One-on-ones & managing people

I was just reading Ben Horowitz’ chapter One-on-ones from his quintessential book The Hard Thing About Hard Things and it’s reassuring to find out I’ve been doing the same thing during the past year.

The thing about books is they formalize what you already know or are doing. In case you didn’t know it yet, then there’s an opportunity to learn. Win-win!

I do one-on-ones quite irregularly, just to make sure they don’t seem obligatory. Here are the questions Horowitz listed in his book:

  • If we could improve in any way, how would we do it?
  • What’s the number-one problem with our organization? Why?
  • What’s not fun about working here?
  • Who is really kicking ass in the company? Whom do you admire?
  • If you were me, what changes would you make?
  • What don’t you like about the product?
  • What’s the biggest opportunity that we’re missing out on?
  • What are we not doing that we should be doing?
  • Are you happy working here?

It’s important to realise an effective one-on-one requires the manager to act as an active listener, i.e. you’re making bottom-up happening.

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