The gap between knowing and doing is where most leadership fails. Fine Lines is a weekly newsletter for leaders who'd rather be right than comfortable. Each Tuesday one idea from research and real experience; examined with enough rigour to be useful and enough honesty to sting slightly. If you want frameworks and inspiration, there are better newsletters. If you want your thinking challenged, you're in the right place.
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3 things that don't sit right
Published 3 months ago • 4 min read
November 11, 2025
Hi Reader
(3-minute read)
Three things keep coming up in conversations, in my own work, in what I'm reading.
I knew they were connected somehow but I couldn't quite put my finger on how.
First, why brilliant strategies keep dying between the planning and the doing. Second, why our leadership development efforts produce people who need permission instead of people who take initiative.
Third, why companies and sports clubs that plaster their values all over walls seem the least likely to actually live them.
Of course, none of this is new.
But watching it happen in real time, across different sectors, different levels means it's become harder to ignore. It’s at the point of acceptance now as ‘normal’ and I believe that’s a slippery slope.
So this week, three short pieces about what I've been chewing on. No grand theory. Just me thinking out loud about some things that don't sit right.
Image Credit: Josh Frenette
On Strategic Execution
I’ve been sitting drinking coffee, looking at an empty beach and thinking about why most strategies fail. Is it because they're bad strategies? Or because nobody figured out how to actually execute properly? I read (forget where!) and wrote down this quote about strategic success demanding a "simultaneous view of planning and doing" and it's kept nagging at me. Most leaders I talk to are either brilliant planners or brilliant doers. Very few are both. They plan in one room, then walk into another room and expect people to execute. Like there's some clean handoff between thinking, planning and acting. I know there isn't. That gap is here The Strategy goes to die. What struck me recently (listening first-hand to a football club CEO struggle with this exact thing) was how he kept separating "what we're going to do" from "how we're actually going to do it." It was like two different conversations on two different days. No wonder his team was looking busy but producing f£$k all. Strategy and execution aren't sequential. Just the same things happening at different speeds but travelling in the same direction.
On Leadership Development
If you’ve been reading Fine Lines and my video posts on YouTube, you’ll see that something's been eating at me about how we develop leaders. You keep trying to create them by rote; through programs and frameworks and competency models. But the best leaders I've encountered learned by being given room to figure things out. There's a line from Ed Catmull (Pixar guy) about assembling different kinds of thinkers and encouraging their autonomy…offering feedback when needed but being willing to stand back. That "stand back" part is what most leadership development is blind to.
Honestly, you can't help yourself. You see someone struggling and jump in with the answer. And then send them off on a course to “address that development gap”. Gives you the dopamine hit of feeling helpful. Bullshit. It actually kills their learning because you’re pushing them into a conformist model. Developing leaders doesn’t really occur through curriculum and intervention, does it? But a better way could be developing them through restraint, no? What I mean is, for example, you knowing when to let someone work through something that you could solve in five minutes….even if it takes them days. It’s clear to me that most leadership development programs optimise for the wrong thing. They optimise for leaders who know what to do or know how to win an argument towards one definite answer or position. What is actually needed are leaders who know how arrive at solutions and how to figure out what to do when nobody's there to tell them. But look around, there’s not too many shining examples of that, are there? It’s time to start getting that right, because the fish rots from the head down.
On Values and Change
Something contrarian that nobody wants to hear….healthy cultures aren't stable. They're constantly shifting. Which means protecting your core values requires changing how you protect them. Bit of a mouthful so read that again. It kind of sounds contradictory. Maybe it is. But I keep seeing leaders treat their values like museum pieces, that is, something to preserve exactly as they were when the organisation was founded. But the world's moved on. For sure, the values matter. But how about the way you live them out? How much grey matter do you invest in that? How do you live and express the needs to evolve? Or are you turning your head to look away as they become empty words on walls. And as long as it doesn’t go tits up on my shift, then so what? The tricky part is figuring out what's core and what's just how you used to (or still do) do things. Most leaders can't tell the difference. They confuse "this is who we are" with "this is how we do things around here." One's worth fighting for. The other's is just your inertia masquerading as values. Nonsense that you want to believe….just like the fables you read on the back of a bourbon bottle about craft, heritage et al. (See Wright Thompson’s quote below). If you’re not eyes forward on the primary locus of attention then Rome will burn while you’re busy fiddling.
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