The 2nd Tommi Forsstrom Hypothesis: Effective CPOs are Executives First and Product Leaders Second

Tommi Forsstrom is the Chief Product Officer of Workstep. He is a product executive that specializes in flipping startups to scaleups—ie. navigating the scary adolescence that begins at product-market fit. He’s on a mission to pull product / engineering and design leaders out of the product development bubble to grow a new generation of Chief Product Officers.

In this episode of the Product Science Podcast, we cover how a company needs to focus their operations in order to scale up to the next level, what role executives play for an organization, how to translate product values to founders & investors, and what role trust plays in your executive team.

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Resources

Questions We Explore in This Episode

As much as we want to think that if you get the product right, everything else falls into place, it's not true. Product people really deeply need to understand the other layers of the onion: what it means to operate a product, sell it, market it. All this stuff is so critical.

What was Tommi’s journey into Product like? How did he pivot from Engineering to Product and why? What is exciting about a company that is finding its product market fit? What was it like working at Teachable? How big was Teachable when he joined? What were the engineering & product teams like at Teachable? What was it like working with Teachable’s founder Ankur Nagpal?

What is the difference between a company’s founding and its scale up? How far can a company get by being founder driven? Is it better to get the widest range of customers or to segment and focus on those most impacted by your product? What are the benefits and drawbacks of being based on founder vision alone? How do you scale up once you achieve product market fit? What self imposed obstacles need to be cleared once a company has hit the growth stage? Is product market fit everything a company needs to focus on?

What is another way to look at Tech Debt? Does a company help or harm itself in the long run when focusing on building all of its tools internally? When does it make sense to pivot towards 3rd party SaaS tools? Should companies just use SaaS tools from day 1 instead?

What do you look for when joining a new company? How can an empathy map of a company, its executives, and investors help you learn if the company is a good fit for you? To be effective in product, how much of the organization’s practices do you need to understand? What disciplines do those in product need in order to have an effective impact on an organization? Do you need an MBA in order to be effective in product? What changes for you when you move up to the executive levels?

How do you translate product concepts to a board of executives? How can you translate your customers and the customer journey into KPI’s and hard data? Is high shipping rate the same as being highly productive? How do you get other executives to value the insights that product people have?

What value does trust have in an executive team? How can you apply product principles for conflict resolution? As an executive, what do you represent first, your discipline or the organization? What is an ideal size for an executive team? How can you tell if a company has a well functioning executive team? What advice does Tommi have for those interested in reaching the next level of their career?

Quotes from this episode

“As product people, we're so well-trained to understand our customers, get deep in there and get into their brain. And we do such a bad job at it with other people and teams around us.” @forssto via Click To Tweet “As much as we want to think that if you get the product right, everything else falls into place. It's not true. Product people really deeply need to understand the other layers of the onion: what it means to operate a product, sell… Click To Tweet “Product is the hub of the wheel. And that's a servant position, everybody else is relying on you to get the hub right. But you can't if you don't understand all the spokes that connect to it.” @forssto via Click To Tweet

 

Transcription

Holly: This week, on the Product Science Podcast, I’m sharing my second conversation with Tommi Forsström. Tommi recently began as Chief Product Officer at WorkStep. He’s a product executive that specializes in flipping startups to scale-ups, i.e. navigating the scary adolescence that begins at product market fit. He’s on a mission to pull product engineering and design leaders out of the product development bubble to grow a new generation of chief product officers.

Holly: Welcome, Tommi.

Tommi: Thank you. That sounded so much fancier when you said it.

Holly: It’s fun being introduced by somebody else, right? It always makes you sound more professional.

Tommi: It really is. Man, I should charge more for my services.

Holly: So, Tommi, in case some of our listeners didn’t hear your first episode, let’s do a quick 10,000 foot view of what your career has looked like.

Tommi: Yeah. And just for the record, after this is recorded and released, I hope nobody ever listens to the first one because … it’s crazy, you’ve been doing this now for quite a few years.

Holly: Yes.

Tommi: I think we spoke four or so years ago … three?

Holly: Probably. Yeah, three or four years ago. Yeah.

Tommi: And that’s been a pretty transformational three, four years in my career. So maybe it would be fun for somebody to listen to these episodes back-to-back and be like, how is this the same person?

Holly: Right.

