Managing Up When Your Manager Is the Problem
A difficult manager is one of the most common career challenges. Here's how to diagnose and navigate it.
First: Categorize the Problem
Bad managers fall into recognizable patterns:- The Micromanager: Doesn't trust you, needs to approve everything
- The Ghost: Never available, provides no direction or support
- The Credit-Taker: Claims your work, blocks your visibility
- The Bully: Uses fear, publicly criticizes, plays favorites
Each requires a different response.
Second: Document Everything
Before taking action, start keeping records:- Decisions made and their outcomes
- Commitments your manager makes (and breaks)
- Your contributions and their impact
This protects you and clarifies your thinking.
Third: Attempt the Direct Approach
Many bad managers don't know they're bad managers. One honest conversation might change things. Frame it as: "I want to do great work here. Can we talk about how to make that easier?"
Fourth: Build Alternatives
If direct approaches fail, your options are:- Find a new role internally (bypass the manager)
- Wait out your manager (they might leave first)
- Leave the organization entirely
Don't wait indefinitely. Set a timeline.
What This Looks Like in Practice
The Scenario: Alex, a first-time founder who had built a company from zero to $5M ARR, was exhausted. The board wanted to bring in an experienced CEO to scale to the next level. Alex wasn't sure if this was a vote of no confidence or a natural evolution—and whether stepping aside meant failure.
What He Did: Instead of reacting emotionally, Alex created space for clarity:
- He talked to three other founders who had gone through similar transitions
- He worked with an executive coach to separate his identity from the company
- He explored what role, if any, he wanted in the company's next chapter
The Outcome: The conversations revealed that bringing in a scaling CEO was common and often the right move—it wasn't about Alex's abilities, but about matching skills to stage. He negotiated a transition to Chief Product Officer, where he could focus on what he loved (building product) without the CEO responsibilities that drained him.
Two years later, the company hit $20M ARR. Alex was energized again, and glad he didn't let ego drive a reactive exit.
The Lesson: Founder transitions aren't failure—they're evolution. The question is whether you're in the driver's seat of that transition.
What You'll Walk Away With
Our structured session produces concrete artifacts, not just conversation.
Decision Snapshot A clear-eyed assessment of your current situation—what's true, what's not, and what actually matters for your decision.
Fork Recommendation A specific direction (stay, go, or pivot) with the reasoning behind it, so you understand not just what to do but why.
Risk Map Everything that could go wrong with your chosen path, and how to mitigate each risk before it materializes.
Conversation Scripts Exact language for the hard conversations you need to have—with your boss, your partner, recruiters, or anyone else.
14-Day Action Plan The specific steps to take immediately after our session, so momentum doesn't stall.
30-Day Roadmap The longer-term plan for executing your decision, with milestones and check-in points.
These aren't templates—they're customized to your specific situation, role, and constraints.
Ready for Personalized Guidance?
Every situation is different. If you want help thinking through yours—with someone who's seen hundreds of similar cases—consider working with a coach.
What you get:- A structured conversation to clarify your situation
- Frameworks tailored to your specific circumstances
- Scripts you can actually use
- A clear action plan