THE PROGRAM
Executive Strategic Thinking with AI
Three sessions. Six weeks.
Strategic thinking with AI,
applied live to your actual challenge.
A structured engagement where we work together on the real decision in front of you, using AI as a thinking partner that finally moves at the pace you actually think — and works at your altitude.
You don't learn about AI. You learn to think with it — on something that actually matters to you, with the longer-term perspective and the outlook to lead from.
45 minutes · complimentary · no pitch
WHAT THIS IS
What this actually is
This is not training.
Not a framework.
Not a course on AI.
It's structured strategic thinking, with AI as the medium, and your actual situation as the focus of our work together. There's nothing to translate from a generic case to your reality — because we work directly on what's in front of you.
The focus might be:
A single challenge
Something you've been working through. Often the one that won't resolve on its own.
A set of connected issues
Multiple moving parts —
people, time, money, risk — that you need to think through together.
A mix of what you’re
carrying
Several things on your plate that
need to be seen in a coherent way.
You leave with two things, woven together. The first is clarity on what you brought into the work. The second is the durable capability to do this kind of thinking again — on your own, on whatever comes next.
And the point isn't more thinking, alone. It's the confidence to lead — and to create the conditions within which your team, and your organization, can do their best work too. This is the clarity that lets you do that deliberately.
WHERE THE WORK LEADS
Shaped to where you’re leading
The value of strategic thinking with AI isn't in how fast we move. It's in how much the work becomes yours.
That's because of where these sessions lead. The point isn't to make you a faster thinker on your own. It's to give you enough perspective and clarity — and the confidence to use AI as a strategic thinking partner — so you come back ready to lead.
You’ve imagined what's possible, seen the second- and third-order moves, and shaped the conditions your team and your organization need to do their best work.
THREE SESSIONS
How the sessions unfold
The work moves across three sessions, each with its own altitude. Each begins higher than the last ended.
SESSION 1
Finding the footholdent
You bring the challenge — the one you've been carrying, in whatever shape it currently has. The first session is where we surface what's actually in front of you and find the place to stand.
We work in real time. I work the conversation across altitudes, zooming in when it matters, rising when the bigger pattern needs to come into view. You think out loud; AI keeps pace, holds the whole picture, surfaces what's connected to what.
By the end, we've shaped the situation together. You'll have a working sense of where the throughline runs, what matters most, and the foothold you need to lead what’s next.
SESSION 2
Building the outlookt
Session two begins higher than session one ended. It picks up at altitude — because the work I do between sessions sets the table at a higher level. The conversation is captured. What we made sense of together is consolidated. I look across it for what wants to come forward next.
In session two, we deepen and pressure-test what emerged. We zoom out until the landscape makes sense from above, and zoom in where the detail decides the move. The craft becomes more visible as we work — you start to recognize how the conversation is shaped, and how it could be shaped by you.
By the end of session two, you can feel what strategic thinking with AI makes possible.
SESSION 3
Leading from altitudet
The third session is where the work consolidates. We synthesize where we've been — what shifted, what's clearer now, what the throughline became as it sharpened. You walk through what you'd say, what you'd decide, what you'd ask of your team. The thinking has weight; the next steps have ground under them.
You leave with the documents that carry the work forward, yours to use: a captured throughline, the synthesis of what emerged, a record of the thinking you did. And the ongoing capability to do this thinking again — on your own, on whatever comes next.
What you walk into next, you walk into differently. With the perspective to see the whole, the outlook to lead from, and the confidence to create the conditions your team and your organization need to do their best work.
THE PACE
At the pace that lets it land
These sessions start at the beginning with the end in mind. And they move at the pace that lets the thinking land. Some sessions move quickly because the work is already alive. Others slow down because something important needs to be untangled. Both are right. The depth and direction are yours to set.
What I bring is the craft of strategic thinkingwith AI — reading the conversation, choosing the moves the situation calls for, and pacing the work so it integrates into how you lead. Part of the craft is leaving enough room for the questions only you can ask– so the work is yours. That's where the value lives.
THE CRAFT
The craft beneath the conversation
Behind every session, there's a discipline. Seven moves I work with — not a sequence to follow, but a repertoire to draw from.
In the conversation, these moves don't appear in order. They appear as our work calls for them, and that work is always non-linear.
We rise to a higher pattern when something needs a broader perspective.
We zoom in when the detail matters.
We reorient when the situation shifts.
What I bring is the choice of which move, when — and the throughline that holds it all together. You won't be tracking the moves. You'll be in a conversation that flows — and notice, only afterward, how much ground we covered.
BETWEEN SESSIONS
The sessions are 90 minutes. The engagement isn't.
Between each conversation, I do the work that makes the next one count.
The full thread is captured — prompts visible, thinking organized, a document you can return to and actually use. From that, I distill what mattered: the throughline of what surfaced, the nuggets worth carrying forward, the questions worth sitting with.
Where something connects to a tool, a framework, a book, or a reference from my own practice, I send it your way. One useful thing — chosen because it fits what's in front of you right now.
I draft the working agenda for next time. So we pick up where the thinking is, not where the last conversation ended.
The thinking accumulates.
The clarity compounds.
WALK AWAY WITH
A real challenge advanced
Not a hypothetical, not a generic case. Something that actually matters to you, moved forward.
Documents that capture the work
A throughline of the strategic journey you just took, the synthesis of what emerged, and a record of the thinking you did.
Confidence with AI as a thinking partner
Not the AI you've read about, but the AI you've actually worked with — on your own terrain, on what's actually in front of you.
Confidence to lead from this work
The perspective to see what matters, the outlook to act on it, and the confidence to create the conditions for your team to thrive.
INVESTMENT
A single fee.
A complete program.
FULL ENGAGEMENT FEE
Three sessions, all the work between them, and the full set of documents you take with you.
$5,000
Canadian dollars
The discovery call is complimentary.
No obligation.
WHAT COMES AFTER
Three paths. All yours to choose.
Continue Solo
You'll have the clarity, the capability, and a working relationship with AI to carry forward — on your own, on whatever comes next. The engagement is complete in itself.
Continue with me
Some leaders want an ongoing thinking partnership — sessions at your pace, on what's emerging next. We pick up where the work left off, whenever you need it.
The conditions you create for strategic thinking with AI become a shared capability — across your leadership team, on what matters most. The work spreads from one to many.
Expand to your team
Executive Strategic Thinking with AI
WORK WITH MARY
Strategic clarity.
The confidence to think with AI.
The judgement to lead from both.
A 45-minute discovery call. No pitch – just a real conversation about what’s in front of you.