Tommi: So anyway, short, short, short summary of what I do. I was supposed to be a math teacher, became an engineer instead, back in the late ’90s. Did engineering and then engineering management for like 10 years. Moved to New York City in the early 2010s. Realized there’s such a thing as product management and that that’s everything that I love about what I had thought as engineering management at that point.

Tommi: Basically, the full story is I was a CTO at a small startup. And somebody asked me, as we started scaling, “Well, why don’t you hire a product manager?” I was like, “What the hell is that?” And I started Googling, found some [inaudible 00:02:12] from the West Coast. And I was like, “This is everything I love about my work. Why would I outsource this to somebody else?” And immediate career pivot mode … and this is about a decade ago … transitioned to product manager. Realized, when I got to product, that I actually care a little bit more about the environments, the cultures, the practices, the processes, the orgs, that build products more than the actual products themselves. It’s a horrible thing for a product person to say by the way, but I’m saying it anyway.

Tommi: And then once I got there, to product leadership roles, where I got to design the machines, I was like, “Wait a minute, this whole shareholder value, valuation principles, P&Ls, business leadership, executive team work, this is cool. This is super exciting.”

Tommi: And somehow, that’s now led, for the last couple of years, to me defining my role as an executive first and product leader second; or major in business, minor in product, if you will. And getting really passionate about the weird life cycle stage between early stage, the exploration, that then culminates into product market fit if you’re lucky, and the adolescence that starts from that moment, the growth stage, the scale-up stage, the whatever you want to call it. Because it’s the most unique part of a company’s life cycle.

Tommi: I just finished my tour of duty at Teachable, where I joined two and a half years ago, right at that, “Oh shit …” I don’t know if we can swear here, but I’m going to do it anyway.

Holly: Yeah, it’s fine.

Tommi: “Oh shit, we have product market fit. What now?” And then spent two and a half years scaling the company up to where we went through an acquisition and the company’s significantly larger now. And just exited because, just like at the end of Mary Poppins when Mary Poppins leaves the Bank’s family, it’s like, she leaves because she knows the Bank’s family can now continue on, on its own.

Tommi: And so I’m now taking some, hopefully, well-deserved time off, advising, mentoring, coaching; founders, companies, leaders, product managers. And hopefully increasing leverage by talking to your listeners through this medium as well.

Holly: Yeah. Awesome. Well, I’m super excited to hear as much as you can share about your journey at Teachable. So tell us from the beginning, when you joined Teachable, what was the state? Obviously they’d just found product market fit, but how big was it? How many engineers did they have? And what did the product team look like?

Tommi: Yeah. It was 15 million annual revenue, give or take. Product team was kind of nonexistent, there two product managers, two or three designers, and a very competent head of design; luckily recently hired. There was about a couple of dozen engineers, with a really good VP of engineering in place. And a total headcount of Teachable at that point was about 100, give or take. Actually, I think I was employee 101 so it was pretty much exactly 100.

Tommi: And when I left in December … not to go into too many details so I don’t lose any of my RSUs for NDA infringement … but about 60 million annual revenue, give or take. Part of Hotmart company, which is the company that acquired us, and we’re talking multiple hundreds in revenue and well into the four figures in head count. Teachable itself was about 230 in head count. And the technology team, like product management, product design, engineering, product operations, and product marketing, was about 125 FTE. So that’s the bookends of my journey there.

Holly: Oh yeah. I love joining a company at that 100 person-ish stage. I think that’s a really fun time to get involved. What was the product practice like when you joined? You mentioned there weren’t many product managers, so I’m curious what it looked like?

Tommi: I’m going to throw a couple of personal hypotheses that are semi-strongly held at this point, in that Teachable looked exactly like a company should at that point, which is it was built solely on the back of founder vision, founder instinct. Ankur Nagpal is seriously one of the fastest moving, smartest people that I’ve worked with.

Tommi: And Teachable, at that point, had really been built just on the back of Ankur building a team to hustle and grind behind his vision. And that’s what a company coming into product market that really usually should look like. It’s just a lot of spaghetti on the wall, even more spaghetti on the floor that didn’t stick, and pretty much a company just solely harnessed to execute that founder vision, and also a founder that, up until then, had been in every decision in every nook and cranny. Because, to be honest, that is the most efficient way to build into product market fit.

Tommi: But the problem is obviously that that does not scale, it doesn’t function when you get into the exploitation phase, where you need to take a product market fit and ride it to its maximum. And so Teachable was exactly there, it was huge product footprint, because, again, when you hustle and grind you build and ship a lot of things that honestly yield the value, but an ultra strong core product market fit, really good customer base, really talented people, and strong financials and all that good stuff.

