24 Constructive One-On-One Questions To Ask Your Manager

Ask your manager these questions during your 1:1s to take control of your career growth and fast-track your skills development.

August 25, 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?

Armed with the right questions, you can transform your one on ones with your manager from casual catch-ups to the most valuable hour on your calendar.

Read on for our pick of the very best one on one meeting questions for anyone looking to take their personal and professional development into their own hands.

How Do You Prepare For A One-On-One Meeting With Your Manager?

Turn up to a one-to-one with your manager unprepared and you’ll pass up the perfect chance to get clear on what you need to do to get on track for a promotion, pay rise or professional development opportunities. 

An easy and effective way to prepare for a check-in with your manager is to note down smart questions to ask your boss ahead of time in a one-to-one template. This will lay the groundwork for a productive one-to-one where you and your boss touch on everything that’s important to you.

Your manager will appreciate it if they can always trust you (and other direct reports) to come to your meetings with a list of talking points , questions for first 1:1, constructive feedback and action items prepared.

Try Assembly to make it as easy as possible for your people to prepare for one-to-ones, geet good topics for manager meetings and get comfortable with a 1-1.

What should I ask my manager during a one-on-one?

To give yourself the best chances of rising up the ranks in your company and having great team meetings, you should look to establish these things in every one-to-one with your manager (especially a new boss):

  • That you’re on the same page as your manager in terms of what your priorities should be
  • That you understand how to effectively manage up
  • That you’re on the right path to achieving your career growth goals
  • That you’re doing your best work

Here’s a closer look at how to tick each of those boxes with some simple questions you can ask in any one-to-one.

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

Questions to ask boss to make sure you’re on same page as your manager

The most important part of any one-to-one is making sure you and your manager are on the same page when it comes to how you should be spending your time.

Focus on the wrong to-dos and you could have a stressful performance review session, set your career aspirations back, and potentially even put your job security at risk.

If you only walk away from a one-to-one with one thing, make sure it’s that you’re spending your time on what your manager wants you to by asking questions like:

  1. What should be my priority right now? (were my priorities this past week the right ones?)
  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’s our team’s priority at the moment?
  5. What do you want to be done before our next one-to-one?

Try Assembly to see how easy it can make staying on the same page as your teammates and knowing what question to ask your manager (don't forget about the free 1-2-1 meeting template).

Questions To Help You Manage Up

Some bosses like to be kept in the loop with everything through a daily update. Others prefer you to figure out the small things yourself and only come to them when you need help on the big decisions.

Some managers like to communicate through Zoom calls, others through Slack. Some prefer their reports to take the lead on one-to-ones, while others like to set the agenda.

Do you know how your manager likes to work or what their management style is?

Figuring this out and adapting to it is one of the smartest things you can do for your career prospects and your professional relationship (plus it shows off your leadership skills). In addition, work-life balance becomes easier and more enjoyable.

Ask these manager feedback questions during your one-to-ones to quickly get to grips with how to best manage up (or jot them down in your meeting agenda):

  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?
  4. How can I make your life easier?
  5. What are your priorities right now?
  6. What’s worrying you the most at the moment?
  7. Is there a team member that needs help?

Questions About Your Career, Professional Growth, and Career Path

If your manager is in your corner they can open all kinds of doors for their employees to develop grow your skills. They can help you take on more responsibility, and build progress within the company.

Letting them in on your career goals and aspirations is therefore one of the best things you can do for your career growth and overall employee performance. After all, they’re the person who’ll have the biggest impact on where you’re heading beside yourself. You might be surprised about how far they can help you go.

Think about it from their point of view. Who are they going to trust with more responsibility: a teammate who doesn’t show any interest in stepping up, or a direct report that makes a point of discussing their career growth in each of their one-to-ones?

So, be sure to ask these career development 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?
  5. What steps can I take right now to progress my career with the company?
  6. What learning and development opportunities are there within and outside of the company?
  7. How can I improve my management skills to become a successful manager in the future? What do you look for when hiring managers?

Questions To Help You Improve Your Performance

If your manager could pick a dream trait for their reports to have, it would probably be a desire to seek out and listen to feedback

Any manager worth their salt can help you get better at your job. Taking the initiative on soaking up the wisdom they have to offer will not only fast-track your skills development. It’s also a surefire way to form a great working relationship with them.

These are the questions to ask a supervisor during your one-to-one meetings to get better at what you do as fast as possible:

  1. What do you wish I did less of? More of? Where should I spend some focused collaboration time?
  2. What are my biggest weaknesses? My greatest strengths?
  3. Where do you think I should be focusing more of my attention?
  4. Should I put more focus on improving my soft skills or my hard skills?
  5. What do you wish I took more ownership over?
  6. Do I have any blind spots that are holding me back?
  7. Is there anyone in the company you think I could be learning more from?

The Final Word

There's a lot of traditional wisdom that says you shouldn't ask too many questions when meeting with your manager, especially questions to ask a new manager, or you risk seeming like you know it all. That's not the case (or shouldn't be with good company culture).

Good questions can get your manager to see things from a different (often better) perspective and learn more about your personal life.

The right questions will help uncover areas that need to be strengthened or improved and make your 1-1 meetings with your manager more productive (check out these questions for how to provide useful feedback for managers).

And whether or not you ever get to ask your manager these questions directly, they're a great way to evaluate your current job situation. You can use them to gauge where you stand career-wise and make sure you have a strong handle on your work-life balance. Keep these in mind as questions to ask new managers and set yourself up for success.

Take your one-to-ones with your manager to the next level with these simple questions, our five tips to make one-to-ones successful, and our advice on how to give meaningful feedback to a manager.

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