🚩 Tactical Memo 061: 20 Years In, One New Boss, and He Was Gone

Read time: 7 minutes

👋 Hey, it's Justin. Welcome to Tactical Memo, my weekly newsletter for leaders who plan to win the next decade of work.

If you want practical guidance you can use at work this week, you're in the right place.

👉 Why Read This Edition: You'll get 15 principles for managing up that protect your job when your boss changes, and 1 question that tells you if you're already at risk.

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The research that should scare you

A 2023 study published in Personnel Psychology, led by Ravi Gajendran at Florida International University, ran four studies with 1,313 respondents to test something called "Managing Your Boss," or MYB. The finding was simple. Employees who proactively understood their boss's goals and work style got better performance ratings from those same bosses.

The researchers also found that MYB matters most when the work is unstructured and when managers give little direction. In other words, the messier the job, the more managing up decides your fate.

Read that again.

Your performance review is a measure of how well your boss understands your work. That's a different thing than the work itself. One you control. The other you have to build.

People learn this after they've already lost.

The call I got last month

A friend of mine called me three weeks ago. He'd been at the same company for 20 years. Senior role, strong track record, the kind of guy who knew where every body was buried in the org. He'd survived three reorgs and two acquisitions. He'd survived a CEO change.

He didn't survive his new boss.

The new boss had been in seat for nine months. My friend told me the story like he was still confused about how it ended. He'd been at the company two decades. The new boss had been there nine months. In every meeting, my friend made sure everyone knew which one of them had the institutional knowledge.

He corrected the new boss in front of the team. He'd jump in mid-sentence to "clarify" things. He'd say "that's not how we do it here" in front of peers, and he'd say it again in front of the new boss's own boss. He talked over him in steering committees. He rolled his eyes when the new boss pitched an idea that my friend had seen tried and fail in 2014.

He thought he was being helpful. He thought 20 years of receipts gave him the right to be the smartest voice in every room.

The new boss heard something different. The new boss heard a guy who was openly undermining him in front of the people he was trying to lead.

Nine months in, the new boss made a call. My friend was on a list of three names handed to HR, and he was the one who got cut.

20 years. Gone in a 22 minute meeting.

What he missed

When we talked, I asked him one question. Did you ever stop to think about how you were making him look in those meetings?

He paused for a long time. Then he said, "He should've known I was trying to help."

That's the whole story right there. He confused institutional knowledge with authority. He thought tenure gave him the right to teach the new boss in public. The harder he leaned on his 20 years, the more the new boss heard a threat instead of an asset.

None of that is how it works.

When a new boss arrives, the clock starts. You have a window, maybe 90 days, to install yourself as someone they trust. If you don't fill that window with trust, you'll fill it with friction. And friction with a new boss has a shelf life. Once the new boss has labeled you as the guy who undermines him, that label is very hard to peel off.

My friend didn't manage up because he'd never had to. His old boss did all the work for him. He'd built his career on a relationship, and he confused the relationship with a skill. When the relationship left, he had no idea how to build a new one. So he leaned on the only currency he had left, which was being the guy who'd been there longest. He swung that currency around like a club. The new boss felt every swing.

That's the trap. If you've never had to manage up, you don't know if you can. And you'll usually find out the hard way, by losing.

15 principles for managing up

These are the rules I've worked from, and the ones I've coached operators and managers through when their boss changed, when they got a new skip-level, or when they were trying to crack into a senior team. None of these are theoretical. I've watched every one of them play out.

1. Learn how your boss reads information. Some bosses want a one-page summary. Others want the full deck, and a few only want a five minute hallway conversation. Find out in the first two weeks. Ask them directly, "How do you like to be updated?" Then deliver it that way every time.

2. Bring solutions, not status. A status update is a debt. You're asking your boss to spend energy figuring out what to do with the information. A solution is a deposit. You tell them what's wrong, what you're doing about it, and what you need from them. Three options on the table, and your recommendation at the bottom.

3. Surface bad news first. Bad news travels up slowly, and that's why bosses get blindsided. Be the one who tells them on Monday morning, not Friday afternoon. Bosses don't fire people for problems. They fire people for surprises.

4. Understand what your boss is being measured on. Your boss has a scorecard. If you don't know what's on it, you can't help them win. Ask. "What does your boss care about right now? What's the thing keeping you up at night?" Then map your work to those answers.

