The AI Stress Test
A one-day commercial diagnostic with an AI gap audit built in.
You think your story holds up. You think your growth motion is working. You think you have a handle on AI. All three rarely hold once someone trained to find the lines that will not hold pulls them apart. Better me than your buyer, your board or the press.
The diagnosis
Three things tend to break in a CEO’s first hour with me. The story has been told a hundred times but never stress-tested by a sceptic. The growth plan looks tidy until you ask what the three real constraints are. The AI strategy is either three pilots going nowhere or a budget line nobody wants to defend.
The story sounds fine in your head and it sounds fine to people who already agree with you. It falls apart the moment a smart outsider asks the obvious follow-up. Investors notice. Buyers notice. Journalists certainly notice.
The growth plan looks tidy in the deck. Under operator scrutiny it usually hides three constraints nobody has named and a transformation programme that will not survive contact with reality.
The AI gap is the newest of the three. A lot of executive teams cannot name a single workflow they have rebuilt, a role they have redrawn, or a competitor they have priced against on AI-leveraged unit economics. The gap is widening every quarter.
My background covers every side of the commercial table. I spent the first decade of my career as a national technology and business news journalist at the Financial Times, the Economist Group and the Daily Telegraph. After that I was Commercial Director at Virgin Money and Thomas Cook, running FTSE-scale transformation programmes. For the last few years I have advised teams at IBM, Microsoft, Google, Cisco and Cognizant on deals, messaging and growth, and I run an AI agent stack in my own business every day. The AI Stress Test puts every one of those lenses on your company in a single day.
How the day runs
The first half of the day is your narrative. We start with the opening line and work through it from there. Can you say what you do in one sentence that lands. Why this, why now, why you. What you claim against what you can actually prove. Where you sit next to your sharpest competitor and how you sound against them. The hard questions you hope nobody asks. Whether the people in the room tell the same story or three different versions of it. We put the whole session on tape so you can watch what a buyer sees.
The second half is the AI gap. We map where your team is still doing work an agent should be doing. We look at what your sharpest competitor is shipping with eleven people and a Claude subscription, and what that means for your headcount maths. We look at which of your roles change shape, which disappear, which need rebuilding. And we look at where you are exposed on data, indemnity and the decision-trail your board will start asking about within twelve months.
What you walk out with
You walk out with a tightened narrative the whole team can hold under pressure. You walk out with a growth plan that names three real constraints, three fixes and a ninety-day sequence. You walk out with an AI gap map showing where you are, where your competitors are, and the three highest-leverage workflows to rebuild first. And you walk out with footage you can watch back and benchmark against, so next quarter you can tell whether the work has actually moved.
Format
One day. London or on-site at your office. CEO plus four to ten of your direct reports. Camera, recording, written diagnostic delivered within five working days. Invitation by application — we work with a small number of teams and the calendar is intentionally light.
Who it is for
CEOs and founders whose growth has stalled, whose board has asked the AI question, or whose next raise, sale or launch has to land. If you would rather know what is broken now than find out from a buyer, this is for you.
About Dan
Dan Ilett was a national technology and business news journalist at the Financial Times, the Economist Group and the Daily Telegraph, before becoming a CEO himself and then an advisor on storytelling and growth. He edits The Executive Summary and works with a small number of companies on growth, performance, AI and story.
Earlier in his career he was Commercial Director at Virgin Money and Thomas Cook, running FTSE-scale transformation programmes. He has advised teams at IBM, Microsoft, Google, Cisco and Cognizant on deals, messaging and growth, and he runs an AI agent stack in his own business every day.
Book a 30-minute scoping call
Tell me what is going on and we will see whether the AI Stress Test fits. The first conversation is a half-hour video call. No deck, no pitch.
Or email dan@theexecutivesummary.com if you would rather start by email.