The Agile For Agilists Podcast

Product-Led Growth – How to Capture a Unicorn

March 1, 2023
Album cover for Season 2 Episode 1 of the Agile for Agilists Podcast with a picture of guest speaker Diego Von Sohsten who is the Director of Product as Vidyard as well as a Product Growth Leader.
Agile For Agilists
Product-Led Growth - How to Capture a Unicorn
Having a wildly successful product takes more than solving the right problem for the right users. It also requires paying customers. We are joined in this episode by Director of Product and Growth Strategy Expert, Diego von Sohsten, who shares his experience in his own failed startup and how that has made him a better Product Manager today. Tune in to learn tips and tricks, as well as hear about Diego’s journey from Brazil to Canada and from developer to product manager, and his successful quest to capture that mythical unicorn.


S02 – E01 Diego Product Led Growth


Drew Podwal: All right. That’s probably good. All right, let me pull up my notes. All right. Welcome to another episode of the Agile for Agilists podcast. My name is Drew Podwal, and today I am joined as always with my co-host Brad Nelson.

Brad Nelson: Hi, everybody.

Drew Podwal: Hey, Brad, and today’s a great episode. We’ve got with us a guy named Diego Vaughn Soften. Did I say that right? Diego Vonns.

Diego von Sohsten: Better than I do.

Drew Podwal: better than, right. Amazing. Well, uh, Diego, I, we’ve [00:01:00] been talking about this probably for about a month now, and I’ve just been really excited about this. I met Diego probably, what was it like 2020? I think it was 2020 still.

Diego von Sohsten: so too.

Drew Podwal: Yeah, it was right. Right towards the end of the first year of the pandemic and, uh, Diego, uh, Diego had this wonderful, wonderful Agile, uh, product called Team Worky that, uh, did, uh, uh, natural was it, uh, natural language processing for forms and, uh, retrospectives.

And it would spit out this amazing, uh, uh, view that let you know whether your employees were, were trending positive or trending negative with, with their comments. And, uh, it was just such a great. , great product. And, uh, today we’re gonna talk a bit about that with Diego, but just as a quick introduction, right.

Uh, you know, Diego, you, you’ve said you’ve, you’ve worked for over 13 [00:02:00] years as a developer. You’re one of those amazing developers who’s turned into a product leader. Um, you’re both Brazilian and Canadian, which I, I find your accent to be absolutely fascinating. Um, I, I love the mix. I think it’s fantastic.

Um, and, uh, you know, now you’re currently specializing in, uh, uh, product leadership with, uh, bus, uh, B2B SaaS, um, and focusing on companies through product led growth. Right.

Diego von Sohsten: Correct.

Drew Podwal: Amazing. So tell us a bit about, like, you know, what the past couple years have been like for you at Vidyard. Tell, tell us a bit about what you do there.

Um, give us the high.

Diego von Sohsten: Awesome. Yeah, so I have a lot of fun at the yard. Basically, we are leading our product like growth transformation as you alluded here, and that means splitting the product on the driving seat. Um, often what happens is that you build this amazing product and, uh, the way that you are serving your customer, the way that you are [00:03:00] showing how the product works and building that value perception is with human beings.

And the way you’re selling is with human beings and the way you’re selling too. And what happens sometimes is that once you have that solid understanding of the problems that your products solving, you can actually get it to do a lot of the heavy lifting for you. Whether that means more retention strategies and more engagement strategies, leveraging product, product led onboarding, product led acquisition with virality, and also the ability to transact in the product by yourself.

So, uh, I think we’ve been, we’ve come a long way evolving the PLG strategy at Vigar in a way that if you are an individual, if you’re part of a team, anyone to start using video for sales and or marketing, you can do it yourself. You can set up a free account and the products, the product gives you a lot of value on its own.

And once you’re ready to reach that organizational scale, that’s the [00:04:00] moment when our sales teams get more involved. So it’s a transformation. So it’s no easy work for sure, but it’s also very gratifying. Once you start seeing the progress

Drew Podwal: That’s phenomenal. And it’s like, you know, so rare. I mean, I, I guess it’s not super rare, but like in what Brad and I do with the companies that Brad and I work with, um, it’s so rare to hear, um, you know, product led growth stories, um, you know, firsthand. So I think that’s, that’s really wild. Um, so tell us a bit, you’ve had a couple of startups as well, right?

Like, tell us about your evolution as a, you know, from that, that moment where you were a developer and you were like, I want to be a product manager. I wanna be a product leader, um, through to the startups and uh, you know, tell us a little bit about that, because that’s fascinating to us.

Diego von Sohsten: for sure. Uh, basically I was a developer, um, but I wasn’t very good at that [00:05:00] and I knew that and I wasn’t having fun either. I think I was, uh, pursuing the computer science program. Because, uh, I had a different perception of what that it was gonna bring to me and what, what had actually happened, . But if, if there is one thing I learned as a developer in my first job, uh, during university and after, was that working with customers and understanding the problem, those interactions, having that understanding, having that connection meant way more to me than the time that I spent writing lines of code.

Uh, and while I still carry a lot of that, you know, less about the code and more about the data component, I just love data. I still use SQL in my job. I just adore that. Uh, but I, I eventually learned that product management was a career path. And just by reading about it and talking to people in those, , I could see [00:06:00] myself making that transition.

It wasn’t easy. However, because uh, as you mentioned, uh, I come from Brazil and eventually I, I moved to Canada. But in Brazil, especially in the city that I come from, you have all those large companies have ibm, Accenture, Microsoft. But what happens more often than not is that developers are the workforce. In a place like Brazil, you don’t have necessarily a product manager in those environments. Your product manager is probably North America and Europe or someone else. Uh, so that was very limiting knowing that there were many opportunities in software development. But that, um, you know, if I wanted to go beyond that, I would feel a little bit more limited.

So what I did was to really shift my career towards what I wanted and. The opportunity for me. So I was pursuing my master’s at the time and I had my first startup at the time, which was something a little bit more services and [00:07:00] product oriented. But still, um, once I finished at Master’s, I knew I didn’t want to code anymore and I really wanted to go back to, you know, a full-time job, um, and learn from that.

So my previous job where I started, offered me the opportunity to return as a product owner. As long as I taught everything I learned to the new team that they were for me at the time. And I took it, I took it because I knew that the options were very limited. So, okay, that’s, that’s okay for me if half of my day in the first few months is about teaching people all the time and hand holding them, because eventually I made that transition to a product owner role.

And from there I got into product into a product manager, a more formal job. That’s also when I moved to Canada. Had my second startup and, uh, things eventually progressed.

Drew Podwal: That’s awesome. And, uh, you know, uh, I, one thing that you said there that [00:08:00] I want to call out is you had to teach the, the people that were on your team, I’m assuming, was it the developers or who, who did you have to teach?

Diego von Sohsten: Yeah. Developers, basically what we did at the time, uh, there’s this technology by Microsoft called SharePoint, and

Drew Podwal: Never heard of it.

Diego von Sohsten: technology it’s a technology very used for portals. So whether that’s an internet portal that you use in your organization

Drew Podwal: Oh no, I’m joking. I’ve, I’ve, I’ve heard a SharePoint.

Diego von Sohsten: Oh, you heard of it. Okay. I couldn’t say much because my, my current manager worked at Microsoft developing SharePoint.

Brad Nelson: Oh, wow.

Diego von Sohsten: It’s such a small.

Brad Nelson: So, so I have him to blame is what I’m hearing.

