managemnet company strategy managemanet 28 Questions to Ask Your Boss in Your One-on-Ones

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

28 Questions to Ask Your Boss in Your One-on-Ones post thumbnail image

Good one-on-one meetings between managers and their direct reports address the practical and personal needs of employees, benefiting their performance, growth, and well-being, as well as the success of their team. and the wider organization. However, since managers are often the ones running these meetings, employee needs are often overlooked. 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 stimulate the best conversations.

When she started a new role, Brianna was told she would have regular one-on-one meetings (1:1s) with her manager, Jayden. He accepted this news; he saw this as a good opportunity to interact and be supported and taught by his new employer. But his hopes were quickly dashed. In their initial meeting, Jayden only focused on project updates and then gave him some additional tasks. This pattern continued for weeks and Brianna often left their meetings feeling both micro-managed and unsupported in her progress.

This story, unfortunately, is a composite of many that we heard from employees in our research about 1:1 between managers and their direct reports. As one of us (Steve) described in a recent book, Pleased to Meet: The Art and Science of 1:1 Meetings, a well-integrated meeting addresses the employee’s practical and personal needs (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 growth and success of the teams and the wider organization.

But these benefits can only be realized if the meeting involves constant conversation responding to the needs of employees. And as 1:1 is usually facilitated by managers, they often devolve into answering what is on their mind, rather than the employee. That’s especially true because it’s rare for managers to receive training on how to run these meetings, so they often recycle the dysfunctional practices they’ve experienced.

If you’re in Brianna’s position — if your boss’s approach to your 1:1s leaves you feeling unsupported and unheard — you need to feel empowered to steer the conversation around your needs. 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 key topics to broach in a 1:1, we identified 28 key questions in seven broad areas. categories to help you get the most value from your check-in with your boss. . You can use, adapt, and put it in your own voice as you see fit.

Ask for Guidance and Input

Use these questions to get help from your manager with any tasks or projects you’re struggling with, or to express your need for additional resources, input, or support.

  1. I have some challenges and struggles with X. Can you help me figure out how to navigate and solve X successfully?
  2. Can you suggest any ideas and thoughts on how I can get more support (people, time, funds) to help Y?
  3. What do you think of my idea Z? Do you have any suggestions on how to improve it? Or, maybe you have an alternative idea that I should consider?

Clarify Priorities and Expectations

To make sure you’re on track and working effectively, make sure you and your manager are on the same page. Ask for clarification on what tasks require your most focused attention from their perspective.

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

Adapt to the Organization and Its Strategy

Ask questions to understand how your role relates to the organization’s broader strategic goals and the way its leaders think about the future.

  1. What is going on further down the tree (or in other parts of the organization) that would be helpful for me to be aware of as I work on my important tasks?
  2. To better help me understand the big picture, how does the work I do or the task you give me fit into the broader goals and strategy?
  3. Is there anything the management team is working on or considering that you think I should know about right now because of 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?

Find Career Development and Advancement Opportunities

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

  1. I would appreciate your advice. What can I do to prepare myself for more opportunities or to keep X interested in me?
  2. As you reflect on where the organization is headed, do you have thoughts on how I can improve and improve to best align?
  3. What strengths do you think I have and how will they help in the future?
  4. From your perspective, what should I target for my next career move and why do you recommend that position?
  5. How do we ensure that my skills are best used to support the team and the organization?
  6. How can we ensure that I reach my full potential?

Get Feedback on Your Performance

Check with your manager to see how you’re doing, performance-wise. You don’t need to turn every meeting into an official performance evaluation, but it’s important to regularly check in and calibrate if your manager isn’t doing that himself.

  1. Did I meet your expectations? I would love to learn your perspective on my work performance.
  2. What feedback can you share with me about my performance on X or Y task?
  3. Do you feel that I have overlooked areas when it comes to A or B?
  4. As you reflect on what I am doing at work, what should I start, stop, or continue doing?

Build Relationships

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

  1. How was your day?
  2. How are things for you in general? are you ok
  3. What’s something you’re excited about outside of work?
  4. Is there anything you want to know about me? (If necessary, be prepared to say “I’m not comfortable sharing that, but here’s something else you should know about me.”)

Offer Support

Think of ways in which you can help your manager achieve their goals and fulfill their role. Managers need help, assurance, and support to optimize their efficiency and performance. Just as you expect your manager to support you, see how you can lend them a hand. It also increases the chances of you getting what you need at 1:1.

  1. What are your priorities for 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 Questions

For each 1:1 meeting, choose one or two categories to focus on. You can’t answer them all in every meeting, so you have to rotate or choose the most suitable one at a time. Likewise, choose a few from the questions – you don’t have to ask them all at once. You just want to sample from all the categories over time.

Feel free to follow up on your manager’s answers to your questions. A good follow-up is often a simple “why?” You’ll gain strategic insights into the rationale, motivations, assumptions, and big picture behind your daily work.

Good 1:1 meetings with your manager are essential for your success and the success of your team and organization. Asking the right questions to ensure that those meetings give you what you need will have a huge impact on your work experience – helping you stay engaged, improving your understanding of your role and place in the organization, and improving your relationship with your manager – not to mention improving your well-being.

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