Find the Bad Feeling

Nan Yu was head of product at Linear, which makes project-management software, when Yu said this on Lenny’s Podcast in January 2025. Host Lenny Rachitsky had heard from Linear’s head of sales that Yu keeps digging on customer calls until finding an insight, and asked how. Salespeople sitting in, Yu said, often wonder what the questions are for. This line is the answer.

When a customer asks for a feature, the usual approach is to ask what goal it serves. Yu says that can “miss the reason that they actually feel bad for not having this thing.” So Yu keeps asking why it matters until the stakes come out, as in Yu’s example of a customer who finally says, “I’m not going to get promoted at work.” That answer shows how severe the problem is. People won’t necessarily say how they feel when asked outright; it comes out in a long conversation, once they see Yu understands their side.

In one of Yu’s examples, a customer had a project due sometime in the last quarter of the year and set its ship date to December 30, to put it at the very end. The marketing team objected that they couldn’t ship anything on December 30, when everyone is on vacation, and the customer felt bad enough to never want to put a date on anything again. To spare people that feeling, Linear lets a project’s target date be a whole month, quarter, or half-year instead of a specific day. That customer could have set the target to the last quarter and never had to pick December 30.