Managing Up Without Selling Out

Nobody teaches you this in engineering school.

You can be technically brilliant, ship great work, lead your team well — and still fail because you can't work effectively with your boss.

"Managing up" sounds political. Sycophantic. Like playing games instead of doing real work.

It's not. It's just communication. Done well, it makes you more effective and your boss's job easier. Done poorly or not at all, it limits your impact no matter how good your work is.

What Managing Up Actually Means

It means:

• Understanding what your boss cares about
• Communicating in ways that work for them
• Helping them succeed (so they can help you succeed)
• Building trust through reliability

It doesn't mean:

• Saying what they want to hear
• Hiding problems
• Abandoning your principles
• Sucking up

The goal is effective partnership, not manipulation.

Understand What They Care About

Your boss has problems. Understand them.

What are their goals? What are they measured on? What keeps them up at night?

What do they need from you? Reliable execution? Strategic input? Technical expertise? Covering blind spots?

How do they like to communicate? Slack or email? Detailed or high-level? Frequent updates or only when needed?

What's their style? Hands-on or delegating? Risk-tolerant or cautious? Process-oriented or outcome-oriented?

When you understand these, you can tailor how you work with them.

The Status Update

Most friction with bosses comes from information asymmetry. They don't know what's happening. They get surprised. Surprises make people nervous.

Fix this with proactive updates.

My formula:

• What's on track: Brief. No need for details.
• What's at risk: More detail. What's the risk? What's the mitigation?
• What I need: Decisions, resources, air cover.
• What you should know: Things that might come up, FYIs.

Frequency depends on your boss. Some want daily. Some want weekly. Ask.

The key: no surprises. Bad news should never be news. If you know something might go wrong, share it early. "I wanted you to know this might become an issue" is infinitely better than "This blew up yesterday."

Disagreeing Effectively

You won't always agree with your boss. That's fine. How you disagree matters.

Disagree privately first. Don't surprise them in meetings. Have the conversation 1:1 (see Running 1:1s That Don't Suck).

Come with data. "I don't think we should do X" is weak. "Here's data showing X will cause Y problem" is strong.

Propose alternatives. Don't just shoot down ideas. Offer better ones.

Disagree and commit. Sometimes they'll decide against you. Once the decision is made, execute it fully. Don't sabotage or sulk.

Know when to escalate. If it's truly important and they won't budge, you can escalate to their boss. Use sparingly. Have a good reason.

Making Their Job Easier

Your boss has a hundred things competing for their attention. If working with you is easy, you'll get more support.

Be low-maintenance. Handle what you can handle. Don't escalate every small problem.

Be reliable. Do what you say. Meet deadlines. If you can't, communicate early.

Anticipate needs. What will they ask for next? Have it ready.

Solve problems, don't just report them. "We have a problem" is less useful than "We have a problem, here's my proposed solution."

Make them look good. When your team succeeds, they look good. Align incentives.

Navigating Politics

You might have a great boss. You might have a difficult one. Either way, some navigation is required.

Build direct relationships. Don't let your boss be your only connection to leadership. Build rapport with peers and their bosses (more on this in Stakeholder Management for Technical Leaders).

Understand the landscape. Who has influence? What are the organizational dynamics? You don't have to play politics, but you need to understand them.

Document important things. When decisions are made, confirm them in writing. "Just to confirm, we agreed to X." CYA when needed.

Don't gossip. It always gets back. Always.

When Your Boss Is the Problem

Sometimes you do everything right and the relationship still doesn't work. Maybe they're a bad manager. Maybe there's a values mismatch. Maybe they're just difficult.

Options:

1. Direct conversation. "I feel like we're not aligned. Can we talk about how to work better together?"
2. Seek mentorship elsewhere. If you can't learn from them, learn from others.
3. Outlast them. Bosses change. Sometimes waiting is the play.
4. Transfer or leave. If it's truly broken, move on. Life's too short.

But be honest with yourself first. Is it really them, or is there something you could do better?

The Long Game

Your relationship with your boss is an investment. Built over time through consistent reliability, good communication, and mutual respect.

When you need something — a promotion, resources, support on a risky project — that relationship pays off. Or it doesn't.

I've seen brilliant people stall because they couldn't work with their bosses. I've seen average performers thrive because they could.

Technical skills get you in the door. Relationship skills determine how far you go.

Managing up isn't about politics or games. It's about making the relationship work so you can have more impact. Understand what they need, communicate effectively, make their job easier. Simple in concept, requires practice in execution.