The Mask
The Voice
You know it when you hear it:
The town hall where the C-Suite types talk about “exciting momentum” and “strategic alignment” while people in the same building are cleaning out their desks. Your skip-level asking, “How things are going?” in a tone that makes it clear they hope you don’t really say anything of substance. It’s the phrase “let’s take that offline” deployed to make a question disappear.
I can’t really explain why it sounds fake; the words are technically fine, and the information might even be accurate. Somewhere in between what the words mean, and what you are really hearing, there’s a gap (or a chasm). You feel it before you can articulate it.
That voice grinds my gears to this day. (Cue Peter Griffin)
The Lesson
I didn’t learn ‘authentic’ leadership by leading; I learned it by being on the receiving end of the fake version for years.
Early in my career, I had a string of managers who weren’t bad people. They were fine; professional, competent (probably). Talking to them felt like talking to a corporate chatbot before chatbots existed. That ‘professional’ mask never came off, their tone never varied. Whether it was a one-on-one, team meeting, or a hallway conversation, I got the same flattened, HR ‘approved’ version of a human being.
The performance reviews were the clearest signal. “Keep doing what you’re doing.” In my naivety, I took that as an indicator that I was killing it, or at least doing pretty well. Then the dreaded ‘A&D’, or ‘PM Cycle’ ratings would come: middle of the road 3/5, 1.5% raise. Every time.
Here’s what I find interesting in retrospect: I didn’t distrust these managers; I didn’t think they were lying, maliciously or out of incompetence. I just didn’t trust them enough to take risks for them, or bring them problems early. I didn’t volunteer for the hard stuff (or anything really, by the end of it all). I did my job, collected my paycheck, and kept my head down.
That’s what ‘the mask’ costs you. A thousand small withdrawals of discretionary effort.
The Contrast
Then I worked for Richard. (Hope you read this someday!)
Richard was my manager at a smaller company after I left the corporate machine. Trust took some time to build in both directions; I’d been trained to expect the mask, he had a young, sleep-deprived (new parent), wild variable as the first member of the team he was trying to build.
After a little bit of time, Richard started doing something simple, almost stupidly so: he told me which hat he was wearing.
“Boss hat” meant we were in a conversation where he had to be my manager; he had obligations, constraints, things he couldn’t flex on. I might not like what he had to say, but I’d know why he was saying it.
“Friend hat” meant we were just two people talking; we could both be candid (think safe-space in modern terms). There was still a power dynamic, (he was still my boss) but we were acknowledging it instead of pretending it didn’t exist, or making me guess every time we chatted, and he shut the door.
The distinction sounds small, but it changed everything.
Three promotions in five years. My skills grew, sure, but my core work ethic, personality, and my approach were all the same. The difference was that I actually trusted my manager, so I took risks: I raised problems early, offered up ideas I legitimately thought had merit (even when they didn’t), and put myself out there for opportunities I would have avoided before.
We’re still friends. Hopefully that tells you something.
The Thesis
The mask isn’t about lying; most leaders wearing it aren’t being dishonest. They’re being tonally mismatched.
What they’re saying is technically true, but signals in a way that says: “I’m not actually in this room with you.” They’re optimizing their communication for how it looks (maybe how it can be defended to HR), not how it lands. Performative leadership instead of actual practice of leadership.
I think people feel that gap, far more often than anyone gives credit for sometimes. They may not write memos about it or bring it up in skip-levels; they just… quietly recalibrate. They stop assuming good intent, stop bringing bad news early, and stop volunteering for the hard stuff (again, or anything).
Death by a thousand small withdrawals.
The Fix
The opposite of the mask isn’t “be everyone’s buddy.” Richard still had a boss hat, for sure. He still had to make unpopular calls, represent the company’s interests, and deliver hard feedback (the word ‘deliberate’ still makes me shudder).
The fix is legibility; making the subtext into text.
- “I don’t have a good answer for you yet, and I know that sucks.”
- “This is the part where I have to be your manager, not your friend.”
- “This situation sucks. I’m not going to pretend it doesn’t.”
It’s not about oversharing or performing vulnerability, it’s about closing the gap between what’s actually happening and what you’re saying about what’s happening.
The “Why Now” Conversation
A few months into my current role, I got to experience what this looks like in practice, in a way that has really stuck with me.
We were in the middle of a massive migration—moving thousands of CI/CD pipelines from one platform (you’ve probably heard of it) to a new platform (which you probably haven’t). My team was neck-deep in it, and there was a question nobody could answer: why now? Why this timeline? Why the sudden urgency? Especially after YEARS of relative stability.
I was new enough that I didn’t have the answer either. I could honestly say “I don’t know yet,” and that was fine.
Then I got the answer, behind virtual closed doors. A peer explained: our contract with the current vendor was expiring, and we were approaching a scaling threshold that would trigger a significant cost increase, and we had just made a large acquisition that would require migrating thousands of pipelines to our central platform. Now the timeline made perfect sense; we needed runway to build, test, and at least start migrating before that deadline hit. Otherwise, we would be walking into a contract negotiation with a disadvantage that screams ‘layoffs’ to account for the budget discrepancy.
I was told the information was sensitive, not forbidden to share, but sensitive. The ‘safe’ play was to sit on it, wait for official messaging, and be prepared to support the comms.
Instead, I brought it to my team.
I prevaricated, because I always do: “I have an answer to the ‘why now’ question, and I think it’s important for me to share it, but I’m asking you to keep it within our team for now.”
I explained the reasoning. Contract timelines, cost thresholds, the need for runway.
Silence. Almost uncomfortably so. I had to check and make sure my AirPods hadn’t died.
Then one of my engineers said, “That… explains a lot, actually. Thank you for sharing that.” I could hear the stronger than average sincerity, even through Zoom.
A more junior engineer asked why that would cause a panic if it got out. Fair question. I explained: when you tell people the product they’re 100% focused on is going away, they start dusting off resumes, and might jump ship at the first decent opportunity, especially if they were already on the fence. Better to wait until there’s a plan for what’s next before announcing what’s ending, and reduce the panic, preserve some faith in leadership.
That conversation was the first major crack in the trust barrier, though I did not realize it at the time. I’d told my team, on day one, that I’d be as transparent as I was allowed to be (I technically said “painfully transparent”), but those were just words until I backed them up. After that meeting, something shifted; they were more relaxed, more open, and more willing to bring me problems (or warn me of potential problems).
The Close
I prevaricate constantly. I say “I think” and “I’m not sure” more than most managers probably should. I call myself out for hedging, and usually get a few chuckles for it.
My teams perform better for it.
Not because uncertainty is a virtue, though (it’s definitely not). Decisions need to get made, direction needs to be set, and sometimes you have to commit even when the data is incomplete (hedging risk is implicit here).
But acknowledged uncertainty is safer than performed confidence. “I don’t know yet, here’s how we’ll try to figure it out” gives people something to work with. They can help fill gaps, flag risks, and challenge assumptions.
The mask gives them nothing. Just a smooth, professional surface with no handholds (and occasional heartburn).
People can work with “I don’t know, yet.”
They can’t work with a mask.