Four Things to Do If You’re Struggling With Your Boss

Let’s be honest: managing upwards isn’t just about “aligning communication styles” and “navigating complex dynamics.”

Sometimes it’s about surviving a relationship that’s draining the life out of your work.

If you're finding it hard to work with your boss, and you've already tried being patient, professional and positive, this article is for you.

Try these four specific things this week to take back control.

1. Stop Guessing. Get Clear.

Difficult relationships often stem from misaligned expectations. And when things are tense, people stop talking.

You try to second-guess what they want. You overwork, overexplain or go quiet. It doesn’t help.

So pause. Get clear. Ask them: “What does great look like to you this month? What are your top three priorities? How do you want me to communicate progress?”

Even if the answers are vague or contradictory, you’ve started resetting the relationship. You’re forcing clarity where confusion has taken root.

2. Show Value Where It Matters Most

In fast-paced organisations, senior leaders are under pressure to deliver. If your boss is difficult, there’s a good chance they’re under pressure too.

Don’t just try to be liked. Focus on being useful.

Ask yourself: Where can I take pressure off? Where can I deliver something they’ll be genuinely relieved or impressed to see handled well?

When you make your value visible in the areas that matter most to them, the dynamic starts to shift. You’re no longer a source of friction. You’re part of the solution.

3. Set Some Boundaries

This one’s non-negotiable. If your boss is micromanaging you, undermining you, or constantly moving the goalposts, it’s time to draw some lines.

You don’t have to go in with your fists up. Try saying:“Can we agree on what success looks like here so I don’t need to keep checking in unnecessarily?”or“I’ve noticed the priorities keep shifting. Can we take 10 minutes to agree what’s genuinely urgent and what can wait?”

This is where confidence counts. Your boss isn’t responsible for your boundaries.

You are.

4. Start Planning Your Exit

If you’ve done all of the above and nothing’s changing, listen carefully:

There is no badge of honour for staying in a relationship that damages your confidence, drains your energy, or makes you dread Monday mornings.

There is no shame in leaving a team, or a boss, that doesn’t bring out your best.

And no matter what you’ve been told, moving on is not a failure. It’s a decision to put your well-being and career back in your own hands.

You deserve to work in a place where your contribution is valued, your voice is heard, and your leader has your back.

Want to talk this through with someone who’s helped hundreds of senior leaders navigate exactly this kind of challenge?

Let's have a call.

You don’t have to stay stuck.