For leaders and teams

AI coaching

Working sessions, not briefings. We build on your real work, on your screen, and you use what we build the same day.

Teams take their cue from what their leaders visibly do, not from what the strategy says.

Most stalled AI programs are not stalled on technology or on budget. They are stalled because the people sponsoring the change have never done the work themselves, and an organization reads that accurately and immediately.

A leader who has not used these tools on their own work cannot tell an ambitious plan from an impossible one, cannot judge which of the proposals in front of them is serious, and cannot ask the question that would have caught the problem. That is not a knowledge gap that a briefing closes. It closes by building something.

What a session is

Your work, on your screen, the same day

We start by mapping where your time actually goes, which is usually the first uncomfortable moment. Then we pick something real from that map and build it together while you drive.

You leave with the thing working and in use, not with notes about it. After a few sessions you can build the next one without me, which is the point. What gets built is yours and runs whether or not we continue.

How it runs

One executive, or several

Individually where the work is personal, or with a small group of peers where the value is in comparing how each of you actually spends a week.

A whole team at once

Inside an offsite, or as a standing engagement. Useful when a leadership team needs to arrive at the same understanding at the same time.

Your transformation group

Coaching the internal team that will carry this after I am gone, so the capability stays in the company rather than in a vendor.

Ongoing by design

Monthly rather than hourly. Early results come fast. The change that counts takes quarters, and I will say so.

What changes

01

You can tell a real proposal from a plausible one

The most expensive decisions in an AI program are made by people who cannot evaluate what they are approving. Firsthand command fixes that faster than any amount of briefing.

02

Your team sees you working differently

Adoption follows visible behavior at the top far more reliably than it follows a mandate, which is why this is usually the first move when adoption has stalled.

03

You stop outsourcing the judgment

Deciding what AI should and should not do inside your firm is a leadership question. It cannot be delegated to whoever is most technical.

04

Something is in use on Monday

Every session ends with a working artifact rather than a plan to build one.

Why me

I build my own systems

Including the operating system I use to run my own week. I design and build agents rather than commissioning them, so the sessions are about how the work is really done.

Teaching has run alongside all of it

A computer science teaching assistantship at Princeton, JPMorgan's firm-wide training committee, and a full AI course I wrote and delivered to a school staff with no technical background.

I have coached senior people throughout my career

Always alongside the work rather than as a business, which is a long way of saying I have done a great deal of it.

I have sat where you sit

Transformation at JPMorgan and Citi, transformation functions built from the ground up at Gen II and SEI, and a P&L as a general manager.

When this is the right door

Usually when adoption is stalling, when a leadership team is being asked to approve things it cannot evaluate, or before an operational program starts, because the sponsors will need firsthand command to make good decisions once it does.

Three symptoms, one problem

Leaders who cannot sponsor the change. A transformation group that is busy without producing results. Nobody who owns AI. Those look like three problems and they are one, which is the distance between what AI can do and what your organization will let it do. Coaching, transformation advisory, and the Operating Partner seat are three doors into the same work, and the engagements that work usually use more than one.

Start a conversation

The first conversation is thirty minutes and free. You will leave with an honest read on whether there is anything worth doing.

michael@greatbridgeadvisory.com Or find me on LinkedIn.