share some new stuff about.

[00:40:30] Andrew Michael: Very cool. Well, I want to just say thanks a lot for joining again, Ryan. It's been an absolute pleasure chatting to you today. We'll make sure for the listeners that we leave everything we discussed today in the show notes. If you want to keep up to speed with Ryan's work, that will be there and available for you. And I'd just like to wish you best of luck now going forward. Is there any final thoughts you want to leave the listeners with before we wrap up today?

[00:40:49] Ryan Singer: No, I would just invite anybody who wants to reach out to send me a message on LinkedIn or to write me, just write me an email, You can also check out the website, and you'll find my contact info there. I love hearing from people about what they've applied, what worked, what didn't, where they're struggling. For me, it's this big learning process of what are people doing out there and how are the pieces of the puzzle that I'm working on, how do those things help people and also where can I improve? So please, I would love to hear from folks about their experiences and get connected.

[00:41:27] Andrew Michael: Amazing. Well, thank you so much for joining and wish you best of luck now going forward. Thanks, Ryan.

[00:41:32] Ryan Singer: Awesome, great chatting with you. Take care.

[00:41:34] Andrew Michael: Cheers.

[00:41:42] Andrew Michael: And that's a wrap for the show today with me, Andrew Michael. I really hope you enjoyed it and you were able to pull out something valuable for your business. To keep up to date with Churn.FM and be notified about new episodes, blog posts and more, subscribe to our mailing list by visiting Churn.FM. Also don't forget to subscribe to our show on iTunes, Google Play or wherever you listen to your podcasts. If you have any feedback, good or bad, I would love to hear from you. And you can provide your blunt, direct feedback by sending it to Andrew@Churn.FM. Lastly, but most importantly, if you enjoyed this episode, please share it and leave a review as it really helps get the word out and grow the community. Thanks again for listening. See you again next week.


Ryan Singer
Ryan Singer

The show

My name is Andrew Michael and I started CHURN.FM, as I was tired of hearing stories about some magical silver bullet that solved churn for company X.

In this podcast, you will hear from founders and subscription economy pros working in product, marketing, customer success, support, and operations roles across different stages of company growth, who are taking a systematic approach to increase retention and engagement within their organizations.


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