This one question will instantly improve your 1:1s

(and my full 1:1 agenda)

Happy Tuesday team,

We’re gearing up over here to make a huge announcement on the 22nd of April. An announcement that will be our biggest ever business pivot to date. It’s something we’ve been working on very secretly since last year. But don’t worry, you will absolutely be the first to know (reply to this email with your best guesses 👀).

Oh, and it's officially Q2. Which means we’ve got 3 months of learning behind us and 9 months of opportunity ahead. What you do with yours is entirely up to you.

But one of the best places to start is your 1:1s. Because let me guess… They’ve become just a status update meeting? Or a moaning session?

You run through the task list, check in on the project, ask “anything else?” and wrap up in 20 minutes feeling like you’ve done your job as a manager. Tick.

But deep down, you know. Neither of you left that meeting feeling motivated, connected, or any different than when you walked in.

But it’s so very easy to turn that around (often with just ONE question)…

The problem with most 1:1s

For the business, our 1:1s matter more than you we think. Disengaged employees cost businesses more in turnover, lost productivity and quiet quitting than almost anything else. Your 1:1s aren’t just a cute connection tool, they’re truly a business one.

1:1s are one of the most powerful tools a manager has. And most managers are wasting them.

Here are the biggest mistakes we make:

• Turning them into progress reports. If your 1:1 could be replaced by a Slack message, it should just be one.

• The manager is doing all the talking. Managers who dominate 1:1s think they’re being helpful, but what they’re actually doing is filling the silence where their team member’s honesty should be.

• Staying on the surface. “How are you getting on?” answered with “Yeah, fine.” Fine is not a conversation. Fine is a door you forgot to open.

• Only having them when things are going wrong. By then, you’re already in damage control.

Most of us managers truly care about our people. It’s just that nobody taught us what a great 1:1 actually looks like. So lemme change that today:

The question that changes everything

A while back, I started introducing a new question into my 1:1s, and it was by far the most impactful.

Here it is:

“If you were to hand in your notice tomorrow, what would be the reason?”

Read it again.

This question does something most 1:1 questions don’t… It bypasses the polite, surface-level answer and goes straight to what actually matters to your team member.

It gives them permission to be honest without it feeling like a complaint, and it gives you intelligence you can actually act on.

People don’t usually leave out of nowhere. They leave after months of feeling unheard, undervalued, overlooked or stuck. And they’ve often already answered this question in their own heads long before they hand in that notice.

You’re just asking it before it’s too late.

What to do once you have the answer

There was a time I avoided asking questions like this entirely, simply because I was scared of what I’d hear. What if the team want more money? A promotion? Bigger opportunities? What if they wanted something I simply couldn’t give them? It felt safer not to know.

But the single biggest lesson I learned is this: Not asking doesn’t make the need go away. It just means your team member is sitting on it alone, and quietly making decisions about their future without you in the conversation.

But remember, our job isn’t to immediately deliver the thing they want. Our job as their leader is to take it seriously. To go away and find out if it’s possible, and if so, when. If it’s not possible, say that, honestly and directly. What people can handle is the truth. What they can’t handle is being strung along or kept in the dark.

But here’s where it gets really powerful. Once you know what someone wants, ask them two follow-up questions:

“What are you doing personally to get there?”

“How can we, as a company, support you?”

These two questions change the entire dynamic of the conversation, because suddenly you’re not the sole owner of their development, they are. You’re a partner in it, but you’re asking what they can do to achieve the goal (instead of it all being on you).

As managers, we can for sure open doors, create opportunities, and remove obstacles, but we cannot work for their growth more than they do. The accountability has to sit with them, and these follow up questions just make that clear in the most empowering way possible.

Final thoughts

Your 1:1s are not an admin task. They are your single greatest lever as a manager to retain, develop and genuinely connect with the people you lead.

The managers who get this right aren’t doing anything magical I promise, they’re just asking better questions, listening more deeply, and treating their team members as whole human beings who have ambitions, fears, and things that matter to them beyond the to-do list.

One slightly awkward question. Followed by one honest conversation.

That’s all you need to start.

Peace,

H

P.S. If you want my full 90 Day 1on1 agenda, please use and steal it here.