18 Questions to Ask Your Manager to Improve Your Relationship and Better Manage Up

If you’ve ever had a frustrating boss, you know how true it is: People leave managers, not companies.

… but that doesn’t mean the responsibility lies entirely on your boss to make you love your job.

You play a part in managing the relationship between you and your manager. Put another way, this is what it means to manage up.

The truth is, you have more power than you might think to influence your relationship with your manager. It’s true whether you are trying to turn it from bad to good, good to great, or want to keep a good thing going.

By taking responsibility and deciding to work with your manager to improve your relationship– whether it was good to begin with or not– you can overcome problems and make work much more enjoyable for you and them.

Why is managing up important?

When you start a job, except in rare cases, you can’t pick your manager; if you want the job, you’re going to report to who you report to. And with re-orgs, the person you started out with often isn’t who you end up reporting to.

That puts you in a tough spot, particularly if you aren’t enjoying working for your manager (which, as Gallup found, over 50% of us have had a manager we disliked so much we quit our job).

That’s why managing up is so valuable a skill to master. It can help you overcome whatever problems exist and smooth out the relationship, improving your work experience in the process.

An ounce of prevention is worth a pound of cure…

Things don’t have to be bad for it to be worth improving your relationship with your manager.

Even if things are good, taking steps to meet one-on-one with your manager and learning how you can help improve the relationship can make things even better.

So whether you love your manager, are just getting to know them, or struggle with working with them, getting better at managing up is a great skill to develop. It will make good situations great, and can fix many problems with difficult managers.

14 Questions to Ask Your Manager to Improve Your Relationship and Better Manage Up

18 Questions to Ask Your Manager to Improve Your Relationship and Better Manage Up

Leadership coach and Vistage Chair Beth Armknecht Miller says there are three things you need to improve your relationship with your manager:

“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.

Here’s what I tell them:

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 the needs and demonstrate your understanding of them, the more confidence and influence you will build with your manager.

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.”

To learn your manager’s priorities, anticipate their needs, and communicate with their language requires that you get to know them. The best way to learn them quickly is through one-on-ones.  A recurring, lengthy time meeting with them one on one gives you the opportunity to listen, learn, ask questions, and share what’s important to you. There’s no other time like it.

If you don’t already have them, work to get a regular spot on their calendar, so that you have time to build rapport and get to know them better.

You can’t pick your boss, but you can take steps to improve your relationship and make work a more enjoyable and productive experience.

While ultimately we recommend you find a job and manager you love, these questions can help improve any situation:

*To learn more about how to have effective one-on-one meetings with your manager, read: 7 Essential Tips for Effective 1 on 1 Meetings with Your Manager.

Questions to understand your manager’s goals and priorities

Your manager has certain goals and priorities– but they won’t always explicitly tell you what they are.

Unfortunately, those priorities can impact everything you do and how you do it. This means that investing some time to find out what things are most important to them before problems arise is vitally important.

While in a dream world, they’d always tell you, sometimes you have to ask.

14 Questions to Ask Your Manager to Improve Your Relationship and Better Manage Up

Leadership expert and Lead from the Heart author Mark Crowley suggests doing a little detective work to find out:

“Ask your colleagues to individually share examples of things they’ve done to successfully meet your boss’s needs in the past. You’ll quickly see there are many common denominators – and these practices are the ones you’ll want to consistently provide.

When you feel like you have solid footing with your boss, you can and should ask them directly: ‘What are some things I could do better or differently to help you succeed even more?’”

Here are more questions you can ask to help uncover your manager’s goals and priorities:

  • 1) Here are my top X priorities. Do these align with your priorities? (Make sure you’re doing the things that matter most.)
  • 2) What are your priorities? What wins do you need?
  • 3) What gives you confidence in the work of your team members?

Use the waterline concept to encourage trust and improve communication

Another helpful question to ask is:

  • 4) I learned about the concept of a waterline…what do you consider above or below the waterline?
use the water line concept to manage up well

This applies the “waterline” concept, a great analogy that mega manufacturer W. L. Gore uses to encourage trust and improve communication, but it’s also helpful for understanding their priorities:

“The waterline principle means that it’s ok to make a decision that might punch a hole in the boat as long as the hole is above the waterline so that it won’t potentially sink the ship.

But, if the decision might create a hole below the waterline which might cause the ship to sink, then associates are encouraged to consult with their team so that a collaborative decision can be made.”

Using the water line concept can help make both you and your manager’s lives easier by establishing a defined process for when you really need to check in with the, and when you can be given more autonomy and independence.

As a follow-up, make sure to be clear with your manager about how you’ll treat below and above-the-water-line tasks. For example, you might say, “I’ll keep you informed at a high level, but work independently on above the water line tasks. Meanwhile, I’ll be more detailed, and come to you quickly for things below the waterline if they start having problems.”

learn how they think to manage up well

Questions to understand how your manager thinks + their language

As we talked about earlier, Beth Armknecht Miller reminds us that the third thing she tells people working to improve their relationship with their managers is to, “Use the language and terms that he or she often uses and focus on the topics that are most important to him/her.”