Diego von Sohsten: I, I didn’t want you to elaborate much on Microsoft SharePoint on this podcast, and that’s the reason why

Drew Podwal: Well, so you, you had to teach these people, and, and the thing is, is that, like one of the things I’ve learned in the past two years is that, [00:09:00] you know, sometimes you think about like teaching people as being a drag, uh, but the more time you share with others, the more you have, uh, an opportunity to remain in self discovery as well.

And so even the act of like teaching people, especially when you’ve just learned something new, um, you know, helps you to really. Open that up and evolve what you’ve just learned as well as go deeper. So I, I think that that probably, like, maybe it felt like a drag at the time, but I think it was perfect.

Right? Like,

Diego von Sohsten: a hundred percent. A hundred percent. I think I was able to solidify what I thought I knew. Uh, I think that the moment that you go through it from a teacher instructor perspective, things make more sense in your brain. But also, uh, I, I also bought myself some time in terms of, I was seen as a, as a solid product manager at the time by my, my boss because of my technical skills.

And that’s not what I wanted to happen. I wanted to phase out those technical [00:10:00] skills and ramp up my product skills. So yeah, that definitely bought me time. That helped me, you know, slowly make the transition while ramping up a team and what a gratifying exercise, what a gratifying experience to go through, right?

Being able to bring people who were on the first job and now some of them are still working with Microsoft SharePoint, believe it or not, in 23. Uh, but being able to be part of those people’s journeys. I think that that was super gratifying.

Brad Nelson: Yeah. Yeah. Drew. And I like to talk about martial arts a bunch cuz we know nothing about it. Uh, but some, uh, I, I’ve heard that some masters aren’t considered a master until they’ve taught another master. So there’s definitely validity in my mind too, to teaching is, uh, is the path to mastery.

Drew Podwal: Yeah, I hate that saying, what is it? Those who cannot do teach or something like that.

Brad Nelson: Yeah, I, I’ve heard the same from manage.

Drew Podwal: Yeah. [00:11:00] I, I think that’s terrible. Um, but, um, you know, while we’re talking about, uh, Microsoft real quick, uh, Reminded me like 10 years ago, I had a really good friend of mine, uh, who worked for Frog or still works for Frog Design.

Um, and he had this super secret project, and now it’s not super secret anymore, but, uh, to re-skin the Microsoft Office suite, um, masthead like the, the ribbon up at the top where it says file and view and format and all that, and come up with a better layout for the buttons. Um, he’s a, a creative director at, at, uh, frog Design.

And, um, and I joked around with him. I said, are you gonna bring back Clippy? And he actually, you know, clippy the, the little. You know, paperclip guy, he had to part of his product discovery. Um, he actually had like a week of interview [00:12:00] sessions with the product developer who developed Clippy. Um, and I just thought that was absolutely hysterical.

And, and it’s so funny in Apropo that now you know that, you know, companies like Microsoft, Google, and, and all these other companies are bringing AI into their applications. We might see clippy again, you know, that’s powered by ai. And it might actually finally be the paper clip of value that we were hoping Clippy would be back then instead of that little annoying, you know, grasshopper looking guy.


Brad Nelson: Yeah,

Drew Podwal: so

Brad Nelson: people are sentimental for clippy now. It’s, it’s surprising, like at the time everyone hated on clippy and now people are sentimental.

Drew Podwal: I’m sentimental for the icon. I am not super sentimental for the actual feature

Diego von Sohsten: Yeah. If anything, I think we, we end up, uh, Feeling nostalgic and, uh, yeah, creating stories about how the thing actually worked and maybe didn’t do the job well, but I will take it, [00:13:00] I will try it out. The moment that clip was available again,

Drew Podwal: I probably would too. I’ve been using a lot of AI lately. So, alright, so you moved to Canada and that’s when you started teamwork.

Diego von Sohsten: Yeah, I moved, uh, I think a couple years prior to that. Um, so I still had a, I had a job as a, doing something very similar to what I do now, working B2B SAS for two and a half years as a director of product. Uh, and prior to that I had a very short consulting gig, which taught me a lot about Canada. I was literally going to a mine two times per week and, uh, doing a lot of SharePoint work there.

Uh, more from a business analyst perspective, but, uh, yeah, SharePoint helped. Build my Canadian work experience and then I said goodbye to SharePoint once again,

Drew Podwal: Yeah, I wish. So. Okay, so you’re in Canada, you’re starting Team Worky. [00:14:00] Um, this is kind of the meat of what we wanted to talk about today is, is this experience you had with Team Worky that was, you know, an amazing product. So, um, why don’t you tell us, you know, or the audience, cuz I know about it and Brad knows a little bit about it, but give us the rundown.

What, what was team.

Diego von Sohsten: Great question. If there was one thing that really, um, was a curiosity that I had in my brain all these years working in tech, was there should be a better way to gauge and improve team morale. There should be, uh, I’m seeing more and more teams being distributed. In fact, one of the projects, one of the companies that I worked for, uh, before moving to Canada, Was a global company that had a project in North America.

So I would be communicating with people in the US and people in India, and I could see that there was a lot of appetite for gaging team morale, especially as [00:15:00] people were behind screens for most of the day and working from completely different places. I also work, I was part of teams that were very, teams that had a very clear sense of psychological safety teams that said what they wanted to say in a very radical, kinder approach.

And also part of teams were, there was a lot of pressure maybe from the organization for results and very challenging timelines, and I could see that those teams operated in very different ways. So I had a lot of curiosity about the role of technology in, first of all, assessing where you are as a team in terms of morale, but also helping you improve.

Some situations, uh, that maybe, you know, if you didn’t have technology you couldn’t notice. So that was a problem we are trying to solve, uh, to equip team leads and managers in tech organizations to understand morale in their teams, but also give them strategies to [00:16:00] elevate and build that sense of psychological safety.

Uh, there was a product that I always wanted to have and I don’t think it existed, so I decided to build it. And that experience actually happened while I had a full-time job. So, uh, not something that I’m very fond of or something that I feel very nostalgic about, but having a full-time gig in product while developing a product in an organization is a very challenging task.

And I don’t think I was fully ready for it psychologically, but I definitely went through it and learned a a lot. And that led us to a moment when, uh, COVID happened. And that was a time I think, for many people to practice detaching and changing how their lives were progressing. And I, I basically told myself, Hey, we have been developing this thing for a year.

If I don’t go full time on this, if I don’t really give it a chance to be successful, I’ll always have the question, what if, what if? [00:17:00] And in fact, at the time, the organization I worked for, uh, for some part, wasn’t very supportive of the idea of leaders, uh, having another project outside. So I had to make a choice.

Was I going to ditch my starter in for, for the sake of security, job security, or would I say no to my job security and really gain more depth with teamwork and the problem we, we are trying to solve. I chose the letter. I don’t regret it. I learned a lot and we are truly able to, to meet you. You were one of our earliest doctors.

And one of our biggest fans, so I learned a lot and I’m very grateful for that experience.

Drew Podwal: Yeah, so Brad, what we used it for at Matt Hive right, was um, I reported to this guy Brian, who was the chief product officer.

Brad Nelson: Mm-hmm.

Drew Podwal: when I first got on board, uh, one of the things I noticed that Brian did was all the people that [00:18:00] reported into him. He would send out a Google form to them every Friday, and every Friday you had to fill it out.

And it was what went well this week, what didn’t go so well this week? You know, um, what do we wanna do differently? Like, what are the things that you learned this week? Um, if there’s one thing I should know about, what should it be? And it, it wasn’t that Brian was trying to replace face-to-face conversation, all right?

