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Ep 3. Lean on Kindness


Lean on Kindness

Welcome back to The Chaos of Scale. We’ve covered two of our four guiding principles for navigating The Chaos of Scale: Pause for Quality and Beware the Curse of Knowledge. Today, we’re diving into the third guiding principle: Lean on Kindness.


Now, I’ll be honest—this one is personal for me. On the surface, kindness should be obvious, right? We should all just… default to it. But here’s the truth: kindness wasn’t always my default.


My first job was brutal. Zero kindness. It was very much “dog eat dog,” and it is very easy to default to that mindset in the world of work. Competition over kindness. Watching our own backs instead of watching each others. But over time, I started to feel the impact of showing up differently, leaning on kindness. When I let kindness set the tone, everything changed. Teams thrived, relationships deepened, and the work got better.


Do I always get it right? Absolutely not. I’m human—and so are you. But leaning on kindness is like creating a circular economy of goodwill. It pays dividends in effort, energy, and long-term success.


The Two Options

Picture this: a team member tells you they barely slept and they’re running on empty.


Option one: “Shame, good luck getting through today.”

Option two: “That’s rough. What’s essential for today? Can you drop anything non-urgent? Do you need me to help so you can ease up a little?”


Option one? Surface-level acknowledgment.

Option two? Care, compassion, and investment in goodwill.

And that investment always pays back.


Scaling Is a Marathon

Scale-ups are chaotic, no doubt about it. Pressure is relentless. That’s exactly why you need to build kind spaces where people can breathe, slow down, and recover.


Think of it as an island of time lost now for a river of productivity gained later. When people feel safe to pause and rest, they come back stronger.


And if you’re worried they’ll take advantage? Flip it: if you were exhausted and your leader gave you permission to rest, would you suddenly decide to slack forever? Of course not. Most of us want to show up and contribute. Build your culture for the 97% who will, not the 3% who won’t.


Mistakes Happen

Here’s the other side of kindness: mistakes. They will happen. So when they do, do you default to rage and frustration—or kindness?


I’ll admit—rage is my default. But I also know it kills safety. When people don’t feel safe, they stop experimenting. They stop acting independently. Innovation disappears, and suddenly your team is sprinting through mud.


Kindness keeps the door open. It says: we learn, we adapt, we figure it out together. And believe me, everything is figureoutable (to quote my former business partner, Brad Shorkend).


Kindness Is Not Softness

Kindness doesn’t mean avoiding tough feedback or hard conversations. It means delivering them on a foundation of trust and safety. That’s when honesty really lands, when people lean in rather than shut down.


Kindness sets the tone, even in high-pressure moments. It creates resilience, longevity, and connection. It’s the difference between a culture where people watch their own backs and one where people have each other’s backs. And when people have your back? You can achieve infinitely more.


Your Action Step

Here’s a simple challenge: observe yourself. What’s your default—kindness, or rage and frustration? If it’s the latter, that’s okay. Notice it. Pause. Reframe. Then choose kindness instead. Try it. I promise the results will be worth it.


Business growth is messy. The human side doesn’t have to be.

So, even when it’s the last thing you feel like doing—lean on kindness.



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Eye-level view of a diverse team brainstorming around a table
Lean on Kindness


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