Hey team,
We’re down to the final few hours of enrollment for Fresh Start. This will be the last time I mention it in my emails, and I’m so grateful for the incredible group of managers who’ve already joined.
If you’ve been on the fence, this is your moment. After today, the doors are closed. But back to the matter at hand…
When your boss is the problem
I used to have a boss whose emotions controlled everything.
Before I’d even stepped into the office, I’d catch myself wondering: “What mood is he going to be in today?” Because that would decide how my whole day would go.
If he was stressed, we all walked on eggshells. If he was frustrated, the smallest mistakes blew up into drama. Then if he was in a good mood, we could all breathe again and felt like best mates… Until the cycle repeated.
And this is the part no one warns us about. Sometimes the hardest part of management isn’t your team at all.
It’s managing the emotional rollercoaster of your own boss.
Managers tell me this literally daily:
“My boss’s stress becomes my stress.”
“I feel like I’m babysitting upwards instead of leading downwards.”
“My boss is a control freak.”
So how do we handle it?
We can’t exactly “performance manage” our own manager like we can our team.
And whilst I don’t think we’ll ever 100% figure this out, because ultimately we can’t change people, I have found some solid strategies to navigate it. Let me show you…
1. Understand their priorities
If you don’t know what keeps your boss awake at night, you’ll keep missing the mark.
Frame your conversations around their priorities, and you’ll instantly shift from sounding like a complainer to being seen as a partner.
Example: Let’s say your team is missing deadlines because they’re juggling too many competing requests.
The version most managers take to their boss:
“The team are overloaded. Everyone’s stressed and we can’t keep up. We need more headcount.”
Whilst these things are true, and valid, it puts the focus on your frustrations, which makes it easy for your boss to dismiss as complaining.
The strategic version (aligned to their priorities):
“I know one of your top priorities this quarter is hitting the new client deadlines. Right now, the team are being pulled into multiple directions, which risks us slipping on that. I see two options: either we pause lower-priority tasks or we bring in temporary support. I’d recommend pausing the lower-priority work, because it protects delivery on the deadlines you’ve committed to.”
This shifts the focus: you’re not just raising a problem, you’re showing you get their goals and you’re already thinking in solutions.
That’s what builds trust and influence upwards.
2. Be a strategic partner, not a passive executor
Managers who simply wait to be told what to do will always stay on the sidelines.
The ones who get noticed are those who bring ideas, weigh options, and recommend a path forward. That’s the shift from doer to partner. And here’s how we start really strategically managing up.
Instead of:
“What do you want me to do about this?”
Run with something strategic and solution-focused:
“Here are two approaches I’ve considered. I’d recommend this one because it supports [priority] and keeps us on timeline.”
Over time, this helps your boss trust your judgement, rely less on control, and dial down the toxic habit of micromanaging. When you consistently show up as a partner, they don’t need to hover, they start to let go.
3. Push back to build trust
Here’s the paradox: Saying “yes” all the time makes you less trusted. It’s the thoughtful pushback, the moments you’re willing to challenge, that actually build trust and credibility.
Silence looks like disengagement. But thoughtful pushback shows independence, care, and commitment to the shared goal.
Phrases like:
“Would you be open to exploring another angle?”
“I’m not sure this will land well with the team, can we look at an alternative?”
These aren’t about picking fights. They’re about offering perspectives that might not be visible at the top.
Always making sure it’s done with curiosity instead of ego.
4. Call it quits
Too many of us cling to a familiar hell, staying with a toxic boss or a job we hate.
Change is hard. But is it harder than staying?
With the boss I mentioned in the intro, I eventually realised he was never going to change. No matter how well I managed up, set boundaries, or reframed conversations, his emotions would always dictate the day.
And just like with a toxic ex, I had to make the call to quit and walk away.
Sometimes the bravest form of leadership isn’t managing harder, it’s deciding the environment isn’t right for you, and leaving it behind.
Peace,
H