Knowing What to Ask (and When) in One-on-One Meetings

Discover the questions that will take your 1-2-1s with your boss from casual catch-ups to the most valuable hour on your calendar

October 19, 2022
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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?

Ask your manager the right questions at the right time during your one-to-ones and you can transform them into the most valuable meetings you have all month.

Read on for our pick of simple questions you can use to get on the same page as your boss, make sure you're doing your best work, and get on the right track to grow your career. 

How to ask for a one-on-one meeting with your manager

Regular one-on-ones are your ticket to career success.And any manager worth their salt knows one-on-one meetings are their secret weapon and will make sure you’ve got a regular facetime set in stone on the calendar.

But maybe you’ve got a new manager who hasn’t got around to setting up a regular meeting time yet. Or things got busy and your one-to-one meetings got dropped and haven’t been picked back up again.

Whatever the reason you don’t have regular meetings in the diary with your boss, here’s a simple email script you can use to set them up:


I’d love the chance to meet with you regularly to make sure we’re on the same page about how I should be spending my time (and to find ways I could be making your job easier for you).

Could we set up a regular half-hour check-in every few weeks? 

Happy to meet at a time that suits you, so let me know when would best work for you.


What manager wouldn’t want to receive an email like that? That simple script should get you a regular one-to-one in the calendar in no time.

What do you discuss in a 1-on-1 with your manager?

You’ve got a regular one-to-one meeting with your boss on the calendar.

But what do you talk about?

Well, this face-to-face time with your boss is the perfect opportunity to:

  • Make sure you’re spending your time on the right things. If you and your manager aren’t on the same page about what you should be prioritizing you could both have some serious headaches to deal with down the line.
  • Find out what you could be doing better. Feedback from your boss on what areas you could do with improving in – as well as what your greatest strengths are – can do wonders for your career development.
  • Plan your career growth. A good manager can help you develop the skills and gather the experience you need to take the next step in your career.
  • Discover better ways of working together. Get to grips with the way your boss likes to do things and you’ll quickly become an indispensable member of their team. 

You might not want to cover all of these bases in every one-to-one. But regularly touching on these four areas will help you manage your relationship with your manager as effectively as possible.

What are good questions to ask managers?

You're wasting a huge opportunity if you don’t use your facetime with your manager to make sure you’re both on the same page – and that you’re doing what you need to be doing to land a pay rise or a promotion.

Ask these constructive questions during your one-to-ones to make sure you’re on track to fulfill your career ambitions: 

Priorities to focus on 

The most important part of any one-to-one is making sure you’re not spending your time barking up the wrong tree. Fail to ask the questions that would have got you on the right track and you could seriously set your career aspirations back – or even risk being out of the job.

Make sure you’re walking away from every one-to-one knowing exactly what you should be spending your time on by asking questions like:

  1. What should be my priority right now?
  2. Is there anything I shouldn’t be spending time on right now?
  3. Here’s what’s on my to-do list. Should I add or remove anything?
  4. What do you want to be done before our next one-to-one?
Career growth and personal development 

Having your manager in your corner will open all kinds of doors for you to grow your skills, take on more responsibility, and climb the corporate ladder.

Ask these questions in your one-to-ones to show your manager you’re ready to take on opportunities when they show up:

  1. Where do you see my role evolving in the next year?
  2. Are there any extra responsibilities I can take on right now?
  3. If I could improve one skill before our next one-to-one, which would you choose?
  4. What skills do you think our team is lacking?

Some bosses like to receive regular updates on what you’ve been up to while others aren’t interested in the day-to-day as long as deadlines are getting hit. Some would prefer you ask for sign-off on your ideas, others that you just let them know how they went. Some prefer to speak over the phone, others over email.

Ask these questions during your one-to-ones to get to grips with how your manager like to communicate:

  1. How do you like to receive updates about my work?
  2. What parts of my work do you want to be kept up to date on? And how often?
  3. When’s the best time to get feedback on my work performance?

The people who tend to go the furthest in their careers are the ones who are most open to receiving feedback.

Your manager has been around the block a fair few times more than you. They’ve more than likely been there, seen it, and got the T-shirt when it comes to any problem you’re facing. 

Ask them these questions during your one-to-one meetings and you’re bound to get better at what you do as fast as possible:

  1. What do you wish I did less of? More of?
  2. What are my biggest weaknesses? My greatest strengths?
  3. Where do you think I should be focusing more of my attention?
  4. What do you wish I took more ownership over?

When should I ask my questions in a one-on-one?

Here’s the flow of a good one-to-one.

A status update

You should always start a one-to-one by getting your manager up to speed on everything you’ve been working on, what’s next on your to-do list, and any blockers holding you back from being able to get your work done.

To make sure this part of your one-on-ones are successful, keep a running list of everything you need to update your manager on in a one-to-one template. Then you can simply pull this up and run through it with your boss in your next meeting.

Ask how you can help

A simple way to become invaluable to your manager is to take a moment to ask them how you can help make their lives easier.

This isn’t complicated, but it’s rarely done. The easier you can make your boss's life, the more responsibility they’re likely to give you. And the more responsibility you have, the more likely you are to land a pay rise or promotion. 

You’ll seriously set yourself apart from most of your colleagues by taking a moment in your one-to-ones to ask your manager questions like:

  • Is there anything I can help you with?
  • What are your priorities at the moment?
  • If you could have one thing handled for you, what would it be?
Ask your questions

Last but not least, it’s time to ask any questions you have for your manager. You probably don’t want to touch on every base in every one-to-one. But regularly asking about your career growth, how you can communicate better, and whether you can be doing things better will help you grow your career as quickly as possible.

The final word

Finishing up your one-to-ones with the questions we've listed out here is a simple but incredibly effective way of pouring rocket fuel on your career growth. 

Stick to these tips – as well as preparing properly for your one-to-ones and keeping the one-to-one do’s and don’ts front of mind – will help you make sure you’re always having effective one-to-one meetings with your boss.

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