Top One-on-One Meeting Questions to Ask Direct Reports

Ask your reports these questions during your one-to-ones to make sure they're enjoying their work and are on track to hit all the

October 7, 2022
Press the button to generate random icebreaker questions.
There are 300 more icebreaker questions at the bottom of the article
How would you describe your job to a five year old?
What season would you be?
What is a weird food you have tried? Would you eat it again?
What is your favorite holiday tradition?
Would you go in the mother-ship with aliens if they landed on Earth tomorrow?
What is your favorite season?
Do prefer working from home or the office?
What is your earliest memory of this job?
What is the best thing you have bought so far this year?
What is the earliest book you remember?
If you had to move to another country, which one would you choose?
You are the best criminal mastermind in the world. What crime would you commit if you knew you would get away with it?
What is your favorite movie genre to watch?
What was the last thing you ate?
What person from history would you add to Mount Rushmore?
What is a weird fact you know?
What is your favorite part of working from home?
Were the Spice Girls a good team?
Imagine you can instantly learn any language. Which would you choose?
If you could live in any state, which state would you pick?
Which fictional team is the best team of all time?
What did you want to be when you grew up?
What do you usually eat for a quick lunch?
What simple food will you never eat?
Show us the weirdest thing you have in the room with you right now.
Would you rather stay at a hotel or an AirBNB?
What is your favorite movie genre to watch?
Are you more productive in the morning or at night?
Who is someone in your community that makes a difference?
Who was your most unique pet?
Choose one famous person from history you want on your team during a zombie apocalypse.
What is a good way to give back to the community?
Which song could you listen to over and over again?
Is Hugh Grant funny?
What is your favorite thing to eat for breakfast?
Would you want to have an imaginary friend today? Did you have one as a child?
What actor or actress would you want to play you in the movie about your life?
What is the best super power?
What is your New Years resolution?
You can only eat one food again for the rest of your life. What is it?
What is the best work holiday?
What is the first gift you remember receiving?
Would you rather join Metallica or Backstreet Boys?
What is the best example of a community you have seen?
What is an easy way to do something nice for someone?
Show us your phone background and tell the story behind why you picked this image.
What was your first job?
Pick any band to play at your funeral.
If you could have an unlimited supply of one thing for the rest of your life, what would you pick?
Which superpower would you give to your arch enemy?
What is the most obscure superpower you would want?
What emoji best describes how you are feeling right now?
If you could live in any country, which country would you pick?
Would you rather live in a city or a town?
What is your favorite holiday?
What is something you accomplished as part of a team?
What is your standard office lunch?
What is your most used phone app?
What is your favorite season?
Have you ever won something as a team?
Imagine you are a professional baseball player. What is your introduction song?
Beach holiday or ski trip?
Have you ever been to a funny comedy show?
Would you rather live at the North Pole or the South Pole?
What is your favorite song to sing?
If you could live in any state, which state would you pick?
Imagine you could teleport anywhere. Where would you go right now?
What is the most unusual job you have heard of?
What was the last thing you ate?
You can visit any fictional time or place. Which would you pick?
What do your family and friends think you do all day?
What movie do you wish you could watch again for the first time?
Show us your most-used emoji.
What was the most unique style or fashion trend you ever embraced?
What movie defined your generation?
You are stranded on a remote desert island. Are you alone or with your worst enemy?
What is your favorite knock-knock joke?
Have you ever told someone Santa is not real?
Do you know how to speak more than one language?
On a scale of 1 – 10, how much of a team player are you?
What is your #1 recommendation in this city?
What is your favorite holiday?
What bucket list item do you most want to check off in the next six months?
What is your favorite mythical creature?
What was the first way you made money?
If you could be great at any Olympic sport, which would it be?
Which song could you listen to over and over again?
When did you start liking/hating mushrooms?
Where is your favorite vacation spot?
Do you take your PTO all at one time, or another way?
Which show do you remember most from your childhood?
Which beverage goes best with pizza?
Would you want to have a personal assistant follow you around everywhere and do what you asked of them?
Have you ever met your idol?
What did you want to be when you grew up?
Would you rather live 100 years in the past or 100 years in the future?
What is your hobby?
When you are alone in the car, what volume is the music at?
Imagine you no longer have to work. How would you spend a Tuesday?
What is your favorite type of sandwich?

One-to-ones are a manager’s secret weapon.

They’re the perfect chance to make sure your reports are enjoying their work, feeling part of the team, and on track to hit all their goals.

And for your employees, their catch-ups with their manager is one of the clearest indicators of how well they’re performing and what their career prospects are. 

So it’s crucial that you put plenty of thought and care into making the most from the one-to-one time you have with each of your employees. 

Ask your reports the questions we’ve laid out here to make sure the one-on-one meetings you have with your team are as effective as possible.

What do you talk about in one-on-ones with your reports?

The meat of a successful one-to-one meeting should be spent on getting on the same page as your report about everything on their plate.  

For the best results, come prepared with a list of things you want to cover, but let your employee take the lead. This will give them the chance to mention everything that’s important to them, giving you a sense of what their focus has been on and whether anything is causing them stress. 

