What do you talk about in your one on ones? What questions do you ask in one on ones with your manager? What about one on ones with managers that report to you?
It’s important to understand that your one on ones with individual contributors reporting to you should be treated differently from those you’d have with the managers under you, and even moreso with the one on ones you have with your boss.
Every kind of one on one helps you thrive at work and have great working relationships with your colleagues. Yet, to accomplish this, every type of one on one has different topics to discuss and questions you should ask to make the most of them.
Whether you’re an aspiring manager looking to manage up, want to make a career move into leadership, a senior leader wanting to better manage your team of managers, or a hungry learner wanting to learn more about both, this post is for you.
The post below is broken up into 2 sections:
Click on either of them to jump to the section that applies most to your situation:
- Questions to ask in one on ones with your boss, including tips to help you manage up
- Questions to ask in one on ones with the managers under you to help you better support them
First, we’ll dive into questions to ask in one on ones with your boss to help you better manage up.
Part 1: 23 Questions to Ask in One on Ones with Your Boss
Having effective one on one meetings with your boss is important for a number of reasons. They can help you:
- Get feedback on what you need to improve
- Receive coaching in areas you’re working to grow
- Strengthen your rapport with your boss, improving communication and reducing potential issues
- Offer your ideas and suggestions to improve your team, and how you work
- Avoid surprises and ensure you get good news at performance review time
And that’s just the beginning. As former Intel CEO Andy Grove put it, regular one on ones can offer a 10x return on the time investment for managers:
These meetings are a priceless opportunity. When else do you have the undivided attention of your manager, and have them solely focused on you? Chances are, this is the only time.
Whether your manager is taking advantage of your regular one on ones with you or not, you have the power to take charge of them yourself.
If you’re not getting what you want out of them, then bring some of your own agenda items and questions to change that.
You can create that 10X return just as much as your manager can.
Here are questions you can use to make the most of one on ones with your manager, and get them more engaged in supporting you:
1) Questions to help you take charge of your one on ones
Most managers have good intentions. Unfortunately, whether overworked, overwhelmed, or just figuring things out for the first time, they don’t always have everything perfect for you and your 1 on 1s.
The first place to start is if your manager isn’t being consistent with your one on ones. After all, if they’re not happening, there’s no benefit to be gained.
Use a question like this to get your manager to reschedule the next time they try to cancel a one on one:
- 1) “Okay. I understand you have something pressing, and these meetings are important to me. When can we reschedule our 1 on 1 meeting to?”
This kind of response is useful for three reasons:
- You’re building reciprocity by agreeing to their request, then asking for a favor.
- You’re using “and” instead of “but” which helps build on the conversation instead of making it seem like you’re disagreeing.
- You’re immediately requesting a rescheduled time, making them less likely to forget, or put it off.
To make this even more effective, be prepared to suggest some new times for them to choose from. You can even bring up your calendar if you’re talking in person.
Your goal is to make it as easy as possible to reschedule right away and avoid missed conversations from canceled one on ones.
More questions to help you take charge of your one on ones
There’s a lot more you can do than just make sure your manager sticks to your one on ones.
You can influence what’s talked about in your one on ones, what you get out of each meeting, and whether action is taken on what you cover. You may wish your manager would take charge, but that’s no excuse to keep having wasted meetings.
Here are some more questions you can use to help lead your one on one meetings with your manager to better results and outcomes:
- 2) To get Status Updates out of your 1 on 1s: How can I best give you updates at another time? How about an email, a chat message, or a few minutes in [team meeting X]?
- 3) For Career Advice: What skills do you think are most important for me to work on right now to help me advance?
- 4) I’d like to build a plan for my development. What do you see as important steps for me?
- 5) To encourage note taking: Would you like me to write that down for you, or send you a note later about it?
- 6) To ensure progress happens: What do you think we can both do for next time based on what we talked about? (Lean more about the Progress Principle here. )
2) Questions for managing up
What does your manager think of you? How can you manage up effectively, so you reduce the chance of having problems with them?
Or, even better, how can you strengthen your relationship with your manager?