It was that, um, he couldn’t sustain all of that face-to-face conversation on a regular basis, um, to, to make sure he always had his finger on the pulse of things. And, um, and it wasn’t to say that I couldn’t, you know, set aside a meeting with him if there was something I needed to talk to him about. He had a great open door policy.

It was just, it, it enabled us to kind of track from week to week what was going on. And, you know, at the same time, um, you know, Matt Hive had never really done regular retrospectives before. So Maria and I were looking for a [00:19:00] retrospective tool and teamwork. He seemed to be this thing that could kill two birds with, you know, one stone for us.

Um, and, and so we deployed it in both, uh, uh, team retrospective, uh, context as well as it replaced Brian’s Google forms. And, you know, the cool thing was you could track over time people’s, you know, response and the, the sediment score, I think it was a sediment score, right? Um, that, that you had for each person as well as the people on your teams.

And, you know, there were things about teamwork. Worked really well for us. There were things that didn’t work really well for us there, but the coolest part of it, right. Um, and Brad, I didn’t get to really share this part with you, is that like Diego and I one, we, I found team working on Reddit, which was, you know, go figure.

I found something on Reddit. Um, but, uh, we started [00:20:00] talking and, you know, Diego gave me a little bit of influence over his backlog. Right. Um, and we, you know, he talked to me as a customer in a way that made me feel like my feedback and not just made me feel, but, you know, made me feel, and actually that my feedback was, was valuable to, to him, to you, Diego.

Like, uh, that, that always stood out to me, right? Is you always made time to talk to me as a customer, um, and learn more about our use case and how we were using it and, um, You know, and there were some things that, uh, you did for us that were custom, that maybe other customers weren’t specifically asked for.

And uh, and we always appreciated that. But it was a lot of fun working with you on that while that was going. And we were deeply saddened when, when it went away. And I haven’t really found something that [00:21:00] that really fits the bill to replace, you know, what, what you had with teamwork. So

Brad Nelson: So, so we have you to blame for the bad advice, right? That’s why it doesn’t exist

Drew Podwal: I’m, I’m the reason why it doesn’t exist anymore.

Brad Nelson: so, so I wanna clarify it. It’s a sentiment score, right? Not a sediment

Drew Podwal: Did I say sediment?

Brad Nelson: That’s what I heard.

Drew Podwal: Uh, I think I probably said sediment. Sediment sentiment.

Brad Nelson: maybe it’s the New York

Drew Podwal: It is my, yeah, I have a lot of New York anachronisms or whatever the right word is.

Brad Nelson: Um, so

Diego von Sohsten: lot.

Brad Nelson: very different. Um, I’m still, so, like, I’m still struggling to, to visualize in my head like what exactly this interaction was.

Like, walk me through like the user journey, how you use this.

Drew Podwal: Is that for me or for Diego?

Brad Nelson: Uh, either, I guess. Yeah. Diego’s our guest. Why don’t, why don’t you?

Drew Podwal: Well, okay, so what it teamwork, you had this concept of you [00:22:00] would log in from a user management perspective and you would create teams at a team. I believe, if I remember correctly, had, um, a couple of different roles. There was like an administrator role and there was a manager role, and then there were, there was I think just one member role below that.

Um, and, uh, um, so you could set up your. And then within your team, you could set out, uh, you could create surveys and so you could have multiple types of surveys. So we had a weekly survey that went out every Friday. Um, then we had, at the end of every sprint after we did our retrospective, we had a survey from that, um, just because we were kind of new at doing retrospectives at Matt Hive.

And, um, people weren’t always so keen on speaking up. So this survey was really more for how did you feel this retrospective worked? Um, did it work well? [00:23:00] Did it work? Not so well. You know, so retrospective for the retrospective, but, um, you know, then there were, we had, uh, we had monthly surveys that would go out at the end of a month as well.

Um, and. They were automatic, so they would automatically go out at certain periods of time. So that was one side of it. Then there was the retrospective side of it, right? So, um, you could schedule retrospectives. Um, and the cool thing that I loved was at, instead of like starting a retrospective on the last day of the sprint in the retrospective, I would create the retro board at the first day of the sprint.

I would open it up for everybody and I would say, Hey guys, uh, the board’s open. Here’s the link to the, the latest retro board. If anything works well, doesn’t work well, you know, ideas for what we should do differently. Or, I always added a, a fourth column for shoutouts, right? If somebody, you know, blows your mind and helps you out this [00:24:00] sprint, don’t wait until the last day of the sprint to add it, add it early, because if they added it early, then we could save time in our actually retrospective event. and we could just start talking about the things that were important to talk about. So

Brad Nelson: Hmm.

Drew Podwal: the morning of the retrospective, I would transition it from ideation mode into voting mode, and I would jump on Slack and I would say, all right guys, it’s time to vote. And people would vote. And then when the retro started at like one o’clock or two o’clock or whenever that was, we would just jump right in to talking about the things that had the most votes and, you know, moving down the list.

And um, and it had the ability for us to create action items off of those things. And we even convinced Diego to, uh, to create a plugin for us so we could export it into Jira. Um, so we could have our [00:25:00] improvement item in the backlog, which, uh, uh, was helpful for us. And, um, it was just a great tool. It really worked well, you know, so.

Diego von Sohsten: Yeah. That, that’s awesome to hear. I can, I can tell that Drew was one of our earliers adopters and our exercise is basically, you know, can we find more Drew ? Because he, he’s exactly, he, he, he represents the problems that we’re trying to solve and someone who’s willing to put the time to really solve those problems.

Uh, so that’s something that we, we actually spend a lot of time on, uh, building the community of ready adopters, creating those feedback loops, and really, um, learning from that, a lot of what Drew said inspired. Features that we developed, integrations that we built. Um, we also had integrations with, uh, slack, Microsoft teams, I think at some point of year.

So it was a tool that was deeply integrated into the context of the environment of an Agile [00:26:00] team. Uh, the thing that we learned was that, um, the biggest opportunity for a product like that lied more in the HR space than in their regional space. Where we started, we were so excited about solving the problem, thinking about the Agile team, uh, the new manager or the experience manager, that once to everybody around them, uh, whether that’s a scrum master or team lead.

It didn’t matter much at the time, but we learned that the willingness you pay for the main part for, for the majority things should be low for something like this. And getting support in an organization to fund a tool like this can be very difficult. Uh, so that was ultimately the factor. That led us to not want to pivot and actually close shot the moment that we saw this huge community with a lot of free users engaged, but few accounts that were more deeply involved paying, um, [00:27:00] and you know, providing the feedback more actually.

But we learned a lot and I’m glad that I was able to, you know, meet so many folks like Drew and build those connections.

Drew Podwal: You know what’s funny? I don’t know if you guys are like this or not, but you know, whenever I report a bug, like, or for like in Riverside or whatever the tool is, I always write it almost like a QA tester, you know? Um, and, uh, and it really trips people up and they’re always really thankful. Um, or like the, um, we use a tool called Memo FM that allows people to go to our Agile for Agilists website and record a, a short audio recording that nobody’s used yet.

And you should definitely use it, um, if you’re listening. But I reached out to him because, um, there was some functionality that wasn’t working the way that I expected and. The, the bug that I logged, I not only put in there, you know, you know, that I was trying to [00:28:00] do x type of, um, uh, action so that I could achieve y type of, you know, outcome, um, but instead experienced Z behavior.

I also put in there, and by the way, I found your, um, I found this product by, you know, using this Google search. Um, I was able to get, uh, I found a community of people who were talking about it over here, and, and he loved that, you know, and so I would encourage like people who are, you know, technologists like us to, you know, one, recognize that the people.

