Listening is always hard, and it only gets harder at scale.

When you're leading a team of five or 10 people, feedback is pretty easy. It's not even really "feedback”: you’re just talking. You may have hired everyone yourself. You might sit near them (or at least sit near them virtually). Maybe you have lunch with them regularly. You know their kids' names, their coffee preferences, and what they're reading. So when someone has a concern about the direction you're taking things, they just... tell you.

You trust them. They trust you. It's just friends talking. You know where they're coming from.

At twenty people, things begin to shift a little. You’re probably starting to build up a second layer of leadership and there are multiple teams under you, but you're still fairly close to everyone. The relationships are there, they just may be a bit weaker than before. When someone has a pointed question about your strategy, you probably mostly know their story, their perspective, and what motivates them. The context is fuzzy, but it’s still there.

Then you hit 100#

Somewhere around 100 people, the ground shifts underneath you, as you realize you don’t know everyone anymore. You just can't. There aren't enough hours in the day, and honestly, there aren't enough slots in your brain.

Suddenly you have people whose names you don’t recognize offering very sharp commentary about your “leadership.” They’re talking about you but they don’t know you. There’s no shared history, no accumulated trust, no sense of “we’ve been in the trenches together.” Your brain has no context for processing all these voices.

Who are these people? Why are they yelling at me? Are they generally reasonable, or do they complain about everything? Do they understand the constraints we're under? Do they have the full picture?

Without an existing relationship, it feels like an attack, and your natural human response is to dismiss or deflect the attack. Or worse, to get defensive. Attacks trigger our most primal instincts: fight or flight.

This is the point where a lot of leaders start to struggle. They still want to be open to feedback—they really do—but they're also drowning. They start trusting their intuition about what they should pay attention to and what they should ignore. Sometimes that intuition is right. Sometimes it's just... self-selected, stripped of context, pattern matching against existing biases and relationships.

On top of that, each extra layer of management, each extra level to the top has separated you, and now you’re just not like them anymore. Their struggles are not your struggles anymore.

At 200, it's a deluge#

By the time you reach 200 people or more, feedback isn't an actionable signal anymore. At that size, feedback stops being signal being noise. A big, echoing amphitheater of opinions, each louder than the last, each written in the tone of someone who is absolutely certain they understand the whole system (they don’t), the whole context (they don’t), and your motives (they definitely don’t).

And all those kudos you used to hear? Those dry up. When you had a close relationship with everyone, kudos came naturally. You were just talking. But now folks just expect you to lead, and if they’re happy with your leadership they’re probably mostly quiet about it. They're doing their jobs, trusting you, assuming things are generally fine.

The people who are unhappy? They're loud. And there are a lot of them.

From where you sit, it feels like everybody's mad about everything all the time. And maybe they are! Or maybe it's just selection bias combined with the natural amplification that happens when people with similar grievances find each other. You don't know if this is a real crisis or just three loud people who found each other in a Slack channel. You just can’t tell anymore.

Because feedback doesn’t scale. Humans scale poorly. Your nervous system definitely doesn’t scale.

Why this happens#

Feedback doesn't scale because relationships don’t scale. With five people, you have some personal interaction with everyone on the team. At twenty, you interact with some, but not all. At 100 you still have personal relationships with 10 or 15 people, so there are a lot of gaps. At 200, your personal relationships are a tiny slice of the overall pie.

Making matters worse, as the din gets louder and louder, channels for processing all that feedback get smaller and smaller. Where you once had an open-door policy, now you have “office hours.” Sometimes. When we’re not too busy.

Where once All-Hands meetings had open questions, now you’re forced to take the questions ahead of time. Or not at all.

Even your Slack usage dwindles, because half the time you say anything, someone’s upset with it.

We tell ourselves we're "staying close to the ground" and "maintaining our culture,” But we're not. We can't. Because the fundamental math doesn't work. The sheer volume of feedback we’re getting absolutely overwhelms our ability to process it.

So what do you do about it?#

First, you have to admit the problem exists. Stop pretending you can maintain personal relationships with 200 people. You can't. Nobody can. Once you accept this, you can start building systems and processes that work with this reality instead of bumping against it. You have to filter, sort, and collate the feedback coming in, and you need to do it at a scale larger than your own capacity.

When you can’t rely on “just talk to people,” you need systems that distinguish between:

• legitimate issues
• noise
• venting
• misunderstandings
• and “this person is projecting a whole other problem onto leadership”

That means: structured listening, actual intake processes, and ways to synthesize themes instead of reacting to every single spike.

Build proxy relationships. You can't know 200 people, but you can know 10 people who each know 10 people. You should already have strong, trusting relationships with your leadership team, and then set the expectation that they have strong relationships with their own teams, and explicitly ask what’s on people’s minds. When feedback comes up through this chain, it comes with context. Pay attention.

At small scale, trust is direct: I know you. You know me. At larger scale, trust must be delegated: I trust the leaders who are closer to the work than I am. If you don’t intentionally empower those leaders to absorb and contextualize feedback, you’ll drown. They’re the ones who can say: "I know who said that, why they said it, and here’s what’s actually going on."

Build structured channels for feedback. For example, you can set up working groups to dive into thorny problems. The people closest to the problem understand it better than you do, and they can turn a flood of complaints into something you can actually act on. Or consider starting an "employee steering committee" for the sole purpose of collecting feedback and turning it into proposals. You’re essentially deputizing people who care deeply to listen for you, and then manage the feedback din.

Remember that every angry message is still a person. When someone you know well gives you feedback, you might not like it, but you’re likely to say "Oof. Okay. Let’s talk." At scale, you need to find ways to respond with humanity — even when the feedback you received lacks it.

Close the feedback loop. Let people know when you’re acting on their feedback, and if you’re not going to act on it, let them know that you at least heard it. Nobody wants to feel unheard.

In fact, you'll probably think — if you haven't done it already — that you should have an anonymous comment system to capture feedback. Don't. It's a trap. Anonymous feedback is the most contextless feedback you'll get, which makes it the least actionable. And it inevitably turns out to be contradictory or lacking key information, all those folks feel even more unheard and unhappy than before.

Finally, accept that you're going to get it wrong sometimes, and own that. You're going to ignore feedback that turns out to be important. You're going to overreact to feedback that turns out to be noise. When you make a misstep, be transparent about how you're correcting it.

The uncomfortable truth#

Past a certain size, you have to make peace with the fact that a lot of people in your org are going to be frustrated with you, and you're going to have no idea why, and you may not going to be able to fix it.

Not because you're a bad leader. Not because you don't care. But because feedback doesn't scale, relationships don't scale, and the alternative—trying to maintain authentic personal connections with hundreds of people—is a recipe for burnout and failure.

This is genuinely hard to accept, especially if you came up through the early days when you did know everyone. That version of leadership was real, and it worked, and it probably felt really good. But it doesn't work anymore, and pretending it does just makes things worse.

Note: The photo is of a large crowd gathering for a union meeting during the 1933 New York Dressmakers Strike. That's scaling feedback.