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60 Great Questions to Ask your Boss in a One-on-One Meeting

Leverage your growth and potential by trying out these 60 questions to ask your manager in one-on-one meetings!

By Alexandria Hewko  •   September 1, 2023  •   8 min read

One-on-one meetings are a great time to build rapport with your manager, align on your career growth goals, and work through any challenges you’re facing. If you’re just starting your career or you’re new to having one-on-ones, you might find it nerve-wracking to be highly engaged in those meetings with your boss. It can be especially hard to give or receive feedback from your manager on those calls, too. Yet, one-on-one meeting time is super important for your growth and development—and it’s all about you, so you should make sure to come prepared with plenty of questions to help fuel your career journey! 

How to prepare for a one-on-one with your manager

For most employees, one-on-one meetings with their manager will take place for an hour every week or two. To make the most of your time together, you should come prepared with any questions and concerns that have been top of mind since your last check-in. Keep track of these talking points in a meeting agenda that will be shared with your manager at least one business day ahead of your call. This gives your manager a chance to review them ahead of time and prepare any answers. 

As a bonus, if you write down your questions as you think of them during the week, you’ll be building your agenda as you go! Then, on the day of your one-on-one, you can use the list of questions as a guide for your meeting to make sure each concern is addressed. If you’re looking for inspiration on how to structure the agenda or what kinds of questions you can ask in this type of meeting, take a look at this one-on-one meeting template. If building meeting agendas is new to you, you can also look to AI meeting assistant tools to automatically generate a one-on-one agenda! 

60 questions to ask a manager in a one-on-one meeting

Questions about growth and development 

The primary purpose of hosting a one-on-one meeting between an employee and a manager is so that you both ensure there is time to talk through your career plan, overall well-being at the company, and blockers in your role. Most of your meeting time will likely revolve around these topics, so spend extra time brainstorming what you’d like your manager to help you with in these areas.

  • Given my skills, abilities, and interests, what roles do you see as suitable for my future?
  • Which skills should I improve to do better in my job?
  • What skills do I need to develop for career growth?
  • Are there responsibilities I can take over for career development or network building?
  • Is there any way I could be given responsibility for X? I think I am suited to it and it will help me develop my career.
  • Can you please help my development in X with coaching or training?
  • In your opinion, what is holding me back?
  • What do you think my blind spots are?
  • In your opinion, what are some strengths on which I should focus?
  • With whom should I develop a better working relationship? Can you facilitate an introduction or co-working opportunity?
  • Can you give me an example of how to improve my work based on a recent project I’ve completed?
  • How does my current performance align with where you’re expecting me to be? 
  • Where would you like my performance and skill levels to be in three months from now?
  • How would you describe my working style?
  • If I could focus more intently on one area of my role, what would that area be? 

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Questions to ensure alignment 

There will be plenty of days when you and your manager are too busy or distracted to be able to sync on project goals, timelines, and solutions. Using this one-on-one time together to unblock your challenges will allow you to work faster in your independent time—and it gives you a boost of confidence to know you’re working in the right direction, too! 

  • What are your top priorities?
  • Looking at my to-do list, what is the higher/lower priority? Should anything be prioritized/delayed?
  • What am I expected to report on, and how frequently do I need to deliver those reports? To whom will I present this, and in what manner?
  • Is there a quota or quantitative target for which I should aim? By when do I need to achieve that target?
  • How will I be rewarded for achieving my targets or goals? 
  • Where can I see my progress on my goals? 
  • On whom should I lean for support while you are away on holiday? 
  • Who is the best person to help me answer a question about [product, campaign, or process]? 
  • What is the process to follow if I am having a disagreement with a colleague over a project decision that I’m overseeing?
  • Is there anything I can do differently to help the team right now? 
  • If someone other than you assigns me a task for which I’m not sure I am responsible, what should I do? Who is allowed to assign me work?
  • What is the date of my next performance review? What will I be measured on?
  • What organizational technology or tools should I use for each task for which I am responsible?
  • What is the process for getting budget approval? Does the designated approval person change depending on the amount of budget needed?

Questions about the company culture and motivation

The company’s culture shapes many everyday factors like how colleagues communicate, how fast work is expected to be completed, which activities should be a priority, or how to resolve conflict. The motivation within a company is also impacted by the culture, the organizational mission and values, as well as the compensation and rewards that the team receives. 

