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AI Fluency · For Executives

Deploying AI to your teams
is a strategy.
Deploying it to yourself is a prerequisite.

Hands-on coaching for the people making the decisions, run personally by Philippe Marcotte. In person, at your workstation, working on the things actually on your desk this week.

Four to six weeks. Roughly four hours of contact time per executive. You leave with a personal playbook, real deliverables, and the judgment to lead what comes next.

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What executives are sitting with
The questions you can't answer from a vendor pitch.
We've licensed Copilot. Adoption is flat. Why?
I'm making AI investment decisions but I've never actually built anything with these tools myself.
My team is asking what we're doing with AI. I don't have a real answer.
I keep reading about AI agents going off the rails. How do we deploy this without that being our story?
Our next board meeting is going to be uncomfortable if we can't articulate where we are on this.
From the Founder

Ninety Seconds on Why
This Goes First.

Some buyers want to hear the founder before they read the case. The video makes the argument in voice. The page below makes it in detail.

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30 minutes · No commitment · Run by Philippe.

Step Zero

You can't lead a transformation
you haven't been through yourself.

Most AI initiatives are run by leaders who have read about the tools, watched a demo, maybe tested them for an afternoon. That is not the same as having used them to do real work — and the gap shows up everywhere downstream. In the vendor selection. In the policy debates. In the conversations with the board. In the rollout that doesn't land.

AI Fluency closes that gap first. Before the rollout, before the strategy, before any of the bigger pieces — the people leading the change become fluent themselves. Everything else gets easier from there.

"This isn't a 10–20% productivity story. Done right, fluency is closer to a doubling. A Chief of Staff I coached built an agent in ten minutes that pulled the source data and assembled her monthly town hall deck — the deck that used to take her a whole day. That's the unlock when the tools are matched to the work, and it's the rule, not the exception."
Philippe Marcotte · Sterling North Partners
The trap most executives fall into
Delegating the AI exploration to junior staff or to IT, then trying to make seven- and eight-figure decisions on top of secondhand understanding. The decisions that follow tend to optimize for the wrong things — because they're being made by people who've never felt what's actually changed.
The question that actually matters
Not "which AI tools should we buy?" — but "what does it actually feel like to do my own job with these tools, and what changes downstream when 80 of my employees are doing the same?" The first question can be answered by a deck. The second can only be answered by sitting at the keyboard.
The mistake that costs the most
Rolling AI out to teams before the executives know what good looks like, what bad looks like, and where the limits sit. The well-publicized failure modes — agents acting outside their scope, confident-but-wrong outputs, drafts sent before they were ready — are largely preventable, but only when the people approving the rollout have calibrated their own judgment first. Fluency at the top is what lets the rollout below it land safely.
A Common Question

Building a computer
versus knowing how to use one.

This isn't a coding course. We're not turning non-technical executives into engineers, and we're not asking you to become one.

The cleanest analogy is the most familiar one. Most executives don't know how a computer is built — chip architecture, kernel design, network protocols. They use computers fluently anyway. Email. Calendar. Spreadsheets. Slide decks. They make smart decisions about IT investment, security policy, and software vendors. None of that requires building the machine.

AI is the same kind of shift. You don't need to understand how a model works to draft a board memo with one — or to know when not to. You don't need to be able to fine-tune anything to govern its use in your company.

What we develop is fluency as a user — the firsthand calibration that lets you make smart decisions about deployment, governance, investment, and rollout. The mechanics under the hood are for your engineering team. The judgment is for you.

Why The Executives, Why First

Three Reasons The First
Engagement Lives at the Top.

There are good arguments for starting AI adoption at any level of the organization. Each has trade-offs. None of them avoid this constraint: the decisions that govern the entire program are made by executives, and those decisions are only as good as the firsthand judgment underneath them.

01
First-hand judgment beats secondhand briefings.
Buy-versus-build, vendor selection, governance scope, headcount planning, the policy debates with legal — none of these decisions are improved by reading more analyst reports. They get sharper when you've actually used the tool to draft a board memo, build a financial model, structure a difficult conversation, or process a contract. After that, every conversation about AI in your organization is conducted from a different position.
Once you've done the work yourself, the briefings are recognizable for what they are.
02
Adoption follows the corner office, not the training plan.
If the CEO is on Claude every day, the rollout sells itself — managers see the signal and follow it. If the CEO has it installed and never opens it, no enablement program saves you. The pattern holds across every implementation we've seen. Executive fluency is the lowest-cost, highest-leverage adoption mechanism the organization has, and most companies skip it entirely.
A team takes its cue from what it sees. Not from what it's told.
03
You can't govern what you haven't used.
AI tools fail in particular and often counterintuitive ways: confidently-wrong numbers, agents acting outside their authorized scope, the much-publicized cases of an agent taking actions it should never have been allowed to take. None of these are theoretical, but neither are they inevitable — they happen when broad rollouts get approved by people who haven't yet calibrated, firsthand, where the limits actually sit. Fluency at the top is what lets you set up the deployment properly: the right human checkpoints, the right scope of action, the right governance. The policies you sign, the boundaries you set, and the rollout you approve all get sharper when you've been at the keyboard yourself.
Knowing where these tools fail is what lets you deploy them where they don't.
How It Works

One Executive at a Time.
In Person. On Real Work.

