MGMT Minute: The One Question That Unlocks Your 1-on-1s

Read time: 1 minute

You're in your weekly 1-on-1.
You've covered the usual updates.

Projects are on track.
No major fires to put out.

But something feels...off.

You sense there's more beneath the surface.
Something your team member wants to say.
Something they can’t quite find the words for.

Here's the all-important question I ask in these moments:

"What's the one thing you wish I knew, but you're hesitant to tell me?"

Why it works:

1. It builds trust and safety: When you acknowledge their hesitation, you're signaling it's okay to share whatever is bothering them.

2. It invites specificity: Asking for "one thing" focuses the conversation on what matters most.

3. It surfaces hidden issues: Often, the most important feedback is the hardest to give.

The magic isn't in asking once – it's in asking consistently.

And it turns out, the more you ask, the less you’ll have to.

Some of you might worry that the phrasing might create resistance.

Here are 5 alternatives to unlock similar insights:

1. "What's something obvious to you that might not be obvious to me?"

   → Removes the emotional burden

   → Makes sharing feel like helping
   

2. "If you were in my role, what would you do differently?"

   → Creates psychological distance

   → Turns critique into strategy
   

3. "What's working well that we should do more of?"

   → Starts positive

   → Naturally surfaces gaps
   

4. "Where do you see friction that I might be missing?"

   → Focuses on systems, not people

   → Easier to discuss objectively
   

5. "What would make your job 10% better?"

   → Specific but not overwhelming

   → Solutions-oriented

Try making it an occasional part of your 1-on-1s.

You'll be amazed at what you learn and how it accelerates trust and alignment.

Lead on,
Dave

PS - Want to dive deeper into mastering 1-on-1s? Check out our 1-on-1 Lighting Lesson. It's free! Even if you missed it live, you'll get the recording.

PPS - How do you approach your 1-on-1s? Reply to this email with your best tip – I'd love to feature reader insights in an upcoming playbook!

💡New Managers: MGMT Fundamentals is open for enrollment. In an hour a day over two weeks, we’ll teach you the foundational skills to not just survive but thrive in your new leadership role. Ideal for managers in the first 3 years managing a team.