Tommi: So, to me, a dream scenario, because its brilliant momentum, brilliant foundation had been set, but plenty of work to do to be able to get to the next stage. “What got us here, won’t get us there,” is usually the mantra of that stage. That’s what I look for in a dream scenario, is a company having done the first stage ridiculously well, but also all the drawbacks of having done that first leg of the journey really well.

Holly: So go into a little more detail for us, what are the drawbacks of having done that first leg really well?

Tommi: Well, usually, hustle, grind and instinct have its drawbacks, in that you’ve usually way too much product, there’s a lot of stuff there. Not all of it is great. Not all of it should have been built or kept alive. You usually also have a complete lack of focus in who you’re targeting.

Tommi: So, for example, Teachable, when I joined … and I do want to make sure that I say this with all the admiration to everybody that was there … but it had peanut buttered itself across a number of different customer types and was trying to even expand more. Because usually, at the early stage, it’s all about this frantic expansion. Every idea is valuable. Every new deal is valuable. Which is great, until you get to the growth stage, early growth stage, where that becomes toxic.

Tommi: And so it was just a lot of stuff like that, was essentially coaching the company to be confident. Even though what got us here, which was an utter lack of focus and just doing everything that you can, from here on out that is actually not great. You can grow with a pared-down focus, because once you find product market fit … and also coaching the company, product market fit is not binary, it’s not your whole product with all of the market … the first thing you need to do is excavating what part of your product creates the most value and what part of your customer base is reacting to it the strongest.

Tommi: So that, to me, was the biggest challenge. I say this to a lot of product leaders: product leadership, at this level, is a lot more change agency and psychology than executing a playbook or whatever. It’s coaching individual leaders, coaching groups of people, to rewire their thinking. And that, to me, is the first step always, is showing a group of people that the way they’ve scaled up to this point is going to start hitting diminishing returns, and doing less but better is actually the right way from here on out. So that was definitely the first six months, for sure.

Holly: So how do you show people that? I know, “What got you here, won’t get you there,” is a hard lesson for a lot of people to learn. So how do you help them realize it?

Tommi: Geez Louise, if I had a silver bullet to that … It’s hard. And I think there’s a cookie-cutter answer. And one thing I usually coach people to do nowadays, especially when joining slightly later stage startups or earlier stage scale-ups, it’s: the first thing you got to do is you essentially got to empathy map the founder, the CFO, the board, and you got to get into their mind, like what do they care about out? Because even though, with founders, there’s certain common elements, but they’re still a relatively diverse group of people in how they think about things and what they care about and what they’re worried about.

Tommi: I think I didn’t do this well enough. I don’t think I spent enough time on understanding what motivated and what drove Ankur specifically. It starts from understanding the psychology of where the people you need to influence are, because all change begins with mapping out where you are. It’s one thing to figure out where they need to get to, that’s the easy part, but how do you get them to budge from where they are? And I think that’s one of my retro items, is how do I double down on first understanding the mindset, the mental environment that they are operate in, at that point?

Holly: Yeah. I love that. That’s something I push my clients to do too, the empathy map on stakeholders or founders. It’s really helpful to make people look at all the different impacts that are on those people and help them understand if there’s a behavior that they find really frustrating. Maybe they can understand where it’s coming from better, and then make a path to get from there to wherever they want to be.

Tommi: Yeah. I mean, honestly, this is one of those things that I’ve spent so many brain cycles on. Because I spend a lot of time with different product leaders and we’re a pretty frustrated bunch, you know what I mean?

Holly: Yeah.

Tommi: We’re always ground down to a nub because people don’t let us do the best work that we know, within our hearts, that we could do. And I think one of the most transformational things that somebody’s given me as piece of advice was that … and again, you allowed me to swear, so I’m just going to ride it frivolously … but the advice was, “If you’re always surrounded by assholes, maybe you are the asshole.”

Tommi: And that mantra has come in handy so many times. And usually the way I look at it is: whenever I find myself in a conflict … and I can be a little conflict-oriented sometimes because I like a good debate. I’m an engineer by background, I love debating things. But whenever I find myself walking away from a conflict, just steaming inside, I always try to ask myself, “Was there something that I ignored about what the other person, the other party, the other team, the other whatever, was trying to get across? Or was I just trying to bulldoze my own view?”

