First Principles
Trouble shows up as a question, weeks before it shows up on the burndown.
Richard Phillips, CTO at IFS, on the enabler he turns to when things break — and the person he’d most want to find before December.
5 min watch
Richard Phillips
Chief Technology Officer, IFS
Recently stepped into the CTO seat of an AI business unit — smaller, younger, and moving faster than the organizations he’d led before, adding people almost weekly.
What this conversation is about
Richard arrived recently enough that his answers come from a vantage point most CTOs never write about — the first months, when you can see the shape of a team but not yet its individuals. What struck him was the enthusiasm. A younger, AI-native unit, less constrained by the political drag of the larger organizations he’d come from.
But he has led enough teams to know what the beginning of trouble sounds like. It isn’t a missed date. It’s a question — quiet, one-to-one, arriving weeks after everyone had already agreed.
And when I asked what he’d want to see that he can’t see today, he didn’t ask for a number. He asked for a person.
Three things to take from this
1.
The person leaders turn to in a crisis isn’t the best technologist.
Richard’s answer was unambiguous. When something breaks, he turns to enablers — the people who know the organization, who can walk the political ladder, who have friends in the right places. Because most of the challenges, in his words, aren’t technical. They’re politics, people, egos. Organizational fluency isn’t a soft skill sitting beside your real ones. In the moments that decide outcomes, it’s the load-bearing one.
2.
If you are that person, your work is invisible by design.
The enabler’s job is to make the problem disappear. Which means when they do it well, there’s nothing left to point at. No ticket, no commit, no artifact — the friction got absorbed, and absorption leaves no record. That’s the trap. The work that makes you indispensable is the same work that leaves no evidence you did it. If that’s you, you have to make it visible on purpose, because no system in the company will do it for you.
3.
Your cautious question is data about your environment, not your memory.
Richard watches for the quiet one-to-one — “can I just confirm...” about something already settled weeks ago. If you’re the one asking it, read it as information. Re-checking a closed decision isn’t diligence. It’s what a nervous system does when closed doesn’t feel safe. The question was never whether you remembered. It’s what your body is telling you about the room.
“Most of the challenges aren’t technical. Most of the challenges are politics, or people, or egos.”
— Richard Phillips
Host’s note — Dharma Ramasamy
Richard gave the sharpest early-warning answer anyone has given me on this series, and I don’t think he knows it.
He watches for the cautious question. The quiet one-to-one, arriving late, asking to re-confirm something the team had already aligned on. Most leaders read that as a communication failure and schedule another meeting.
It isn’t communication. A regulated nervous system files a settled decision away and moves on. One running elevated cortisol can’t — the threat-detection loop keeps reopening closed questions, because closed doesn’t register as safe. So the person checks. Then checks again. And routes it privately, one-to-one, because checking in public carries social risk on top of everything else. What Richard is describing is a body telling on itself, weeks before the calendar does. That’s why it works as a leading indicator. Biology moves first. Behavior second. Delivery last. Almost everything organizations measure sits at the wrong end of that sequence.
Then he told me two more things, four minutes apart, that he didn’t connect.
When something breaks, he turns to the enabler — the one who absorbs the politics. And if he could see one thing he can’t see now, he’d want to find the person who will have struggled most by the end of the year, now, while there’s still time to do something about it.
In most organizations, those are the same person. Absorbing friction is metabolically expensive work — reading threat, managing other people’s states, staying regulated while everyone around you isn’t. It accumulates. And it leaves no trace, because the entire purpose of the work was to make the trace disappear.
Richard is watching for exactly the right thing. He just can’t watch everyone at once. That isn’t a judgment problem. It’s a bandwidth problem — and it’s the one thing no amount of leadership skill solves.
Be on the series.
Five more of these this quarter. Twenty minutes, two cameras, nothing to prepare, and you see the edit before it publishes.
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