Who build these products are, are real people. Sometimes they’re, you know, like U Diego or it’s a startup. Other times it’s a big company. But either way, like if you want to be that customer that gets recognized a little bit by the product manager in house, give your feedback in a constructive way. Give them additional [00:29:00] information about how you found the products.

Um, give them your, your sentiment, not sediment, um, but.

Brad Nelson: Yeah, for sure. Uh, that’s something I think that we all learn once we work in software, right? Like, it’s really easy to get frustrated, just be like one star. This is, but uh, see, I caught myself Drew. Um, this is terrible. Well, well, that’s great that you feel that way. And I, I don’t want to like take away your feeling.

Uh, that’s not actionable. I can’t action on that. so, yeah, I definitely think like actionable feedback is really the key for, for any product.

Diego von Sohsten: 100%. I feel that, uh, being a product manager for so long and now in a more leadership position, uh, whenever you look at, uh, the quantitative factor, Whenever you look at those metrics, you know, how many active users do we have on a daily, weekly basis, how many people are completing certain actions? You’re still missing an element, a human element, about how people feel [00:30:00] using your product.

And the worst thing for a product manager is to get those indicators, but you have crickets on what the actual experience look like. It’s anxiety inducing, especially if the indicators look awesome, but nobody’s saying anything. Nobody’s giving any feedback. Uh, so it can be very, um, nerve-wracking, I would say.

And having a community of people like what Drew just described is just a dream for any product person. When I think of, uh, crossing the Chasm, the book and how they talk about as you’re building the experience, you have those innovators right at the beginning with you. Those people who are really excited about new technology.

And they want to give active feedback. Eventually you get to those early adopters. The thing should be a little bit more on the cautious side, but still with a high appetite for trying something new. But then you start getting to the late majority, the early majority, the late majority, the lags, and then it feels very enterprising.

[00:31:00] So I think that the fun of product management more often than not lies in working at the beginning of the chasm, creating those relationships, learning from your customer, because everything that comes after, in my opinion, is a lot about maintaining status quo. And that’s where the product saturates, that’s where the product starts to lose meaning.

So every product, I think, should be thinking about how do we start this again? How do we evolve? How do we think about new problems to solve? How do we grow from here in a way that’s not simply what we currently have? Because honestly, I don’t think that that’s super for a product manager.

Drew Podwal: No.

Brad Nelson: So I do want to add, it’s equally as anxiety inducing and frustrating when you have a podcast that gets no feedback.

Drew Podwal: Yeah, I was thinking that actually while, while Diego was talking and you know, I was thinking that it’s not that we are not getting any feedback. It’s not, we’re not getting feedback. From people who we don’t know, you know? Um, I am like, I’ve gotten feedback from [00:32:00] people who saw the podcast on LinkedIn that I know that I didn’t specifically say, Hey, listen to my podcast.

And that, that was kind of cool. But I, we haven’t yet had that person that nobody knows, you know, neither Brad or I know, uh, to come back and say, I listen to the episode and I hate it. Or I listen to the episode and I love it. Um, and, uh, and like, we want both, you know, we want, we wanna know a little bit of both.

We’ve been looking at our metrics. Um, it’s interesting. I didn’t think the conversation would go here, but it’s kind of apropo. Um, like we’ve been looking at our metrics for the podcast. We use Anchor fm, which allows us to distribute on, you know, many the major, uh, podcasting platforms. And then gives us a dashboard that shows us the metrics on, um, uh, on all the platforms at once.

And, um, There’s a, a graph that shows the drop off rate and it’s, we’re not, we’re right at the place where [00:33:00] we’re starting to have enough active listens in each episode to start to make some early, like, meaningful hypothesis hypotheses, um, about like, you know, uh, like one of the things that we’re, we’re talking about, and I think maybe I.

Messed it up on this podcast already. Um, this episode is that we’ve noticed that sometimes we start the podcast, we chit chat a little bit, and it takes us a little bit to get to the actual subject. And I realize I never actually, I introduced you Diego, but I never actually said what we were talking about today.

Um, that just kind of evolved and I think that that’s something that the early metrics are kind of showing us that we think might be true, you know? Um, what kind of like tips and tricks do you have in your role, right? From like, I’m sure that early on when, when you created Team Worky, uh, that there was probably a period of time where you [00:34:00] got, you had no feedback coming in.

So like how did you go and solicit.

Diego von Sohsten: Great question. Um, I think that especially when you’re starting out, it’s really the bag borrowing steel strategy where the customer feedback is a one thing that you can be striving for. And uh, I think for us it was really important to nail who we were building the product floor so that we could better align the audience with that persona.

In our hypothesis was that by doing that in a far and more of the right, let’s say type of user, they would be more likely to provide feedback. It’s easier said than done because when you’re starting out, you don’t have one persona. Sometimes you have three. You don’t know your positioning statement, you don’t have a lot of money in the bank to fund the business.

You don’t have a huge runway. You’re really trying to prove that you can solve a problem. So it’s easier said and done, but [00:35:00] I think once you’re able to, you know, grow that community, I think the people will be inherently more likely to provide feedback in creating space for the feedback. Whether that’s you reaching out to the customer and doing what it takes to hear back from them, or creating micro surveys on the product that create that opportunity for them to, to share how they’re feeling, uh, and even contextualizing.

How you ask those questions, and when you ask those questions, there’s this whole thing about customer journey mapping and product management where you’re trying to put yourself in the perspective of your audience from the moment that you’re creating an account and having the first experience all the way through what we call activation or a successful onboarding through the, the way that they get hooked and now they’re returning and constantly engaging with your product.

So building up, building up that map for the persona that you really care about and really [00:36:00] contextualize what am I trying to learn along the way for someone who’s a new user and maybe perform specific action for the first time. I think the question is about how was it, tell me the best about it. Tell me the worst about it.

For someone who completely disappeared, your question can be more intentional. Cheer, Hey, we dropped the ball, it seems like. Why is that? And a tiny fraction of those people will actually give you feedback. But if you can really nail that persona and build that community, you’ll have enough to keep going.

And yeah, that’s how I like to approach it. Easier said than done again, especially when you have a very small community.

Drew Podwal: So I’m curious, uh, what were the personas that you had at at Teamwork?

Diego von Sohsten: That’s a great question. Um, my memory isn’t the best, but I can try to answer the question. Uh, we did have one for ScrumMasters, in Agile coaches. We had one [00:37:00] for team leads, we had one for developers, and then we had an icp, an IG customer profile in terms of the size of the company that we are trying to target.

And we had startups and we had mid size organiz. Very open, very broad, but we really wanted to learn and we learned a few things. We learned that, at least when it comes to how people are using our product, ScrumMasters and King leads had very similar jobs to be done and very similar roles and very similar engagement patterns.

At some point we gave a name to the persona and we simplify things, and we thought about that persona and we thought about the user persona, and eventually the decision maker persona would be entering the credit card. Once we introduced a plan, I think, uh, maybe being over, those were the personas we had.

Drew Podwal: You know, I, I love that you said that. Uh, two things. One, you said jobs to be done. I love, uh, uh, was it Clayton Christensen? [00:38:00] Um, I think he passed away in 2020, shortly after the pandemic started. Um, it talks about jobs to be done and the famous story of the McDonald’s milkshake. Um, love that. Uh, and so that’s, that’s one for the, for the references, the, the links for the podcast description.


Brad Nelson: Across the chasm.

Drew Podwal: Across the chasm. Let me write these two down real quick. Cross the chasm and jobs to be done. Um, and now I forget the second thing that was really important, but um, oh yeah. Okay. So this is one that I’ve always struggled with, right? And I’m curious what your approach is, is that, um, I’ve always coached the perspective of you might have a persona that’s a decision maker, [00:39:00] right? Um, and, uh, and has check spending authority or check signing authority that is different from a persona that is your end user.

