28 Questions to Ask Your Boss in Your One-on-Ones

Good one-on-one meetings between managers and their direct reports address the practical and personal needs of the employee, benefitting their performance, growth, and well-being, as well as the success of their team and the broader organization. However, since managers are typically the ones who run these meetings, the employee’s needs are often forgotten. Then it’s up to the employee to ask questions to get the attention they need. The authors’ research points to twenty-eight questions that can drive the best conversations.

When she started a new role, Brianna was told she would be having regular one-on-one meetings (1:1s) with her manager, Jayden. She welcomed this news; she saw it as a great opportunity to get aligned with and supported and mentored by her new boss. But her hopes were quickly dashed. In their initial meeting, Jayden focused only on project updates and then assigned her a few additional tasks. This pattern continued over the weeks and Brianna routinely left their meetings feeling both micro-managed and unsupported in her development.

This story is, sadly, a composite of many we have heard from employees in our research on 1:1s between managers and their direct reports. As one of us (Steve) described in a new book, Glad We Met: The Art and Science of 1:1 Meetings, a good one-on-one meeting addresses both the practical and personal needs of the employee (practical: information, instruction, alignment; personal: the need to be treated with consideration, respect, trust, and support). As such, these meetings are a critical source of growth and support for the employee and promote the thriving and success of teams and the broader organization.

But these benefits are only realized when the meeting includes frequent conversations that address those employee needs. And as 1:1s are typically facilitated by managers, they often devolve into addressing what is front of mind for them, rather than the employee. That’s especially true because it is very rare for managers to receive training on how to run these meetings well, so they often simply recycle dysfunctional practices they themselves have experienced.

If you are in Brianna’s position — if your boss’s approach to your 1:1s has left you feeling unsupported and unheard — you should feel empowered to direct the conversation toward your needs yourself. You can do this by asking smart questions.

Questions to Ask

Based on published research as well as data we collected from nearly 200 employees on important topics to broach in a 1:1, we have identified 28 key questions in seven broad categories to help you get the most value from your check-ins with your boss. You can use, adapt, and put these into your own voice as you see fit.

Ask for Guidance and Input

Use these questions to get help from your manager on any tasks or projects you are having difficulty with, or to express your need for additional resources, input, or support.

  1. I am having some challenges and struggles with X. Can you help me think about how to navigate and address X successfully?
  2. Could you suggest any ideas and thoughts around how I could get more support (people, time, funding) to help with Y?
  3. What do you think of my idea Z? Do you have any suggestions for how to improve it? Or, might you have an alternative idea I should consider?

Clarify Priorities and Expectations

To be sure you are on track and working efficiently, make sure you and your manager are on the same page. Ask for clarification on what tasks need your most focused attention from their point of view.

  1. Given what is on my plate, what should I be prioritizing right now, and can you help me understand why?
  2. As you review my workload, am I taking on on the right projects and tasks?
  3. Am I on track for meeting my goals and your expectations from your perspective? Is any any refocusing necessary?
  4. Is there any context I might be missing about the projects I am working on? For example, what is the reasoning for doing project X? 

Align with the Organization and Its Strategy

Ask questions to understand how your role relates to the broader strategic goals of the organization and the way its leaders are thinking about the future.

  1. What is going on further up the tree (or in other parts of the organization) that would be helpful for me to know as I work on my key tasks?
  2. To better help me understand the big picture, how does the work I’m doing or the assignment you just gave me fit into the broader goals and strategy?
  3. Is there anything that the management team is working on or considering that you think I should know about at present given its potential impact on my role?
  4. What is new in our strategic priorities as a company that you feel I should know about, if anything?

Seek Growth Opportunities and Career Advancement

Come to the meeting with your thinking (however inchoate) around your professional short-term and long-term goals and ask your manager what steps you should take to get there.

  1. I would value your counsel. What can I do to prepare myself for greater opportunities or to pursue X interest of mine?
  2. As you reflect on where the organization is going, do you have any thoughts on how I should improve and develop to best align?
  3. What strengths do you think I have and how might they be helpful in the future?
  4. From your perspective, what should I be targeting as my next career move and why do you recommend that position?
  5. How can we make sure that my skillset is put to the best use to support the team and the organization?
  6. How can we make sure that my full potential is achieved?

Get Feedback on Your Performance

Check in with your manager to see how you are doing, performance-wise. You shouldn’t make every meeting into an official performance evaluation, but it is important to periodically check in and calibrate if your manager isn’t doing that themselves.

  1. Am I meeting your expectations? I would relish learning your perspective on my work performance.
  2. What feedback might you be able to share with me about how I’m doing at X or Y task?
  3. Do you feel I have any spots I’m overlooking when it comes to A or B?
  4. As you reflect on what I do at work, what should I start, stop, or continue doing?

Build a Relationship

Your 1:1 is a critical place for you to build and nurture your relationship with your manager. Allocate time at the beginning or end of the meeting to connect with your manager personally.

  1. How is your day going?
  2. How are things going for you overall? Are you doing ok?
  3. What is something you are excited about outside of work?
  4. Is there anything you would like to know about me? (If needed, be prepared to say “I don’t feel comfortable sharing that, but here’s something else you should know about me.”)

Offer Support

Consider ways in which you can help your manager achieve their goals and fulfill their role. Managers need assistance, reassurance, and support to optimize their efficiency and performance. Just like you’d expect your manager to support you, see how you can lend them a hand. This will also increase the chances of you getting what you need in the 1:1.

  1. What are your priorities over the next X days? What can I do to help you with this?
  2. Where can I offer you support?
  3. Is there anything keeping you up at night that I can help with?

How to Use the Questions

For each 1:1 meeting, pick a category or two to focus on. You can’t address them all in every meeting, so you will need to rotate or pick the most relevant at a given time. Likewise, choose sparingly from among the questions — no need to ask them all at one time. You’ll simply want to sample from all categories over time.

Don’t hesitate to follow up on your manager’s responses to your questions. A great follow-up is often simply “why?” You’ll glean strategic insights into the rationale, motives, assumptions, and big picture behind your day-to-day work.

Good 1:1 meetings with your manager are critical for your success and the success of your team and organization. Asking the right questions to make sure those meetings give you what you need can have a huge impact on your work experience — helping you stay engaged, developing your understanding of your role and place in the organization, and improving your relationship with your manager — not to mention enhancing your well-being.

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