Parenting wisdom for product managers, powered by Lenny's Podcast

When to Rescue, When to Watch Them Fall

Inspired by John Cutler episode

The VP's dilemma of when to intervene versus let teams struggle mirrors every parent watching their kid on the climbing frame.

Your kid's trying to put their shoes on. Wrong feet, upside down, laces a modern art installation. You could fix it in three seconds. Instead you're having an existential crisis about whether this is teaching or child abuse.

John Cutler talks about the VP's hardest call: knowing when to step in versus when to let teams struggle. Congratulations, you've been practicing this at the playground for years.

The climbing frame is perfect. They're reaching for something just barely out of range. If you hover and help every time, they never build the muscle or confidence. Yet if they're truly stuck or unsafe, standing back isn't teaching—it's just you being a sociopath.

Are they building frustration tolerance or about to ragequit childhood? You're running a tiny performance review every twelve seconds. Is this struggle productive or are we all just suffering for no reason?

Welcome to management. The hours are terrible and your direct reports cry a lot.

1-2yr2-3yr3-4yrTeam LeadershipFostering IndependenceJohn Cutler
While this advice is inspired by John Cutler's quotes, it does not necessarily mean they would agree with it. Much like your kids or mother-in-law. If you see something odd though, you can .