Then you can mention anything on your list they didn’t bring up. This can be an effective way of realigning your reports’ priorities without them feeling like they’re being micromanaged.  

At the end of every one-to-one, you should have established what your employees’ goals and targets are and whether they’re on track to achieve them. You should also be aware of any roadblocks you need to remove for them, as well as set expectations for what they need to get done before the next catch-up. 

Book a demo of Assembly to quickly and easily set up one-to-one meetings across your organization. 

How do you prepare for a one-on-one meeting with a direct report?

Most managers treat one-to-ones with their reports as a box-ticking exercise. But set aside just a little bit of time to prepare for yours and you can transform them into the most valuable meeting on your calendar.

Here’s how:

First, track down all the action items that came from your last one-to-one with your report. 

Run through your reports’ to-do lists with them in every one-to-one and they’ll know they need to have made progress on all the action items they agreed to during your last meeting with them. This simple practice makes it very obvious, very fast when someone isn’t managing their time well without you wandering into micromanagement territory.

Alongside your list of action items, note down everything you need to update your report on and any questions you have for them in a one-to-one template. This makes it easy to send them the agenda ahead of time so they have time to prepare, as well as add anything they want to cover themselves.

Taking the time to do this prep work before each one-to-one shows your reports they’re a priority, not an afterthought. 

Try Assembly to make it as easy as possible for your people to prepare for one-to-ones.

What are good questions to ask during one-on-ones with your reports?

Here’s a closer look at how to tick each of the boxes of the ultimate checklist for an effective one-to-one meeting with some simple questions:

Questions to make sure you’re on same page as a report

The most important part of any one-to-one is making sure your report is spending their time on the most important things on their to-do list.

If your team isn’t spending their time productively, they’re going to struggle to hit their KPIs. And the buck’s going to stop with you if you didn’t spot that early and correct course.

Which means it’s no exaggeration to say that your job depends on making sure your reports are working on the right things.  

So, if you only walk away from a one-to-one with a report with one thing, make sure it’s that they’re focusing on the most important things by asking questions like:

  1. What’s your priority right now?
  2. What progress have you made on the action items that came out of our last one-to-one?
  3. Is there anything blocking you from getting any of your tasks done?
  4. Is there anything I can do to help you get more work done?

Try Assembly to see how easy it can make staying on the same page as your teammates.

Questions to help spot how engaged a report is with their work 

An effective one-on-one meeting involves checking in with your employee on how they’re feeling, fitting in with the team, and enjoying their work. 

Giving each of your team members a space to open up about how they’re coping with any challenges they’re facing is a simple but incredibly effective way of making sure your team is happy and engaged. 

This is a particularly important step if you’ve sensed a member of staff has been a bit off or their performance has dropped. Simply asking them how they’re finding things lately and giving them a safe space to open up is often all it takes to get to the bottom of what’s been weighing on them.

Get a sense of how engaged your reports are with their work through questions like:

  1. What have you been enjoying about work lately?
  2. Is there anything you’re dreading about work at the moment?
  3. Have you been finding it easy to get into work lately, or have you been struggling to get into it?
  4. Do you feel challenged by work at the moment or like you're just going through the motions?
  5. Is there anything I can do to help make work more interesting and engaging for you?

Questions about a report’s career aspirations

You should also be regularly touching on your report’s career trajectory in your catch ups with them

Having an open dialogue with each of your team members about their career growth and how they feel that’s developing is one of the most effective things you can do to keep your staff engaged in their work and wanting to stick around.

Don’t make the mistake of leaving a candid discussion of your reports’ career aspirations until their performance review. Instead, ask them these questions during your one-to-ones:

  1. How would you like your role to evolve in the next year?
  2. Are there any extra responsibilities you’d like to take on right now?
  3. Are there any skills you’re interested in developing? 
  4. Do you see your future as a people manager or an individual contributor?
  5. Is there anything I can do to help you realize your career aspirations?

Questions to help improve a report’s performance

You don’t have to be a veteran people manager to know people hate to be told what to do.

Which puts you in a difficult position when it comes to letting a report know there’s an area they need to improve in. Tell them what they’re doing wrong and how to fix it and they’ll leave feeling patronized and embarrassed.

Luckily, some thoughtful questions can help you get your point across without your report losing face. 

Next time you need to give a report feedback on their performance, try these questions:

  1. Do you think there are any areas you could improve in?
  2. If I asked your teammates what your biggest area for improvement is, what do you think they’d say?
  3. What’s one thing you think you could start doing differently to improve that?
  4. What do you think the easiest way to improve that would be?
  5. What can I do to help you improve in that area?

The final word

Ask these kinds of questions during regular one-to-one meetings with your reports and you’ll lay a solid foundation for a happy, engaged, and loyal team that feel comfortable coming to you with any problem that they face.

Browse our Free Employee Recognition Guide

Get the foundational knowledge on creating an employee recognition program that boosts employee engagement and helps them feel valued.

Explore Guide
Employee recognition guide