Performance Managing to the Room or "How to Stop Sucking at This"
Four environments. Four playbooks. All of them suck.
You Will Find Yourself Here
Every manager I respect has the same look on their face when they talk about performance management. It’s not confidence. Or dread. It’s something closer to recognition. Like a soldier describing terrain they’ve crossed before.
That’s because performance management isn’t one skill. Nobody teaches you this, so I will: performance management changes depending on where you are. The room you are in dictates the rules. Most managers run a stale playbook from the last room they occupied and wonder why nothing is working.
There are four rooms. I’ve been in all of them. You will find yourself here too if you do this long enough. They all suck in different ways.
Come! Take a tour with me. 🙃
Room 1: Lifer’s Paradise
It’s impossible to fire someone here.
Not “difficult”. Not “there’s a process”. Impossible. HR has opinions. Legal has concerns. The org has decided, either explicitly or through years of cowardice, that managing someone out is more trouble than keeping them around.
The Kindle Guy
I’ve seen government workers quarantined in roles like this. Pulling six figures. Reading their Kindle all day. Not because they put in the time, but because they were being marooned. Sat in the worst, most unfortunate cubicle in the building. Part of their punishment. Leadership had bet on boring them into quitting rather than doing the exhausting, soul-crushing work of documenting them out the door. The bet didn’t pay off. They’re still reading.
But make no mistake: every Lifer’s Paradise is a leadership failure.
The organization chose this.
And the thing about having a guy reading his Kindle all day in plain view of the rest of the team? He becomes the floor. And when the floor is “produces zero value, suffers zero consequences”, everyone else does the math. If that’s what the bottom looks like, why kill myself to be average?
Stay here long enough and one of two things happens:
You regress to the mean. The Kindle guy is a gravity well. The low performers closest to him get swallowed up first. They were barely trying anyway, and now they’ve got proof that barely trying is fine. And only one of them can truly have the worst cubicle, right? The mid-performers take longer, but being mid, they eventually do the math too: effort isn’t rewarded here. Why try? They stop raising their hands to solve hard problems. They optimize for comfort over craft. And the high performers? They either leave—because they can1—or something worse happens: they stay, and the room slowly blunts every sharp edge they came in with. Give it 18 months and you won’t even recognize them anymore.
You lose your mind and quit. The Professional Caremad—the one who actually gives a shit, who showed up wanting to do great work—looks around, realizes nobody else wants that, realizes it wouldn’t be rewarded even if they did it, and leaves. Often dramatically. Probably writes a manifesto in their goodbye Slack message. Probably right about everything in it.
Room 2: The Degradation Machine
You can fire someone here. The system allows it.
But the catch is that whatever comes back through the machine is worse than what you put in. Fire your mediocre mid-level dev? Get two offshore juniors. 12-hour time zone gap. Never seen your codebase before. Fire your low-performer who at least knows the domain? Get a req that sits open for six months (you aren’t paying enough) and then gets yanked as “reclaimed headcount” ahead of the every-six-months layoff, as predictable as the cycles of the moon. Alas, the promised backfill never materializes. And now you’re doing their job too.
The machine runs on a crude equation: departure = degradation. Every exit is a step down. Every replacement is a dice roll weighted against you.
The Known Quantity
Managers in this room learn fast. Your underperformer who phones it in? At least you can get them on a meeting during normal working hours. At least they know the system. They’re a known—albeit disappointing—quantity, rather than an unknown quantity of chaos.
So you hold on. You tolerate. You optimize for “minimally functional, physically present” over no one at all.
Stay here long enough and one of two things happens:
You become a hostage negotiator with entropy. Your job is no longer building. It’s preventing collapse. You’re not managing performance. You’re just overseeing the decline. You learn to speak fluently in the language of “good enough” and “at least they show up”. You stop dreaming about what your team could be and start bargaining with what it is.
You burn out and leave. Because you realize the machine is rigged. You fought to fire someone. You won the battle. You watched your team get worse anyway. The math only works on a spreadsheet in the CFO’s hands. In reality, you’re hollowed out. Leadership is fine with it because the alternative was either a sale to (gulp) private equity or a competitor buying the book of business, unceremoniously shutting down the founder’s passion project.
The cruel part about The Degradation Machine is that you only figure out it’s rigged once you’ve played a few rounds. After you fought, won, and lost anyway.
Room 3: Summer Camp
There’s no performance bar here. Hell, there might not even be performance expectations. Money’s free. Growth is automatic. The only question is: are the vibes good?
This is every ZIRP-era tech company from 2015 to 2021. Leaders who grew up here struggle to find work anymore if they haven’t evolved. This environment runs on a simple premise: revenue goes up whether you’re at your desk or not, so why would anyone care what you’re doing?
Maximum Variance
The result is maximum variance. You’ve got someone working two remote jobs, present at neither. In the same room, you’ve got someone scuba diving at 2 PM on a Tuesday. And then you’ve got the Absolute Unit. The Locked-In Crushinator. They love the autonomy, they ship constantly because nobody’s in their way asking stupid questions, and they quietly carry the entire fucking company on their back without anyone noticing.
As a manager? You just go with it. Everyone’s cheering you on regardless of results. And suggesting someone might need to work hard, occasionally, is a hostile act punishable by a stern talking-to from someone with “People” in their title. Performance isn’t a concern. It isn’t even a topic. Your job is vibes management. Keep people happy and retained, let venture capital do the rest. Summer camp for adults.
