Managing Up: The Difficult Boss (Or...Are They?)
Part 4: Managing Up Series
So you’ve got a difficult boss.
Sucks to be you.
But also...you’re not special.
Approximately 97% of LinkedIn is keeping you company. Scroll your feed for thirty seconds and you’ll turn up a narcissist, a micromanager, a gaslighter or someone who appears to have escaped from a true crime documentary.
To be fair, some bosses are genuinely grade A mo fos. (Even their mothers think so.)
They bully people. Play mind games. Have favourites. Take credit. Undermine. Create emotional chaos before 9:30am.
No amount of “managing up” fixes the fungus growing on their soul.
We’ll get to those ones. I promise.
But first, here’s something I’ve noticed after many years in corporate land. It doesn’t take much for us to convince ourselves we’ve got a TERRIBLE BOSS.
There’s an interaction.
It doesn’t feel great.
Maybe another.
And before long, we start confusing how they make us feel with who we think they are.
Then we start cataloguing EVERY frustrating interaction as EVIDENCE.
Abrupt = Rude AF.
Challenges my idea = Against me.
Leaves me to figure it out= They have no idea what they’re doing.
Cancels my 1:1= Declaration of war.
Never see them= I’ve been abandoned.
Easy tiger.
Before we diagnose your manager with a personality disorder, let’s consider the less thrilling possibility.
They might not be a bad boss. They just might not be your favourite operating system.
Annoying. Yes. Not the same as bad.
Here’s a few examples worth mulling over before you commit to the diagnosis.
False Positive #1 “Leaves me to figure it out”
Your diagnosis:
They’re LAZY.
They don’t CARE.
They have absolutely no idea what they’re doing.
Or...
They hired you because they trust your judgement. Which is the thing they are PAYING YOU FOR.
They’ve assumed you’ll get on with the job and pull them in when you need a decision made, an obstacle removed or some air cover.
That’s not necessarily neglect. Sometimes it’s autonomy.
And you can’t ask to be trusted to do your job while also expecting to be told exactly how to do it. That requires your manager to leave you alone and hold your hand at the same time. Even Hermione needed a time-turner for that.
The reframe: Ask yourself, are they neglecting me or are they trusting me?
Do this Tuesday: Book fifteen minutes with the boss and settle decision rights out loud. “Here’s what I’ll just get on with. Here’s what I’ll bring to you. Here’s what I’d never touch without you.” Most of what feels like abandonment is simply unspoken. Say it out loud and it stops being a mystery.
False Positive #2 “Abrupt”
Your diagnosis:
They don’t like me.
They’re rude.
They have the emotional intelligence of a garden rake.
Or...
Could it be that they’re busy?
Or that for them, brevity isn’t rudeness, it’s efficiency. They’re actively trying not to take any more of YOUR time than they need to.
They’re the leader whose entire email reads: Approved. The other one crafts a thoughtful four paragraph response opening with, “Hope you had a lovely weekend...”.
Neither of them necessarily values you more than the other.
One just has fewer adjectives.
Communication style tells you how someone likes to communicate. That’s it. That’s the whole data set. Everything else- what they meant, who they are, how they feel about you, is YOUR interpretation. Not FACT.
The reframe: Ask yourself, is this personal, or is this just how they communicate?
Do this Tuesday: Rewrite your next request to suit them, not you. The ask goes in the first line. Context goes underneath, for if they want it. And give options instead of open questions. So not: “Hi! Hope you’re well. Wanted to loop you in on the campaign timings, there’s a bit of history here...” But: “Need a call on Q3’s sales campaign date. I recommend 14th March. 28th March works if we want the extra creative round, but we lose the school holiday window. Happy either way, just need a yes by Tuesday.” Brief people aren’t being difficult. They’re waiting for you to get to the point.
False Positive #3: “Challenges my idea”
Your diagnosis:
They think I’m an idiot.
They don’t respect me.
They’ve made it their life’s work to ensure I never voluntarily contribute in a meeting again.
Or...
Could it be that they simply disagree with your idea?
Not you.
Your idea.
Some leaders genuinely believe it’s their job to poke holes in thinking before the market, the customer or the CFO does it for them.
To them disagreement isn’t rejection. It’s quality control to stop expensive mistakes happening on their watch.
And this is where we usually spiral. We hear “I don’t agree with your idea” and translate it to,“I don’t value you.” It isn’t the same sentence.
Some of the smartest leaders I’ve worked with challenged almost everything.
Not because they wanted to win the argument. Not for the dopamine hit of saying, “Yes... but have we considered...”. But because they believed finding the holes before somebody else did, was the actual job.
