Don't Deprive Growth

The hardest parts of leadership have very little to do with hard skills, and a lot more to do with soft skills, like delivering honest feedback in a way that lands. It’s not that hard to come up with a strategy, but it's pretty hard to sit across from someone and tell them they’re not meeting the bar. To look them in the eye and say, “This isn’t working.” Or, “You’re plateauing.” Or even just, “You can be better than this.”

Leaders rationalize their silence with kindness. “I don’t want to hurt them.” “It’s not the right time.” “They’re going through a lot.” But the real reason, more often than not, is fear: fear of the reaction, fear of being disliked, fear of confrontation, or fear of the organizational drag that might follow. So the feedback stays bottled up, and everyone pays the price.

One of the most important lessons I ever learned about leadership came from the Head of Design at Square Online, well before I stepped into that role myself. I was struggling with an underperforming employee. I had feedback, but I was hesitating to give it. I worried it might create tension and wouldn't be received well. He looked at me and said, “Don’t deprive them of their growth.”

That was the unlock. It reframed feedback not as a confrontation to fear, but as a responsibility to uphold.

Self-Protection Disguised as Empathy

“I thought I was being nice, but I was really just being a coward.” That’s what Julie Zhuo wrote in The Making of a Manager, and it’s one of the most honest admissions about early leadership I’ve read. Avoiding feedback feels like empathy, but it's not. It’s self-protection disguised as care. We say we’re shielding others from pain, but we’re really shielding ourselves from discomfort.

I thought Kim Scott addressed this well in Radical Candor when she said, “Challenging people is often the best way to show them that you care.” The job isn’t to keep people comfortable. It’s to help them grow. And growth doesn’t happen in the comfort zone.

HR Can Either Enable Truth or Muffle It

Too often, HR policies slow down feedback instead of enabling it. Overbuilt PIP processes and legal paranoia. Culture decks that preach candor, but systems that punish it.

When managers are forced to “document for months” or “try coaching cycles” long after they know the outcome, it doesn’t protect people. It prolongs dysfunction. It traps someone in a role that’s not working for them and blocks them from finding the next right fit.

Contrast that with Shopify, where Tobi Lütke famously eliminated PIPs and empowered managers to make clear decisions faster. Or Netflix, where Reed Hastings instituted the Keeper Test: “If someone on your team were to leave, would you fight to keep them?” If not, you owe them the truth and a generous severance, not a dragged-out performance process.

HR should exist. But like any function, it needs constraint. Influence and process must be kept in check. Otherwise, the system stops supporting people and starts shielding them from the truth they need to hear.

The Cost of Silence Is Time

When you withhold feedback, you’re not just stalling progress. You’re stealing time. Maybe it’s six months of quiet tolerance before someone finally gets managed out. That’s half a year they could have spent getting better on another team, in another role, at another company.

Maybe it’s a watered-down critique that takes six tries to land because it was too sugarcoated to be actionable. That’s six cycles wasted on decoding intent instead of building skill.

Time belongs to the individual. Not to you, and not to the company. And it’s finite. If you’re not willing to tell the truth, you’re not respecting that time. You’re robbing them of the very thing they showed up to earn: growth.

This is especially true in design. Early in their careers, many designers flinch at harsh feedback. They think the creative director who shreds their work in critique is an asshole. But talk to them ten years later, and they’ll say the same thing: That person made me better. The professor who pushed them. The design director who made them redo the same screen ten times. The peer who asked the one question they couldn’t shake. It all felt harsh in the moment, but it left a mark. It sharpened their eye. It built their craft. It didn’t waste their time.

Feedback Cuts Both Ways

Delivering feedback doesn’t just help the person on the other side of the table. It strengthens your leadership, too. To give meaningful feedback, you have to clarify what matters, like your expectations, your standards, and your view of what great looks like. You’re forced to reflect on what you're willing to tolerate, what you’re trying to build, and what your team deserves. That process makes you more precise and more aligned with your values. It also holds you accountable for upholding them.

Feedback is a mirror. It reflects the manager as much as it does the report. Avoiding it doesn’t just stall someone else’s progress. It limits your own. If you’re serious about becoming a strong leader, this isn’t optional.

The Outcome May Hurt. That Doesn’t Mean It Was Wrong.

Sometimes the feedback lands and sparks growth. Sometimes it sparks resistance. And sometimes it sparks an exit. All of those are valid outcomes. Letting someone go isn’t a failure. It’s often the most honest and healthiest move for everyone involved. Maybe they tapped out their growth curve on your team. Maybe the role isn’t right anymore. But you don’t get there unless you’re willing to be honest.

At Square, we had moments like this all the time. The design and engineering culture rewarded honesty over comfort. During Design Reviews and Hack Weeks, teams would tear down and rebuild projects in days. People gave direct feedback in real time. Nobody was shielded from the truth, and that’s exactly why the teams kept growing.

Truth is the Expectation

There’s a quiet, insidious belief that letting someone “just keep going” is the more compassionate thing to do. It’s not. Letting someone drift for another quarter, another cycle, another year without clarity and honesty doesn’t protect them. It stalls their growth and it weakens your role as a leader.

Sometimes, people do leave because of a manager. When feedback is missing and growth slows, top performers start looking elsewhere. They want to be challenged to get better. If their manager isn’t helping them do that, they move on (and rightly so).

But it’s also true that some people leave because the bar is high. Because the expectations are clear. Because the direction is strong and the pace is fast. And that’s okay. Not every environment is right for everyone, and not everyone is ready for the growth being asked of them.

Your job as a leader isn’t to control who stays or who leaves. It’s to make sure people know where they stand. That means being honest. Not months later. Not after they’ve already checked out. But when it counts.

Tell the truth. It’s what you're expected to do.