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Technology Leader Coach · The Hundred Days
From most senior engineer to the exec conversation in a hundred days
A first-time CTO at a regulated fintech, promoted from inside. Brilliant at the old job, and nobody had told them it was a different one, or that the regulator now had their name.
The situation
The engineering lead at a payments fintech was made CTO on a Monday. By Friday the CEO wanted a technology strategy for the board, the engineering team wanted their old lead back, and the new CTO was still reviewing pull requests at midnight because that was the one place they still felt competent.
Underneath the normal first-month chaos sat something sharper. The firm operated under the FCA's Senior Managers and Certification Regime. The new CTO was now the named senior manager for technology and operational resilience. If something went wrong with the platform, the regulator would not be asking the engineering team. It would be asking them, personally.
What was in the way
Three of the seven coaching areas were on fire at once. Identity and transition: the thing that had made them good, being the person who knew the answer, was now the thing holding the team back. Influence and translation: the board and the regulator both spoke a language the CTO had never needed, and the technology strategy they had drafted was forty pages of architecture. Judgement: they were being asked to sign off on operational resilience statements, outsourcing arrangements and incident reports with regulatory consequences, and had no frame for how certain they needed to be before signing.
The first ninety days are not about proving you can still do the old job. They are about proving you can stop.
What we did
Fortnightly sessions through the first hundred days, with a line open between them for the week something landed badly. The first session was a drawing: the function as it was, the function as it needed to be in a year, and the arrow between them. The CTO kept it on the wall.
On identity, the work was permission. Permission to stop reviewing code, said out loud to the team, with the engineering lead role delegated in week three rather than month six. The loss was real and we treated it as real rather than pretending it was a promotion with no cost.
On influence and translation, the forty pages became one. Who are the five people whose view of technology shapes the budget? What do they believe, and why? What is the one thing you could change this quarter that would move that belief? The board paper that came out of that had a number in the first paragraph and no architecture in it at all.
On judgement, we built a simple frame for regulated sign-offs: what am I being asked to attest, what evidence would I need to be comfortable, who has seen that evidence, and what would I say to the regulator if it turned out to be wrong. The CTO used it on an outsourcing arrangement in week six and declined to sign until two gaps were closed. That was the moment the CEO started treating them as a peer.
Team and organisation and career and resilience came in later: a leadership structure for the team so the CTO was not the single point of failure the regulator would worry about, and an honest conversation about the pace, the pressure and what the CTO would need to sustain it for more than a year.
What changed
By day one hundred the CTO was running the technology conversation at the exec table, had a one-page strategy the CEO used in an investor update, and had passed their first regulatory attestation with evidence they could point to. The engineering lead role was filled from inside. The midnight code reviews had stopped.
What they kept
The drawing on the wall. The sign-off frame, which the CTO now teaches to their own leads. And the habit of asking what the board believes before telling it what is true.
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