Brian Bailey

November 20, 2023

Make room for ambition

You start a new project. The pitch outlines the problem and boundaries of the solution. There's an appetite, like three weeks, that captures how much time it's worth investing.

It's time to jump in.

You add some to-dos. Have a kickoff call. Mock up a few approaches, throw together a dead simple UI, or spike a potential data model.

All good things!

But the early stages are exactly when you should let your mind wander a bit.

Is there a simpler way to solve the problem?

Does the solution have costs we'll regret later?

Is now the time to finally fix a lingering frustration or limitation in the codebase, or bring this UI inline with recent improvements elsewhere?

Are we layering more on top of assumptions that are worth questioning?

The boundaries of the solution should be porous, not impenetrable.

Most of the time, the answer to these questions is no, but just for a moment, while a project is still fresh, give yourself permission to explore and rethink — to be ambitious.

But how do you walk the line between rapid iteration and pushing the boundaries? It's easy to get lost as you explore, then realize half of the appetite is gone and you have little to show for it.

First, time box your exploration. A promising idea will usually reveal itself quickly. The hope is to find a straight shot where there wasn't one, an alternative that cuts with the grain better that what's in the pitch. If there's a roadblock every few steps, it's probably not a better way. Don't hesitate to move on.

Second, treat it as a side quest. You don't have to be formal or highly structured about it — "We've going to spend three days trying an alternative approach."

In fact, it's often better to explore quietly and in parallel when you can. Get started on the pitched solution while you see if your idea holds promise. Go above and beyond. Your excitement and motivation is a sign that there's something there. Skip the debates about whether it's worth exploring — get real, prove it out, and report back.

It can be a bit of a high-wire act, so proceed with caution if you're just getting started with Shape Up or the team is less experienced. There's risk that you blow past the appetite if you explore too long. You also don't want to get distracted by minor details or start shaping what's already been shaped. It's time to build.

The bigger risk, though, is that inflexible boundaries deprive the organization of the team's insights, creativity, and experience. Now and then, there's a better way. You won't know unless you take a moment to look.

About Brian Bailey

Head of Product Strategy at 37signals, the friendly people behind Basecamp, HEY, and ONCE. Find me elsewhere at bb.place and @bb.