Knowing how to effectively manage up is an important part of taking charge of your career; the relationship you have with your manager impacts everything from the projects you are assigned, the recognition you receive, your compensation, and promotions and new opportunities.
Leadership coach and Vistage Chair Beth Armknecht Miller says that the relationship you have with your managers can transform your career:
“Over the years, I have had the opportunity to coach many rising stars on their relationship with their manager, which is often the most critical to their success in an organization.”
Miller says there are three key elements to effectively managing up:
1) Know your boss’s priorities and goals. When you know his/her priorities, you can tailor the information you share during meetings and conversations with them. And when you are able to assist your manager in accomplishing his/her goals, you are demonstrating you are dependable and take initiative, two highly coveted traits managers look for in their employees.
2) Anticipate the needs of your manager. The more you anticipate their needs and demonstrate your understanding of them, the more confidence and influence you will build with your manager. They’ll trust you more and more.
3) Talk like your manager. Use the language and terms that he or she often uses, and focus on the topics that are most important to him/her. This aligns you and them to achieve goals for both of you.
One on one meetings with your boss are the perfect place to do all three of these things.
By asking the right questions, you can uncover their priorities, goals, needs, and their language and communication style. This helps you succeed in your career and becomes information you can use to improve your relationship with your manager.
Questions for uncovering your manager’s needs, goals, and language
By asking the right questions, you can discover all kinds of useful information to better understand and work with your manager.
Here are questions you can use to better manage up with your boss:
- 7) What are your priorities? What wins do you need? (Uncover your manager’s goals and priorities, which could be different than yours.)
- 8) What parts of my work are most important for you to be up to date on often? Where do you trust my work and I can be more autonomous?
- 9) What causes you to feel stressed about my work? What gives you confidence?
- 10) What have team members that frustrated you or were challenging to work with done or failed to do? (Avoid these things to keep your manager happy with your work.)
And questions to help you anticipate your manager’s needs:
- 11) Would X be helpful for you? How would you change it? (Great if you have an idea to help you or the team)
- 12) What do you recommend I do when I get stuck on [area you’re weaker in]? (What do they want you to do when you get stuck? Also a great way to get them to coach you)
- 13) If I need help with something, what’s the best way to get your input or support? (Useful if they have a hands-off management style and for finding out how they want you to go about getting input/support from them)
Listen carefully to what they have to say, and practice active listening skills to ensure you understand them. In many cases, the requests they’ll make will be totally reasonable and just as easy to do as the other way you might have planned to do things.
Want to further tune up your 1 on 1s, and get better at managing up? Here’s where to start:
- Learn how you can improve one on one meetings with your manager: 7 Essential Tips for Effective 1 on 1 Meetings with Your Manager
- Some of our best Advice for Managing Up at Work from Experienced Leaders
- If you liked the above questions, here are 18 Questions to Ask Your Manager to Improve Your Relationship and Better Manage Up
3) Questions to drive your career growth
Improving the relationship you have with your manager is one of the most important elements for your career growth.
Thanks to the law of reciprocity (if you do something for me, I’m more likely to do something for you), if you’re helping your manager out in a few ways, they’ll be more likely to want to help you.
Fortunately, most managers aren’t like Dilbert’s boss. They have your best interest in mind, and want to help you succeed. However, they are unlikely to have your career top of mind nearly as much as you do.
You need to show it’s important to you and keep it top of mind for them.
Asking the right questions in your 1 on 1s can help open up your career to grow in a variety of ways. Like the other questions we’ve discussed today, your initiative to ask about your career growth can help get the ball rolling towards many positive results for you.
- 14) What are the most important areas I need to master to get promoted here?
- 15) What skills gaps do you feel I have? (Remember: your manager is the person who will have to advocate for your advancement, so their opinion matters a lot.)
- 16) What kinds of milestones do I need to hit?
- 17) What are key habits you feel make someone successful in [your new role/ the role you want next]?
- 18) Can you help me get approval / or do you have budget for X? I think it will help me grow because…. (Talk about getting a book, a course, conference, etc. that will help you in your career)
- 19) What would it take for you to feel I’m ready for [desired role/promotion]?
