Leading

Pair on Hard Problems

Published on Jun 11

If I made a list of my favorite meetings over the years, none of them would be an update meeting or a one-on-one.

They'd all be the same kind: two or three people in a room with a hard problem, and the work getting better in real time. New ideas surfacing. Healthy rumble and debate. Alignment by the end.

Every one of those meetings started with someone who had the courage to ask for help.

So why aren't most meetings like this?

Part of it is politeness — asking a teammate to pair on a hard problem means asking for their time. But the deeper reason is that we treat autonomy as the prize. Asking someone to get into the problem with you feels like admitting you can't handle it alone. So we grind in isolation and present work when it's "ready."

Jean-Michel Lemieux, who led engineering at Atlassian and Shopify, has the best line on this: "Without alignment, autonomy is squandered."

Here's the uncomfortable truth: not asking for help is bad for you and bad for the business. The work is lower quality. It takes longer. And the trust that gets built in rumbles and debates never forms.

Pairing isn't just an engineering practice. It works on a pricing decision, a customer issue, a hiring call, or a strategy you just can't crack. It's one of the few meetings that's almost always worth the time — for everyone in the room.

Pick the problem you've been grinding on alone and ask someone to get into it with you. Skip the update. Have the rumble. Rinse and repeat.