WATCH AND LISTEN ON
The companion
Ask AI for a recommendation and you'll get what's in the guidebook: Madame Tussauds, the Angus Steak House, a katsu curry at Wagamama. Fine, if fine is what you're after. Nobody listening to this is shooting for fine. This episode is about pushing the machine past the average answer, and investing in the stuff it can't fake: warmth, judgment, taste, reading a room. That isn't the soft stuff. That's the job.
1. Escape the average answer
Ask AI a question cold and it gives you the safest, most common response. Fine for a first draft. Fatal for anything meant to stand out. Henry's fix: ask for the answers most people would never land on.
“Give me five options for [X]. Skip the obvious ones. Sample from the edges: unexpected, a little risky, the kind of thing most people wouldn't think of. For each, tell me the trade-off.”
Leader's note: Next time a team member brings you an AI-assisted plan, ask: is this the median answer? It is a fast test for whether real thinking actually happened.
2. Interrogate the claim
Kirsty photographs a product label and asks AI to separate validated claims from marketing spin. The same move works on any vendor one-pager or pitch deck that lands on your desk.
“Here is a vendor page. Separate the evidenced claims from the marketing language. What would I need to verify independently before trusting this? What is a comparable option worth checking?”
3. Talk, don't type
Wispr Flow turns speech into text anywhere there is a cursor: email, Slack, first drafts. Good for the admin you quietly resent. Your brain moves faster than your hands, so let it.
1. Agenda vs impact
Kirsty's rule: two things happen when you speak. Your agenda (the content, the notes, the data) and your impact (are people listening, do they like you, are you having fun). Before your next high-stakes room, split your prep in half between them. AI can write your agenda, it cannot deliver your impact. If your prep is 100 percent content, you are competing where the machine is strongest.
2. What are you modeling?
Kirsty's family weren't stressed about her failing, so she never learned to fear failure. Teams work the same way: people don't do what you say, they respond to your energy. Next time you go into a situation, simply ask yourself, “What energy am I bringing into the space?”
3. The AI-smell test
Take a message you recently sent that AI helped write. Read it out loud. Rewrite one paragraph the way you would actually say it to the person's face. That gap is your voice. Protect it in anything that carries your name.
Transcript coming soon. It will live right here, in full, for every episode.