Three "what about...?" questions when considering Shape Up

I sometimes hear from CTOs and VPs of Product who started adopting elements of Shape Up, and some doubts are holding them back from going all the way. They have some "what about..." questions, especially around the planning aspects. They ask: How is it possible for a "real" B2B company to work without a roadmap, or to make bets at the last moment before a cycle starts?

That "no roadmap" style of working has a lot to do with the structure of Basecamp, where Shape Up was born: they're self-funded, profitable, and free from external pressures. That gives them the luxury of deciding turn-by-turn where to go without making promises ahead of time.

Lots of companies don't fit that description. And actually, it's not necessary to embrace a "no roadmap" attitude. Shape Up is all about shipping. It's about building that muscle that lets us decide what we want to do and how much time we want to spend, and then accomplish that. If we can't ship projects one-by-one, it doesn't matter how wise or aligned our big picture strategy is — we won't be able to execute it.

On the other hand, we do need to combine our shipping muscle with strategy. That means defining how individual projects add up to bigger goals, setting expectations about the future, and managing people and capacity along the way.

So let's take a closer look at those "what about..." questions.

"Making bets at the last minute doesn't seem realistic"

This question touches one of my favorite evolutions of the method in the past couple years. In Shaping in Real Life, we teach a work step called "framing." Framing is about making the business case to spend time on this project instead of whatever else we could do. Shaping takes time, so we need to build the case for a project before we start shaping. The betting table as described in the book is much too late in the process!

If your company is like Basecamp and has the luxury of shaping multiple things in parallel and then just picking one of them, then betting at the last moment is fine. But most companies aren't in that situation. There's limited time, limited resources, and we need to align on that one thing that is most important to do next. Framing is the work we do to figure out what that next thing is, before we invest time in shaping it.

(Even at Basecamp, before they shape anything, there is an informal understanding that project A is more likely to get resources than project B, so they know to focus on shaping A first.)

In practice, projects go from raw idea to framed opportunity to shaped concept to a build team through a series of green lights. As a result, I've stopped using the term "pitch" for shaped work. It gives the misleading impression that you first shape something and then make the case to do it. It's really the other way around. We have a reason for doing something, we shape it down, and then, once the concept is crystalized, we give the green light to spend our precious build time on it. That's why I talk about "packaging" the shaped work rather than "pitching" it now. The pitch — the attempt to sell and align others — happens earlier, at the framing stage.

"I can't imagine a successful business without a roadmap."

Of course we need to have an idea of where we're heading at a bigger time scale than six weeks. The thing is, the reason we're talking about Shape Up is because we want to improve our shipping muscle. So we have two different topics in the air: One is about project formation and execution — our ability to set our sights on something and ship it as we intend. The other is the question of which projects to pursue and ship at what time.

The place where we get into trouble is when we conflate these two. When what we call the roadmap is really a bunch of promises to deliver specific functionality on specific dates. It's nearly impossible to understand what the concrete solution should look like for something that's beyond the horizon of six weeks. But we can certainly decide which problem areas to tackle, which aspects of the business need attention, and what kinds of projects we want to pursue or let slide over the next quarter, half, and year.

The link between these two subjects is, again, framing. Our strategic goals inform our decisions about project formation — which individual efforts we want to frame, shape, build, and ship. Projects and strategy are linked, but not the same.

The relationship between shipping and strategy is like driving a car. First we learn to control the machine. And then once it becomes an extension of ourselves, we can concentrate on the route we want to take and the task of navigation.

"If we focus so much on getting projects 'done', does it mean we can't iterate anymore?"

This is a legitimate question for teams who are used to agile sprints. In the world of sprints, everything can get better the next time around. That sounds nice, but the flip side is less rosy: everything can get better because nothing is ever done.

For companies considering Shape Up, "nothing is done" is the world they're trying to get away from. When you're trying to move things forward, the value of iterating over time goes down and the value of making step changes goes up. There is a trade-off to be made, where we decide to be more intentional about what we're going after and what "done" means. Tactically, this means learning to do more shaping and spiking before we jump into time commitments and Figma and code.

Zooming out a little, we get some great news. We can break this trade-off and have our cake and eat it too. The better we get at targeting something and shipping it as intended, the more freedom we obtain to decide what's next. Instead of unfinished work and debt, there's clear space ahead. It's the car analogy. As skilled drivers, we decide where to go. We can define "done", ship the project, and jump to a completely different area. Or we can say "that was great, and the feedback is amazing, let's reinvest" and make that area even better. The key is that we decide where we want to be, instead of slogging through iteration after iteration because we didn't know where we were going.

To learn more about framing, running shaping sessions, and how to ship what you intend — without doing Shape Up "by the book" — check out the Shaping in Real Life course. Sales just opened for Cohort 3, running October 9-23. The course is limited to 20 participants, and consists of self-paced video lessons, exercises with feedback, and two interactive group sessions. For all the details, check out the course page.