Culture is Deep Work

We just had our annual Dolphin Summit. It was awesome – it always is. Every year we seem to find a better way to Summit. And this year, reflecting afterward, I realized we needed to stop doing something we’d been doing for years.

We have a tradition of giving core value awards – recognizing three Dolphins who exemplify our three core values. It is intended to be a way to celebrate and reinforce what matters to us. I try to keep it light and fun and try to make it about the team. But in practice, one Dolphin winning means other Dolphins don’t. I could feel it. This wasn’t reinforcing our “Elevate the Team” culture. These awards were working against it. So we’re stopping it. It’s a small thing. But these small things matter.

I think about that moment because it captures something I’ve learned over 25 years: culture work is never done. It IS the work. You can get something right for a while, and then it drifts. Or you set something up with good intentions and it creates the wrong effect. You have to keep paying attention. Keep adjusting.

But the ongoing nature of culture work isn’t just about adjusting what you’re doing. It’s about going deeper into understanding who you actually are.

Culture doesn’t start with picking aspirational statements and ranting about them to the team. It starts with really knowing yourself. What you genuinely care about. What behaviors feel natural to you. What kind of environment you intrinsically want to work in every day.

That sounds straightforward, but it’s not. It’s intimate and uncomfortable as you dig into deeper layers. It requires real honesty about who you are versus who you think you should be. It’s easy to pick aspirational values that sound good. It’s much harder to acknowledge what you actually value in practice.

We spend time thinking about who we are and what we want to emphasize in our stated core values. Put them on paper. Share them with the team. Highlight example behaviors. Hire and fire around them. We genuinely try to identify what’s true to us, not just what sounds impressive.

But it feels like a life-long journey to fully understand myself and our team. I thought I valued certain things. I thought I was a certain kind of leader. And some of that was true. But some of it was who I wanted to be, not who I actually was.

That gap creates problems. Your real values show up in your decisions whether you acknowledge them or not. You can say you value one thing, but if your actual behavior contradicts that, everyone sees it. And then the stated values become meaningless.

So the work of knowing yourself keeps going deeper. You learn things about yourself by watching what you actually do. By noticing what makes you uncomfortable or upset. By seeing patterns in your decisions. By paying attention to the moments when you make important decisions and examining why.

The discovery work isn’t just about you as the leader either. It cascades. The leadership team needs to know themselves individually and as a collective. To understand their own values and behaviors. To see where they’re aligned and where they’re not.

And then it extends to the whole team. Culture is ultimately about who you are as a group. What you believe together. How you behave as a group. That can’t be manufactured from the top down. It has to be discovered and built through who you bring in and how everyone shows up.

We have three core values at Smart Dolphins: Love Your Dolphin Life. Elevate the Team. Find a Better Way. Those aren’t aspirational statements. They describe who we actually are. They came from watching ourselves, not from brainstorming what would sound good.

The business changes. Your team changes. You change. So the understanding keeps going deeper. You think you’ve figured something out, and then you realize there’s more to learn. You can’t separate culture work from the work of understanding yourself and your team more deeply. They’re the same thing.

Once you know who you are – or at least who you are right now – the hardest work begins. You have to make decisions that align with that.

The real cultural work happens in people decisions. Who you hire. Who you keep. Who you address when they’re off track. Who you ask to leave. Every one of those decisions teaches your team what you actually value, regardless of what’s on the wall or in the handbook. Those decisions get really hard when performance and culture don’t align.

One of my mentors, Gary Pica, says “you get what you tolerate.” I’ve proven that true more times than I’d like to admit.

We’ve gotten more disciplined about this. We do quarterly reviews where the leadership team evaluates every person against our core values and their role. When someone is “off track” – a phrase that’s become meaningful here – we address it.

That sounds systematic. But it’s not easy. It’s hard every time. Especially when someone has been with you for years. Especially when they’re good at their job but misaligned in how they work or what they believe about how we should do things.

This is where culture actually gets built. It’s not in the moments when you talk about your values. It’s in the moments when living those values is impactful and you make the decisions consistently with those values.

We also try to reinforce culture in smaller, repeated ways. We have a peer recognition system where people acknowledge each other for living our values. It’s active – people use it regularly. And it spreads the work of culture beyond just leadership. These points of recognition are usually related to our values and culture – they’re meaningful.

Recently we did 360-degree reviews for our leadership team. All five of us scored highly. The feedback showed real alignment, appreciation and trust. It felt like validation that the work is real, not just aspirational.

The moments that define culture are the ones that cost you something. Saying no to revenue because a prospect doesn’t fit. Addressing a top performer’s behavior even though it’s uncomfortable. Catching yourself reinforcing the wrong thing and being willing to change it.

I don’t think you ever “finish” building culture. You’re always discovering more about yourself and your team. Always making decisions that either reinforce what you believe or contradict it. Always adjusting as things drift or as you learn something new. And if you’re paying attention, you keep getting better at it.

What’s this 25/25 stuff about?: 25 YEARS, 25 INSIGHTS – Reflections on Growth, Leadership and Resilience | Smart Dolphins IT Solutions Inc.