The Hidden Patterns That Sabotage Technical Leaders (And How I Rewired Mine)
Why behaviours that got you promoted start working against you—and how to rewire them before they become career-limiting
Many technical leaders hit the same invisible ceiling: when the very behaviours that once helped you stand out, start working against you.
The confidence to challenge conventional wisdom got me noticed as a developer. The willingness to argue for better solutions made me valuable. But somewhere along the way, intellectual confidence became arrogance, and healthy debate became the need to win every argument.
I can spot patterns like these because I did most of them to the extreme (my best stories will cost you a pint).
With distance, you can see quirks calcify into a lethal reputation: hard to work with. When you can’t play well with others, your ideas die, your influence shrinks, and opportunities pass without you even knowing.
As I found out, if you don’t address them voluntarily, a crisis eventually will.
Comfortable Dysfunction
At the end of 10 years at my previous company, I lived in what psychologists call the region beta paradox — being comfortable in situations that were uncomfortable, simply because the pain wasn’t sharp enough to force change.
We were on an earn-out, so I told myself the politics didn’t matter. But stuck inside a larger organisation that didn’t value technology, I found myself fighting daily battles. Over time, I stopped getting better.
Worse, my behaviour became dysfunctional. I wasn’t just tolerating the environment — I was adapting to it in all the wrong ways. I grew strangely comfortable in dysfunction, normalising patterns that should have been red flags.
Neuroscience is sobering: repeat a behaviour long enough, and it becomes your default. My stress tolerance made it worse. I had developed a dangerously high capacity for bad situations — and I stayed far longer than was healthy.
“Smart” but Stuck
Instead of using my deep knowledge of the business to help people navigate complexity, I weaponised it.
When PLC executives wanted simple stories for analysts, I rolled my eyes. When they set up a 40-person data team, I basked in the thought of “they don’t know what they’re doing.”
I should have honed in on what I could control: linking their goals to mine, finding ways through the nuance. Instead, I obsessed over what I couldn’t. Psychologists call this locus of control — the difference between focusing on what’s in your hands versus external forces. I’d outsourced mine completely.
Without the right people around me, those patterns didn’t just persist — they started to set.
It escalated to the point where, as the People team told me, “the choice to remain with the business is no longer your decision.” The wake-up call I’d been subconsciously avoiding.
Learning that age-old lesson that if nobody is giving you feedback, don’t assume you’re doing fine.
When Strengths Turn Toxic
The patterns that once were strengths — being contrarian, refusing to play the corporate game — had become liabilities because they hadn’t evolved with my environment.
In my twenties, contrarianism made me stand out. In my thirties, it made me difficult. In a corporate machine, it became career-limiting.
I was the corporate equivalent of those kidults you see in Brighton, living in the same way they did in the 20s, but the outfit no longer fits. Same clothes but stretched over all the wrong places. The lack of change made visibly sad.
That new company ran on politics and ego. I had plenty of ego, but none of the nuance. One CEO dinner summed it up: sycophants choreographing airport pickups, rehearsed taxi conversations, and a “most inspiring CEO?” parlour game at the table. My “I don’t buy into the cult of personality” answer didn’t exactly extend my tenure.
I told myself I was being authentic. Really, I was just using that story to justify being a dick instead of adapting. A conscious response would have been either: work within the system strategically, or have the self-confidence to walk away.
Instead, I carried on. For a year, I repeated the same behaviours, convinced that being “resilient” was enough. But resilience isn’t strength — it’s dysfunction in disguise when it keeps you in the wrong room.
Crisis doesn’t create your patterns. It just makes them impossible to ignore.
Get Your Mirrors Back
The real change came when I finally left that feedback desert.
At loveholidays, I had a CEO who told me exactly what he thought — to my face. Direct, timely, honest — and refreshing. No politics. No second-guessing. It removed the anxiety (apart from what I actually needed to focus on). You always knew where you stood, which meant you could fix it.
That directness reset my growth. After years of people tiptoeing around me, I was back in an environment where feedback was unavoidable — and improving became possible again.
Which is why friends like Jason matter. Only the other week he told me: “You focus entirely on the relationships where you made mistakes and completely ignore all the positive impact you’ve had.” He was right. I was still doing it.
You never outgrow the need for mirrors. Friends. Leaders. Anyone willing to tell you the uncomfortable truth. They don’t eliminate your patterns, but they stop you drowning in them.
Pattern Interruption
Seeing the patterns was only half the battle. The real work was installing new responses before crisis forced them.
Brazilian Jiu-Jitsu is a microcosm of immediate feedback. My reliance on strength and aggression recently resulted in a dislocated finger — which forced me to slow down. Instead of making me worse, it gave me options. I could finally apply techniques I’d “known” for years but never used.
Slowing down didn’t weaken me; it made me effective. The same is true professionally.
I built habits to keep the feedback loop alive:
Somatic work: Noticing early signs of tension before they trigger old behaviour.
Journalling + shadow work: Naming the pattern. Asking: what’s the trigger? What’s the payoff? What would the opposite look like?
Deliberate reps: Choosing the slower response. Asking a question before countering. Leaving space instead of filling it.
Each one was a small interruption — a way to stop running the same script and install a better one.
The Second-Time Advantage
Pattern recognition doesn’t just help you personally — it makes you far more effective professionally, especially in leadership.
Take our recent Platform Vision work — a CEO initiative that required me to actually understand his intent before acting. The old me would have either dismissed it or steamrollered my own interpretation. This time it became a genuine collaboration with our VP of Engineering, CPO, and CDO.
Crucially, this doesn’t mean giving up my opinion. Collaboration isn’t passivity.
When our CDO suggested a name for the vision, it wasn’t quite right. Instead of dismissing it or forcing my alternative, we noodled on it for days until we had something we were all happy with. That patience — trusting the process and each other — created a stronger outcome and deepened trust across the team.
Second-time round gives you an advantage: you don’t stop making mistakes, but you spot the pattern sooner, course-correct faster, and turn collaboration into your edge rather than your blind spot.
Your Pattern Recognition
Carl Jung said life begins at 40 — until then you’re just doing research. I think that’s generous. Left unchecked, the “research phase” just means calcified patterns you’ll eventually have to unpick. The earlier you start, the less painful the rewiring becomes.
Integration isn’t about becoming someone new. It’s about becoming conscious of who you already are — and choosing which patterns you keep.
This isn’t a tidy success story. People still think I’m challenging and opinionated (a dick). The difference is, now I can see it happening, course-correct faster, and surround myself with people who’ll call it out before it hardens into reputational damage.
What I’d tell any technical leader climbing toward their first senior role:
Don’t mistake stress tolerance for strength — it can keep you in bad situations longer.
Find people who’ll tell you the truth and listen to them — even when it stings
And most of all, don’t wait for a crisis to do the work. Patterns don’t vanish. They harden.
Here’s one rep to start with: next time someone challenges your approach, pause and notice your internal state. If you feel that familiar “THEY DON’T UNDERSTAND” frustration rising — that’s your cue. Slow down. Instead of defending your position, ask “help me understand” and mean it. Keep asking until you can reframe their position so accurately that they say “that’s right.”
Only then do you know you’re working toward the same ends.