The reframe: Ask yourself, are they attacking me... or pressure testing the idea to make it stronger?
Do this Tuesday: Bring the holes yourself. “Here’s the idea. Here are the two things I reckon you’ll push on and here’s my thinking on both.” You’ll stop being cross examined and start being consulted. Same idea. Completely different meeting.
The Rapid Round
Cancels your 1:1. The calendar is not a love language. Ask to move it rather than reading it as a verdict. And if it’s cancelled four times running, that’s not a mood, it’s a pattern and now you’ve got something concrete to raise instead of a grievance to nurse.
Never see them. Some managers are stretched across too many people and too many meetings and are pathetically grateful when someone tells them exactly what they need and how long it’ll take. Access is usually available. It’s just rarely offered.
The Receipts
Version A: Approved
I once had a manager, back when I was consulting, whose entire feedback vocabulary was one word. Approved. Go for it. On a big day, I’d get: Yep, good.
The first two months I was a bit miffed. I’d send something I’d worked on for a week and get back one, two words, if I was lucky and a full stop.
So I decided she wasn’t reading them.
Then I decided she didn’t rate me.
Then I got a call from a leader in a completely different part of the business, about a small project they needed help with. My manager had put my name forward. Turns out she’d been talking about me for months.
Just never to me.
She was one of the best managers I’ve ever had.
Approved doesn’t mean I can’t be bothered with this. It meant I trust you. Go.
Version B: The head tilt
I once had a manager who was by every visible measure, lovely.
Remembered my boyfriends name. Asked for my opinion on things and actually waited for the answer. And he’d ask how I was really doing. With the pause. And the head tilt.
The same man decided he wanted me out of my role and never said a word to me about it.
What he did instead was mention it to someone close to him who worked in the same industry. Who mentioned it to one of their leads. Who then reached out to me, casually and warmly to say he’d heard I was looking at new opportunities and ask whether I might be open to hearing about a role.
Three people, to avoid one conversation.
The part my manager hadn’t accounted for was that I’d worked with that lead years earlier. I knew him and I knew exactly who he was connected to.
So about ninety seconds in, I knew exactly where it had come from.
Then I went back to work and sat across from a man who wanted to know how I was really doing.
Warmth is a communication style too. It tells you how someone likes to sound.
It doesn’t tell you how they’ll behave when it counts.
One of them never told me what she thought of me, while the other told me constantly. Only one of them was on my side.
Ok, but what if they actually ARE a Toxic Mo Fo
Some of them are. This isn’t a piece about how your boss is secretly lovely and you’re the problem.
So here’s how to tell the difference.
Pattern or Incident? Everyone has a bad Tuesday. One sharp email after a steering committee meeting is a human being under pressure. The same email every week is not a bad Tuesday. Moods you have to ride out. Patterns you can plan around.
Everyone or just you? If they’re brusque with the entire team, that’s their operating system. If they’re warm with everyone and sharp only with you, that’s information and it’s worth finding out what’s driving it.
Behaviour or impact? This is the real test. Good leaders challenge ideas. Toxic ones make you feel like a moron for having ideas. So ask yourself, do you leave the interaction with your boss clearer or smaller? Clearer is a difficult style. Smaller is a difficult boss.
And the honest bit
Whilst we’re thinking about this, it’s worth asking what you’re contributing to the dynamic.
Not because it’s your fault. Because it’s the only half of this you actually control.
If you bring half formed thinking, you’ll get challenged harder.
If they only hear about problems once they’re on fire, they’ll start checking in constantly. Which you will then describe to your friends as micromanaging.
Point is, some of the friction could have some of your fingerprints on it too. And that part is fixable.
Prosecutor or Detective?
When we’ve decided someone is THE PROBLEM, we misread their behaviour, wish they were different and talk smack about them to anyone who’ll sit still long enough.
We appoint ourselves prosecutor, gather the evidence and build the case. And we win precisely nothing, because there’s no jury, no verdict and you’ve still got the same 1:1 on Thursday.
The people who get ahead spend that same energy on detective work instead.
What does this human respond to?
What makes them itchy?
What makes communication easier instead of harder?
That’s managing up.
Not waiting for an operating system upgrade that isn’t coming. Working with the human in front of you.
Basically: you can be right about your boss, or you can go be successful with the one you’ve got.
Choose carefully.
Managing Up: Boss Whispering 101
Planning to just wait it out until you get a better boss?
Bold.
The next one will be different, but not easier. And you’ll be starting the decoding from scratch.
Boss Whispering 101 teaches you how to translate the cryptic one line email, tell genuinely useful feedback from someone having a stressful Tuesday and stop reading every new request as an act of psychological warfare.