Understanding a Strategy and Acting on It Are Two Different Things

Every leadership team (alright - most leadership teams) I've worked with can tell you their strategy. Not many of their people can tell you what it actually asks of them, day to day. That gap - between understanding a strategy and acting on it - is where most execution problems actually live, and it doesn’t only have to do with clarity.

Take Customer Success as one clear example. Nearly every CS team I've worked with has the same strategic direction: become more commercial. Sometimes that means owning both retention and upsell. Sometimes it means new KPIs tied to commercial activity. The leadership is usually clear about it. The team usually understands it.

And still, the first move rarely comes.

I used to think this was a communication problem - the strategy hadn't landed, or wasn't specific enough. Usually it isn’t. Ask a Customer Success Manager what "more commercial" means and they can tell you. What stops them is fear. Fear of breaking the one thing they're currently measured on - the relationship - in pursuit of something newer and unproven. And that fear is not irrational. If the company has recently been through layoffs, or a well-regarded colleague has been let go without any obvious wrongdoing, the fear of consequence in the building increases exponentially. Understanding the strategy was never the hard part. Believing you'll survive acting on it is.

This is where most organisations get stuck, and it's worth naming why. Dave Logan, John King, and Halee Fischer-Wright's Tribal Leadership model describes most companies as sitting in what they call Stage 3 - a culture built around individual ability rather than collective effort, or as I call it - a team of individuals. In a Stage 3 culture, people watch what's actually done, not what the strategy document says, becuase there isn’t as high a level of trust in the company and its ethos as one would believe. So if everyone around a CSM is playing it safe and doing as they have always done, that's the real culture they're reading - regardless of what leadership has announced.

Which means clarity on its own doesn't move anyone. What moves people is watching someone else survive the risk first.

I've seen this again and again, across teams and functions, not just Customer Success. A team sits on a clear, well-understood strategy and goes nowhere - until one or two people take the first uncomfortable action. Not because they were told it was safe, but because someone showed them it was possible. That's when the rest of the team starts to move. Psychological safety, in practice, isn't granted from the top. It's built sideways, one visible test case at a time.

This is the real difference between a team that executes and a team that doesn't. Teams that execute embrace new and uncomfortable activities early, and let the discomfort do its work. Teams that don't try to think their way into a new way of acting - and end up acting exactly the same as before.

Strategy documents describe a destination. They rarely describe who's going to take the first risky step, or what that first step looks like.