Over the last few weeks, I’ve been teaching a workshop about sales. We get together on Zoom for an hour every week to discuss – and practice – a more authentic approach to selling.
I made my first sales at five years old at Robin’s Pumpkin Patch. Selling is a part of my work today. But I’ve always meant to study sales and persuasion more deliberately, so this workshop format provided me the excuse.
Last week, in a discussion of empathy and connection, I asked the workshop participants a question: “What characteristics make a good therapist?” Or, if you prefer, what makes someone feel like a safe and trusted presence in your life?
It’s not usually their credentials or how convincing they are. It’s how they show up. It’s the way they listen, make space for you to think, and are okay that you don’t have everything figured out. A good therapist isn’t trying to steer you toward a particular outcome, but instead helping you discover what’s true for you.
That same kind of presence is at the heart of my approach to sales.
The most effective salespeople aren’t pushing hard for a yes. They’re not over explaining, and they’re definitely not trying to be impressive. They’re doing something much harder – and much more generous. They’re holding space, asking real questions, and listening closely enough to help someone gain a clearer understanding of what they need.
In that way, sales and therapy aren’t that far apart. Both rely on deep listening, curiosity, and a quiet confidence. They’re about helping people see something they couldn’t quite see on their own – not because someone told them, but because they finally had space to recognize it themselves.
When sales are done this way, it stops being about persuasion. It becomes about partnership. It becomes a conversation that respects the other person’s agency. And when that’s the foundation, a sale – if it happens at all – feels more like a mutual decision than a transaction.
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Homework
This week’s homework is to compliment a stranger on the street. Pick out someone in the grocery store or on the sidewalk and compliment them on something trivial – their hairstyle, an article of clothing, the brightness of their eyes.
When I started this habit a few years ago, I was scared. Before I spoke, my heart would beat fast and my palms got sweaty. Today, I compliment strangers with ease. More significantly, I feel more comfortable speaking up in public and I’ve never had someone respond poorly.
Next time you are in public, find something about somebody nearby to compliment and let me know what happens.
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3 things I’ve loved this week
Framework I’m thinking about
Hanlon’s Razor
Hanlon’s Razor dictates that we should never attribute to malice that which can be adequately explained by stupidity. I recently discovered this principle—and agree!
AI video that blew me away
Skydiving Gorilla promotes LA dental office
I saw this TikTok video, which was created with Gemini’s Veo3. Unsurprisingly, that dental practice is now completely swamped. But as someone who makes videos professionally—I’m pretty stunned by what’s possible.
Book I’m reading
Empire of AI: Dreams and Nightmares in Sam Altman's OpenAI by Karen Hao
Several books about Sam Altman and OpenAI were published recently – one with his full cooperation, one without. Empire of AI is the second of these.
The title is a nod to the fact that empires typically have a few big winners while the vast majority suffer to produce their spoils. This book is a well-reported, high-octane read that delivers a scathing account of OpenAI and Sam Altman’s rush to dominate the AI race. One thing’s for sure: Sam Altman is an incredible salesperson!
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When you're ready, here's how I can help
Read these books - Responsive: What It Takes to Create a Thriving Organization is a book for any startup founder or enterprise change lead. And if you want to learn to do a handstand, read out How to Do a Handstand.
A different kind of creative agency - Clarifying your narrative is critical in order to sell. My agency Zander Media helps startups and global brands clarify their message and create video that change consumer behavior.
Join us in September - Established in 2016, Responsive Conference is an annual summit that brings together 300 executives, founders and entrepreneurs who want to work better. Join us at Responsive Conference 2025 and equip your teams to respond to change!
Until next week,
Robin
