Leading The Person Above You

I had a conversation that you need to know about if the manager above you is (put simply) hard work. 

A senior manager with more than 30 years of leadership experience told me her most pressing challenge. She leads a division that works hard and keeps falling short. Above her sits a CEO who doesn't do detail, doesn't cope well with bad news, and would rather talk at you than listen. So she's holding both ends. A team that needs clear direction, and a leader who makes the work harder than it needs to be.

 If you've felt some version of that, you're not the only one.

She's up against one of the hardest parts of any manager's job, and it's the one we almost never name out loud. Managing up.

We'll talk all day about leading a team. We rarely talk about the skill of leading the relationship above you, especially when that person is hard to read, or hard to tell the truth to.

When managing up becomes managing around

 Here's what usually happens. You start managing around them. You filter. You soften. You share only what you think will land, and only the version of it that will land well. You tell yourself you're being strategic, reading the room, protecting the team from the fallout.

But that's not managing up. It's self-protection at its finest. And the tell is this: you're deciding what your leader gets to know based on how you think they'll react, not on what they actually need to lead well.

Over time that quietly makes you the buffer for their blind spots. And it costs you. It costs your credibility, because eventually the softened version catches up with reality.

Real managing up runs the other way

It's relational. It starts with getting genuinely curious about how the person above you actually works.

Not their personality type. Not how they "process". Something more specific than that. Do they take in information by reading it slowly on their own, or by talking it through with you? Do they trust numbers, or stories about people? Do they decide in the meeting, or two days later once it's settled? When you bring them something hard, do they need a moment to react before they can think, or do they just want you to get to the point?

You already have this data. You've watched them do their job plenty of times. You've just been using it to predict their moods instead of using it to lead the relationship.

The move most people skip - ask:

 "What's the best way for me to bring you an update in our one-on-one? Do you want the pre-read, or the three-minute version in the room?"

 "When something's gone sideways, do you want to hear it early and raw, or once I've got a plan attached?"

 These questions get missed constantly. And this is where the dynamic shifts, almost straight away.

Name it out loud

Those questions are a big part of why I built the Relational Agreement. Most working relationships run on assumptions nobody ever said out loud. How we share information. How we give each other feedback. What happens when something goes wrong. We absorb the other person's habits and hope we've read them right.

The Relational Agreement makes it explicit. It's a simple, shared way to name how you'll actually work together, so it stops being something you guess and becomes something you've agreed on. It works with the person above you, and it works just as well with your own team.

None of this means becoming a mind reader, or shaping yourself around their comfort. The point is that you get to be more honest, not less, once you know how to deliver the truth in a way they can take in. A CEO who struggles with bad news doesn't need you to hide it. They need you to bring it in a way that gives them somewhere to go with it.

The harder question underneath

How do you set an expectation with the most senior person in the room, when the whole dynamic makes that feel impossible?

That one doesn't have a clean answer, and I'd be suspicious of anyone who handed you one. But it usually starts smaller than you think. Not a big confronting conversation about how they lead. One clear, specific ask, in the moment it's relevant.

"For me to get this right before the board meeting, I'll need a decision from you by Thursday. I know you'll want all the detail before we walk in, not during."

You're not managing their behaviour. You're being clear about what you need to do your job well, and letting them meet you there.

Where this leaves you

The manager I spoke to hasn't changed her CEO. That was never the point. But she's starting to stop managing around him, and start leading the space between them.

If you're caught in the middle of something like this right now, the question I'd sit with isn't "how do I handle them". It's this: where have you been softening the truth to protect yourself, and calling it relationship strategy?

The Relational Agreement is a free tool you can put to use this week, with your leader or your team.

 Download the Relational Agreement →