Click to extend mobile menu
Click to view cart
Living As A Leader Blog
HOME / BLOG / Overcome the Challenges of Managing Your Manager

Overcome the Challenges of Managing Your Manager

By: Glenn Marczewski

Overcome the Challenges of 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 Mandarin 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/Mandarin 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.”


Lead Upward Infographic


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 manager. 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.

  2. 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 Register Now




Join Your Peers!
Get our blog delivered to your inbox.

Serving Clients Across The Nation

We currently serve organizations across the USA.


Learn how you can become certified in our Leadership Development System and bring Living As A Leader to your company. 


Serving Nationwide

Contact Us
Phone: 262.505.5405

Linked In
©Living As A Leader 2019