Empowered ShapeUp

ShapeUp by Basecamp is an awesome, practical, and pragmatic introduction to the process surrounding product management. It offers great tools to describe and prioritize what to build and when. However, it also describes power dynamics that will slow you down and potentially kill your team’s motivation. It will also lead you to build the wrong features as you scale.

ShapeUp is designed to be top-down. Leadership writes pitches, decides which ones to deliver, and hands them over to a team of designers and engineers to build. Yes, the solution fidelity leaves room for the team to leave their mark on the final product, but that’s about it.

Above is an informative video by Jason Fried from Basecamp talking about how they run product strategy. It’s great, but notice that only 3 out of 80+ people at Basecamp are part of the pitch process.

I have sadly seen many founders introduce ShapeUp and use it as a top-down micromanagement framework. That works for some, but I think that there is a better option.

At Whimsical we have five product teams. As VP Product, a member of the executive team and the manager of the product department, I am responsible for maintaining product strategy, leading my team, and answering many non-product-related questions. I simply do not have time to develop pitches of a high enough quality that I would feel comfortable risking my team’s time and the company’s money.

I have a ton of respect for the quality of the product that Basecamp has built, and it’s working for them. Over the years, however, I have learned that I am no Steve Jobs or David Heinemeier Hansson. I need to substitute my personal lack of genius with empowerment and leadership.

ShapeUp at Whimsical

People that know me or have read other posts on my blog will know that I am a huge fan of Marty Cagan’s take on how to structure product teams. The core is building empowered teams (he even wrote a book about it).

At Whimsical we are mixing what Marty Cagan has taught us about empowerment with ShapeUp.


This is the core product piece that I, as the VP of Product, own. This is my “pitch” on what the future of Whimsical is, and how to get there. Writing a good strategy is many things, and while I don’t want to even try to get into details here, it’s a document that sets a long-term plan for what Whimsical could be in the future. Think of it as a concept car, a prototype made of clay, without an engine, and with wheels that can’t turn. It provides a direction and might include some design ideas, but as the car manufacturer gets closer to releasing the car they will work on all the little details. Chances are that no car manufacturer will ever release a car that is 1:1 with their concept car, but it still served its purpose by showing their team and the public a direction.


An empowered team doesn’t function without clear goals. This is where I, as the leader of the product organization, take the company’s overall goals and marry them with the product strategy. From there I derive concrete goals for each of the product teams that they can deliver on and feel excited about. We use quarterly goals and have cut down the cycles we run to 5 weeks of work and 1 week of cooldown to be able to fit two cycles within a quarter.

Our goals are inspired, but not tightly guided by the OKR format. As a leader, I decide on the objectives and then work with my team on the key results (how to measure the success of the objective).

We try to always have the goals ready two weeks before a new quarter starts. This allows the teams the time needed to shape work for the first cycle that starts the first week of the new quarter.

The Team

The team consists of a product manager, designer, tech lead, and a number of developers depending on the scope of the team. The product manager, designer, and tech lead form what we call the product trio.

At Whimsical it’s not the leadership team that writes the pitches, it’s the product trio. They are the people who best know their product and customers, and are best suited to speak to how we achieve our goals. The individual developers on the team are also more than welcome to participate in the process, but are not required to take part.

The trio will run a dual-track process where they focus on writing and developing pitches for the next cycle while they also deliver on the pitches that were selected in the betting table for the current cycle. The trio will run a mix of discovery efforts to evaluate both the problems and the solutions that they outline in the pitches, helping us to have a higher certainty that we are building the right thing.

Product Jams

Product jams are bi-weekly meetings where our CEO, the Head of Engineering, the product trio, and I discuss the pitches that are being shaped. It’s the product trio that leads the meeting and the agenda. Leadership is not in the meeting to make decisions but rather to share feedback, knowledge, and thoughts on the direction of the individual pitches. The meeting is very much inspired by Pixar’s concept of Braintrusts.

Betting Table

For sanity’s sake, we do a betting table for each team. We are not fans of long meetings, and with five teams we would slowly run out of energy if it was one big meeting. Participants of the betting table are our CEO, the Head of Engineering, the product manager of the team, occasionally 1-2 other stakeholders, and me.

All members of a betting table will have had at least 2-3 days to read through and comment on each pitch before the betting table. On the call, the product manager will walk through each pitch and we will discuss it as a group. We usually agree easily on which ones to select for the cycle, but if we disagree I am the final decision maker, allowing me to set the right direction for the teams. After the betting table, the team will end up with a number of pitches that they have created to finish and deliver. When the team delivers on features I also have a final say on its release. I rarely use that saying and let the teams do their thing.

The flipped power dynamics of Empowered ShapeUp

This leaves us with a process where I, as the leader, have multiple ways to control the direction:

But the team owns and is empowered to drive:

This moves most of the power to the team and leaves me with more time to think about the strategy, build a great team, and lead, and it allows us to pour more raw, amazing brainpower into solving hard problems and driving the business forward.

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