A lot of you are reporting to leaders who are brilliant at the strategic and technical parts of their job, and yet surprisingly poor at managing people.
I’m not talking about actively malicious bosses. I’m talking about the ones who change their mind every three days, fail keep you in the loop, or fail to back you up whenever you need them too.
If that’s you right now, I empathise, because it’s exhausting to report to someone like that.
Research consistently shows that the relationship with your direct manager is one of the single biggest factors in whether you stay in a role or leave. More than the work itself, and more than the pay, and more than the company values.
A difficult boss doesn’t just make your day harder; they can seriously undermine your confidence and suck the joy out of a job you might otherwise love.
So, how do you manage upwards when the person you report to is making your professional life more difficult than it needs to be?
When the usual advice falls short
Common advice about managing upward usually focuses on making yourself more likeable in the eyes of your leaders. Things like adjusting your communication style, mirroring their energy, or giving them information the way they prefer it.
Those are good tips, but they’re not enough. You need to understand what’s actually causing the friction and then be much more deliberate about how you work with them.
I’ll walk you through the four most common complaints I hear from clients about their difficult bosses. For each complaint, I’ll suggest what you can do, give you some actual words to use and describe what success might look like.
Complaint #1: They keep moving the goalposts
You present your strategy, they ask for changes. You make those changes, and then at the next meeting it turns out they wanted something completely different. And the cycle then repeats itself.
This usually means one of two things. Either they’re under pressure from above and that pressure keeps shifting, so they’re redirecting it onto you. Or, they genuinely don’t know what they want and are using your iterations to figure it out.
The tactic here is to give them two chances, and after the third time this happens, have a conversation about it. Not at the point when you’re feeling frustrated, but in a separate, calm one-to-one.
What you can say is:
“I want to make sure I’m using our time well. I’ve noticed that when I present work to you, the direction often shifts between conversations. I’d like to understand what’s driving that so I can get ahead of it. Is this coming from changes in what the exec team needs, or are we still working out the right answer?”
And they’ll usually tell you. If the answer is that it’s shifting priorities from above, you can say: “That’s helpful. Would it be useful if I gave you two or three options at each stage so we have some flexibility as things change?”
Or if they’re still figuring it out: “Got it. Would it help if we worked through the strategy question first before I go deep on anything? I can put together a one-pager with a few possible directions and we can test which one feels right.”
What success looks like here is not that they stop changing their mind, but that you understand why it happens and have a process that works with it rather than against it.
Complaint #2: They keep you in the dark
Decisions get made that directly affect your work but you only find out about them afterwards, or worse, you get blindsided by your boss in meetings because they haven’t shared critical context with you.
This usually happens for one of two reasons: either your manager doesn’t see information-sharing as part of their role, or they’re so overwhelmed that communication is the first thing that drops off their radar.
Here’s what you can do: create what we call in coaching a forcing function, which is essentially a structure that makes communication as low-effort for them as possible.
Set up a short weekly check-in of about fifteen minutes with a standing agenda that you send them the day before. When proposing it, say: “I’ve noticed I sometimes get blindsided in meetings because I don’t have the full picture of what’s happening at your level. I know things move fast up there. Would it help if we had a quick weekly check-in, just fifteen minutes, where I can ask you three questions? I’ll send them to you the day before so you know what’s coming.”
The three questions are: what’s changed at your level this week that I should know about? What’s coming down the track that might affect my work? And is there anything you need from me?
They can respond verbally in a quick call or via email, but the key is sending those questions ahead of time so they can prepare their thoughts without feeling put on the spot.
You’ll know this tactic has been successful when you stop being blindsided (for the most part) and you have enough information to do your job effectively.
And again, you’re not trying to change their communication style or turn them into someone they’re not, but you’re simply building a routine that works around their limitations.
Complaint #3: They don’t back you up
This is the boss who won’t support you when you need them to, who doesn’t back your decisions publicly or privately, and who doesn’t fight hard enough to get you the resources you need.
You know the type, whenever you need them to pipe up, they go conspicuously quiet.
This is a tough one to navigate and my non-medical diagnose here is that this behaviour is usually due to insecurity or self-preservation on their part. They either don’t feel confident enough to advocate for you, or they’re too worried about protecting their own position to put themselves on the line for you.