Um, what’s your approach on that? Because, you know, um, like I, I’ve always broken it down by. Who has the influence over the, the, the spending and, and you know, maybe the people, actually, lemme take a step back where, what’s most important here actually is that I remember I worked at a very, ma I’m not gonna say the name, a very major publisher of education content, right?

Um, ed education textbooks, like one of the biggest in the business. And my job was as early in my career to build custom media, um, uh, custom media learning management environments, right? Um, for students. And I’ll never forget [00:40:00] when they talked about the customer, they were. Talking about a student, they weren’t talking about a parent, they weren’t talking about a teaching assistant.

Right. Um, and they weren’t even talking about the professor. They were talking about the 83 year olds, um, you know, white stodgy guy, department chair with the, the leather patch and the, the pipe. You know, that, that should have retired years ago. And so we were building these digital experiences completely devoid of, of any of the users that were actually gonna be touching this product.

It was just like we were building it to be palatable and, and likable by the person who, and, and that was it. And, and as a result, like, and I think that’s why digital learning sucked for so long, you know, especially like until [00:41:00] like about 2010 or. A little bit after that when, but, um, tell me a bit about like how you build personas for those different types of, of users.

The, the person who has the ability to sign the check versus the person who’s an actual user.

Diego von Sohsten: The good news on that topic, I think, is that there is a movement in size about people having more and more budget power in ability to make decisions than before. Uh, the whole persona topic, I think it evolved a lot from the two thousands and 2010s and 2020s. Uh, 10 years ago, we were seeing a world where, to your point, products were being built to cater to the decision maker’s needs, not to the ic, the individual contributor, the end user.

And what happened was that you’re selling probably, uh, an enterprise contract that lasted a year or more in dissatisfaction for the person using your product. [00:42:00] Didn’t matter as much when renewal time came, it was about did that one person want to renew the contractor? Not. And what I think is changing, especially in the 2020s, is that there’s more and more power to the user a whole.

Uh, you know, one of the reasons behind product type growth is also that idea that users can adopt things by themselves in organizations that are more and more acknowledging that. Um, you know, talking about my, my current employer, it’s a video solution for sales and marketing and many of our users are creating a free account, and that’s how adoption starts with that one user that has a very clear problem, aligns with our personas, just covers our product experiences, the, the, the aha moment, and then eventually brings a coworker who brings another coworker.

And now you have the critical mass in the organization of people who really enjoy the product. So [00:43:00] we have people who pay for their own licenses and we have people who are part of a more enterprisey type of subscription where there is a decision maker. So I think that the process around adopting a tool hasn’t uncovered that, you know, even the end user has some budget power.

Some people are purchasing software and expanding it, paying with their own credit card. To me, that’s a very good change that unleashes a lot of positive change across the board. And also decision makers on the other side are more and more supportive and mindful of what their peers and their teams are saying.

So they are making, uh, I think less often than before decisions about, you know, choosing the wrong product. They’re listening, they are listening to their teams. So it’s such a positive change, I think.

Brad Nelson: That, that’s awesome. Yeah. Yeah. I like to always say that like, customers and users aren’t always the same. Right? Like you have the person paying versus [00:44:00] the, the people actually using it, which I think is the point. And yeah, I, I see that in my own organization where enough people start using a tool that then it becomes a conversation of, should we have an enterprise license for this instead of everyone doing their own, um,

Drew Podwal: Even in Agile coaching, the same is true, right? Like the, the people who usually, you know, are the, the, the sponsors for Agile coaching and, um, you know, they’re, they’re looking for a transformation to occur for their team, you know, um, the people who benefit from that right away oftentimes are, you know, it’s supposed to be the stakeholders, right?

It’s supposed to be, well actually it’s supposed to be the customers. Um, but, um, you know, oftentimes the people who benefit from that at first are, you know, the teams, um, you know, when. Ooh. And, and it, it’s a misalignment of, of needs and understandings that occur there. And, you know, I don’t know actually, Brad, where you’re [00:45:00] at.

Brad Nelson: Mm-hmm.

Drew Podwal: personas for like that? I think that would be an interesting activity if you’re not like, creating personas for the different types of coaching engagements. Right? And a persona for the, the person who has the spending authority versus the persona for the person you’re gonna be interv interacting with on a daily basis.

Um, and things like that. Um,

Brad Nelson: Yeah. Uh, it’s, it’s not something that we do a lot, but it is something we have done. And then I was also trained in Prosci organizational change management. And, and that’s a pretty standard process in Prosci, is identifying your personas. Um, that’s not something we typically use for an Agile transformation, adoption, whatever we’re calling it today, uh, because pro side tends to be a little bit more prescriptive, follows more of a PMI type approach.

Uh, it’s funny, I’m actually writing about this right now, but, uh, like that doesn’t [00:46:00] work so well with something as complex as an organizational change.

Drew Podwal: Yeah. I, I, I, one of the things, and we’ve talked about this, is that, you know, we gotta walk the walk and talk the talk, you know, and, and, uh, like whenever I’m interviewing with professional services or Agile professional services organizations, you know, I’m always asking them about like, well, what’s their internal communities of, what do they, what the internal communities of excellence look like?

Right. Um, do they have weekly lean coffees for the coaches to come together? Do they do monthly open spaces? Um, and, you know, a lot of them do that, but there’s, there’s some out there that just, you know, they put the coaches out on engagements and, you know, maybe some coach has, you know, stood up a Slack server and now the coaches are coming together to talk about things and, and trade notes.

I, I call it, um, Comparing chessboards and, and [00:47:00] hypothesizing moves with other coaches based on what your chessboard looks like or what their chessboard looks like as a way of, uh, ensuring cross-functionality and growth. But I mean, the reality is, is that that’s a product, right? Like a pool of Agile coaches that, um, goes out on various engagements with the team is a product, and a product is a problem solver that solves the problem.

That’s the end user’s job to be done. And you know, as Agile coaches, our end user’s job to be done, unfortunately most of the time is get more stuff done faster. Um, but if we know that about their persona, um, I actually had a call about this kind of thing today. Like I know that like. , I can be overly dogmatic and, and focus on too much of the culture side, um, for my customers, uh, tastes.

And, uh, if I put together some [00:48:00] personas for them, it’ll help me to develop my products of, of Agile coaching service, uh, services better. So,

Diego von Sohsten: Yeah, something that I’ll probably add. I think that the process around creating crouching those personas will probably vary depending on the service or the product that you’re offering When you have a product, like what we did with Teamwork Key and we were acquired, acquiring hundreds and hundreds of people each month, uh, in terms of users, um, we could afford to not have all the answers.

So we had an idea of what our personas were, but it was so early to have the level of, of understanding. So basically what we did was to follow up with the people who were returning to the products, the people who are experiencing. And having a very open conversation about, Hey, tell me about your day-today mapping.

Now jobs should be done, basically running jobs should be done interviews, which is something that I still do [00:49:00] to, to this day. And eventually you start find patterns you don’t to who are using your product consistently to start to find patterns. You, you get to that at a 10 20 mark and now you have enough to hypothesize who the personas that your product solving problem for are.

And now you can ask questions about how many more people fit this criteria? Can we have a, can we grow, can we build a, a healthy business by serving these two or three personas? But yeah, I, I like to keep things very loose at the beginning because more often than we have more questions.

