Product Comms Series #12 | John from Toast

Jack Lancaster | Co-founder & CPO
February 27, 2024

Having John Cutler on the Product Comms Series was so much fun! This episode is full of gold.

John is a Product Leader at heart and shares his wisdom from experiences gained at, Zendesk, Amplitude and currently at Toast. We talk about communicating strategic frameworks and the power of simplicity.

I am certain you will enjoy this one!

Key Learnings

✅ Strategic Communication Must Guide Decisions: It's crucial that strategic frameworks communicated by leadership are not just memorable, but actively guide everyday decision-making within the organization.

✅ Avoid "Decision Drift": Ensure that discussions lead to concrete decisions that are remembered and acted upon, preventing the need to rehash the same conversations.

✅ Embrace "Powerful Simplicity": Communicate complex strategies in a simple yet powerful manner that encourages deep understanding and engagement from the team.

✅ Test and Iterate Communication: Like A/B testing a landing page, it's important to test strategic communications within the organization to ensure they resonate and drive action.

✅ Prioritize and Focus: While broad visions like "build a bank the world loves to use" can be empowering, they must be accompanied by focused priorities to prevent spreading efforts too thinly across too many objectives.


John Cutler (00:00)

Sure. John, background in product management and UX, and before that, some business analyst roles, and then a prior life as a musician. Probably the last seven years, mostly been in eight, have been in B2B SaaS companies. So that's kind of, I guess, where I've inhabited. Not a lot of B2C recently, although I did that in the past. And then I write a lot. I write a newsletter every week, and like sharing frameworks and things like that. So...

Yeah, that's my passion and I live in Santa Barbara with my kid and partner.

Jack (00:34)

Cool. Thanks. Obviously, we're here to talk about kind of product communication. So communication is obviously a fabric of running through everything we're doing. And, you know, we're all in cross-functional teams and those teams are in departments and in organizations. So we're obviously communicating every day and there's a lot of things that can go wrong with that. And I'm sure you've got a lot of interesting experiences around where it hasn't quite worked. If you'd like to dive into a couple of those, that would be super interesting, I think, to share.

John Cutler (01:05)

Sure, I can think of a couple examples ranging from the very simple maybe person to person and then maybe person to organization too because that's interesting. I think what comes to mind is that often around strategy.

There's strategy development and then strategy deployment. And so what you often see in a company is maybe there's a lot of kind of back room strategizing and a lot of conversations and that gets deployed. So, you know, one particular experience that stands out for me is, you know, being an employee in a company and looking at the sort of deck or the presentation during a kickoff or in all hands and seeing, you know, these three or five strategic pillars.

And it's very sticky, it sits in your mind, everyone's nodding their head. You know, at least initially they're nodding their head. It's sort of all inclusive too. You know, you scratch your head and you think, wow, I can fit almost anything I can do into those things. And then ultimately, when it comes down to making decisions, no one ever looks at it again. Or that was my experience, right? So I think that, you know, that's one facet of communication is that,

You know, often we try to crystallize things into very memorable models or simple models that people can, the organization can understand. And that does a job as a leader to communicate something very concisely. But it is communication and you have to ask yourself why you're doing it. So when people, you know, it's there sticks in your head.

But if it doesn't guide decisions, that was my experience in that case, right? It didn't really, no one, it just became this artifact that no one ever looked at again. Six months later, people don't remember it at all, but it was certainly like a highlight of an all hands. So that's one example I can think of communication. Going right down to the sort of micro level or local level, I think that what a lot of us experience, what I've experienced certainly on Teams are, what I would call this sort of decision drift problem, where you invest tons of time to talk over something. And in my particular experience, one example I'm remembering is, I mean, geez, there were hours and hours and hours of meetings. And we're all talking, and we're all creating meaning in that moment. But somehow the minute that we walk out of the room, it just drifts away.

And one week later, we're having those same conversations again to do it. And I think that in retrospect, I think one of the things that causes that is, you know, a lot of those conversations, you're met with a complex problem, and what you do is you try to make a Tetris trade-off game of it. You know, you sort of bang your head against it as a team, and I can remember designers in the room and engineers in the room, and we've got this complex problem, and you try and desperately to thread the needle across the problem, you know, if we just did this, if we could just, you know, 30% of an engineer, 30% over there, and what if this re-architecture works, and maybe the design system can do this, and maybe, you know, you're banging your head against it, and you're desperately trying to do a good job, but ultimately, the trade-off is untenable. And that's what I tend to think about that is, you can feel it in communication when someone creates a wedge in the problem that cracks open the problem and somehow there's a sense of relief. You know, someone comes in and says, you know what? I don't care about that customer segment right now.

