Crystal ball 1-on-1s

March 25, 2018 · 3 min read

1-on-1s are my favorite management tool. Not only for managing direct reports; sideways and upwards management need 1-on-1s, too. Here’s my general definition for a 1-on-1:

  1. Reoccuring - Whether it’s weekly, bi-weekly, or monthly, set a cadence and stick with it.
  2. Informal - Don’t bring a strict agenda; try to spend the time actively engaged.
  3. Focused - Don’t bring your laptop. Set your phone on ‘do not disturb.’ Get out of the office, if possible.

If you’re unfamiliar with 1-on-1s, there are a ton of great intros1. So instead of rehashing the whys and hows, I’d like to share a question I’ve been asking at my 1-on-1’s lately:

Look into a crystal ball and see us at our next 1-on-1. You just told me you had a really great week2. What was great about it?

There’s a few things that I like about this question.


It can be hard to help your reports, colleagues, or managers with the things that are frustrating them or keeping them from getting work done. The crystal ball is an opportunity to imagine that any blockers — too many meetings, needy stakeholders, organizational uncertainty — don’t exist. Sometimes, that’s enough to see a way through.

I have a friend who talks about “the future, where everything’s better,” which is a clever way to dispel skepticism. Sure, it’s fiction, but it gives everyone permission to ditch the drag of current problems.


The crystal ball question is open ended. The answer can be simple: “I got a lot of sleep.” It can be complex: “I finally figured out how to delegate!3” By focusing on the future (where everything’s better), you open the conversation to a huge number of possible topics. The answer can kick off your 1-on-1, or provide a nice tag on the conversation.


No matter the answer, make sure to follow up on it between now and your next 1-on-1. Connecting your conversations allows for short 1-on-1s (mine are usually 30 minutes), while still producing meaningful outcomes.

Ask away

Give the crystal ball question a shot, and tell me what you think. Do you have any go-to tools for 1-on-1s? Any do’s or don’ts? Share 'em with me on twitter. ✌️

Footnotes & References
  1. Start here, with Josh Pigford’s great overview. ↩︎

  2. I usually do my 1-on-1s weekly, so if you’re on a different cadence, substitute that period here. ↩︎

  3. Real talk, this is my answer most of the time. ↩︎