Top-Down vs. Bottom-Up Roadmapping

Let me go in a slightly different direction. One of my favorite posts of yours is called execution beats strategy every time, and I think another way you phrase it is, execution eats strategy for breakfast. I think you put that somewhere. I'd love to hear about this because I completely agree.

And I think one of the things that you learn is if you have great strategy, perfect strategy but poor execution, you don't win because your strategy never makes it to the market. And what's even worse is that you have learned nothing. You don't know whether it was your strategy that was wrong or whether it was your execution that was wrong, all you know is you didn't win.

Some examples include their priorities in product roadmap are driven by a 100-year vision that comes from Tobi, the CEO. And the core product teams don't have metrics or KPIs. They're essentially banned. And instead, decisions are made based on taste, and intuition, and building towards this long-term vision.

All this is just the tip of the iceberg. Dovetail wants to give everyone in their organization instant access to their customers at any time. From roadmaps, discovery, to strategy sessions and more, it's never been easier to make customer-centric decisions.

So let me ask you actually about that. So planning right now is just crazy. How does anyone plan a roadmap when there's just like, "Okay, GPT-5 is out." Okay, great. What works for you for setting actual a roadmap and a strategy for your team? How far out do you plan? How often do you have to rethink everything?

Yeah, let's start with some basic definitions, which is as you asked, what is product strategy? And if you think back to the Headspace example, this sort of comes to life as well. So product strategy, strategy sits between the mission and vision and the plan.

The output of all of this is what I call the comprehensive preparation readout. It is a single master deck where you sort of have the behavioral insights meta analysis, you have the UXR insights meta analysis, you have a download of the leadership interviews, you have the competitive stack charts, you have the adjacent roadmaps, and you have a section on user observations.

You fell in love with building products for a reason, but sometimes the day-to-day reality is a little different than you imagined. Instead of dreaming up big ideas, talking to customers and crafting a strategy, you're drowning in spreadsheets and roadmap updates, and you're spending your days basically putting out fires. A better way is possible.

So let's segue to the evangelize step, which I think I always talk about. I always think about the Seinfeld meme of when he is trying to get a car reservation where he shows up and they don't have his car and they're like, "We have your reservation, we just don't have your car." And he's like, "That's the most important part of the reservation.

But those documents, to me, are the charter. So, "What is your mission, your vision and your strategy?" The goals, "What are you aiming to do and how are you going to measure success?" And then the roadmap, "What is the thing that you're shipping?

And I've kind of noticed two things about this framework for myself. One, I've actually noticed that teams often work their way from the bottom-up, versus top-down. They start with a roadmap. They're like, "What are all the things we're going to ship?" Especially early on. And then they kind of work their way into a charter. But I think it's really, really worth it to start from the top-down.

That's a thread I want to actually follow up on, is just the power of culture and values and things like that. But before we do that, let me just summarize maybe the top five attributes and kind of traits you just shared and then I have a two part question around this. I wrote these down.

So for example, I recently wrote about something called the leadership, the Pyramid of Leadership, self awareness. And it's a simple model, but it goes deep how I want it to go deep. So the idea is that at first we know nothing about ourself and then the next level is that we start to become self-aware, but believe the whole world is wired just like we're wired.

And then the last one is standardizing your processes, your cadences for strategy check-in. So it's like, hey, we do roadmap check-ins every month. These are the people that need to be in the room. We do quarterly planning sessions with executives, and this is the inputs to it, this is the outputs to it, here's the decisions we make in this meeting. This is what we review.

Where the gaps come between that and becoming an executive is interfacing with the board, understanding the financials super deeply so that you can create revenue projections off of what your roadmaps and your product's strategy is going to be.