How to Manage your Manager

How to Manage Your Manager by Glenn Marczewski

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!”

While we seemingly got along fine, the difficulty was in our communication, and I don’t mean the English/Chinese language barrier…

He would come into my office without advance notice and urgently ask my team and me to switch tasks and gather data in a report before his upcoming meeting.

Since he was relatively new, he didn’t seem to have a handle on what our department was and wasn’t responsible for. The sales team was more efficient at putting these reports together, because this fell under their responsibilities. What took us an hour or more, a member of the sales team could do in minutes.

His unexpected visits caused us a great deal of stress because it jeopardized our ability to finish our time-critical procedures, potentially putting our customer’s shipping dates at risk. Many of these shipments were worth hundreds of thousands of dollars each.

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.”

[Blog interrupter graphic here linking to Lead Upward Shopify]

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, the 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.

Download our FREE Lead Upward Cheat Sheet.



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