Or, you know what? It's gonna be okay if this is crappy for now or something like that. And so I can remember in that situation, the trap is believing if we just bang our head against it enough, we can find that special trade off to go through it. And the thing, the wedge that opened it up is typically some kind of decision or a new perspective or someone saying, you know what, we're just gonna release it in a week and see what happens. Or conversely, I want us to get this right and I'm willing to put these things to the side to do it. So I think that's another experience that comes to mind in communication setting. I'll probably think of the third one I can think of is just Yeah

Jack (05:08)

Maybe, sorry, I'm just gonna jump in because I think it's interesting to kind of double click on a couple of those. So, I mean, maybe the first one, if we just rewind back to that for a second, becoming this communication from typically leadership around strategy and they've given this broad vision, this deck that goes and sits in a draw at some point.

If you're doing that, if you're the leader of the organization or, you know, you're the product leader, you're communicating that to people. How do you, A, make that something that people look at again? Um, because I think that that's important. And B, how do you make that something that people can make decisions against? Because you of course don't want it to be super prescriptive, right? You want to, that there's this whole idea of giving freedom. The team should choose how to solve the problem, but if you give them a blank page, everyone's going to go off in different directions as well.

John Cutler (06:04)

Well, so I think that one interesting concept there is if, sometimes I think in two by twos, and you think about that on one axis, it's powerful and not so powerful. And the other one is highly prescriptive and highly general and open-ended. I think what people underestimate is it's possible to give open-ended feedback that's also very, very powerful.

And I call it sort of powerful simplicity or graceful simplicity. And so what you get a lot is that a lot of these like pillared frameworks and things like that, they're not very graceful and they're open-ended. So that's where they fit in the thing. Now if you're very prescriptive and you tell a team do this, that's not very powerful, but it is very prescriptive. It just tells them exactly what to do.

So I think the trick is just like making anything simple and useful. It's easy to make something simple and not useful. You just take everything away and then there it's simple Is that it just takes work in crafting that kind of language in such a way to do that? and the example I always give was given to me by a friend who worked at Netflix and You know what he said that they circulated there's you know, we were gonna be HBO before HBO could be Netflix and On the surface has a very simple statement. It's like 12 words or something eight words.

But it actually, if you unravel it, there's so much depth in that particular statement. So it's a powerful simplicity. And I think that that's what people get confused with communicating these things on a comp They think, I gotta make this simple because, for some reason, most people just are gonna process the basics or something like that. And yes, some people will, but you've also got a lot of talented problem solvers who are gonna peel it away at different levels.

You know, so it just takes practice, I think. And you also have to usability test it. You know, what happens, I think, a lot is that, you know, you get leadership teams or whoever, and they kind of, it just falls to someone's responsibility at the end of the time to make that slide. And none of them think it matters for them. They believe it's somewhere this kind of like performative slide that just needs to be there, but none of them are thinking about it. So in fact, they just, they just delegate it to someone else to do those slides because they don't really care. And so that's where the magic happens is like, what happens if they use ability tested against each other and say, is that powerful simplicity?

Is that going to, is that going to encourage new ideas versus just block and to think so very actionably though, that could mean you just test out these statements against you find a reasonably passionate problem solver in your company and you test it out with them and you say, you know, what, what does this put on the table? And what does this take off the table? And how do you feel about that? And if you see their brain turning and maybe they don't get the first answer right, but they get the second and third answer right. As they start to wrap their head around it, you know, you have something powerful. If all they do is they just kind of nod their head and said, sure boss, that sounds good. It just means that they're just taking what you've said and putting it to the side because they just don't feel it's helpful and they already have their plan in their mind and they're just like, yeah, see you later.

So I don't know if that helps, but that's my sort of take on it.

Jack (09:18)

Yeah, that's really interesting. I think two, two points that reminded me of first is almost like it's, it's almost like you're AB testing a landing page, like the hero section, right? And, you know, you're like, what's the conversion who's going to actually click through here, or are you just going to look at it and bounce because you're confused or, you know, maybe you'll read down and then you'll, you'll turn. And the second thing is that I thought about was, uh, at N26, I remember our, our strategy towards the end of my time there. So this was 2019.