Why is it important to use your manager’s language when communicating with them?

It works for the same reason the human mind often naturally imitates another’s speech when talking to someone with an accent. According to a University of Riverside study on the phenomena:

“This unintentional imitation could serve as a social glue, helping us to affiliate and empathize with each other.”

When you adopt your manager’s common terms and language, you’re connecting and relating to them better.

Build strong lines of communication with your manager

Even better, the more you work to understand how they think and can communicate from the perspective of the things that matter most to them, the better you can work with them. Understanding how they think and communicating from that perspective is just another level of effective communication.

Here are more questions you can use to help you get into your manager’s mind and pick up on their language:

  • 5) How can I build more trust with you on the work I do? (Great if they’re a micro-manager)
  • 6) What is most important to you to be up to date on for progress I’m making? Where do you trust my work and I can be more autonomous?
  • 7) What causes you to feel stressed about my work? What gives you confidence?
  • 8) What part of my work are you most comfortable and familiar with? What parts of my work are things you haven’t done as much yourself? (This is understanding their Task Relevant Maturity)
  • 9) What have your best team members you’ve enjoyed working with done when working with you that you liked? 
  • 10) What have team members that frustrated you or were challenging to work with done or failed to do?
manage up by thinking ahead to what your manager needs

Questions to help anticipate what your manager wants

Much of managing up is learning about your manager, so that you can anticipate what they’ll want. The better you can do that, the more they’ll trust you, and you’ll strike a balance between them being hands off, and supportive when you need it.

Being able to anticipate what your manager wants can also help overcome one of the most common workplace issues: poor communication.

Many issues develop because an employee is afraid or hesitant to open up. They fear they’ll be bothering their manager, so they never say anything (nor does anyone else). Over time, the issue gets worse until it’s too late.

But the reality is, it’s often misplaced fear. At least in the case of a good manager– as Flexport engineering manager Jason Crawford echoed:

You see things that your manager doesn’t, so bring up problems you think they should know about. A good manager will be excited to learn from you, and thank you for the information. Meanwhile, even a bad manager may welcome you bringing up a problem if you also come to them with suggestions for a solution.

This is a great question to help you do that:

  • 11) I noticed problem X and was thinking Solution Y could help. What do you think of that? 

After asking the question, consider following up with, “How could we make that happen?” to try and nudge the solution along and make sure action is taken to actually resolve the issue. If you can also provide context on why the problem is important, this can help them understand why you prioritized bringing it up, and why you should do something about it.

Here are then a few more questions to help you understand and anticipate what your manager needs:

  • 12) Would X be helpful for you? How would you change it? (Great if you have an idea to help you or the team)
  • 13) What do you recommend I do when I get stuck on <area you’re weaker on>? (What do they want you to do when you get stuck / need help? This is also a great way to ask for coaching versus waiting for them to coach you spontaneously.)
  • 14) At what point do you want me to ask you for help versus figure it out on my own? (When do they want you to stop trying to figure it out on your own and ask for help?)
  • 15) If I need help with something, what’s the best way to get your input or support on something? (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)
  • 16) What’s one thing I could do differently or better that would make your life easier?
  • 17) How could a recent project or task I did be put in a format that’s easiest for you?
  • 18) What do you need to report up our chain of the work I do? How can I get it in a format that’s easy for you? (If their boss has to write an email report, then some text may be good, but if, for instance, they have to make slides, then sending them slides or image-friendly information could save them a lot time.)
manage up good or bad

Learn how to manage up effectively

Whether your relationship with your manager is good or not so great, use these questions to improve the situation moving forward. There’s a good chance no one has ever asked them these questions proactively, so you’re likely to impress them at best or at the least get them thinking more about h

Manage up more effectively by:

  1. Knowing your manager’s priorities and goals
  2. Learning & anticipating their needs
  3. Understanding how they think and communicate

In addition to these tips, make it a priority to build rapport with your manager. The more you both know each other and appreciate what makes each of you uniquely human, the easier it will be to work together. You can find something in common with just about anyone if you get to know them (start here).

Great rapport with your coworkers:

  • Makes communicating issues easier due to greater comfort with each other
  • Gives you more opportunities to give (and receive) feedback
  • And reduces the chance of miscommunications occurring

Prioritize building rapport, especially through your one-on-ones you have with them, and you’ll find managing up and asking the questions we suggest today will become much easier.

You can’t pick your boss, but you can take responsibility and improve the situation yourself by better managing up. By asking a few of the right questions and acting on what you learn, you can make work a much more enjoyable and productive experience for you and your manager.

use the water line concept to manage up well

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