Brad Nelson: Yeah. I, I, I like that point too. You, you hit on something that’s very important to me, and, and that’s using data and research to build your personas, because that’s where people get in trouble too, is they build their personas off of assumptions. A and sometimes that’s all you have. To your point, when you’re starting, all you have are assumptions.

[00:50:00] Uh, but understanding that and that there’s risk in that is something that, uh, is very important. And, and, and on the data and research, uh, topic, uh, some, something I’ve been kind of sitting on here is, you know, early on you had mentioned like getting feedback from fantastic users like Drew and Drew always gave the perfect feedback.

Uh, but when you get this feedback, how did you decide which feedback was worth investing in? And, and which feedback was like, we’ll, we’ll set this aside and see if we get more of it.

Diego von Sohsten: Right. Yeah. I think that that’s when having some sort of ideal on your personas can be helpful because we had a lot of people using our product at the time. There was also a point, an inflection point where we had to make a decision. Do we want to continue down this path? Do we want to serve hr? We were even offered a government grant at some point to create a version of our product that [00:51:00] said HR and Serve hr, but keep the same functionality and shut down our Slack integration.

Will keep the Microsoft teams one because that’s the one that they were using. And you know, many people will say, Hey, I’ll take the money because we are new. We are starting out, but we didn’t because it felt like the type of change that would not, would not align with the product we originally had in mind and the, the personas that we had, the community we had built at that time, maybe financially it was the right decision to make with the product because HR has a more clear path to budget.

Then from my perspective, from my experience with teamwork, then working with team leads in a dev team. Uh, but we didn’t want to build that product, so we really stuck to it. And maybe we were too stubborn when we shouldn’t. But from the perspective of serving [00:52:00] those personas, what were the decisions that would allow for, you know, expanding reach of the product by, um, you know, addressing this feedback?

We’ll be able to help teams grow in sizes. We will increase account penetration or team penetration metrics on the product. We’ll be more likely to convert an organization from free to pay, because now we have more people experiencing value. So we had basically a checklist. What are the questions that we want you to answer before we prioritize something?

Uh, ability to grow accounts, ability to monetize accounts. Um, and, you know, ability to get better at the problem we’re trying to solve versus solving a brand new problem, which we are not good at. Uh, so many teams will have different frameworks, you know, rise exercises, rise frameworks or things like that.

But impact for us, in a prioritization framework was about answering those questions that were important to us.

Drew Podwal: I remember [00:53:00] early on one of the conversations that we had, I think it was with you, it might have been with another company, but I’m pretty sure it was with you. Uh, we talked about this idea where, like me as an Agile coach, um, Would be able to have a coupon code that I could give to, uh, a client that I was working with that would allow them to, um, to have a trial of it for a period of time.

Um, and, you know, maybe even a discount or something like that based off of that, or, or, um, or potentially I think we talked about, uh, where, where I would get a commission on it or something like that. Um, cuz I, and I remember you, were you, I think you had this idea early on that the path to success was to find a lot of coaches, because coaches work with a lot of clients and, you know, if we can create that, that coach persona to [00:54:00] attract coaches, then they can be the persona that, that, um, multiplies the, uh, the, the clients that way.

Was that, that was, we talked about that, right? Am I remembering correctly?

Diego von Sohsten: I think so, and we even implemented that at some point.

Drew Podwal: Yeah. Yeah.

Brad Nelson: Yeah. That’s interesting. See, my experience as an Agile coach going into organizations is I don’t feel very empowered to bring tools with me. Like that is something that we’ve, we’ve discussed internally at my company. Uh, my company is a tooling technology company first and foremost. So we have all these cool tools that can make our, our customer’s life’s easier.

Uh, and we’ve talked about doing partnerships with things like desktop and, and uh, you know, we use mural and those sorts of things, but it, it’s really hard to get companies to want to adopt new tools. Either they already have one that’s like close to it or like it has to go through security. And the, from [00:55:00] my experience, this is my opinion, I don’t think the freebie approach works.

Like, I don’t think the free trials work at a mega corporation because there’s a lot of overhead into installing and like the security and then like, Uh, band listing it afterwards. If they don’t want it, then I think a lot of them are just like, no, that’s okay. That’s too much work for, for a little time.

Drew Podwal: Yeah. It’s funny you say that. I, um, with, uh, my partner Dimitri, uh, United Parts of Chicago with Zoho, we were pitching early on a, uh, a product services organization. Um, they came to us, they wanted Zoho, and we pitched it and I said, Dimitri, like, we’re gonna have to go through, we’re gonna have to go through their security at some point, right?

Like, so we need to make sure that everything that we do stays away from touching specific types of data, you know? [00:56:00] And, uh, I said, I, I have a feeling like we’re gonna get far on this pitch and. We’re, they’re gonna ask us at some point if we have government security clearances and, and it’s gonna just be lights out for us at that point.

And, uh, sure enough, that’s what wound up happening. We, they, they got so excited about the different functionality that we could do that it, the, the topic of integration came up and I was like, trying to backtrack that off the table. And, um, but you know, I have found that I have had the opportunity. It’s usually, it’s with smaller companies where, where they don’t have the tools yet.

Right. Um, like there was one customer that they were like 150 people and they were running their software development outta Trello still. Um, and I was like, what are you guys doing? Like, you know, how, how are your developers putting up with that? You know? Um, . But, [00:57:00] um, you know, those are the kind of customers that are open to looking at the tools that I have used and the bag of tricks that I’ve used.

And, you know, um, if there’s not, if it’s not an enterprise company and there’s not security and things like that, but even at enterprise companies, right, like, it’s still so heavily siloed where, where a manager or usually a director, like, has some discretionary budget where they can afford to pay for a small product as long as they keep it under the radar and it’s probably not the right thing that they should do.

It’s probably never gonna be like at a, at like a Pratt and Whitney or, you know, Fuji America where they’ve got government contracts and stuff like that. Um, you know, but like at hbo, like we had. Definitely had tools that we probably shouldn’t have purchased that should have gone through it, that we were using.

Um, or, uh, I think one of the things [00:58:00] that we had was, wasn’t, uh, wasn’t Jira Service Desk, I think it was like ZenHub or something like that. And when it finally, when they finally caught winds that we had a license, it turned out there were like 12 other departments that each had their own license for this thing.

Um, and they were like, no, only one license now. And it’s all gotta go through it. And, um, and then everything, all the gears ground to a halt because everybody was trying to figure out who’s requirements were gonna be the requirements to, to, to set up the enterprise level account. And it wasn’t gonna work for this department and it wasn’t gonna work for that department.

It was just a nightmare. But,

Brad Nelson: Yeah. Yeah, I’ve experienced that too.

Drew Podwal: s.

Brad Nelson: Um,

Diego von Sohsten: feel like a, a category of products that really fits what you just explained here is probably the Figma of the world, where every company I’ve heard of is using a mix of lucid charts and FEMA and mural and. You, you don’t [00:59:00] even know, uh, how those decisions are made. And making a decision in terms of enterprise adoption gets really hard because now you have teams with your own preferences.

And I think that maybe that’s a consequence of product like growth share, more fragmented product adoption in organizations, especially in categories where you have a high saturation, where you have very strong players and the market is very divided. That ends up reflecting in the company itself. So I find that super interesting.

Drew Podwal: Well, like, you know, one of the, one of my super secret P super secret powers has always been, I know that Whene, whatever client engagement I go on. , if they’re using Jira, it’s likely gonna be a mess. It’s likely not gonna be configured correctly, right? Most companies, they hire, and I’m doing the air quotes, a Jira administrator, but they’re really just a Jira coordinator at best, you know, and that there’s nobody on site that actually understands [01:00:00] Atlassian at an enterprise level.