5. Adapt to their pace, not yours. If your boss moves fast, you move faster. If your boss is deliberate, you slow down and bring depth. Andy Grove wrote in High Output Management that a manager's job is to multiply the output of the people around them. Your job is to make that easier, not harder.

6. Make them look good in front of their boss. This isn't politics. This is math. Your boss's reputation is built on what their team produces. When you give them a clean win to take upstairs, you're investing in the only person who can promote you.

7. Don't make them guess what you want. If you want a promotion, say so. If you want a stretch project, ask for it. Bosses aren't mind readers, and the ones who try to be usually guess wrong. Be direct. "Here's what I want in the next 12 months. Here's what I'm doing to earn it. What am I missing?"

8. Manage their calendar awareness. Know what's on your boss's plate this week. If they have a board meeting Thursday, don't drop a five-alarm problem on them Wednesday night. Time your asks. The same request lands differently on a Monday than a Friday at 4 p.m.

9. Translate your work into their language. If your boss is a finance person, frame your work in revenue and margin. If they're a product person, frame it in customer outcomes. The work doesn't change. The frame does.

10. Build a relationship before you need one. The time to invest in your boss is when you don't need anything. Stop by their office. Send them the article you read on the weekend, or ask how their kid's soccer game went. By the time you need political capital, it's too late to start saving.

11. Don't compete with your boss in public. This is the one my friend broke, over and over, for nine months. He corrected the new boss in meetings and rolled his eyes whenever a new idea got pitched. He thought he was adding value. The new boss heard him saying, "I should be in your chair." Disagree all you want in their office. In front of the team, you make them right. Even when they're wrong. The room is the wrong place to teach your boss anything.

12. Push back hard in the room, then get behind the call outside it. Stanley McChrystal wrote in Team of Teams that a high-performing team debates hard internally, but rows in the same direction once a call is made. Apply that to your boss. Tell them they're wrong with the door closed. Tell the team they're right with the door open. Anything else is mutiny, and bosses end mutinies quickly.

13. Document the wins they didn't see. Your boss doesn't see 80 percent of what you do. Keep a running log of your wins, in their language, and feed it back to them once a month. Frame it as context, never as bragging. "Wanted to flag that the migration came in two weeks early and saved us $180K. Team did a great job."

14. Read the room when their boss is in it. When your boss's boss walks in, your job changes. You're not there to perform. You're there to make your boss look like the leader of a strong team. Speak when asked, and defer credit every time. Let your boss be the protagonist of every story told in that room.

15. Build a second sponsor. This is the one my friend missed. Never let your career rest on one relationship. Find another senior leader who knows your work, sees your value, and will speak for you when your boss isn't in the room. If your only champion leaves, you go with them.

The principle behind the principles

Here's the thing every one of those 15 principles is really about.

Managing up is the recognition that your boss is a customer. They have constraints and pressures you don't see. Your job is to make their job easier. When you do that consistently, they protect you and promote you, and they take you with them when they move on.

When you don't, you're a line item on a list.

Bob Iger wrote in The Ride of a Lifetime that the people who succeeded around him were the ones who anticipated his needs and removed problems before they reached his desk. The ones who made his life easier so he could focus on the big calls.

That's the bar.

Make the call this week

If your boss has been in seat less than 12 months, or if there's any chance of a change coming, do these three things by Friday.

Ask your boss how they like to be updated. Then change your communication to match.

Write down what your boss is being measured on this year. If you can't, schedule 20 minutes to ask them.

Identify one senior leader who isn't your boss and put a coffee on the calendar. Build the second sponsor before you need one.

That's the work. None of it is hard, and almost no one does it.

One question

When your boss leaves a meeting you were both in, do they feel bigger or smaller for having you in the room?

Sit with that one for a minute. It's the only question that matters.

My friend never asked it. For nine months, his boss left every meeting feeling smaller. Then his boss got tired of feeling that way and made a call.

20 years of equity doesn't survive that. Neither will yours.

Don't wait for a new boss to find out how you handle this. Look at the boss you've got, and ask the question. If the answer is "smaller," you have work to do this week.

If this helped you, send it to someone who could use it this week.

Until next time,

Justin

✍️ From the Desk of Justin Bateh, PhD
Become an indispensable AI-era leader