  • What is the company’s mission and values? 
  • What is the leadership team doing to actively practice the company values?
  • Am I measured based on any factor related to aligning with the company culture, such as how well I practice the company values?
  • How are teams rewarded for good work? Will the same rewards apply to me?
  • How frequently are compensation increases distributed, and what factors measure the level of increase earned? 
  • How fast is the company growing, and what are managers doing to support that growth rate?
  • If I need time off for a personal responsibility or medical appointment, how do I get the time off? Will it be paid or unpaid time off?
  • What tools or resources are available to me to support my mental health in the workplace?
  • What is the company doing to support work-life balance? Is there anything specific you are doing differently for your team?
  • How does the leadership team keep the rest of the organization in the loop about results and upcoming plans for the company?
  • Does the company support remote work? Are there specific geographic regions that we’re limited to working in?
  • In meetings, do I need to have my camera on? 
  • To whom should I talk if I feel there is something uncomfortable or wrong in the workplace environment? 
  • What is the process for dealing with conflict?
  • What are the most common communication channels for  [process, team, or project]? 

Questions for managing up

A great way to showcase your own management skills is to manage your own boss a little bit. This means providing feedback, holding them accountable on their promises, and helping them improve, too. 

  • When can I expect feedback on X?
  • What is your standard availability if I would like to book extra time with you?
  • What do you need support with right now?
  • What can I do more/less of to ease your responsibilities?
  • Do you have enough availability to help me with X?
  • What can I expect from you during [project or process]?
  • Who else can help me solve this problem?
  • X is one thing that I would like you to do more of to help me do X; can you do that?
  • Where can I find the information for X?
  • Who will be responsible for approving this decision? Can I reach out to them directly?
  • What makes you feel confident about your team?
  • What goals are you expected to achieve right now?
  • What is your preferred form of communication?
  • How much of [process] would you like me to take over?
  • When is a good date to check in with you about X? 

5 Minute video recap

Bonus! Tips for asking good questions

Effective questioning during a one-on-one meeting with your manager can pave the way for better communication, personal growth, and job satisfaction. Here are the top 5 tips for asking good questions in those settings:

1 Prepare in advance

Don’t go into the meeting without some preparation. Take the time to jot down the questions or topics you wish to discuss in your meeting agenda. This allows you to articulate your thoughts clearly and ensures that you don’t forget to address key issues. Knowing what you want to ask will also make the meeting more efficient.

2 Be specific and clear

Ambiguous questions often result in vague answers that don’t provide much insight. Make your questions as specific as possible to get actionable and meaningful feedback or instructions. For example, instead of asking, “How can I improve?”, you could ask, “Could you provide some specific examples of how I could improve my project management skills?”

3 Prioritize your questions

Make sure to prioritize your questions, starting with the most pressing or important ones. Organize your meeting agenda in Fellow to ensure the most important questions are the first in the agenda. This ensures that critical topics are addressed even if you can’t get through your entire list. It also signals to your manager what you consider to be the most crucial issues needing attention.

4 Ask open-ended questions

Open-ended questions invite discussion and give your manager an opportunity to provide detailed feedback. Questions like “Can you help me understand what the priorities are for our team this quarter?” or “What are your expectations from me for this upcoming project?” can provide you with valuable insights.

5 Be open to feedback and follow-up

When you ask a question, be prepared for the answer, even if it’s not what you want to hear. Use the opportunity to delve deeper by asking follow-up questions. For example, if your manager suggests you need to improve in a particular area, you could ask, “Could you provide more details or perhaps suggest some resources that could help me improve?”

Free one-on-one meeting template 

As you jump into one-on-one meetings, you can try a meeting template to give you some inspiration and structure for your next check-in! 

Parting advice 

Knowing which questions to ask your manager in a one-on-one meeting is essential to help you make the most out of your time together. Thoughtfully preparing for your one-on-one is important for ensuring you ask the right questions, but it does require you to set aside some reflection and organization time in advance. If you need a little extra help, Fellow’s new AI feature helps you automatically create a meeting agenda for your next check-in with your manager—saving you time and allowing you to be prepared!

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