37signals · Product sense · Mid · 45 to 60 minutes

A stuck HEY feature with a fixed time budget

37signals is a software company best known for Basecamp and the HEY email service. Answer this product management case and get it graded line by line against a weighted rubric.

problem framing
prioritization
product judgment
stakeholder management
execution planning

The situation

You are the PM working on a meaningful workflow change inside HEY. The work entered design with a clear target experience in mind, and the team expected to use the current cycle to shape it into something ready for implementation. Midway through design, the concept is not coming together. Important edge cases keep appearing, the interaction feels heavier than expected, and the team is no longer confident that the current direction will create enough value to justify the effort. The tension is that this work already has a fixed time budget for the cycle. Engineering needs clarity soon so they can plan implementation work or shift attention elsewhere. The design lead wants a decision before the next review: keep refining the current concept, cut it down to a smaller version, pause for more input, or revisit the brief and use the remaining time differently. Leadership expects progress this cycle, but there is no promise to ship a specific design yet. You need to recommend how the team should proceed now, given limited time and incomplete certainty.

What to produce

A one page product decision memo, 700 to 900 words.

Your answer must

State the decision that must be made now and the main uncertainty blocking progress.
Define 2 to 3 credible paths forward for this cycle and compare their tradeoffs on user value, quality, risk, and time.
Recommend one path and explain why it is the best use of the remaining cycle budget.
Describe the next 3 to 5 actions you would take before the next design review, including who should be involved and why.
Specify what success would look like by the end of the cycle, even if the work is not ready to ship.

Constraints

Keep the current cycle time budget fixed, do not ask for extra time.
Work only from the information in the prompt, do not assume new user research or detailed product metrics are available immediately.
Stay within HEY, do not propose a broad company wide reorganization or multi product redesign.

Format

Use short headings and bullets where helpful. Lead with your recommendation, then support it.

How 37signals actually played it

The co-founders describe a feature in HEY where the team changed direction mid-design. The key shift was moving from specifying an outcome to diagnosing the real problem, helped by a design meeting that got to the root cause and early involvement from an executive. The pivot kept the original time budget. A useful case of fixing the problem statement before the solution.

Diagnose the actual problem instead of specifying the outcome you assumed.
Keep the appetite (time budget) fixed when pivoting.
Early executive involvement can save time later.
A roadblock can be the trigger for a better idea.

Built from A Product Pivot (REWORK podcast transcript) by Jason Fried and David Heinemeier Hansson, 37signals.