Tommi: And it’s so crazy because, as product people, we’re so well-trained to understand our customers, get deep in there and get into their brain, look at their activities. And we do such a bad job at it with other people and other teams and other important entities around us.

Holly: Absolutely. And it’s so important to be effective in the workplace, to be able to do that with all the people around us too.

Holly: Okay. So when you got there, it had these challenges. And in the first six months a lot of it was helping them realize what they needed to focus. What were some of the next challenges that you saw?

Tommi: I actually realized I should have tossed a couple of tactics in the there that might be valuable for a few of your listeners, especially my time at Insight really helped me. So, before Teachable, I was working for a major venture capital fund, Insight Partners. And one of the things we often did for their portfolio was essentially just segmentation exercises. It’s so common for companies in the growth stage to try and serve way too many different types of customers. And it’s shocking how much value you can get from just slicing and dicing your customer base.

Tommi: It depends on your product and your market and your whatever, with what type of segmentation makes sense. Is it geo? Is it demographic? Is it whatever? But once you find the right segmentation, and you can clearly show through just raw KPIs and a little bit of qualitative research on top of that: who is your product really providing product market fit for? It can make a meaningful difference. Because when you’ve got those LTV, NPS, ARPU, whatever retention numbers, cleanly sheeted, and segmented, it can make a meaningful difference in how well you can focus moving forward. Because then you can use those numbers to back into: what does focus look like from a business outcomes perspective and from a growth trajectory perspective?

Tommi: So if you can nail that down and if you give a company that jolt of direction … because that’s the other thing that’s often endemic at these companies, they’re very shortsighted. You usually get to product market fit with just maniacal focus on the current quarter. Which again, it’s good, you’ve been conditioned to chase the hell hounds of runway depletion off your tail for a couple of years.

Tommi: So, usually, I find it’s a mistake to get overly ambitious with vision and five year strategy at that point because the company’s probably not ready to ingest that, it’s not ready to operate on that spectrum yet. What you need to do is at least get momentum, a direction. Something that’s like, “Okay, if we run in this direction, good things will happen. And then we’ll build the story out after that.” Because then, once you’ve got that momentum, you can focus on the next problem, which is basically, “Okay, can this machine even run? Where can we get this to go?” And that’s when the org building; hiring, firing, establishing culture, practices, processes, all that stuff starts kicking in.

Tommi: And usually there’s a bunch of … I hate calling anything tech debt because I think tech debt is a lazy label to gloss over just bad strategic decisions. But it’s quite common to have not invented here syndrome, because in the early stage the scarcity is on money. You can’t afford SaaS tools, but your engineers would happily burn a couple of weekend hours building your analytics tool. There’s usually a bunch of stuff you’ve built on your own because it was cheaper to build the simple version than to send money to some fancy SaaS company. But that starts eating at you really fast.

Tommi: So one of those six month things is that you have to start identifying and eliminating any superfluous footprint. Get rid of anything that should just be a third-party SaaS tool and just replace it with vendors. And the same thing with your product. You need to start hunting down opportunities to pare down the footprint, both from a technological footprint side … meaning, is there something in this architecture that could just be replaced by different types of platforms to reduce the cognitive overload of your team, both product engineering and design? Every little thing that people are going to be maintaining and shepherding is such a cognitive drain at scale. So eliminating any reason that’s going to start holding things down.

Tommi: Because another endemic problem in this stage is that the CEO is already having a nervous breakdown of, “We used to ship 20 things a week and now we haven’t shipped anything in 20 weeks. What the hell?” And the, “What the hell,” is really just the things you’ve been shipping, the 20 things a week you’ve been shipping, are now this mountain you’re handcuffed to. And your footprints out of control. Maybe you’ve got 10 times the engineers you had, but nine out of 10 of those engineers are just maintaining and doing service requests and dealing with a bad architecture.

Tommi: And then always, on the executive team level, it’s just like tech debt, tech debt, tech debt. Which, at the end of the day, it’s like, “Sure, there’s probably a couple of things that are just … you cut a few corners.” But at the end of the day it was like, “Well, we shift too much product or we made bad decisions on not using a vendor and now we’re managing up our marketing side on our own CMS,” or something like that.

Holly: Interesting. Are you able to share any specifics of an area that you pared-down? You realized, “We had shipped too much here and we need to make this simpler”?

