I figured out a magic question that I use at the beginning of every single 1:1 meeting, or any meeting I have with another individual, be it a direct report, skip level, investor, boss, whatever. Ready?

Magic Questions

First, I have to say, I spend every day seeking Magic Questions. If you know me, you know that I am always searching for hacks that make my efforts more effective.

A healthy part of my time as a UX leader was devoted to thinking about the perfect things to ask at a given moment. When you nail the perfect question, you unlock the most insightful answers, which is the most effective way to get to the right solutions.

The Magic Question for 1:1s

This question assumes you are meeting on a regular cadence with the other person, and the question is really easy:

So, how is it going?

Now there are a few tricks to asking this question:

1. It should be the first thing that you say to the other person. I mean, maaaaybe you can have a little small talk first, but use this question when you round the corner to the meat of the meeting.
2. You should ask it in the same way, with the same tone, every single time.
3. And the tone you use has to be normal, boring even.

Finally, the most important part: You have to listen and observe the speaker as they respond. Nine times out of ten, the response will not be anything interesting. They will simply say, “fine” or “oh you know, work is busy but good” or “great!”. You won’t think twice about it.

But then, every once in a while, you’ll notice something different. A slight twinge in the person’s voice, or a hesitation before they respond. That is the moment where there is likely something you can help with.

When you notice that difference in tone, dive in. Ask, “are you sure?” You can also point out whatever you noticed. Most of the time, this will help open up the conversation so you can move forward and improve things.

That’s it! It’s easy, as long as you are diligent and attentive. I hope this helps!