And it’s just a bunch of, you know, coordinators who are doing the best that they can to, you know, keep the lights on which year and accommodate everybody’s needs. Um, the other side of that coin though, is that I also know that if they are. If the customer I’m, I’m working with is lucky enough to have their own Jira instance, that that needs to be protected because as soon as that gets cannibalized by the actual enterprise license, that all of their ability to make those administrative changes that they had are gonna go away, you know, um, and uh, um, and so yeah, in, in those instances, like my first job to do is to find the Jira IT coordinator slash administrator and get them to love me so that this way I [01:01:00] have the ability to influence them a little bit and maybe get lucky and get an admin account so that I can do some of my own Jira admin.


Brad Nelson: Sweet talk ’em. Send ’em some treats.

Drew Podwal: yeah,

Brad Nelson: Yeah. Few winks. Yeah. I love it.

Drew Podwal: so. Getting back on to, you know, let’s go back to team working. Right. Um, one of the things that we wanted to talk to you about today was, you know, fast cycles of failure, right? And looking at failure as an opportunity, right? As opposed to this badge of, of shame and whatnot. And, you know, you’re on the other side, right?

You’re doing really well, you’re loving your job. Um, you’ve got, you know, great insight. What were the, what were the opportunities of failure for you along the way with teamwork? Like what were those aha moments and, and how has that helped you to be better as a product leader today?[01:02:00]

Diego von Sohsten: Yeah, what a great question. And I think that’s something that comes to mind immediately is, uh, the part about self discovery. And when you are creating a new product or when you are building an organization, you will probably take on a more generalist type of role. You have more jobs to be done per se, and a lot of that magic that led you to that moment will probably be a fraction of your day.

I’m a product person and I was probably spending 25% on my day on product management, and that was a moment when I realized that that’s probably not something that, at least based on how I’m feeling now about the world, that’s not something I want to pursue again anytime soon. In seeing constraints, I miss having eight hours per.

To talk to customers and work with my team to build something meaningful, put something out there, learn, raise, repeat, and [01:03:00] uh, yeah, I think that, you know, maybe could have been a different story in terms of being a funded startup in a more, you know, uh, busy, uh, environment with more funny opportunities. We were in the Canadian prairies with not a whole lot going on, especially at the peak of the pandemic.

So we had to go boots and we had to make decisions there. But still, I’m glad that that happened because I learned that my role, what really excites me is doing product management. It’s not to build a startup. The self-discovery, to me was huge to me alone, that that made the whole thing worth it, . Um, and also I think I was able to put myself in the shoes. Let, let me take a step back. I was able to build more empathy for how sometimes C level and product management don’t necessarily align on everything [01:04:00] and the healthy tension that exists. CEOs and C level folks are building a company, they’re building a culture. They have very tough decisions to make and product people are building a product and you only can’t afford to build the product if you have the money.

if you have the talent, if you have the culture, if you really want to go far. So, uh, being the same person doing two things, I almost led me to those moments when I was like, okay, am I making this decision from the perspective of getting more users using my product so I have a better pitch deck to show potential investors?

Or am I making this decision from a product standpoint because it will retain users, it’s the right thing to do. It’s about building for the future. And that constant conflict was just killing me. . I felt like, Hey, give me a CEO to work with right now and I’ll take on any health attention that’s inherent to [01:05:00] that work dynamic.

Because yeah, I don’t excel at that. And that tension actually creates a lot of opportunity and great decisions. You know, often you’re meet in the middle and you make a decision that benefits the customer, that evolves your product and it’s financially viable. Um, so yeah, that’s one of the main things I learned.

Uh, I created more and more empathy for people who are building organizations and I understand why. You know, when I have my product, like growth conversations, I’m always saying fix retention first. Don’t go after acquisition. But I understand why people go after acquisition. I understand because I was there.

Um, so yeah, knowing where I think I can be more happy and where I can provide better results in what I really like doing, uh, acknowledging some of my strengths and some of my weaknesses and being able to build a career [01:06:00] that, you know, taps into my strengths in empathy for people that I work with. All of that I think may be so much more attractive in my job.

And, yeah, more chill too. Uh, less, uh, imposter syndrome, less, you know, frequent questions about what am I doing? No, I think I understand what’s happening and, uh, they will be healthy tension and that’s okay.

Brad Nelson: That’s awesome. Yeah. That’s the same reason why I usually tell people I don’t wanna start my own business. They’re like, you’re an Agile coach. Like, you know how to run a high, you know, performing organization. Why don’t you start your own business? And like, it’s because I, I like doing what I do. As soon as you start a business, you’re no longer doing the thing you’re passionate about.

Um, So I, I think that’s, that’s very astute of you to discover. Uh, and, and I’m curious, so you mentioned more empathy for, for organizations. Your current company is a b2b. Correct.

Diego von Sohsten: Correct.

Brad Nelson: So do you feel like that made you better at your, [01:07:00] at being a product owner? Product manager at a B2B organization?

Diego von Sohsten: 100%. 100%. Um, many of our customers are actually tech companies. Some of those are tech companies that just started out, and the CEO is a salesperson. Of course, we also sell to enterprise organizations, but knowing that that’s such a significant fraction of our customer. Definitely impacts, you know, how we approach customer research, the questions we ask, the decisions we make.

Um, and I think it’s contagious here, right? The type of, uh, experience, given that I’m a manager, being able to share those experiences with my team as well, without them having to build through everything themselves. Of course, I hope that they will, you know, do things in their careers and learn a lot by themselves.

But being able to, you know, get those nuggets and being able to share that with [01:08:00] folks, um, and make other people’s lives easier, whether that’s internally or externally, whether that’s a customer or a peer, uh, I think it can be really.

Drew Podwal: So thinking about like, you know, most companies out there today are not, you know, product led. Right. Um, they are sales led. Right. And especially like enterprise level companies that I don’t even know how they’re led. I guess they’re steering committee and, and, you know, uh, board member led, but, um, , they have product managers there, they have product owners there.

Right. Like what would you say to people who are kind of like stuck in this role of that product owner or product manager that that doesn’t get to talk to the customers, right? Because there’s sandwiched through so many degrees, so many departments, and so many layers. Like what ideas do you have for them to try to get closer to the customer, to, you know, carve out the space to create personas [01:09:00] even though they’re not given the time to do it?

Like where, what would you say to that kind of person?

Diego von Sohsten: a fantastic question, and I think I found myself there in some of those situations here, and maybe they’re not on my LinkedIn, uh, , but I’ve definitely been in environments like that before. And first of all, I think you, you probably won’t be able to systematically provide awesome results if the environment around you doesn’t foster that. But I also think that if you have, you know, a coach that represents who you want to be in the company that you wanna work for and the values of things that you wanna learn, et cetera, et cetera, I think you can make an impact even in the most bureaucratic organization. I remember in the first job that I was talking about and how I was offering the product owner role, I went on vacation.

It was a very waterfall company. [01:10:00] Waterfall everywhere. I went on vacation and my manager was basically the, the CEO of, uh, the, the regional division that I worked at. She sold a project to a customer and, uh, a project that historically would take a year to be complete. She claimed that in two months we would be able to accomplish the same outcome.

I was on vacation, I was in Japan, . I was very far away. I did not know what was happening. And when I returned I was like, oh my gosh. Okay. We are in waterfall, in environment, a very large, she promise was me. How do we make this work? And by the way, she said, do not use Agile. I don’t wanna see anything related to Agile here.

