Three ways funds use this
Across the portfolio: the same session in every company. A board or leadership session run in each portfolio company against the same four questions, so the operating partner can compare like with like and see where the risk and the value actually sit. The formats are at board away days and briefings.
Portfolio CEO and founder dinners. A chaired dinner for the chief executives or founders across a portfolio, under the Chatham House Rule, built around one question that matters to all of them. Peers say more to each other than they say to their investors. How the evening runs is at board dinners.
Alongside the operating team. A sounding board for the operating partner or platform team on the leadership and people side of AI, and help turning what the portfolio learns into something the next company can use. It sits next to your technical and commercial specialists, not in place of them. The standing relationship is described at board advisory.
What I look at in a portfolio company
Which decisions the machines are making. In pricing, hiring, credit, customer service and reporting, and whether anyone at the board decided they should.
Who can stop each one. A named person with the authority and the skill to override it, and evidence that somebody has.
What the people must stay able to do. A company that has automated the junior work may be quietly losing the people who will run it in five years. I call that the missing rungs. It is a value question as much as a people one. See also capability debt.
Whether the AI story is true. What management says about AI, to you, to customers and in its reporting, set against what it operates. Overclaiming now carries legal and litigation risk; see AI-washing.
Whether the spend is working. Which AI investments to keep, and which to stop. See which AI investments should we stop.
For venture capital and platform teams
Early-stage companies are often building AI into the product itself, which brings the same questions in sharper form: what the customer is trusting the product to decide, who at the company can tell when it is wrong, and what the founders will need their first fifty hires to be able to do.
Platform teams use this for founder programmes and portfolio summits: a keynote that gives founders a working language for those decisions, a workshop on one company’s own product, or a founders’ dinner. The keynotes are at keynotes.
Why I do this work
I have sat on both sides of the table. I founded EtonX and saw it acquired by Eton College. I ran corporate development at HarperCollins, led international growth at Quizlet across more than 60 countries, and was brought in as Executive VP at Avallain to reposition the business for growth in AI. I have held board seats at EtonX, TeacherMatic and Whitefox.
So I know what an investment case looks like the night before a board meeting, and what a portfolio company says to its investors that it would not say to a stranger. My book, SuperSkills (Kogan Page, 2026), is about the human judgement that sits underneath all of it.