Tommi: Yeah. I mean this is definitely not something where it’s particularly secret, but subscription management was a good example. Every SaaS company, if you’re selling your wares as subscriptions, you’re going to have to start charging your customers some way. And all the good tools to do that, like the Recurlys and Chargebees, and especially the higher end like Zuoras, they cost an arm and a leg. And especially because they dip into your cash flow because they charge you as a percentage of your MRR, I don’t think any early stage companies should necessarily go with them. Because it’s not that hard to just whip up a checkout and have Stripe in the background and be over and done with it.

Tommi: The problem is that the complexities of doing subscriptions at scale are going to start killing you. And if you have tens of thousands of customers it’s a major drain, because subscriptions are really hard, they’re really complex. I mean, I did somewhat forcefully run through, “We need to get rid of all this homegrown subscription, like homegrown checkouts and homegrown …” We had a surprisingly big percentage of our technology labor just bound to managing our ability to sell, essentially, a simple SaaS product to our customers. And at the same time, because what you’ve done on your own is usually probably the simplest possible way, we were completely handicapped in exploring pricing and packaging, exploring custom deals, and all that stuff, because none of our own stuff supported it.

Tommi: So we did eliminate all of that and move over to Chargebee. And that’s just one of the many examples of where it’s still so common for me to see things like marketing site CMSs, or analytics tools, or even the whole data stack, it’s just homegrown stuff. And there’s an abundance of mature vendors out there who, for less than half of a single developer’s annual salary, would be happy to provide the infrastructure.

Holly: Excellent. That’s a really good example. Thank you for sharing that.

Holly: So once you get through paring down some things, how long does that phase of the journey tend to last?

Tommi: Honestly, that’s a journey where that doesn’t really ever end. It’s more like the part of the journey that is changing the mindset. Because, again, the mindsets are usually more embedded into the culture than the actual tools. It’s just teaching the org that you don’t have to command and control everything. You don’t have to own every piece of code. Not every one of the use cases you’ve invented for yourself that forced you to do a custom thing are valid. And teaching the company to yearn for that freedom, that we’re only investing our really expensive efforts into what’s going to strategically differentiate us. Because it’s usually, once you build everything yourself you infatuate yourself with your homegrown things. And there’s a little bit of a Stockholm syndrome there.

Tommi: So it takes time to unwind all the stuff that a company builds in their early stage. But the mindset shift has to happen, where the company starts hating superfluous resource drains. You know what I mean? And that’s the thing that needs to happen pretty fast, is you just have to be able to get that point across, is that if you extrapolate this to even bigger scale it’s going to be an even bigger burden and an even more expensive burden.

Holly: Absolutely. So tell me more about some of the other elements of being a product leader at a scale-up, after obviously changing mindsets so much? But what are some of the other key themes that you like to talk about?

Tommi: I mean, honestly, especially at my time at Insight where I got this beautiful cross-section of just … I mean their portfolio is really impressive and I got to work with some really cool companies and some really cool leaders. And I got a good cross-section of leaders that were struggling and leaders that, despite their excellence, were hitting brick walls. And got to do a good diagnostic of: what is the common elements?

Tommi: And I think one of the things our craft, our industry, really needs to look in the mirror with is: we’re a little too eager to stay within our own bubble, within the safe space of the product world. We have all these brilliant thought leaders, like the Melissa Perris and the Marty Cagans and the John Cutlers, who I love and respect to no end. But we sometimes forget that it’s almost like a reverse Superman thing, where, when you leave Krypton, you’re powerless.

Tommi: If you go waving a Marty Cagan book into the executive team, you’re going to get slapped in the face and thrown right out. Because as brilliant as Marty is, a lot of the stuff that we hold as self-evident, and as almost axiomatic, is completely powerless when you’re in front of a CFO or a CRO or even a CEO or a founder. I think what we really need to challenge ourselves, especially people hitting VP and CPO seats … I mean, definitely CPO, but even VP seats … you got to start rewiring your brain to be business first, product second.

Tommi: Also, what I mean by the whole building a new generation of product executives, I really think what I’m saying applies to all product leaders not just product management leaders, but engineering leaders, design leaders, where our collective ability to, number one, come together and understand that product is not product management, product is engineering design and product, and everything that needs to come together to build the thing the company makes money out of.

