Leadership and bootlicking aren’t as far apart as we’d like to think. The only real distinction is how much you’re willing to bend your spine to stay in favor.
But once managing up becomes your main focus, you risk losing touch with the people you’re supposed to lead. And over time, chronic suck-ups stop paying attention to the work and the people doing it, and focus almost entirely on how they’re seen above.
Naturally, when you’re working 50+ hours a week, you might wonder how anyone manages their boss without losing their soul.
The answer is surprisingly simple. At some point, we’ve all had the thought: “What if I just agree with everything my manager says? It would barely inconvenience my dignity, and I’d have a promotion”. Most leaders stop there, impressed with their own survival instinct. Some take it further, refine it, and invent what we now call a "Career strategy”.
The risks of managing up
The trap is choosing the path of least resistance, or what I’d call becoming a “Yes manager”. It feels like you’re protecting your team by agreeing instead of pushing back. But in reality, you’re just eroding your spine. And your team sees it. And they can tell the difference when you’re being a shock absorber and when you’re being a doormat.
To put managing up into perspective: “Aligned with leadership” usually means going along. “Protecting the team” often means taking the hit yourself.
We tend to dislike managing up because it feels like corporate theater. And I don’t make fun of suck-ups for ideological reasons, I do it because I find them really weird.
That disconnect becomes obvious in everyday moments. I recall one time when a middle manager was asked by their team whether the new project deadline was actually possible. He spent a few moments stumbling over the question before reluctantly answering “The VP seems optimistic about the timeline”.
Now, I’m no expert in media training, but as I frequently tell the managers I’m coaching, the correct answer to "Is this a disaster?" is always "Yes", immediately followed by a plan. You can always reveal later that your fingers were crossed out of frame when you told the VP you’d "make it work."
Protecting your team without losing your spine
Managing up isn’t about showing off your own performance. Your role is creating space for your team, presenting their work in the metrics, language, and priorities that actually matter to your boss.
Over time, I’ve learned a few ways to protect my spine while managing up.
Telling the boss that my team is “tired” doesn’t get through, but when I frame it as “the team’s workload is outpacing what we can realistically do” usually does. It felt awkward at first, but it actually works.
I’ve also learned that “We can’t do that” rarely helps. Pointing out trade-offs works better. That means explaining that taking on that one new project might mean another, even a VP’s favorite, gets delayed. Using their priorities as a shield has protected my team without causing a fight countless times.
And from time to time I do the calendar audit exercise. If most of my week is spent in alignment meetings and none of it defending my team’s focus time, it’s usually a sign I’m letting things slide. Keeping that balance in check has made a bigger difference than I expected.
The bottom line
I’ve realized the difference between leaders and office politicians isn’t salary or perks. It’s who gets to say “No”. Protecting your team, keeping focus, and managing up effectively all come down to that.
For example, if you would ask a developer whether they’d rather be alone in a room with a random bug or a random "visionary" manager, they will choose the bug every time. The bugs just crash the app. Visionary managers crash the culture, ask for a "quick sync" on a late Friday afternoon, and then vanish for another one of their “team retreats”.
That’s why, at the top of the hierarchy, it’s not about favor with the CEO, but about who earns the trust of the people doing the work.
That’s right, the team wins again.
See you next week.
P.S. If you want to learn more about How to say “NO”, check out my last week’s newsletter.