Questions for 1:1s with your skip level and above

Published Wednesday, September 14, 2022

At the beginning of my career, the only one-on-one meetings I had were with my direct manager. The idea of talking to their boss or their bosses’ boss was terrifying.

But now I’ve been around a while and gained some seniority, and I’ve found myself having fairly regular 1:1s with people way above me in the org chart. Instead of being terrified, I think of these meetings as super valuable opportunities to learn from folks with serious power and influence at the company. It’s important to use this time wisely, so I always try to prep some good questions in advance.

Here’s some starter questions that’ve proven pretty helpful for me.


  • What are your hopes and dreams for our team?
  • How do you want to see our team grow?
  • What could this team look like in the future?
  • What’s something visible + valuable you’d like to see get attention in our area of responsibility?


  • What’s the biggest tech challenge for our team/department?
  • What are some hard decisions coming up for our team/department?


  • What do you think is the most overlooked area of the business?
  • Where do you think we’re behind, that other companies are excelling at?

3 things

My CTO at my previous company always liked to close out company meetings with “Three Things”:

  • 3 things getting you up in the morning
  • 3 things keeping you up at night