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How to coach employees? Ask these 1-on-1 meeting questions

Micromanage less and coach employees more by asking these key 1-on-1 meeting questions.

The key to coaching employees lies in a single, straightforward choice: The 1-on-1 meeting questions you choose to ask.

You may be raising an eyebrow at this. Surely, you’ve heard enough hype about how “you need to be holding one-on-ones as a leader.” But the role that one on one meetings play in coaching employees is egregiously overlooked.

One-on-one meeting questions are possibly the most effective mechanism we have as leaders for coaching employees. When we invest in asking the right questions during our 1-on-1 meetings, our tendency to micromanage our team can be circumvented.

For instance, if we incessantly ask “What’s the latest on X?” or “When will this be finished?” during a one-on-one meeting, and we’ll likely come across as overbearing.

But choose to ask the right 1-on-1 questions (I share 16 of them below in the “Ask these questions…” section), and you help that employee feel encouraged about their work and equipped to go solve the problems ahead of them.

Let me show you what I mean.

Focus on these 4 things in your 1-1s to coach your team.

First, to coach your employees, your one-on-one meetings should be focused on understanding a few things:

Their perception of the current state: How does your team member see themselves and their performance? Ask questions during your one on one meeting that gives you ample information about their point-of-view of how they currently see their work situation. It’s massively important to understand this, otherwise, you won’t be able to coach someone to make progress.

The ideal outcome of where they need to be: How does where your team member is currently at, match up to where they need to be, in terms of their performance? You want to get clear on what “success” is – and if the other person understands this too. Ask 1-on-1 questions that reveal to you both how you know when a project has been successful.

What your team member is most motivated by: What does your team member seem to want most for themselves, professionally? What do they seem to be most motivated by? A big part of coaching employees well is being in tune with what the other person ultimately cares about. Their aspirations can help you ask questions to help the other person remember and zoom in on this for themselves.

What’s holding your team member back: What’s likely holding them back from where they need to be, in terms of their performance, and/or from what they desire most professionally? The best coaching one on one questions illuminate how the person is either (1) unintentionally holding themselves back or (2) hasn’t considered a problem from a different angle. By asking questions around what’s getting in the way, you can help an employee see for themselves how to solve a problem.

Focus on gaining clarity in these four areas, and you’ll be able to coach an employee during a one-on-one meeting. By the 1-on-1 questions you ask, you’ll help a person see obstacles in a new light, and come to the right conclusion themselves.

Looking for more detailed guidance on one-on-one meetings? Make sure to check out our 1:1 module in Canopy.
Learn more

Ask these 16 one on one meeting questions to help coach your team.

All right. You’ve got the framework for approaching coaching employees during a one-on-one meeting. Ready for the exact 1-on-1 questions that I recommend asking?

Here are the 16 questions you should ask if you want to coach your employees during a 1-on-1:

First, ask questions that reveal how do they see themselves and their performance…

  • How have you been feeling about your performance lately?
  • In your view, did anything fall short of your own expectations?
  • In your view, did anything fall short of the team’s expectations?

Then, ask questions that reveal where they need to be…

  • Is it clear to you what is “quality” work?
  • Is it clear what “success” ultimately looks like?
  • How do you know you will have been successful?

Afterward, ask questions that reveal what they want most…

  • What motivates you the most about this project?
  • What have you been most proud of what you’ve worked on?
  • What’s been energizing you lately about the team, if anything?

Lastly, ask questions that reveal what’s likely holding them back…

  • What do you find most demotivating about this project?
  • What are your biggest time wasters?
  • What do you feel confused about?
  • How am I unintentionally getting in the way of progress?
  • Is there anything that feels harder than it needs to be?
  • Is there an easier way to do what you suggested?
  • Is there another solution that isn’t immediately apparent?
Looking for more detailed guidance on one-on-one meetings? Make sure to check out our 1:1 module in Canopy.
Learn more

From these questions, surprising and meaningful insights will emerge. You’ll help your direct report realize that they tend to rush their work. You’ll help them see that a problem they were stuck on wasn’t so insolvable after all. And, you may also learn that there are in fact things you as a leader are unintentionally doing to hold someone back from doing their best work 🙂

This is all part of coaching employees well. After all, at its core, coaching is about helping your team figure something out, themselves. Coaching enables the agency they already have. You’re not doing the work for your team when you’re coaching employees – you’re helping a team solve problems for themselves, and make the best choice on their own.

There’s truly no better way to do this than by asking the right 1-on-1 meeting questions.

Start by asking these 16 one-on-one meeting questions here, today.

👉 Looking for more one on one questions and agenda templates to coach employees? Look no further: We’ve got these (and more!) all in our on-demand training program. See for yourself, and try Know Your Team for free today.

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Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.