Navigating Uncertainty is Product Management

Ryan Singer, Head of Strategy at Basecamp, shares how he manages projects with unknown requirements, eliminates blockers, and avoids unnecessary meetings.


Most of the product managers that I know have had the experience of spending weeks or months planning a development project, only to find out that things end up being more complicated than expected. Whether it’s unforseen hurdles or new customer requests, there are always surprises.

This doesn’t mean that the planning wasn’t done properly. Rather, unexpected challenges and opportunities are simply the nature of building products in the digital age. Accordingly, Ryan says that we need new planning and management processes that take this into account.

Ryan differentiates between the work of figuring out what to do and actually getting it done. These require two very different skill sets and frames of mind.

At the beginning of a development project, there are a nearly infinite amount of unknowns. There will be countless assumptions and ideas that you can’t validate until you start building.

This uncertainty is what often causes projects to stall. Someone doesn’t know how to solve a given problem, so they get stuck.

Ryan recommends isolating independent parts of a project and plotting them on what he refers to as a “hill chart” so that you can spot where pieces are stalled and solutions or decisions are needed. By working on the pieces that are unknown, you can get answers sooner and avoid blocking other pieces of the project.

An added benefit of this is approach is that it reduces the amount of time you waste in meetings. Ryan communicates asynchronously with the people who are working on pieces of the project that are still on the “uphill” portion of his chart. In other words, the pieces with the most uncertainty. This enables everyone else to stay focused on working on the pieces of the project with with more defined steps.

You’ll learn a lot from this episode about project management and planning.

Here are the highlights:

Ryan Singer

Head of Strategy at Basecamp

Ryan’s Recommended Resources on Navigating Uncertainty

What Ryan is Reading Right Now

Ryan’s Favorite New Product Outside of Work

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