The Kindness Trap

This week, I had three(!) separate conversations with senior tech leaders that revealed a troubling pattern. Each of these accomplished executives. People who’ve built teams, shipped products, and driven significant business outcomes. Yet, each of them shared the same frustration: their teams weren’t delivering the results they expected.

But here’s where it gets interesting. When I dug deeper into how they were addressing these performance gaps, I discovered they were all making the same critical mistake.

The “Kindness” That Kills Growth

Each leader described a similar scenario. A project would wrap up, results would fall short of expectations, and when it came time for the post-mortem or one-on-one feedback session, they would soften their message. “It’s fine,” they’d say, even when it clearly wasn’t. “We’ll get it next time.”

Their reasoning was understandable, even admirable on the surface:

They didn’t want to seem controlling or micromanaging They believed their reports should learn from natural consequences They wanted to give their teams freedom to innovate and find their own path to greatness Sound familiar? If you’re nodding along, you’re not alone. This “kindness trap” is endemic in tech leadership, especially among those who’ve risen through the ranks by being collaborative and empowering.

Without clear feedback about where reality diverged from expectations, their team members were left to guess what success looked like. This led to them making the same mistakes repeatedly because no one had the courage to point them in a better direction.

Think about it from your report’s perspective. You’ve just completed a project, and your manager says “it’s fine” when you can sense their disappointment. What are you supposed to do with that? How do you improve? How do you know what to prioritize differently next time?

This ambiguity doesn’t create freedom… it creates anxiety and stagnation.

Conversely, when you provide specific, actionable feedback about what could be better next time, you’re giving them a gift! You’re showing them exactly where to focus their energy for maximum impact.

And when you establish clear boundaries and direction, you’re not limiting creativity—you’re creating a playground for innovation. The most creative solutions often emerge when people understand the constraints they’re working within.

The Framework for Courageous Clarity

So how do you escape the kindness trap without being seen as a micromanaging control freak?

Start with these three principles:

**Replace “it’s fine” with “here’s what I observed.” **Instead of glossing over disappointments, describe the specific gap between expectation and reality. “I was expecting X, but we delivered Y. Let’s talk about what happened and how we can bridge that gap next time.”

**Turn learning moments into teaching moments. **Rather than hoping people will figure it out on their own, actively guide their development. Share your experience, highlight patterns they might not see, and offer concrete suggestions for improvement.

**Define freedom through boundaries. **Give your team crystal-clear objectives, constraints, and success criteria. Then let them innovate freely within that framework. You’ll be amazed at how much more creative and confident they become when they know exactly what game they’re playing.

This is enough to get you started, but if you want to go deeper I highly recommend reading High Output Management by Andy Grove. And if you’ve already read it, maybe it’s time to read it again? I think I’ve read it 5-6 times by now and each time I get a new insight.

Wrap Up

If you’ve made it this far it should now be clear to you that kindness in leadership isn’t about avoiding difficult conversations. It’s about respecting your team members enough to tell them the truth about their performance and giving them the tools they need to excel.

Your reports don’t need you to be their friend. They need you to be their leader. And sometimes, the most loving thing a leader can do is be uncomfortably clear about what needs to change.

The next time you’re tempted to say “it’s fine” when it isn’t, remember: silence isn’t kindness. Clarity is.