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Session insight · 17 September 2026
Why does leading feel so lonely, and what can a technology leader do about it?
Leadership is lonely because the fears and habits we bring to the chair were learned long before we got there, and most of us have never looked at them. Jerry Colonna's answer is inner work: understand what you were taught, go first on honesty and ask better questions instead of pretending to have every answer.
Jerry Colonna was a venture capitalist before he was an executive coach, and has spent the best part of twenty years coaching founders and chief executives, latterly through Reboot, the coaching firm he co-founded. His starting point, in the room with hosts Andy McMenemy and Steve Maxwell, was simple. The loneliness of the chair is real, and it is rarely caused by the chair.
He told his own story to show what he meant. His father lost his job when Jerry was a child, and the lesson he took from watching what followed was that he could only rely on himself. That belief carried him a long way. It also showed up, decades later, in his marriage and in how he led, long after it had stopped being useful. The conversation moved from there through childhood conditioning, the difference between resilience and self-reliance, what psychological safety actually asks of the person at the top and what it looks like to drop the mask at work.
The tone was honest and often personal. It closed on a responsibility: leaders get to break the unhelpful patterns they inherited, before they pass them on to the next generation.
Seven takeaways
Better humans make better leaders.
Jerry's core belief. The inner work you do on yourself is not separate from your leadership. It is the foundation of it.
The behaviours holding you back were taught with love.
Playing small, avoiding attention, refusing help. These patterns usually came from someone trying to protect you. Understanding that makes them easier to unlearn.
Psychological safety starts with the person at the top going first.
You cannot ask your team to be open if you are not willing to be open yourself. Leaders have to model honesty before they can expect it from anyone else.
Honesty matters more than vulnerability.
Vulnerability can feel like a loaded word. Jerry prefers honesty and transparency. Adults can sense when something is untrue, and pretending everything is fine when it is not breaks trust fast.
Resilience is not the goal. It is the path.
Bouncing back from hard things is not something to aim for on its own. The real goal is learning how to handle the ride so you are not constantly thrown by it.
Your job is to ask good questions, not to have every answer.
Quoting Peter Drucker, Jerry reminded the room that pretending to have all the answers creates more pressure and less trust. Admitting uncertainty, then working through it together, builds a stronger team.
Ask yourself how you have been complicit in creating the conditions you say you don't want.
Asked with curiosity rather than guilt, this is one of the most useful tools for any leader trying to break old patterns instead of repeating them.
“How have I been complicit in creating the conditions I say I don't want?”
Jerry Colonna, the question at the heart of Reboot and of this sessionWhat this means for technology leaders
The technology seat is structurally lonely. Your peers on the leadership team are not your peers on this. The board sees you as the person with the answers. Your own team needs you to be steady. So the honest version of "I don't know yet" has nowhere to go, and the habits Jerry described, self-reliance above all, fill the gap.
Three things follow from the session. First, find somewhere you can say the unsayable. Not a feed, a room, with people carrying the same weight, where nothing leaves. That is the reason The Curious Mindset exists. Second, go first with your own team. The engineer who tells you about the outage early does so because you told them about your mistake first. Third, swap "I have the answer" for "what's the actual question". In a job built on uncertainty, that is not weakness. It is the work.
And Jerry's question is worth carrying into your next difficult week. Where have you been complicit in creating the conditions you say you don't want?
Be your best self.
Invitation only, free and a person at every step. If you lead technology and you'd rather not do it alone, ask to join.
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