Executive time is the scarcest resource in any organization, and any engagement that ignores that fact is dead on arrival. The format is built around the constraint: surgical, one-on-one, in your environment, on the work that's already on your calendar this week. No webinar series. No e-learning portal. No "AI 101" deck. The first session produces a real deliverable, not a slide on what's possible — maximum impact, minimum drag on the calendar.

Who shows up

Run personally by Philippe Marcotte, Sterling North's Managing Director. No junior coaches, no rotating staff, no co-pilot in the corner. Same person, every session, start to finish — and reachable directly between them.

Session 01
Install & First Deliverable
Two hours · in person
Claude Desktop, the Cowork app, the browser extension, and the relevant connectors are installed and configured correctly. Then we don't talk theory — we pick something already on your desk this week (a board memo, a customer reply, a financial analysis, a hiring decision) and produce it together. By the end of the session you have a real, finished deliverable.
Between Sessions
You Use It. Philippe's On Call.
One to two weeks
The format is a small push on your calendar by design — but the work between sessions is real, and sometimes the moments are real too. The night before a board meeting when the agent is acting up. The morning of an investor update when a tool isn't doing what you remembered. You call Philippe directly. Phone, email, text. No queue, no intake form, no ticket. Between sessions matters as much as the sessions themselves.
Session 02
Raise the Ceiling
One hour · in person
We review what you attempted independently. We resolve the obstacles. We raise the ambition: more complex use cases, multi-step workflows, agent-style tasks where appropriate, and the connections to your actual systems (calendar, email, files, CRM) that change what's possible. By the end, your repertoire is meaningfully larger than what's typical for an executive.
Session 03
Consolidate & Close
One hour · week four
A final session to consolidate progress, document your individual playbook, identify the two or three workflows you'll keep using, and close the engagement cleanly. Your playbook is yours — written in your context, with your prompts, for your role. It's not a generic cheat sheet, and it's not something you'd hand to anyone else.
Total contact time per executive: roughly four hours over four to six weeks. The ratio is intentional. The work happens in your own use of the tools between sessions — that's where fluency actually develops. Our job is to make sure the path between sessions is productive, and that you don't waste time on the obstacles other people have already cleared.
What You Leave With

Deliverables, Not a Certificate.

Most executive AI training programs produce a feeling of having attended something. AI Fluency produces actual artifacts you can point to and use. There is no completion email. There is the work itself.

Per Executive
What each leader walks away with.
  • A working setup. Claude Desktop, Cowork, browser extension, and the connectors that matter for your role — installed, configured, and tested. No "I'll get to it later" tab open in your browser.
  • Three to five real deliverables. Produced during the sessions and the weeks between. The work is yours, drawn from your current calendar — board memos, financial analysis, hiring scorecards, customer communications. Tangible artifacts you'd be willing to send.
  • A personal playbook. A short, written reference capturing the use cases, prompts, and workflows that actually fit your role and your habits. Not a generic guide. The version of this for a CFO and the version for a CEO look nothing alike.
  • Calibrated judgment on failure modes. You'll know — from having seen it firsthand — where these tools confidently produce wrong answers, what kinds of tasks should never be left unsupervised, and what the right human-in-the-loop looks like for the work you actually care about.
Across the Leadership Team
What the organization gets out of it.
  • A consolidated readout. Cross-cutting observations from coaching the whole leadership team — what worked, where the friction sits, what should come next. Useful for the board conversation, useful for the strategy work, useful for sequencing what comes after.
  • An aligned signal. When the senior team is fluent, the organization stops getting mixed messages about whether this is real. The rollout that follows — whether it's a pilot, a strategy mandate, or a full transformation — lands on prepared ground.
  • A credible answer to the board. "Here is what we have done, here is what we have learned, here is what we are doing next." Specific, grounded, and informed by the team having actually used the tools — not by a consultant's assessment of what they should think about them.
  • A foundation for everything else. Strategy work, AI Workers, AI Solvers, full transformation — every subsequent engagement is faster and sharper because the people steering it know what they're steering.
Where This Fits

The First Step of Almost
Every Engagement We Do.