Stay here long enough and one of two things happens:
You become complicit in the delusion. You stop asking hard questions because the answers never matter. You learn that the path of least resistance is also the path of most reward. Why rock the boat?
The music stops. The money runs out. The board wants “discipline”. Suddenly everyone cares about performance, and you realize you have no idea who on your team can actually perform. Your 10x person who was carrying everyone? Gone. Poached by a competitor offering “Summer Camp too, but with better comp”. You’re left holding the bag with a team of lifestyle optimizers and the overemployed, and now you need to build a performance culture from scratch with people who think accountability is a four-letter word.
Summer Camp is an enigma. It simultaneously produces your best and worst people, and you won’t know which you’ve got until it’s too late. The same lack of oversight that lets your best people thrive lets your worst people hide.
Room 4: Buy the Wine
This is where most good managers think they want to be.
Leadership tells you: “If this isn’t your dream team? Manage them up, manage them out. Do whatever you need to do. Want to bring in people you’ve worked with before? People from the talent pool? We’ll pay them—really well. Build your dream team. You’re a professional. This is why we hired you. Go for it.”
Fuck yeah, right? Your dream team! Finally.
Nowhere to Hide
Here’s the reality check though: you’re going to be held accountable for the results. Brutally. Clinically. Because they gave you the decree. The autonomy. The budget to just buy the wine instead of trying to turn water into it. And now there’s nowhere to hide.
This environment is higher pace, higher pressure, higher stakes. Salary goes up and to the right from Rooms 1 through 4. You’re probably operating from a position of strength. And paradoxically? That actually makes it harder. You’ve tasted the playoffs! Now you need to be a perennial title contender. You’re either proving you can be profitable, tracking toward an exit, or—in true unicorn fashion—showing you can grow and be operationally efficient. You’ve got a rocket ship and you’re aiming for the moon.
Your investors want to see Mars.
Stay here long enough and one of two things happens:
You level up. You recognize that the skills that got you here won’t get you there. That old cliche. You stop trying to save people and build the team you need later, rather than the one you think you can mold now. You get comfortable making hard calls fast. You grow into the leader the org needs for its next phase. You learn to just buy the wine.
You flame out. You cling to the hero mentality. You spend six months coaching someone who should’ve been gone in six weeks. You miss your numbers because you were too busy being everyone’s mentor instead of building a team that doesn’t need one. Leadership loses patience. They gave you the keys. The budget. The autonomy. But you squandered it playing savior. So they replace you with someone who performance manages to the room they’re in. Because they’re holding you to the same dream team standard.
The cruel part? It takes solid instincts or hard-won experience to recognize you need to change. To let go of the identity you built in rooms 1 through 3. To stop being the scrappy underdog coach who does more with less, and become the ruthless architect2 who does more with more.
Not everyone makes that jump.
The Trap is Muscle Memory
In Rooms 1 through 3, your job was “get the best out of what you have”. You couldn’t afford better people. You couldn’t beat competitors in the talent pool. You weren’t getting more. You weren’t getting better. So you became really good at dragging mid-performers up a level. At coaching. At handholding. At being the hero who turns average teams into good-enough teams through sheer force of will.
That skill doesn’t work here. But it’s worse than broken: it’s actively destructive.
A leader I respect—sharp instincts, trajectory pointing straight up—had lived through this transition. They told me once, in a moment of reflection, that they were looking at the team they’d built and regretting it. They’d tried too hard to push their people to be the team they thought they could be, with all the handholding and help they needed to get there—and to sustain it, it turned out—instead of just having the hard conversations.
They regretted not letting those folks fail. Not managing them out. They’d leaned on the only skill that made sense in the previous iteration: squeezing performance out of what you have. But in Room 4, that’s a trap. You end up spending all your time dragging a mid-performing team forward instead of doing the work that actually levels you up.
But, yes! You can turn a mid-performing team into a high-performing team if you pull enough hair out. But you’ll also be stuck there. Unable to scale. Unable to think strategically. Spending day-in, day-out being a hero at the tactical level. “Managing up” mid-performers in this environment is expensive, wasteful procrastination.
The Room Is the Strategy
So back to the thing I promised to teach you: the room you’re in determines which playbook works. There is no universal performance management strategy. There’s only the right strategy for this room, right now.
…and It Shifts Beneath You
And the transitions? When you stay at a company long enough to live through the shift? That’s the hardest part to survive. It’s where managers get absolutely destroyed if they aren’t prepared. The room shifts underneath you. Funding dries up. Leadership changes. The board gets “serious”. A competitor forces your hand.
The manager who thrives in the Lifer’s Paradise—patient, political, working the system—gets eaten alive when they need to just Buy The Wine. But that same manager burns out in The Degradation Machine, firing people into a void that turns “good enough” into “worse”. The manager who rides the vibes in Summer Camp? They wake up one day with no team left to manage, swallowed up in the latest RIF, with no idea how it all happened.
The question isn’t “am I good at performance management?”, it’s “Which room am I in, and am I willing to change who I am as a leader to manage to it?”.
Your highest performers are always the ones to leave first when shit hits the fan, by the way. Canaries in the coal mine. They have options. They’re in demand, even in an employer’s market.
You can be “ruthless” and still human. Explain to your team that the room has shifted, give them a real chance to adjust to the bar, and give them a soft landing if they genuinely try, and can’t. But move quickly. Don’t hedge.