Dear Coach: A Bad Manager Is Threatening My Dream Job

January 12, 2023   |   Julie Diamond

Dear Coach,

After paying my dues for many years while growing the requisite skills for my dream job, I finally got promoted into a role that felt like a perfect fit. In addition to it being a great role with opportunities for a significant amount of visibility, I was working for a super-sharp leader who I was excited to learn from.

Unfortunately, three months into the role, said leader got a job offer at another company that was too good to refuse. I was bummed but understood, so I took a deep breath and kept my fingers crossed that the new leader would be good as well.

Spoiler alert: she isn’t. One year into this role, and it is a complete mess. My new manager is incredibly indecisive and fearful, refusing to rock the boat and insisting on getting buy-in from everyone. The consequence of her indecision is that all my work gets caught in a gripping bottleneck—it’s so deeply frustrating that I’m contemplating leaving my role, but it’s hard to let go because, theoretically, this is a fabulous opportunity for me.

What do you think—should I stay, or should I go? 


Bottlenecked & Bothered

First, let’s unpack this. Your question tells us that:

  • The gap between your expectations and experience is huge and it is creating a lot of frustration for you.
  • You identify the problem as being your new manager, but perhaps there are other contextual issues creating her timidity.
  • While you identify the obstacle, you don’t identify allies or ways around the bottleneck that you’ve discovered.

So, exactly how is your problem a power problem? A few thoughts:

  • You are constrained by your positional power, and you want your boss to remove obstructions and pave the way for you.
  • While you see the role as a big opportunity for yourself, so much of it seems dependent on the boss, which makes us wonder….
  • Perhaps your emotions and reactivity are getting in the way of finding alternatives for how to get things done. You could be overly indexing on the problem rather than finding solutions.

What’s the Solution?

While you may not have the positional power in this situation, perhaps you do have the expert and personal power that you need to widen the bottleneck—so it’s time to change your approach.

To be able to respond effectively, you’ll need to do a few things, including:

  • Think about who is in your circle of influence and how they can help you get things done.
  • Remember that people in power need your help! Your manager is clearly sinking—how can you help her (which will, in turn, help you)?
  • Use your audience awareness. Be more curious (and not just reactive) about your boss’ mindset, what drives her timidity, and what she might need to feel bolder.

A good first step is to meet with people in your circle of influence and ask for their guidance. Even if they can’t directly help, they might have contextual insight that could inform your position.

Once you’ve gathered thoughts from your circle, spend some time getting curious about your boss before scheduling time to speak with her. When you do sit down together, you can simply ask her what she is so unsure about, and why? What does she need to take bolder steps? And what can you do to make her feel more secure and able to take some risks?

If a candid conversation about her doesn’t move the needle, then share with her your need to take bigger risks and have more visibility. Let her know if there is some other way she can support you. 

Managers are people too, and often all it takes is some good ole fashioned candid yet compassionate communication to get on the same page.


Each month we answer questions we often get from the leaders we work with and unpack how at the end of the day, every problem is a power problem. If you have an issue you just can’t solve, get in touch! We’d love to answer your questions in an upcoming Dear Coach post. Find us at [email protected], or on LinkedInFacebook, or Twitter.