AI Fluency stands on its own — a leadership team can do it, take what they need, and stop there. Most don't. The conversations that follow it tend to be more grounded, more specific, and faster, which is why most clients use this as the doorway into the rest of the work. Below is how it sits next to the other three offerings.

A note on sequencing

Fluency does not have to come first. There are situations — a clear, urgent Solver mandate; a transformation already underway with a strong internal lead — where it doesn't make sense to slow down. We'll tell you that on the strategy call. But for most organizations approaching this for the first time, the four-to-six weeks invested at the top pay back across every subsequent engagement.

Right Fit / Wrong Fit

Who This Is For.
And Who It Isn't.

AI Fluency is a particular shape of engagement, and that shape doesn't fit every situation. Better to be honest about that up front than to disappoint either party halfway through.

Right Fit
Where this engagement actually pays back.
  • CEOs, COOs, CFOs, founders, division GMs, VPs, and Directors — decision-makers who haven't built with these tools themselves but are about to make significant calls based on what they can do.
  • Leadership teams that have licensed tools (Copilot, Claude, ChatGPT) but haven't seen the adoption or the impact they expected.
  • Executives who are about to commission strategy work, transformation work, or significant AI investment, and want to be operating from informed ground when they do.
  • Companies under pressure from a board or an investor to articulate an AI direction — and who want that direction to be earned, not pieced together from talking points.
  • Senior leaders who'd rather work through real deliverables on their own desks than sit through a curriculum.
Wrong Fit
When something else makes more sense.
  • ×
    Anyone looking for a webinar series, a standardized curriculum, or a generic AI training program. Those exist, they're cheaper, and they're a better fit when scale matters more than depth.
  • ×
    Organizations that want a credentialing program — certificates, attendance records, completion percentages. We don't issue any of that.
  • ×
    Executives who can't make four to six hours of in-person time available over a month and a half. The format doesn't compress well.
  • ×
    Executives who are already comfortable building with these tools — you don't need this. Your time is better spent helping us coach the rest of your leadership team, who probably do.
  • ×
    Teams whose problem is technical implementation, not leadership fluency — those situations are better served by a Solver, a Worker, or the right hire.
  • ×
    Anyone hoping to be told that AI will solve specific business problems for them. We won't oversell. The judgment about what AI is and isn't good for is what you're acquiring here.
Philippe Marcotte
Who Coaches You

Philippe Marcotte, Managing Director & Founder

I led AI and analytics transformation engagements at McKinsey as an Engagement Manager a decade ago, then built and operated a venture-backed network of tech-enabled medical clinics where I had to implement it myself rather than recommend it. Since late 2022, I've been using AI tools in my own day-to-day work — writing the prompts, breaking the agents, fixing the deployments, and seeing what executive fluency does — and what its absence does — across more than a dozen organizations. I run these sessions personally. They're not delegated to a coach who learned this last quarter.

The First Conversation

Start With a
Strategy Call.

A 30-minute conversation, no obligation, where we figure out whether AI Fluency is actually the right starting point for your team — or whether something else (a Solver, a strategy mandate, a transformation diagnostic) makes more sense given where you are.

If Fluency is the fit, we'll walk through how the engagement would work for your specific leadership team — who, in what order, on what timeline, and at what investment.

If you already know this is what you want

The call is still the right starting point — we use it to confirm scope, identify the right participants, and align on timing before producing a Statement of Work.

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A note on timing

Philippe runs every engagement personally, so capacity is the real constraint — typically a handful of Fluency engagements running in parallel at any time. If your window matters — a board meeting, a fundraise, a leadership offsite — flag it on the strategy call. We'll find the way in if we can, and we'll be honest if we can't.

Strategy Call
A 30-Minute Working Conversation
Not a sales call. We use the time to understand your situation and recommend the right shape of engagement — Fluency, Solver, Worker, Transformation, or none of the above. We say no at least as often as we say yes.
What we cover
  • Where your leadership team is on the AI fluency spectrum today
  • What decisions are actually pending — and what would need to be different to make them well
  • Whether Fluency, a Solver, a Worker, or a Transformation is the right next step
  • If Fluency: who in scope, in what sequence, on what timeline
  • A realistic range on investment and what the SOW would cover
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Free · No commitment · 30 minutes

Where to Start

Before you ask your team
to change how they work,
be the proof that it works.

AI Fluency is the cheapest, fastest, highest-leverage place to begin. Most of our clients start here. Talk to us about whether it's the right place to start for yours.

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