• Maya Grossman

How To Handle a Difficult Manager

About a decade ago I learned who you report to has a massive impact on your mobility and your ability to level up. I have had the pleasure of working for managers who were force multipliers - the kind of managers who lift everyone around them, and I have had my fair share of 'less than perfect' managers. If you are experiencing the latter, keep reading. This week's question is all about dealing with a challenging manager:




Okay, this is going to be a long one.

The way I see it you have two options: 1. Invest time and effort to change your relationship with your manager for the better. 2. Find a new job. I usually start with the first option, I do my best for 3-6 months and if that doesn't work I refresh my resume and start looking. If you are like me, let's talk about building a better relationship with your manager. The first thing I want you to remember is that your manager is a person. They have feelings. They get hurt. They question themselves. They get scared. They worry about their job. It's easy to forget, but as one of my previous CEOs told me: "I'm your manager but I'm also a human being". I'm telling you this upfront because I want you to have empathy. You'll need it. Step #1: Define your goals Looking at D's question I assume her goals are to: 1. Have authority and decision making power 2. Have direct access to the SVP 3. Be able to deliver great results Step #2: Figure out what is (actually) blocking you 1) D doesn't feel like she is in charge. Why?

  • Her manager is intimidated by her (she has more experience)

  • Her manager wants to look good in front of his boss (SVP)

  • Her manager doesn't trust her

  • Her goals are not in line with her manager's goals

2) She doesn't have direct access to the SVP. Why?

  • Her org doesn't have regular skip-level meetings (HR)

  • Her manager doesn't trust her (afraid she will go behind his back)

  • The SVP isn't aware that she wants this 1:1 time

3) She isn't able to maximize her potential. Why?

  • Her manager doesn't trust her

  • Her manager wants to have the last say because they feel insecure (less experience)

(*There's always the chance that the VP is just an a-hole, but let's assume the best about people) Step #3: Create a plan Now that we know what could be causing D's problems, let's address the real issues. D can't change the fact her manager may not be the best person for the job. What she can do is figure out how to make the most of the situation. D needs to build a better relationship with her VP, get him to trust her, and as a result get more autonomy and support. How can D do that? This may come as a shock, but sometimes you need to manage your manager! 1. She needs to get to know her manager as a person. I once scheduled a "coffee chat" with my boss and just asked him questions about his life, family, hobbies... it was one of the best conversations we had and it helped both of us open up. 2. She needs to understand her manager's goals - what is he trying to achieve? What would make him look good in front of the SVP? D needs to ask herself: how can I align my goals with my manager's? How could my work make a positive impact on him? (I'm not suggesting she should do the work and her manager takes the credit, that's a big no-no. She should find ways to include her manager in her plans and give him credit for "empowering" her. That way they will both share the fame). 3. Over-communicate! When there's a trust issue it mostly stems from miscommunication or lack of communication. D needs to make sure her manager is a thought partner. Include them in every step of the way from ideation to execution. Make them feel included (even though you are running the show) and make sure they always know what she is working on. It may seem like a lot of work, but once D will establish more trust she won't need to do all of that. 4. Have her manager's back. Yes, it should work the other way around too, but D can set an example by standing up for her manager. Cover for them when they are caught off guard, be their eyes and ears and share information they may have missed. Treat them the way she would like to be treated. If D does that for a few months she should be able to gain trust, and that will lead to more freedom and fewer clashes. D and her manager will be working together towards a shared goal. When her manager trusts her, D shouldn't have a problem scheduling skip-level meetings. As long as she keeps her manager in the loop they should be happy for her to have face time with a senior leader. If all else fails... D can talk to her manager. Have an honest conversation about the situation and bring up how she is feeling. It's important not to make it an attack on her manager, but rather a review of the situation. D needs to explain that she wants to build a better relationship and that she wants to know what she could do differently to be a better team member to support her manager. Managers are people and they can have blind spots. Sometimes just bringing it up to their attention can help. What if it doesn't work? That's when you go to plan B. You find a new job or a new manager (move internally). It sucks because it's not your fault, but the alternative is to stay in an environment that makes you miserable... you deserve better. What are a few months of job search in comparison to a few years of misery? I hope you only get to work with multiplier managers, but if you ever have to deal with a challenging manager - this formula has helped me build trust and completely change the situation and it could do the same for you.


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