Skip to Content

Overcome the Challenges of Managing Your Manager

 April 11, 2019   By Glenn Marczewski


Main Content
Overcome the Challenges of Managing Your Manager

So what do you do if you struggle with “managing your manager?”

Having difficult conversations with your manager can be one of the biggest challenges in your career, even when you typically get along with your boss.

In fact, this was the case with a former employer of mine. 

When the CEO of our North American sales branch retired, the corporate president hired a new general manager from China to replace the CEO. 

The new GM spoke decent English, and I took the initiative to learn to speak a little Chinese to further improve my relationship with him. 

He would greet me in the morning with a smile, a hearty slap on the back and a loud, enthusiastic, “So handsome – You’re Tom Cruise!” 

The difficulty was in our communication, and I don’t mean the English/Chinese language barrier…

He would come into my office and urgently ask me or my assistant to create reports that we weren’t responsible for or accustomed to creating. 

Not only was this disruptive to our time-sensitive daily demands, our manager’s requests could be better handled by our colleagues who were hired for and skilled at putting these reports together in far less time than we could have.

His unexpected visits caused us a great deal of stress because they put us at risk of missing customer deadlines and not completing tasks that our co-workers were waiting on in order to do their work. 

Nonetheless, no one wanted to look incompetent, so we would drop what we were doing and switch focus to his sudden request.

Maybe you find yourself in a situation where you don’t know how to “manage your boss.”

Manage your manager confidently

Whether you need to manage your boss’ expectations, make a request for development or resources, or discuss other issues you’re uncomfortable with, talking with your boss can be challenging for a variety of reasons:   

  • Not knowing what to say
  • Not wanting to offend him
  • Not wanting to be dismissed
  • Uncertainty of how she will respond
  • Past history
  • Workplace politics
  • Fear of retaliation

The main thread throughout all of these is fear of a negative outcome, as well as discomfort during the process.

So how can we overcome the fear of having a difficult conversation with our boss?

Preparedness goes a long way in easing the fear and uncertainty that goes into having what we call a “Lead Upward” conversation.

Here are some tips from our Virtual Leadership Course, Lead Upward: Six Strategies for Influencing People of Power

  1. Schedule Time to Talk

You don’t want to ambush your boss. Catching her off-guard may cause her to get defensive or feel rushed if she is preoccupied. Requesting scheduled time to talk will help make sure your manager will be able to give you her full attention, undistracted by any other pressing tasks and demands.

  1. Ask Yourself, “What’s in it For Him?”

Take some time to think about how your request can benefit your manger. Finding a mutually beneficial outcome will increase the chances of success in your request to your boss. For example, if he could be more intentional about who is best suited to assignments, output would be more timely. 

  1. Plan Your Conversation

Your time, as well as your manager’s, is important. Having a plan for what you will say and how you will handle your boss’ concerns will help you feel more at ease during the actual conversation. 

If you want to learn a step-by-step process to confidently plan and hold a Lead Upward conversation with your boss, check out our NEW online course:

Lead Upward

At Living As A Leader, we offer a Leadership Development Series designed to produce leaders that can positively shape the cultural environment, reduce turnover and achieve crucial business initiatives. We do this by providing training, coaching and consulting with a focus on pragmatic communication tools for leaders at all levels of your organization.

For more information, contact Steph Collins at

About the Author

Glenn Marczewski

Marketing and Communications Manager, Living As A Leader®

As a copywriter, blogger, videographer, editor, graphic designer, musician and sound engineer, Glenn brings his diverse creative arts background into every aspect of his role as Marketing and Communications Manager.

Email Gelnn Glenn's Bio



Sign up for an Information Webinar

Find out how our Leadership Development Series can help you and your organization improve the employee experience and drive business results through more effective leadership.

Register Now!

Related Blogs

Please wait while we gather your results.
The Power of Seeing People as People

The Power of Seeing People as People

Work is undergoing its biggest transformation in decades –– and as a result people are re-evaluating what they want out of their careers.

October 14, 2021 | By Living As A Leader

Read More

How Leaders Can Improve Accountability

How Leaders Can Improve Accountability

The most effective workers know how to hold themselves accountable for results. Because of this skill, they become successful and get promoted to positions of leadership.

September 16, 2021 | By Living As A Leader

Read More

Back to School Advice for Leaders

Back to School Advice for Leaders

The best leaders realize that learning never ends. There are always opportunities to grow your skills like listening to your team, providing valuable feedback and balancing accountability with inspiration.

September 2, 2021 | By Living As A Leader

Read More