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.

February 29, 2024
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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 on one conversation 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.

Book a Demo with 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 meetings with other team members, 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?

Book a demo of 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?

8 Q&A Tips for One-on-One Meetings with Your Manager (Beyond the Basics)

1. My manager seems hesitant to answer some questions directly. What should I do?

Remain calm and professional. Briefly rephrase your question for clarity. If they continue to avoid the topic, it might be best to table the discussion for later or seek guidance from HR if necessary.

2. How can I handle disagreements with my manager during a one-on-one?

Approach the situation respectfully. Express your perspective calmly and professionally, focusing on solutions rather than accusations. Be open to hearing their perspective and explore potential compromises.

3. How often should I schedule one-on-ones with my manager?

The frequency depends on your workload, company culture, and individual preferences. A common timeframe is bi-weekly, but discuss with your manager to establish a mutually agreeable schedule.

4. I'm hesitant to ask certain questions, even though they're important. What can I do?

Consider writing down your questions beforehand to gather your thoughts and practice phrasing them respectfully. You can also preface your question by expressing your hesitation and emphasizing your desire to learn or understand.

5. Can I use these same questions with a potential new manager during an interview?

While some questions like understanding priorities and career development opportunities are relevant, tailor most questions to the specific role and company. Focus on acquiring information about the position and team dynamics, showcasing your research and genuine interest.

6. What if my manager doesn't ask me any questions during our one-on-one?

Don't wait for them to initiate all the discussion. Come prepared with your agenda and questions, and gently guide the conversation towards mutually beneficial topics.

7. How can I ensure my one-on-ones are balanced, covering both work and personal goals?

While the main focus is work-related, briefly mentioning personal goals or aspirations can demonstrate your overall well-being and commitment. However, maintain professionalism and avoid oversharing.

8. Is it appropriate to take notes during the one-on-one meeting?

Taking notes demonstrates your attentiveness and helps you recall key points later. However, ask your manager's permission beforehand and ensure your note-taking doesn't hinder the conversation flow.

Remember, one-on-one meetings are a valuable opportunity for both you and your manager. Use these questions as a starting point, adapt them to your specific needs, and prioritize open and respectful communication for a successful outcome.

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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Frequently Asked Questions

Is Assembly SOC 2 compliant?

Yes, at Assembly, security is a top priority. Each quarter, we have ongoing security work that is everyone’s responsibility. While we maintain a strong security posture, it was important for us to prove to our customers that we do everything we claim to do. This led us to pursue a SOC 2 Type II report that would provide evidence of our compliance with industry gold-standard security practice.

What's the ROI for employee recognition?

There is study after study showing that employee recognition leads to increased engagement. This in return creates an environment where employees are happier and more motivated which increase productivity and reduces voluntary turnover significantly. In order to filled critical roles, companies tend to spend nearly twice the value of an annual salary. Assembly is an investment in your employees that supports your bottom line.

Does Assembly offer longer-term contracts?

Yes, we will offer contracts for companies with longer-term agreements to help larger customers have more certainty around future costs.

The minimum agreement term is a 12-month subscription.

Does Assembly offer onboarding support?

We do and for FREE! Any new customer needing further support to get started with Assembly to ensure you're set up for success can request custom onboarding support. Improving your employee experience is about much more than just using our amazing software; it’s about transforming your business to create a workplace that people love. That’s much easier to do with the personal support and advice from our passionate people experts.

Is there a free version of Assembly?

Yes. We offer a completely free plan for up to 50 team members. This plan is intended for teams or organizations that are looking to get started with an employee engagement tool. Keep in mind, this plan is limited in features.

All customers can open an Assembly account for free and get started without a credit card. Then you can change plans as necessary.

How much do rewards cost?

At the time of redemption (when your employees exchange their points for a paid reward) you'll pay face value. If a reward is a $10 Amazon gift card, your cost will be $10. All paid rewards are billed for on a monthly basis.

The good news is that you don't have to pay for rewards upfront because we only charge you when points are redeemed, not when they're earned.

Does Assembly offer discounts?

We offer discounts or educational or charitable organizations. In order to secure a discount, you'll first need to book a demo with a customer support specialist.

For all other organizations, we are willing to consider longer-term agreements in exchange for discounts. To set up annual plans or longer, you will need to book a demo with a customer support specialist.

How do I cancel my plan if needed?

If you're on a month to month plan, you can go here and cancel anytime. If you're having concerns or need help setting up your account for success, you can always book a demo with a customer support specialist.

If you're on a longer-term custom plan, you'll need to reach out to your customer support specialist to cancel your account or email us at support@joinassembly.com.

What customizations are available?

Great question! You can customize your core values to match your organization's to boost and track alignment. You can change your currency from the 🏆 emoji (our default) to any emoji of your choice. You can swap our logo for your own. You can also set up company culture rewards such as, "Lunch with the CEO," "Buy a book on us," and so much more!

Who can give or receive recognition?

While we recommend a peer to peer set up where anyone in your organization can give or receive recognition, you can set up Assembly however you want. If you need to limit the people who can give or receive recognition, that's perfectly fine and can be done from your Admin, here.

What integrations are available?

Assembly connects to the tools your employees use every day to offer an easy, seamless experience with minimal change management.  

Assembly has integrations with HCM/HRIS systems like ADP, Google, Office 365, and Slack. We also integrate with communication tools like Slack and Teams so you and your employees can access Assembly wherever they work now.

What's your average adoption rate?

That depends on the company's permissions set up. That said, over 90% of the employees on Assembly's platform are recognized on a monthly basis. That means nearly every employee across all of our customers are receiving regular recognition from their peers, managers, or leadership. We're extremely proud of this.

Must rewards be set up to use Assembly?

They are not required. You can use Assembly without having rewards set up. However, we don't recommend it if you intend to have a high adoption and usage rate. You can always keep the costs down by offering internal culture rewards that are fulfilled by you internally.

Are points required to use Assembly?

No, you can remove allowances from anyone or everyone. It's up to you but we do recommend using points whether they're worth a real dollar value or not. Companies that use points have a much higher engagement rate even if those points don't exchange for real dollars.

Could find the answer you are looking for?

Please schedule time with an expert and we will help you to get all your questions answered