Please don’t. So we secretly had our first Agile project, She didn’t know what was happening. She would come to the [01:11:00] office, she would start seeing all those chicks on the, the walls, and she would see those meetings with people standing and what’s happening. Basically what happened was that we got back to the Y, we talked to the customer, we recalibrated on what problem they were trying to solve.

There was Microsoft SharePoint evolved. So we had to leverage the most out of that. You know, there are many benefits for sure. There’s a lot of out of box, out of the box stuff. So we really, we created those biweekly spreads. We created this touchpoint at a two month mark, and we negotiated eventually two more months, but we were able to deliver a lot of value very quickly. And that actually surprised my boss at the time. She was like, how did you do that? I didn’t think you’re gonna make it. Um, and the company became more tolerant and more open to Agile and eventually, you know, uh, we had another credit owner and eventually people doing infrastructure work, working with, you know, Azure when it was starting [01:12:00] out and selling 365 licenses.

Now they had chicks and standups and sprints. Um, so I don’t know like that, that was something that I think I was able to influence an environment that was very against what I stood for, but it was the only way. And because it worked, it was able to unleash a transformation. But I’m talking about a company with 35 people, so it gets exponentially hard at Enterprise.

So yeah, I do think you can make an impact, uh, if you can work with people who were there, people who can help guide you. But, uh, eventually if the company, if the culture, the environment, doesn’t change with you, I do think that it’s worth reflecting on, you know, what excites you, where do you wanna work, what do you wanna do?

Um, but yeah, a little bit of a convoluted answer.

Drew Podwal: No, I love that. I, sorry, go on, Brad.

Brad Nelson: oh, I was just gonna say, what I heard [01:13:00] is you don’t have to call it Agile to, to do or be Agile, which, which I love.

Drew Podwal: Yeah. Yeah. I, so what, what stood out to me is, is that like, and I, I’ve said this a lot on the podcast before, is it’s those engagements that suck, right? It’s the ones that are really hard that. Like well organized that you learn the most from that will make you a better product owner, product manager’s, scrum master.

Right? Um, and uh, and like the whole time you’re gonna be wishing that you were at a company that was product led, right? A company that did get Agile and things like that. But, you know, we often forget that the opportunity that’s in front of us in those moments is that opportunity to learn how to deal with things when they’re not picture perfect and rarely are they ever picture perfect.

So, um,

Brad Nelson: Yeah. Yeah. I, I wanna highlight that last thing you said. Rarely are they picture perfect. Like we get in [01:14:00] our heads, especially as Agile Agilists, we have this like picture in our head of we’re gonna go work and like, we’re gonna live in, in, uh, what was that commercial? Like the corner of Perfect. In, in something in great.

Drew Podwal: It’s like Little Orphan Annie, right? Little. Or like the, the idea that my real parents are gonna come and they’re gonna hire me and they’re gonna be Agile. It’s gonna be an Agile company, , you know? Um,

Diego von Sohsten: That that resonates so much with me. And that’s something that I’m always telling my team, especially more junior product managers when I’m doing my coaching, take certain things with a grain of salt, especially in product management and in the product like growth world. There is a lot of content out there, but I don’t think that that represents the reality of most organizations And having someone who had those experiences kinda, you know, bring the reality, bring those conversations to the teams, makes such a huge difference.

I’ve seen people leave an organization [01:15:00] cause the way that AB tasks were being run wasn’t the way that they read about it. But you know, more often than not the person writing how you should write an ad test maybe didn’t even have that exposure. You’re talking about very theoretical content. With, uh, not a lot of applicability.

So yeah, acknowledging that the world is far from perfect and really making the most with the tools you’re given and creating the opportunity yourself, you know, that’s what I did. I feel like in every job I had to create my opportunity because it wasn’t handed over to me, and not everybody feels that way.

Maybe not everybody operates in the same way, but I think that the go-getters of the world, they can create their opportunity in.

Drew Podwal: Well, and that brings us back to the original topic, right? Which is how do you go from being a developer to a product owner or product manager, right? Is is having that mindset, it’s having the, the mindset [01:16:00] of, um, thinking outside of the box, thinking to the left and the right of, of your lane, um, being bold and brave, being charismatic, you know, so, Well, guys, we’re at the, uh, hour and 15 minute mark.

We’ve been talking for quite a while. This has been a great discussion. I definitely want to have you back to talk more about like, what it’s like being at a, a product led company. Um, you know, I wanna unpack that. I, I want to unpack it, I want to check the DNA on it, and I want to replicate that. Um, you know, but, uh, um, I think a great topic would be, you know, to unpack further, like how do you transition from sales led to product led?

Um, how do, like, I’d want to know things like. in your job right now, you mentioned that you wish you had a CEO back when you were a team workie, right? Like, well, you know, today in the [01:17:00] job where you’re at right now, where you do have that ceo, you do have that side of the organization. What’s your role now in providing the guidance and the insight that helps them to make those kinds of decisions, you know, um, in a way that protects being, uh, you know, product led company.

So, um, what do you guys have for last licks before we get off? Um, what would you like to say to the audience, Diego?

Diego von Sohsten: Yeah. Um, I think we’ve covered a lot and, uh, the time definitely flew by. Uh, what a great conversation. Uh, I would say that I think, uh, the way we were wrapping up the conversation is how I would like to, to leave it as well, uh, creating your own opportunity and yeah. Going a little bit beyond what’s obvious, what’s right in front of you.

Exercising a little bit of lateral thinking I think taught me a lot, and I don’t regret any of that. Uh, I think that, you know, there are definitely scars here and there, but they [01:18:00] all taught me something and I wouldn’t change, I wouldn’t have done anything differently. So, yeah. Um, yeah. Let’s, uh, let’s, let’s do what feels right and let’s exercise the life of thinking in our lives, because I think it’s,

Drew Podwal: Yeah, I love that. What about you, Brad? What do you got?

Brad Nelson: Uh, so it’s a pleasure meeting you, Diego. This was the, like Diego and I met right before this call, so it was a pleasure meeting you. It was definitely enjoyable for me. Uh, I think I’m gonna touch back on the whole, we don’t have to call it Agile. To, to be Agile. Uh, and, and I’ll have to listen back to, to the episode, which I always do anyway.

Um, but I feel like we’ve said Agile way less this episode, but we, we were talking about, uh, true, like business agility and, and that’s so important because agile’s almost become com commoditized. And, and it’s like its own, like you said earlier, Drew, like, what’s your product? Like, that kind of like irks me a little bit.

[01:19:00] Maybe that’s another podcast where it’s like agile’s become the product and not the solu like, and a product solves problems, but people treat it like it’s the end all be all right. I, I adopt Agile, or I install Agile and then all my problems go away. But they don’t know what their problems are. So that’s what I loved so much about this, was that we were able to talk about Agile without necessarily having to call it out every

Drew Podwal: I feel like you’re using the word Agile repeatedly to make up for the fact that we didn’t, we didn’t say it enough in the episode.

Brad Nelson: you caught me, Drew.

Drew Podwal: ha. Well, I, you know, I, I think this is great. Um, Diego, you’ve always been an inspiration, um, and I’ve always loved working with you. Right. Uh, and I’m so glad we got to carve out the time for, for such a great topic.

So thank you both. Brad. Thank you always for being my podcast partner in crime. And, uh, yeah, we’ll come back next week with another episode.

Diego von Sohsten: [01:20:00] Fantastic. Yeah. Thank you all so much. What a great conversation. Nice meeting you, Brad. And uh, yeah, hoping I’ll be back eventually, and happy to talk more about.

Drew Podwal: Cool.

Brad Nelson: Awesome. Thank you.

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