The kind of strategic goal of the company was build a bank the world loves to use. And what was pretty interesting about that, like, I think it was empowering. We were like, okay, it's the world. They love it. So there's two components there that are definitely persuasive. I think what was challenging about it was that it also meant kind of a lot of things were important at the same time. And this was...

This was where it went the level down where it was like, all right, we've got 15 priorities and they're all competing. And, you know, when you're trying to add, uh, sub accounts and you're trying to launch in Brazil and the UK and the U S at the top, at the same time, that creates an axis of complexity, which is, you know, infinitely

John Cutler (10:33)

You're like, you're competing against New Bank, Monzo, and any bank in the United States simultaneously. It's like, no, no small problem. This is going to be easy. This will be great.

Jack (10:36)


Exactly, and adding your own functionality as you're going. So it was like kind of, you know, what do they say, like changing the, changing the wheels on a car as it's in motion.

John Cutler (10:53)

Well, I mean, one thing to think about there too, I've been thinking a lot about this. In an organization that doesn't have a lot of dependencies, I think there's actually, this is gonna sound really weird, but I think there's actually a place for these kind of just throw, this can sound bad, just like throw away statements. Because ultimately it's the leaders of the different teams that are gonna like craft this thing. I think the problem though happens when there's a lot of dependencies between the groups.

So I think that a lot of corporate communication advice sort of is leftover advice from companies that were either very functionally divided. Like it doesn't matter. I mean, marketing is gonna set their goal. That becomes one of the goals. Sales is gonna set their goal. That becomes one of the goal. Products can set their goals, becomes one of those goal. And therefore these high level decks are much more performative than meaningful at all. They're just like a checkbox that people do. I think the challenge is that when you have either a lot of dependencies between the groups and they need to act together. You need layers of meaning below those high level statements for it to feel actionable, even for your most passionate problem solvers.

Like you have to put your most passionate problem solver against that statement and they're like, oh, okay, is this a three year strategy and eight year strategy? Do we really need to architect and make a platform for all the world? All the world in eight years, all the year in 15, all the world in two years, like, what are we not gonna do because of this statement? Like, that's what your most passionate problem solver is gonna do. And so you have to think about that. Like, I think it's just an interesting balancing act.

Jack (12:34)

Yeah, absolutely. And I think you touched on something interesting there, which is what you're not going to do, right? Like, I think that there are inherent trade-offs in there and we were trying to do too many things. And I mean, this is something I think like plagues me in every product team I've been in is like, now we're going to be really focused and we're only going to do the one thing. And then the one thing becomes like, you know, 1.5 things and becomes two things and three things.

And, and it's just this complete illusion of progress with parallelization where you think that you can do those things. And, you know, even in a very small team, you ignore the interdependencies between those kind of vertically, and you really ignore also just the context switching of people, right? Like, so, you know, you're not going to be able to just work in a silo, five teams working on their each thing. They're going to be interdependencies.

John Cutler (13:12)


And even if that dependency is leadership, even if that dependency is the budget, you know, I mean, ultimately they're all chasing the same budget to get these things. And I think it actually, one thing I've noticed is no one wants to admit that they're highly dependent on other parts of the org. So realistically, they're kind of like, I think we're pretty independent, you know, just give me our budget, we'll take care of it. Most of the dependency problems get pushed down to the front lines and those are the people who need to deal with it anyway.

So it's like, you get this organizational fiction about it. And I think this also, you know, relates to this concept of communication where in an ideal world, teams would push back in an ideal world, people wouldn't take on more than they could realistically in a lot of companies you have talk about communication challenges. You have those centralized teams that are overwhelmed that people have stopped trusting a lot that people are working around.

They're trying to communicate that they're overloaded, but they're not doing a great job of it people are communicating that they can't trust that team and that's like inherently threatening to this particular thing. And so one of the things is that, in terms of a communication challenge, if you're one of those shared teams, it's extremely, you enter this sort of cycle of doom in terms of how you communicate, because if you're negative, not negative, but if you're just pushed back on everyone, then they'll hyperanalyze how you're allocating your time and that's gonna not work.

And then if you say, yes to everything, of course, that's going to doom what you're doing anyway, too. So I think that, yeah, it's especially hard in organizations for those teams that have to manage the parallelization. Um, and meanwhile, every other team wants to pretend that they're fairly independent. Uh, so that's kind of the fun challenge, I think.

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