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The Stress Test

Why you aren't selling, where AI is leaving you behind, and what to do about both.

A one day workshop that exposes the weaknesses in your story, your growth motion, your change performance and your AI gap. Before the market does it for you.

See The Stress Test dates How it runs
Dan Ilett, founder of The Proposition
Start with the playbook

Want it on paper first?

The companion read for the Stress Test workshop. How the C-suite actually buys. ~30 pages.

Start with the playbook

Selling to the C-Suite. Free.

PDF arrives by email. You will also start getting The Executive Summary — Dan's weekly briefing for CEOs. Unsubscribe anytime.

The challenge

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 under scrutiny.

You have a story you have told a hundred times and never properly stress-tested. You have a growth plan that has never been pulled apart by someone who has run one. And you almost certainly have an AI position that 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 sceptic 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. I have since 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 Stress Test puts every one of those lenses on your company in a single day.

What we do in the room

Seven angles on your narrative. Then the AI gap audit.

  • The opening. Can you say what you do in one sentence that lands.
  • The why. Why this, why now, why you.
  • The numbers. What you claim and what you can actually prove.
  • The market. Who you are really up against and how you sound next to them.
  • The hard questions. The ones you hope nobody asks.
  • The team narrative. Whether everyone in the room tells the same story or three different versions of it.
  • Camera and recording. We put it on tape so you can see what the buyer sees.

Then we map your AI gap. We look at where your team is still doing work an agent should be doing, what your sharpest competitor is shipping with eleven people and a Claude subscription, and which of your roles change shape, disappear or need rebuilding in the next twelve months. We also look at where you are exposed on data, indemnity and the decision-trail your board will start asking about within a year.

Walk out with

Five outcomes from a day in the room.

  • Know where your message is falling short. Every weak line in your story exposed and rebuilt.
  • Know where you and your team need to improve in delivery. Honest read on who lands the room and who does not.
  • Learn where your business sits on growth capability. A clear map of the three constraints holding the next phase back.
  • Get direct leadership feedback from our independent assessment. No vendor pitch. The real read from someone who has run the transformation programmes.
  • See your AI gaps and opportunities. Where you should be, what you should be doing, and the risks and threats you need to see now rather than in twelve months.
Who it is for

B2B tech founders and exec teams about to raise, pitch, launch, sell or face the press.

Anyone whose next six months depends on telling a story that holds.

Who it is not for

One group should book a different room.

  • Anyone looking for media training in the soft sense. This is interrogation, not polish.
Format

Live in London.

Founder plus core team. Up to eight in the room.

Format

Live in London

Attendees

Up to 8

On camera

Yes

Booking

One company

From the room
“The Stress Test was utterly brutal but within 30 minutes we knew exactly why we weren't selling and where the product was wrong. Dan is very honest which is painful at times, but it's saved us a fortune in waiting around to find out the even harder way.”
Ben Lilly · CEO, Giant Leap Digital
Book The Stress Test

Next available dates.

Private session. One company per date. See available dates →

Dan Ilett, founder of The Proposition
Who runs the room

From asking CEOs the hard questions to running the transformation programmes inside FTSE companies.

I have worked every side of the commercial table. I spent years interviewing CEOs as a journalist for the Financial Times, newspapers and online media. I founded Greenbang (50,000 readers, quoted by the UN and European Commission) and was the founding editor and investor in CoinDesk.

Inside FTSE companies I served as Commercial Director at Virgin Money and at Thomas Cook, where I ran transformation programmes that changed how big organisations sell, grow and prove their numbers.

That work has unlocked over $1bn in revenue for clients, and I have advised teams at IBM, Microsoft, Google, Cisco and Cognizant along the way.

Dan Ilett · Founder, The Proposition · Editor, The Executive Summary