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Before the day · Page 29

One challenge or four?

For you only

My default is one. One brief, four teams, four competing answers to the same question. That gives you the sharpest possible decision at five o'clock, because the judges compare like with like and the sponsor picks a direction, not a vibe.

There are honest exceptions. At Ionian we ran four challenges, because Spyros, the founder, treated the day as experimentation, a scan across product directions rather than one bet. That works, with a cost you should accept knowingly: every extra challenge divides the comparison. Four challenges means four separate one-team answers and a softer decision on each. One challenge means four answers to one question and a hard decision about it.

Decide what the company needs from the day, a decision or a map, and set the number of challenges accordingly.

One challengeA challenge per team
What you getFour competing answers to one questionA scan across four directions
The decision at 17:00Sharp: pick the strongest answerSofter: a go/iterate/no-go per direction
JudgingLike against likeEach build against its own brief
Best whenOne decision is stuck or expensiveA founder wants to explore the space
The riskAll four teams find the same local answerNothing gets compared, everything gets a maybe

If you run multiple challenges, keep the shape identical: every brief still names a user, a context, and a goal, and every brief still passes the calendar test, because every brief still needs its five users at 15:30. Four challenges with four different user types quietly quadruples your recruiting. Read that sentence again before you say yes to a founder in scan mode.

The trade is always the same: the tighter the brief, the sharper the decision. The looser the brief, the wider the discovery. A private day buys a decision.

Sources: "How to define a good challenge", productbuildday.com/resources, 2026.