How to Win Over Your Boss

How to Win Over Your Boss

It’s true that most of us spend more time with coworkers and business partners than with our own family members. What is it we’re doing to cultivate these relationships? Are we getting everything out of these workplace relationships we need to make us successful?

In Getting a New Boss? Interview Again for Your Job,

Outline three steps to get yourself “rehired,” 

  1. Update your resume.
  2. Set up a meeting.
  3. Present yourself.

Now, I happen to think that this sort of “me-centric” approach can easily backfire. But, the original post does have some decent points and Claman herself has a disclaimer at the end, “I find that the higher up you are, the less successful the “rehiring” method is.”

In any case, if your boss isn’t behind you 100 percent, it can make your life miserable. Believe it or not, you can win him over just by asking a few questions that show him you “get it” and are management or senior management material. Whether he’s newly promoted, newly hired, the result of a merger or acquisition, or has been your boss forever, here are:

10 Simple Questions That Will Win Over Your Boss

  1. Ask what he thinks you can do to be more effective.
  2. Ask what her top three priorities or goals are.
  3. Ask what you can do to make him more effective.
  4. Ask what you can do to make the team more effective.
  5. Ask if he’s interested in knowing what will make your job easier.
  6. Ask what her take is on the company’s top priorities and goals.
  7. Ask what he thinks you should do differently or improve upon to be more effective.
  8. Ask if she’d like to meet periodically, one-on-one, and if so, how frequently and what format would she like the meeting to take. Then set it up.
  9. Ask what his philosophy is on your shared functional responsibility, whatever that is, i.e. marketing, HR, IT, engineering, finance.
  10. And, if the meeting’s open-form and you feel it’s appropriate, ask about her background. Most people like to talk about themselves and how they got there, as long as they don’t feel like they’re being grilled, pumped for information, or played in some way.

In case it isn’t obvious, you don’t just plop down in your boss’s office with a notepad and start an inquisition. Ask for a one-on-one meeting because you’d like to know what you can do to be more effective and help him be more effective, wherein you ask a few questions, as appropriate, etc.

And, contrary to the aforementioned HBR advice, do not tell her about your role and your team. Instead, ask if she’d like to hear your perspective on your and your team’s role. If she says, “absolutely,” then set it up. But I still say it’s better to ask for her perspective on your and your team’s role. Get the difference?

And whatever you do, don’t present yourself, your resume, or your achievements either. Frankly, your boss, new or old, isn’t primarily interested in any of that stuff. He’s primarily interested in meeting his objectives and helping his boss meet hers.

The closer you come to demonstrating that that’s your priority as well, the sooner you’ll win him over because you “get it.” And the sooner you’ll be viewed as management or senior management material.


  • Don’t be overly vocal when you disagree with something your boss has done. It will get back to your boss.


  • Communicate with your boss as often as possible
  • Don’t be afraid to share your ideas with your boss, especially if they can help increase productivity or make someone’s job easier. Many times a good idea can add to your boss’ positive impression of you, thereby leading them to believe they are doing a good job themselves.
  • hope these tips will help you make your boss a happy one and make him feel that, by hiring you, he made a good choice. So, good luck!


  • Don’t overdo it. There’s a thin line between keeping your boss happy and becoming the office “Brown Noser”!