The approach here is to make it easier for them to back you up. So, before any situation where you need their support, brief them in advance, give them the talking points, and make sure that backing you up feels not only low-risk to the, but also makes them look good in the process.
For example, let’s say you’re negotiating budgets. What you could say is: “I know the budget conversation is coming up on Thursday. I wanted to give you the key points for why we need that additional investment, in case it comes up. The main arguments are X, Y, and Z. Would it help if I sent you a one-pager you can use?”
When people feel prepared rather than put on the spot, they’re far more likely to actually speak up for you.
The other thing that could help is lowering the stakes for them. Insecure people tend to avoid big public commitments because the risk feels too high, so instead of asking them to fight a major battle on your behalf, you could ask for smaller, more specific support. Not a “Hey, I need you to push the exec team to approve my budget increase” but rather “Would you be willing to say in the meeting that you’ve reviewed the numbers and they make sense to you?”
Success here is not that they suddenly become your biggest champion, but that you get the specific support you need on things that actually matter, by making it as easy and low-risk as possible for them to give it.
Scenario 4: They just don’t like you
Sometimes the chemistry between two people is just completely off, and there’s no rational explanation for it. They simply don’t like you. And when it comes to managing difficult relationships, this often feels like the hardest nut to crack.
If you’re the only person on the team having this problem and your peers all seem perfectly fine with your boss, then that friction you’re experiencing is almost certainly personal. Maybe you remind them of someone from their past, or maybe they preferred another candidate for your role, or maybe your personalities just clash in a way that has nothing to do with your actual competence.
It’s also possible that you don’t particularly like them and they’ve somehow picked up on that, which creates a feedback loop neither of you can break.
The reason this is a potentially dangerous situation is that when someone doesn’t like you, no matter how professional they are, it can sometimes leak into how they represent your work, how much benefit of the doubt you get when things go wrong, and whether they advocate for you behind closed doors.
They might not be actively undermining, but you’re probably not being actively supported either, and in organisational politics, neutrality from your boss often works against you.
Now, there are definitely things you can do to build better rapport and improve how people perceive you, and I’ll cover that in a future episode. But when you’re dealing with a boss who fundamentally doesn’t like you, those tactics rarely move the needle enough to matter. What you need to focus on instead is protecting yourself while you figure out whether this situation is sustainable.
First, document everything importnat. Confirm all decisions in writing, and after any conversation where something was agreed, send a brief email: “Just to confirm: I’ll do X by this date, you’ll handle Y.”
Second, keep a clear record of your successes so that when something goes well, there’s tangible evidence of it.
Third, build visibility elsewhere in the organisation by volunteering for cross-functional work and making sure that people at your boss’s level can see what you actually do and how you do it.
And fourth, maybe find yourself a mentor outside your reporting line and say to them: “I’m finding my current reporting relationship quite difficult. Would you be willing to meet every few months so I can get your perspective on how I’m doing more broadly?”
I suspect that none of these tactics on their own will magically improve the relationship, but they will allow you to keep doing your job and stay confident while knowing your reputation isn’t entirely in one person’s hands.
What to do when it’s not fixable
If you’ve tried the right approaches consistently for three to six months and the relationship is still affecting your ability to your job properly, or damaging your reputation, or costing too much emotionally, set yourself a deadline. “I’ll give this until end of Q2. If these things haven’t improved, I’ll start looking.”
Then get ready. Network. Sort your finances. Update your CV. Leaving a difficult boss situation isn’t failure, but staying too long while trying to convince yourself it’s magically going to get better is a mistake.
And before I wrap up, let me turn this around. If you manage people yourself, are you perhaps the difficult boss?
Are you the one changing your mind without explaining why? Keeping your team in the dark? Going quiet when they need backing?
Difficult boss behaviour is often invisible to the person doing it. You think you’re being decisive and agile, but your direct reports experience it very differently. Or you think you’re shielding them from unnecessary politics, but they’re showing up to meetings feeling clueless about what’s going on around them.
So, if this article made you think “Hah! My boss does that,” ask whether you might be the villain in someone else’s story too.