Tommi: And, number two, we need to learn how to think business, think shareholder value, think fundraising, think P&L. Because all the things that we instinctively talk about when somebody asked us to, “Hey, can you do five minutes at the board meeting? Or can you present to the executives?” All the things that we instinctively talk about is noise to them. And the unfortunate thing, as much as we want it to be like, “We meet you halfway, you come halfway as well,” they’re not going to. We got to go all the way. We need to talk in their language. We need to understand the problems and the opportunities that they are thinking of and how they want to communicate, even if we do that without compromising at all on the things that we hold important to our craft.

Holly: So how do we do that, without compromising on those things?

Tommi: We learn. It’s basically like you’re dropped into a foreign country without knowledge of the language. You got to learn the language. You’ve got to put the time in. I mean, I’m not telling anybody to get an MBA, that’s overkill. But learn the language of business. There is a very clear glass ceiling in your career, as a product leader, as a product executive. Basically, you need to be able to credibly be a CEO, is the level you need to aspire for. You should be able to start your own company. You should be able to run a company to really be an effective CPO.

Holly: Yeah. So some of the things that you need to learn to speak their language is a lot about speaking about the finance and the dollars?

Tommi: Yep. Yep. I mean, especially in growth stage companies and especially in venture capital backed growth stage companies, if you don’t understand how valuations come about; what is important, what is not important for revenue multiples and all that good stuff, and also how venture capital works, how venture capital deals work, what the logic is, what’s investible, what’s not investible, what’s the difference between seed rounds, A rounds, B rounds, whatever, you have to be fluent in those. You have to be fluent in understanding how the game works, what people care about.

Tommi: Also, you need to be able to talk in terms of a CFO. You got to be able to take a P&L and just read every line item and understand what goes into them, what doesn’t. What’s COGS? What’s OPEX? What’s CAPEX? What’s the difference? All those kinds of things. Talk about things like CAC and LTV, and be fluent and credible.

Holly: Mm-hmm (affirmative). Absolutely. Did that come as a surprise to you?

Tommi: I’m a pretty candid person and I admit my flaws, but it took me pretty much 15 years to get to that realization, both in terms of, number one, it’s critical … because I had risen through the ranks of product development so I thought it’s all about the scrums and the sprints and the experiments and the empathy maps. I thought, “That’s it. If you get those right, you’re good.” And it took me a lot of doors getting slammed in my face to realize maybe there’s something wrong with my approach, or the language I use, or whatever. Yeah, it definitely surprised me that that was the case.

Tommi: And then the other shocker was that it was surprisingly easy to learn. This stuff, the language of finance, there’s this intentional obfuscation that makes it scarier. It takes you a couple of years to even freaking remember what order the letters in EBITDA are, let alone what they stand for. And if you remember the words, what do those words actually mean? But it’s a pretty simple concept.

Tommi: And so there’s this weird layer of obfuscation to incredibly simple concepts. And the same thing with P&Ls, they’re incredibly threatening because they’re kind of complex. But once you start digging in through the layers and you read a couple of really good S-1s, public filing documents that are well-crafted, and honestly it’s super simple at the end of the day. I don’t know if it’s meant to keep laymen out of their world, but I think product people should be bolder about just jumping into that seat and learning.

Holly: Yeah, I think that’s really valuable, especially when you’re in venture funded startups. Understanding that whole world, not just of how finance works, but how the financing works, that’s really valuable.

Holly: I know for myself, it’s been a thing where it can be really frustrating. At the beginning of the time, when you start speaking to funders and you realize that they want to talk a different language from product people, and you’re like, “But don’t you care about all of these things? About who our user is and how much they love our product?” And they’re like, “Well, show me the numbers.”

Tommi: Yeah. And the funny thing is, of course they should care. What we do, product-centric companies are the future of the world. And some of the biggest companies out there, justifiably, are very product-centric, very product-minded. It’s just acknowledging the unfortunate fact that most businesses are still run and operated by people who got their training in a late industrial stage era, where most of it was just managing complex networks of highly predictable atoms, essentially.

Tommi: Building a product, which is this glorious mess of a puzzle building, versus setting up a new lipstick line, for example, which is like, “Okay, we need this many more trucks, this many more factories, or this many more production lines. And here’s the distribution.” You know every single little thing that goes into it, it’s just really complex.

Tommi: But most companies are still run by people with a very deterministic view into business. You can either think of that as some sort of inherently bad thing in the world or you can think of it as just like a reality that you need to navigate. And I’ve at least found myself much happier when I got from the, “Everybody’s wrong, I’m right,” mindset, to, “Let’s see how I can make this work. Let’s see how I can get good outcomes from a suboptimal starting point.”

