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1:1 Meeting Questions

This is my list of questions to ask in a 1:1 meeting. I have added commentary to help you understand my thoughts on them, what they are trying to achieve, and how well they work. While the wording of questions is often deliberate, I don't always strictly adhere to it.

There is a companion post that shares more about how to use this guide and general advice on running 1:1 meetings.

The questions have been divided into sections:

I prepare for a meeting by selecting a question or two from the sections I want to cover (rarely all of them in one meeting). Often, these provide a fallback if not much has been brought up in the introduction. With longer-serving employees, I rarely dip into these questions. For new team members, I find myself here often.

Note that I test and rotate questions regularly based on their intent and effectiveness. If a question isn't working, I remove it. If I think of one or see one elsewhere that I like, I'll add it and try it.

Many of these questions require trust to get good answers. But by asking them, listening, and, where appropriate, acting or providing more information and context (without getting defensive), they will build trust.

I have given my indication of how much I like a question with stars ★ from 0-3. I don't list bad questions here (unless they are untested and I'm not sure yet), so even 0 stars is good.

Introductions​

How's things?​

Wording is not important, but your interest should be genuine. Stay quiet and avoid the temptation to jump in too early. An answer would normally start with some personal stuff (weekend, etc.) and move into professional stuff. The personal side is important if you want to build trust and relationships. It also gives you a good temperature check into how team members are doing.

On its own, this question often naturally leads into what your report wants to talk about.

When working in the office, I liked to have 1:1s in local (quiet) coffee shops. The change of environment was very conducive to the meeting, and in that case, this section happened on the walk.

Is there anything you want to talk about this meeting?​

Even if the first question naturally leads into something, you should follow it up early on with this one. If the first topic is a big one, you can break and say, "Before we spend all the time on this, was there anything else you wanted to cover?"

You should also share things you want to cover (after they have shared!) and then use this to pace the meeting appropriately.

Role Questions​

How can I help you get things done?​

Even if it yields nothing, it's a good one to ask as it shows you care about supporting them.

What are the biggest time wasters for you each week? ★​

Should be covered in an effective retro but sometimes catches things by encouraging thought into time wasters.

What, if anything, feels harder than it should be in your day-to-day work? ★​

Variation on above but emphasis on "harder" vs. "wasted"

Are you happy in your role? What could make it better for you? ★​

To be used sparingly but can be very insightful. Requires trust.

Team Questions​

If you were running the team, what would you do differently?​

Variation on the CEO question focused on the team.

What's a problem we have on our team that I might not know about? ★​

Works better when you have more distance (e.g., skip level).

What's our biggest challenge as a team?​

OK.

How can we step up as a team this week?​

Untested.

If you were me, what question would you ask yourself?​

I haven't really tested it in 1:1s, but it's a good reverse question. The intent is to help someone talk about something they are finding it hard to bring up.

Who is doing a great job on the team? What have they done? ★★★​

You get really nice feedback here. It often highlights something you weren't quite aware of and is something you can share with the other person in their 1:1!

Company Questions​

If you were the CEO, what's the first thing you'd change? ★​

Tends to be most effective on senior reports and those that have been at the company a while. Unlikely to yield much for mid-levels and below or new hires, but it's still nice to be asked.

Are there any aspects of our culture you wish you could change? ★​

Good.

As a company, do you think we're behind the curve on anything in particular?​

OK.

When have you been disappointed with a decision or the direction that the company has gone in the past quarter? ★★​

Good. It lets you hear potential problems and also provides an opportunity to explain the context behind things.

What rumors are you hearing that you think I should know about?​

Untested. Not sure when I would use it.

What is keeping you at [company]? ★★​

To be used gently and very infrequently. It is both a temperature check on happiness in role but also a way of surfacing what reports value about the company (e.g., mission, team members, culture).

If you were to leave [company], for what reasons would you? ★★​

As above, but from another angle. Good at revealing things that could be actual deal-breakers and lets you address these before they cause a good employee to leave.

Professional Development​

Professional development is a difficult section. I don't like to force it and instead go by the employee. I tend to hire people that have a strong desire to learn, and therefore the need to encourage them here is rarely needed. This section then becomes more about ensuring I'm supporting them in the right way and am aware of what they would like to learn.

My preferred way of doing professional development starts with an energy / skill matrix. More on that another time.

How do you feel about your professional development? Are you happy with the way you are learning and progressing?​

Good.

Is there anything that I or others in the team are doing you're interested in getting involved with? ★★​

Designed to pick up things like they are keen on learning but aren't getting the chance to work on because someone else is doing it or it's something you could delegate but hadn't thought of.

Is there an aspect of your job you would like more help with or coaching? ★​

Good. And has value even if the answer is no, as it makes you approachable in the future if there is something.

What can I hold you accountable for next time we talk?​

For those that have said they like the accountability to have the motivation to do things they want to. Used rarely.

Feedback for Them​

This isn't a question but a deliberate section I fill in ahead of time if I do have feedback for them.

Feedback for You​

I try and ask one of these often. It's not just about the answer but leading by example when creating a feedback culture. By showing you are open to feedback, desire it, and act on it, others will be less defensive.

You are looking for answers though, and that is why there are many questions in this section. It can be very hard to draw out feedback, so there are lots of different approaches here.

Being petty, what do I do well running the team, what could I do better? ★​

"Being petty" is key here as it removes the mental blocker of "I don't think that's big enough."

What is one thing I could experiment with doing differently this month to help you more? ★★​

Is easier to answer as it's not critical but something new. "Experiment" is a key word as well as it shows you're open to try it even if you aren't sure but also doesn't commit you to sticking with it.

What is everyone around me neglecting to share with me?​

Don't think I've used this. Very situational when you sense something is up.

How have you felt about my level of presence/support over the past month? ★​

Good temperature check, but I also use it when I feel my presence has been low, acknowledging I feel it has been an issue.

What do you like about my management style? What do you dislike? ★​

Good, though I haven't seen it yield much in "dislike."

Is there anything that would be productive for me to re-explain to our team?​

Surfaces something that you take for granted (e.g., how the new data pipeline/deployment method/service works that you understand super well and may have explained but isn't as clear to everyone else).

What's something you'd like to share but is a little stressful to bring up in person?​

I have never used this. I'm not sure when I would.

What do you wish I did less of? More of? ★​

Ask in two parts. "Less of/more of" is less harsh than "stop/start." It's easy to raise something when asked this way.

Is there anything I do or my process that makes a part of your job harder than it otherwise would be? ★★​

I like this. There must be something. Don't be defensive. Think about it. Sometimes the answer is explaining why it's important and needed and worth the time they are "wasting." Sometimes you can make small tweaks to improve things. Sometimes you should just stop!

Is there anything you would like us to use this meeting for or would like to go over in this meeting in future? ★​

Good to ask every now and again. 1:1s should adapt to the needs of the report.

What did a former manager do that you valued, which I haven't adopted yet? ★★★​

I love this and often ask it to new employees after they have had time to settle in. At some point between 1-3 months normally.

Ultimate Fallbacks​

For when you are getting very little response from someone. This is rare in 1:1s but can be more common in skip levels, particularly with juniors.

Some of these are repeats, but it's designed to be looked upon mid-meeting if you don't already have a good rapport with the person and so need to build that versus ending the meeting.

Tell me about the project you are currently working on?​

It's very hard for someone not to be able to talk about this.

What do you like best about the project you are working on?​

Variation or follow-up to above.

Who is doing a great job on the team? What have they done? ★★★​

Repeat question but works well here.

What do you like best about working at [company]?​

OK.