- 20) What do you feel are my strengths? How could those help the team more and help me advance in my career? (More on the value of focusing on your strengths here)
Checking in on your progress
A conversation is only the beginning. Once you’ve established what you need to work on, and where you’re heading, you need to make progress on it regularly.
As you begin making progress, use questions like these to check in with your manager to see how you’re doing along the way:
- 21) Do you feel my skills are improving in the areas we identified I need to work on?
- 22) What are the biggest barriers I still have to [the next promotion, raise, goal you’re working towards]?
- 23) What would make you feel totally ready to advocate for me?
Some of these questions can be scary. You may not love what you hear, but it will get the elephants out of the room. If there’s a weakness your manager sees or something holding you back, you need to know.
It’s much better to hear these things on a Tuesday afternoon mid-quarter than it is to have a big surprise at the end of the year. By then, you want to have made progress and fixed those issues.
Being brave and taking charge of your career is how you advance faster. It also demonstrates to your manager you’re serious about your career.
Asking tough questions and really listening to your manager is the best way to make sure the effort you put in is noticed and headed in the right direction.
No one cares more about your career than you. If you want to learn more about developing your career, and how to help others do the same, check out these posts:
- More on driving your own career growth
- An option to consider if your company doesn’t have many promotions is to look at these ideas: Employee Development: How to grow your employees when you can’t promote them
- What to do if you can’t figure out what your goals are: How to help when your team member can’t answer “What are your career goals?”
- Think about your career by asking yourself these questions we encourage managers to ask their teams: How to Help Your Team Achieve Their Goals
Part 2: 51 Questions to Ask in One on Ones with Your Managers
When you’re at the level in an organization where you manage others who also manage teams, your impact is exponential; not only do your efforts improve or hurt your team, but it trickles down to their teams as well.
Gallup calls this the “Cascade Effect”:
Unfortunately, many leaders make the mistake of not checking in regularly with those on their team that are managers. That’s a huge mistake.
As you can see in the chart, a disengaged manager will cause their team to disengage, too. That can get very expensive fast both in lost productivity and lots of turnover.
Support your managers with regular one on ones
Just because someone was promoted does not mean you can give them less support. In fact, they need more help and guidance from you.
When you abandon your people right when their Task Relevant Maturity is at its lowest, you crush their morale, and hurt they and their team’s ability to succeed. You can do better.
The best way to help your managers is to keep your regular one on ones with them. The questions to ask in one on ones with them may change, but the importance of the meetings does not.
If anything, one on ones become more important.
You and your managers’ time is precious. Don’t waste your one on ones with them on status updates. These one on one meeting questions to ask a manager under you can help you get to the root of key issues that can have an out-sized impact for your managers and their teams.
[Ed Note: If you’re looking for questions to ask in one on ones with an individual contributor, these 1 on 1 Meeting Questions Great Managers ask Their Teams can help.]
Questions to ask about the Multiplier Mindset
Being a multiplier (or in your case exponential) is a key mindset to have as a leader. You have the ability to improve the performance of everyone you manage, which compounds quickly.
Your managers have the same potential.
These questions to ask in one on ones with managers will help you explore the multiplier mindset with them. By asking them, you will ensure that they have the right habits and are thinking about how to be multipliers themselves.
- 1) What’s one thing we could do for you to help improve the performance of your team?
- 2) What’s the biggest thing preventing your team from getting more done, or done better?
- 3) How much time do you spend in meetings? Are there any you don’t feel you need to attend?
- 4) How much time are you spending on individual work? What about managing? (Are they investing enough in their team?)
- 5) If we had budget to get you any one thing for you to make you better at your job, what would you want?
- 6) If we had budget for any one thing for your team to be more effective, what would you want?
- 7) Am I available to support you when you need it? What is a recent example that comes to mind? (Explore this and do more of what they liked, or find out what you can do differently)
These questions can help you think about how you can improve your team of managers, which means making a change that helps a whole group of people be more effective.
