Deciding without taking it personally

A small team makes dozens of decisions a week, and most of them reject someone’s idea. A proposed feature does not get built. A design is replaced. A pricing plan loses to another. Each choice is about the product, but the person whose idea lost can easily hear it as a verdict on them. The person deciding, knowing that, may soften or delay the decision to avoid giving offense.

Kevin Hale, who co-founded the online form builder Wufoo with two partners and took it through Y Combinator in 2006, is credited with naming this as the hardest part; the talk or post the line came from has not been traced. Wufoo became known for having every member of its small team answer customer support, an approach it called support-driven development.

Both reactions make decisions worse. The person who lost the argument digs in next time, or stops proposing things. The person deciding learns to wait until a choice can be made without anyone noticing, which usually means waiting too long.

A common case is the feature a founder built personally. It shipped early, and almost nobody uses it. Removing it is the right call and feels like an insult to the person who wrote it. Teams that handle this well talk about the feature as a past bet, placed on the best information of its time, and not as a piece of anyone’s judgment on trial. The fix is mostly procedural: argue from evidence, such as support tickets, usage numbers and customer interviews, so that the question becomes what the data shows rather than whose taste wins. A team that answers support together shares the same evidence, which makes this easier.

Some decisions cannot be depersonalized. Firing someone, splitting with a co-founder or cutting a colleague’s project is personal by nature, and pretending otherwise reads as coldness. For those, honesty and care matter more than distance. The skill is knowing which kind of decision is on the table, and not using the language of evidence to avoid a conversation that is about a person.