Holly: So what are some of the other principles or lessons you’ve learned along the way?

Tommi: I mean, I think product people are usually pretty curious by nature. I mean, that’s why we get into product, is that we’ve tried every freaking thing before and no hat seemed to fit. And then we get into this hodgepodge career, which is a refuge of the indecisive. But I think continuing to leverage that curiosity is something that I need to remind myself at all times. Because especially once you get to executive roles, where it’s more about horizontal excellence, how well can you understand sales and operations and marketing? Rather than: how good are you at your own domain, your own function?

Tommi: I think we should be increasingly curious about immersing ourselves with other functions, other departments, other domains. Even though I want every product person to keep listening to Holly’s podcast, I think you should also listen to marketing podcasts or … I don’t know if operations podcast exists, but I’m sure books do. But immersing yourself into: what are the other ultra critical aspects of running a successful business? Because just having a good product, as much as we want to think that: get the product right, everything else falls into place. It’s not true. And as product people, we really deeply need to understand the other layers of the onion: what it means to operate a product. What it means to sell it. What it means to market it. All this stuff is so critical.

Tommi: And it can be overwhelming because it feels like we need to become these weird renaissance people that just know everything about everything. But you need to have a fairly strong cursory understanding of how a really good modern marketing org works, how a really good sales ops pipeline works. Because, at the end of the day, especially in a software product company, we are the hub of the wheel. And that’s a servant position, everybody else is relying on you to get the hub right. But you can’t if you don’t understand all the spokes that connect to it.

Holly: Mm-hmm (affirmative). So one of the things that I’m thinking about from what you said is: I spoke to somebody once that told me that once he got into an executive position … he actually started trading places with someone else in the executive organization once a month, every year. And it really hit home on this message that once you’re an executive, you’re an executive first and the discipline comes in later.

Holly: I’m curious if you can elaborate on … does that sound like a good idea to you, trading places? What do you think?

Tommi: It sounds scary as heck. But it sounds like a brilliant … I mean it’s a very bold move and I can think of a million reasons why it would be a horrible idea. But, in principle, it sounds amazing. Because yeah, that’s exactly the level of empathy and trust, because basically it’s a huge leap of faith to let somebody else do your job and vice versa.

Tommi: But, to me, that’s a really strong indicator of an executive team that is really a team. Because I have a fairly strongly held hypothesis that meaningful percent of dysfunction that we see is either bad strategy or a badly functioning executive team. Which, obviously, that can be a contributor to the first one. But executive teams that don’t know how to function as a team, and especially as a first team … so, again, being an executive first and functional leader second … it just permeates the ranks. It cascades through.

Tommi: I mean, one of my favorite books of all time, at least in the business side, is Five Dysfunctions of a Team. And I think that that fable just captures that landslide moment when a non-functional executive team learns to be each other’s first team really beautifully. Because so many companies, especially growth stage companies because they usually can’t afford to hire seasoned executives. So usually growth stage companies hire people who are product executive is basically just a functional leader, the engineering executives is just a functional leader. Same thing with the salesperson, the marketing person, the finance person, is they are people who identify with their craft first and foremost, and the executive team job is just like a “seat” around the table.

Tommi: Because it takes a couple of rounds around the block to understand that executive jobs are different than functional leadership jobs. But when your entire executive team is basically just functional leaders it turns into almost like the UN, where people just come in, spend the hour a week talking in a cross-functional setting, only to go back to their functional silos after it and spend the other hours of the week in their functional bubbles.

Tommi: And so I think there’s some critical things I now look for nowadays in functional companies. And one of them is the ability to keep the executive team small. I mean, I like magic numbers. I’d prefer executive teams of at most five people. Because it’s such a leading indicator to: can the company strategize and execute cross-functionally? And not just product, but the whole company strategy. Can it be cohesive and uniform? It’s incredibly driven by: can the executive team, just those few individuals, truly come together, without functional bias, without infighting, like, “Oh. Sales this, marketing that, product whatever,” and really the focus and emphasis on that.

Tommi: Before, it’s like: how can we get the best possible product? Or the best possible marketing org? Those are important. But if the executive team doesn’t work well, none of it will be of any benefit and it’ll just lead to a lot of infighting and friction.