You may be surprised what a few small changes can do to improve things for your managers and their teams. By asking them these questions, you’ll get them thinking about the big picture, and out of their day to day hustling.
Questions to ask how things are going with their team?
Unfortunately, work isn’t all sunshine and rainbows. There are conflicts. People can burn out. Valued staff can become bored. Turnover can spike, or morale can plummet after an unpopular decision.
These are all issues a manager must learn to deal with, and may want your advice on handling. Even better, they often can use your help in catching and fixing such problems before they become too big and devastating.
- 8) Who do you think is at risk of leaving the company? How could we save them?
- 9) Who are your top performers? Why them?
- 10) Do you feel everyone on your team is properly compensated based on their performance?
- 11) Who on your team is struggling right now? What tactics are you using to help them?
- 12) What’s the best idea or suggestion you’ve heard from your team lately?
- 13) How do you solicit ideas and feedback from your team? How often?
- 14) What’s one thing we should stop doing?
- 15) What’s a recent situation where you’d like my advice on how to handle it now, or next time?
- 16) How did you think [situation] went? How could we improve that together?
Fixing problems when they’re small is one of the best ways to keep your managers out of reactivate management mode (aka- fire fighting). By asking these questions, you make it clear they can safely discuss issues with you before they’re massive problems. You also get them thinking about exactly the kinds of things they should be doing and asking of their own teams.
Questions to ask about resources they need & how they perceive you
With changing teams, and new goals, comes new challenges. What was the right mix of resources and support previously may not work now. The best way to find out is to ask. Whether it’s a new team, or a manager you’ve worked with for a long time, these questions can give you fresh perspective:
- 17) What’s one thing I could do to better support you?
- 18) What’s the biggest bottleneck or blockers that affects you and your team doing their jobs well right now?
- 19) What would you change if you had my job? Why that?
- 20) What do you want to know about my job and responsibilities now?
- 21) What would you do to help the person replacing you if you had my job?
- 22) Is there anything in my job you feel you don’t know that you should?
Self awareness is hard. It’s not always clear how much your managers understand about what you do.
Having an honest discussion about what they don’t know about your job, and how you can better support them, can go a long way towards dispelling any myths, and strengthening your working relationship.
Sometimes this may be tough medicine to swallow. However, it’s better to tackle these issues while you can fix them, than a manager losing a large portion of their team, and them being frustrated at you for a lack of support.
As things change at work, this can become a moving target. Consider revisiting these questions semi-regularly to see how what they need evolves.
Want more questions like this right at your fingertips while you’re having a 1 on 1? Then sign up for a free trial of Lighthouse and keep all your 1 on 1s organized and covering the right topics.
Questions to ask how they’re feeling?
After initial excitement fades from a promotion, the real work begins. This isn’t always easy for people, especially if they’re new to management.
Asking a few questions about how they’re really feeling can be a huge relief for them as they spend most of their time helping their team with their problems.
- 23) How is managing your team going for you?
- 24) How is your / your team’s workload? Too little, too much, or the right amount?
- 25) How do you feel about your balance between doing individual work vs. managing? Do you feel like you’re doing too much or too little of either?
- 26) What is your favorite part about being a manager? Why that?
- 27) What is your least favorite part about being a manager? How do you handle that?
- 28) What do you want to do next in your career? How can I help you get there?
- 29) Are you happy in this role? What could make it better for you?
- 30) If you could go back to your old job, would you want to? Why?
- 31) How do you feel your work/life balance is? What would you want to change, if anything?
Sometimes the simplest questions are the most powerful. Making sure your managers are happy in their roles is a great way to ensure their teams are happy too.
No one benefits from working for someone who doesn’t like their job. It’s also why companies like Netflix make it safe for managers to return to individual contributor work if they decide they don’t like managing anymore.
Questions to ask about how they manage & grow their people
If you’re developing managers on your team, it’s important to make sure they’re building and maintaining these habits with their teams, too. Of course, the example you set is one of the most important parts, and these questions to ask in one on ones with them can help as well:
- 32) How often are you having one on ones? Does that feel like the right frequency for everyone?
