How to Manage Up When You Have a Difficult Boss

Work is tough—and sometimes, it’s not because of the workload but because of the people you work with.

If you feel like work has been extra hard lately or if you’re struggling with difficult colleagues, it’s because, well… work is hard, and you do work with challenging people. You’re not imagining it.

There’s nothing worse than dealing with bad leadership or an incompetent boss. Every week, I work with clients who are struggling to navigate situations where:

• “My boss doesn’t listen to me.”

• “We’re short-staffed, and my manager doesn’t seem to care that the team is burning out.”

• “My manager openly admits they don’t know what their role is—and they don’t actually do their work.”

• “My boss said she’d call me when she needs help… and that’s it.”

I’ll save my comments on why incompetent people end up in leadership roles because today’s focus is on helping you navigate these tough workplace dynamics.

And I’ve got two words for you: managing up.

What is Managing Up? (And Why Should You Care?)

Before we dive into strategies, let me acknowledge something important: managing up is not your job. It shouldn’t be.

In an ideal world, your manager would be the one making your work experience smoother, not the other way around. But here’s the reality: understanding how to navigate a difficult boss isn’t just about making work easier—it’s about protecting your own time, energy, and sanity. It’s a skill that helps you advocate for yourself, set boundaries, and position yourself as a leader in your workplace.

So, if you’re feeling stuck with a challenging boss, here are four strategies to help you manage up.

1. Evaluate the Health of Your Relationship

Before jumping into problem-solving, take a step back and assess: What’s the current dynamic between you and your boss?

• Do you generally have a good working relationship but feel like something’s off lately?

• Is your boss hands-off and disengaged?

• Are they reactive, defensive, or constantly stressed?

• Do they undermine your work or fail to give you direction?

The way you approach managing up will vary depending on this relationship. If your manager is well-meaning but overwhelmed, your approach will be different than if they are dismissive or difficult.

Understanding where you stand will help you apply the right strategies moving forward.

2. De-escalate Tense Situations

One of my favorite workplace communication tactics is de-escalation—because let’s be honest, managers often let their stress spill onto their teams.

Whether it’s pressure from above, lack of training, or their own personal insecurities, their frustration can trickle down to you. But when you sense tension rising—when they’re speaking over you, ignoring you, or getting defensive—you can use de-escalation to redirect the conversation.

Try using these phrases:

🔹 “Hey [Boss’s Name], it’s not my intent to make this more frustrating than it needs to be.”
🔹 “Hey [Boss’s Name], lately there’s been a disconnect between us working together—what’s your take on that?”

These phrases call attention to the tension without adding fuel to the fire. They also invite your boss to respond, giving you valuable insight into why they’re acting the way they are.

3. Speak Their Language

Once you’ve diffused the situation, the next step is to ensure that your communication lands. Because often, workplace conflicts arise when people talk at each other instead of with each other.

For example, if you’re a healthcare administrator working with a clinician, you likely communicate in different ways—one more business-oriented, one more clinically focused. Or if you’re in marketing reporting to a finance leader, your priorities and language might not align.

When managing up, frame your requests and concerns in terms they understand.

• Instead of: “I need more time to complete this project.”

• Try: “If we rush this project, we may miss key details that will cost us more time later. Can we adjust the deadline to ensure we get it right the first time?”

Adapting your communication to fit your manager’s perspective can make your conversations far more productive.

4. Control What You Can Control

At the end of the day, some workplace challenges are beyond your control. You can’t single-handedly fix your boss’s leadership skills, and you certainly can’t change who is in charge.

What you can control:
✅ How you communicate your needs.
✅ The quality of your work.
✅ The boundaries you set.

When you focus on what’s within your control, you protect yourself from unnecessary stress and frustration. Do your best, document your efforts, and take pride in knowing you contributed positively—even if your boss didn’t make it easy.

Managing up isn’t easy, and it shouldn’t be a skill you have to learn. But the reality is, many middle managers lack the training, resources, or time to lead effectively. This creates a glaring gap in the workplace, and that’s exactly why I focus on helping professionals like you use communication to make work better for everyone involved.

If you’ve ever had to manage up, I’d love to hear from you! What strategies have worked (or totally flopped) in your experience? Drop a comment or share your thoughts—I’d love to continue the conversation.