Deborah Webster

Speaking

The conversation the room needs to have

Sessions for boards, investors and leadership teams. I bring fifteen years of assessing chief executives, founders and investors into the room, and leave it with sharper questions than it walked in with.

Keynotes · Masterclasses · Board sessions · Investor gatherings · Moderated conversations

Topics

  • 01

    AI and the Human Factor

    The technology may be new. Human nature isn't. How judgement, character, wisdom, incentives and imagination shape what powerful technologies become — and why virtues and vices matter more as the stakes rise.

  • 02

    What Gets Funded Gets Built

    Capital doesn't just finance technology. It shapes the incentives, behaviour and decisions that determine what gets built, what gets rewarded and who benefits.

  • 03

    The Power of AI Isn't Speed. It's Direction.

    AI can make us faster. The bigger opportunity is to make us more capable — strengthening judgement, ingenuity, mastery and agency rather than outsourcing them.

  • 04

    How Investors Get Hacked

    Investment decisions are made by humans before they are made by models. How narrative, founder charisma, cognitive bias, social proof and incentives distort judgement — and what investors can do about it.

  • 05

    What Should Humans Get Better At?

    As AI takes on more cognitive work, what should we hand over and what should we deliberately keep practising? On judgement, mastery, ingenuity, agency, wisdom and the capabilities worth strengthening.

I accept a small number of engagements each year.

Tell me about the audience, the date and what you want the room to leave with.

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