24 Constructive One-on-One Questions to Ask Your Manager

Explore top 1:1 questions to ask your manager, tips for effective preparation, and strategies to maximize each session's value.

April 18, 2025
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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?

One-on-one meetings with your manager are invaluable opportunities for personal and professional growth. These sessions are not just about receiving feedback; they are a platform for open communication, career development, and building a stronger working relationship. 

To make the most of these meetings, it's crucial to ask the right questions. Here, we present a guide to essential questions that can help you gain insights, align with your manager's expectations, and advance your career.

The Importance of One-on-One Meetings

One-on-one meetings are a powerful tool for building strong relationships between managers and employees. They provide a platform for open and honest communication, allowing employees to share their thoughts, ideas, and concerns. 

Regular one-on-ones can help to:

  • Improve communication and reduce misunderstandings
  • Increase employee engagement and motivation
  • Enhance collaboration and teamwork
  • Identify and address performance issues
  • Develop and implement growth plans

Preparing for One-on-One Meetings

To get the most out of one-on-one meetings, it's essential to prepare in advance. Here are some tips to help you make the most of your meetings:

  • Set clear goals and objectives: Identify what you want to achieve from the meeting and prioritize your discussion topics.
  • Review performance data: Look at your recent performance, including successes and challenges, to inform your discussion.
  • Prepare questions and topics: Write down questions and topics you want to discuss, and be prepared to provide feedback and suggestions.
  • Be open and honest: Be willing to share your thoughts, feelings, and concerns, and be receptive to feedback and guidance.

What Questions Should I Ask During a One-on-One Meeting?

To improve your chances of advancing within your company and having productive meetings with team members, it is important to focus on a few key areas during every one-on-one with your manager—especially if they are new to the role. These include: clarifying expectations and goals, exploring career development opportunities, and identifying ways to boost productivity and efficiency. 

Here is a closer look at straightforward questions you can bring to any one-on-one.

Questions to Help You Understand Expectations and Goals

Understanding your manager’s expectations allows you to align your efforts with team and company goals, while also clarifying your priorities and responsibilities. By learning how your performance is evaluated, you can focus on the tasks and projects that matter most. 

Asking these questions about expectations demonstrates your commitment to supporting team objectives and helps you direct your efforts where they are most needed:

  1. What are your expectations for my role in the upcoming quarter?
  2. How do you measure success for my position?
  3. What are the team's top priorities right now, and how can I contribute?

Questions to Seek Feedback and Help You Improve

Constructive feedback is important for continuous growth, and asking for it shows your commitment to improving your skills and performance. By identifying key areas for development, you can create a focused plan for professional advancement. 

These sample questions highlight your openness to feedback and your drive to grow in your role:

  1. Can you provide feedback on my recent projects?
  2. What skills should I focus on developing to advance in my career?
  3. Are there any areas where you think I could improve?

Questions About Career Development and Opportunities

Gaining insight into potential career paths within the organization can motivate you and help shape your long-term goals. Showing interest in specific projects may open doors to opportunities that align with your aspirations. 

Asking about these topics reflects a team-focused mindset and a willingness to contribute to shared objectives. Here are a few examples:

  1. What opportunities for advancement do you see for me in the company?
  2. Are there any upcoming projects that align with my career interests?
  3. How can I better support the team and contribute to our success?

Questions to Help You Build a Stronger Relationship

Offering support to your manager demonstrates a proactive attitude and can help strengthen your working relationship. Learning their preferred communication style also enhances collaboration and leads to more effective interactions. 

Here are some questions to show your dedication to building a positive, productive dynamic with your manager:

  1. How can I make your job easier?
  2. What communication style do you prefer?
  3. Is there anything I can do to improve our working relationship?

Questions to Help You Navigate Challenges and Changes

Proactively addressing potential challenges showcases your problem-solving abilities and readiness to handle issues directly. While gaining insight into your manager’s approach to conflict resolution and staying informed about upcoming changes enables you to adapt quickly and stay aligned with your team’s goals. 

Here are some examples:

  1. What challenges do you foresee for our team, and how can I help address them?
  2. How should I handle conflicts or disagreements within the team?
  3. What changes do you anticipate in our department, and how should I prepare?

Questions to Enhance Productivity and Efficiency

Asking about productivity tools and time management strategies demonstrates your commitment to working efficiently and continuously improving. It also helps you manage your workload and concentrate on high-impact tasks. 

A few sample questions include:

  1. Are there any tools or resources you recommend for improving my productivity?
  2. How can I better manage my time to meet deadlines and deliver quality work?
  3. What are some best practices for prioritizing tasks?

Questions to Encourage Open Communication

Setting a regular meeting schedule promotes consistent communication and ongoing feedback. It also encourages open dialogue and helps you better understand your manager’s communication preferences. 

Some questions to ask are:

  1. How often would you like to have one-on-one meetings?
  2. Is there anything you wish I would communicate more frequently?
  3. How can I ensure that I'm keeping you informed about my progress?

Questions about Fostering a Positive Work Environment

Showing a willingness to help create a positive work environment and  help your peers strengthens collaboration and team dynamics shows your dedication to fostering a supportive team culture. 

A few question to ask might be:

  1. What can I do to contribute to a positive team culture?
  2. How can I support my colleagues in their roles?
  3. What do you enjoy most about working here, and how can I contribute to that?

Parting Thoughts

One-on-one meetings are a powerful tool for career development and building a strong relationship with your manager. By asking thoughtful and constructive questions, you can gain valuable insights, align with your manager's expectations, and identify opportunities for growth. Use these questions as a guide to make the most of your one-on-one meetings and advance your career.

The key to a successful one-on-one meeting is open communication and a genuine desire to learn and grow. Approach each meeting with a positive attitude and a willingness to engage in meaningful dialogue. By doing so, you'll not only enhance your professional development but also contribute to a more productive and harmonious work environment.

FAQs

What are the benefits of having regular one-on-one meetings with your manager?

Regular one-on-one meetings help improve communication, build trust, align priorities, and provide valuable feedback for career growth. They also create opportunities to discuss challenges, set goals, and strengthen the manager-employee relationship.

How can I make my one-on-one meetings more productive?

To make your one-on-one meetings more productive, prepare an agenda with key topics, bring questions related to your performance and career growth, actively listen to feedback, and follow up on action items discussed in previous meetings.

What should I avoid during a one-on-one with my manager?

Avoid being unprepared, dominating the conversation, or only focusing on negative topics. Instead, balance your discussion with progress updates, constructive feedback, and career aspirations while maintaining a professional and solution-oriented approach.

How do I follow up after a one-on-one meeting with my manager?

After your meeting, send a brief summary of key takeaways, action items, and deadlines discussed. Regularly check in on progress before your next meeting to ensure alignment and accountability.

Browse our Free Employee Recognition Guide

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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.

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