- 33) What has come up in your one on ones lately that I should know about, or you’d like help with?
- 34) When was the last time you praised each of your team members?
- 35) Anyone need performance improvement? Why?
- 36) Who is close or ready for promotion? For what roles?
- 37) Who are the best people on your team? What are they doing well?
- 38) How can we help your best people be more successful?
- 39) If you had to promote someone to [role x] who would you recommend and why?
- 40) Do you feel [team member x] is ready to advance? How can we work together to help them grow?
Identifying stars is a great way to ensure good people stick around. By supporting them and showing a path before you need them in a new role you avoid them looking for growth outside your company.
Meanwhile, helping with underperforming or problem team members can be a relief for a manager’s entire team.
Questions to talk about handling change
Not all change is popular. And even for changes that are welcomed, buy-in and long term success is no accident.
These questions can help navigate the broad objections and implementation issues from the front lines so they trickle up to leaders like you.
- 41) What do you and your team think of the recent changes?
- 42) What tweaks would you make to [change x] to help you and your team?
- 43) What are you and your team’s biggest concerns about [change y]?
- 44) I’m thinking about making [change z], how long would it take to privately solicit feedback from your team on it?
While ideally, you’ll get some feedback on changes before a public announcement, that’s not always possible. By checking in whenever you can about a change, you demonstrate you are listening, and care about what they think.
If you make adjustments based on valid feedback from your managers and their teams, this can be especially valued, and increase buy-in for you as a leader. This line of questions can also then provide you a forum to explain to your manager why a decision was made, which they can then selectively share as well.
Questions to talk about managing up to you
Your relationship with your team of managers is just as important as their relationship with their team members. However, it’s easy for someone like you a few layers up to become buried in work and demands and lose sight of this.
Asking questions like these can help identify problems and opportunities for you and your managers to work better together. You can also use these to teach them how to better manage up to you:
- 45) Do you find it easy to communicate with me? What makes you feel that way?
- 46) What’s one thing I could do to make things easier for you and your team to keep me informed?
- 47) What do I just not understand about you or your team that if I did, things would be better?
- 48) How often do you think is the right frequency for us to get on the same page?
- 49) How would you prefer to update me? (Work with them to balance this with your needs)
- 50) What do you think is fair for me to expect from you?
- 51) What do you think is fair for you to expect from me?
These questions on managing up can open a very healthy dialogue. Once you’ve heard their perspective, they’re more likely to listen to and appreciate yours. Then, you can find the common ground needed to work better together.
By creating clear expectations and opening safe communication in your one on ones, you will help your managers be more successful in their role and specifically in working with you.
As a company grows, communication becomes more difficult. By investing in one on ones and asking the right questions, you can combat these challenges and ensure you focus your time on the highest impact areas to help your managers.
These 51 questions to ask in one on ones are a great place for you to start.
Even more further reading
Whether you’re looking to make the most of your relationship with your manager as an employee, or you’re a senior leader who wants to help grow and develop the managers under you, we have additional guides to help.
Additional resources for managing up and working with your boss:
- 7 Essential Tips for Effective 1 on 1 Meetings with Your Manager
- 9 Expert Tips for Managing Up at Work from Real Leaders
- How to Get Status Updates Out of Your 1 on 1s (and what to focus on instead)
- 18 Questions to Ask Your Manager to Better Manage Up
- 3 Ways to Better Manage Up By Developing Empathy
- How to Convince Your Boss to Start 1 on 1s With You
Additional resources if you’re a senior leader who wants to know how to develop your managers and become a better leader:
- 12 Questions for Your Team to Become a Better Coach at Work
- Crisis Leadership: 18 Questions to Ask Your Team in a Crisis
- 15 Skills Senior Leaders Must Master
- How to Use Skip Level 1 on 1s to Majorly Improve Your Managers as a Senior Leader
- Leading Happy Teams: 5 Ways to Keep Your Team Happy in a Recession
- 11 Essential Tips for Effectively Managing Remote Employees
Want you & your managers to make the most of your one on ones with your teams?
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