Holly: So how can a mid-career products person, thinking about either their own company or joining a new company, how can they tell from the outside if there’s a well-functioning executive team at the company?

Tommi: Pretty, pretty hard. But in the interview process you’re almost always going to talk to either somebody from your function that’s in or near the executive team. You have to start learning to ask somewhat poignant questions. Nobody’s going to tell you, “Oh yeah, our executive team hates each other and they can’t agree on anything,” and whatever. But you can always start asking things like: what’s driving the company’s success? And if you get super myopic answers, like if the product leader is just answering, “Oh, product innovation, blah, blah, blah.” No, it’s not. There’s no company ever where it’s that simple, where just product innovation is paving the way. There’s always marketing excellence or sales excellence and a well-running operations machine.

Tommi: And if you are high enough, like director level or one level removed from the executive team, you might be able to meet executives of other functions. Trying to ask questions that’ll showcase the trust between functions or departments, and the trust between executives, will tell you a whole lot. And it’s easy to mask or fake trust in explicit questions like, “What do you think about the other execs?” Everybody’s going to say, “Oh, they’re wonderful professionals. Super great. I love working with them.” But when you start asking indirect questions about department to department relationships you’re going to start seeing the cracks, if they exist.

Holly: Yeah, that makes sense. I love the idea that you have to be interviewing them as much as they’re interviewing you when you’re looking at a new job. And I think the higher up you go, the more true that is.

Tommi: Absolutely. I mean, a lot of people say, “Oh, you should be doing your due diligence like an investor.” I think you should be doing your due diligence 10x more than an investor. Because if you are an investor, you can write as many checks as you’ve got liquidity. When you’re an executive, you’ve got one check to write. Unless you happen to be Jack and your co-CEOing Twitter and Square, you don’t have time for multiple companies so you got to do your due diligence to a much more rigorous level than an investor would.

Tommi: The problem is, most companies, they’ll weirdly enough run their hiring processes as if they have all the power. You know what I mean? It’s so weird. We are going through an unprecedented era of us, as employees, having all the power. Every product manager listening to this, I’m not telling you to quit your jobs or get a new job, but there’s 20 different companies that would hire you by the end of the week and would throw crazy money at you. We have all the power right now. I’m going to regret saying this once I’m on the hiring end again, by the way. But we have all the power, but all the companies are still running recruitment processes as if they’re interviewing somebody in a one directional way, when they should understand that if it’s ever been at two-way street, right now it is.

Holly: Yeah. So what advice would you give to the aspiring products leader who’s trying to find the right next step for their career.

Tommi: Well, who knows how long this current environment of opportunity lasts? So if you’ve got a good thing going, keep riding it. But if you’ve ever thought of changing jobs, this is a really good time to do so. But beyond that, from just skills wise, as early as you can, branch out from just immersing yourself in the product management lore. Read the Cagans, read the Perris, read everything Cutler puts out there. Listen to every podcast Holly puts out there. But, as early as you can, start dialing out from just the product bubble, read the S-1s, do a little bit of investing on your own.

Tommi: Nothing teaches you better than having some skin in the game just to start getting interested in how the money around the products that we build work. Because that’s going to be the superpower that’ll propel you to the next stage. Because you get to VP level just by the razzle-dazzle of impressing other product people. But you will never retain an executive job without being able to razzle-dazzle a CEO. And I can guarantee you, quoting stuff from this interview or a product thought leader, it won’t get you there.

Holly: Mm-hmm (affirmative). That’s good advice.

Holly: So if people want to follow you, where should they go?

Tommi: I’m pretty active on all the socials, except I guess I’m not young enough for TikTok. Maybe I’ll start my product TikTok channel very soon. But, anyway, Twitter, @forssto is a good place. My website, forssto.com, has a pretty good list of things where I’m active.

Tommi: I’m horribly inactive with my newsletter and my blog, but every now and then there’s a burst of creativity and I start putting stuff out. So I’m the worst creator out there. I do everything that people tell you not to do, which is I have these short bursts of massive output followed by long periods of total inactivity. I’ve made my peace with it. I have no intention of being thought leader, so I’ll just share when I feel like sharing. So if you’re ready for horribly unthrottled output, follow me on all the socials.

Holly: Awesome. Thanks so much, Tommi. It’s been a pleasure catching up.

Tommi: It’s been wonderful. Let’s do this again in three to four years.

Holly: Yes!