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.

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.

I was on a call with a client recently and found myself saying that the human desire to listen to Homer recite The Odyssey is timeless. Even when AI voices become as good as today’s best voice actors, listening to the best in the world tell stories is always going to be worthwhile. Or as Pixar animator Bobby Podesta said to me recently: “Storytelling is a method of value exchange.”

Today’s essay is about taste, an increasingly important skill in our noisy world.

I’ve raved before about Ezra Klein’s new book, Abundance. But I haven’t heard Ezra talk about his craft of writing before listening to a recent interview on the How I Write Podcast. The conversation covered the state of media and the role of AI, but the most interesting topic was the role of an editor. According to Ezra, a good editor is not somebody who makes sure that spelling and sentence structure are correct, but somebody who has taste. Taste, he says, is one of the most valuable skills – in writing and beyond.

I was reminded of a short blog post I read by up-and-coming author Billy Oppenheimer. Before he was a writer, Billy was a ski bum who supported his lifestyle by working part-time as a barista. And he argues that taste – understanding what customers want to drink, how they prefer their lattes, and providing exceptional service – is something that AI can’t replace, even if it does replace his writing career.

I developed taste growing up around my mother’s artwork. From the age of four, she would show me her work, ask for my opinion, and listen carefully to my feedback. I’ve never met a professional artist more open to feedback.

The aesthetic sense I developed as a kid has been a driving force behind my work at Zander Media. I’ve never struggled with a brand direction or critiquing our videos.

In an AI-enabled world, discernment is increasingly important. Creating work that moves people is a valuable skill. Taste is never going away.

My AI avatar logs into Zoom to chat with your AI avatar. Sounds great – fewer meetings! But then what? What happens when AI takes over both our mundane and creative tasks?

This question has been haunting me lately.

If you’ve been following along with the Snafu newsletter, you know that I had an AI inflection point a few months ago amidst attempting to buy my first home.

Even as I was confronted by the painful bureaucracy of trying to buy a house in California, my learning accelerated far beyond anything I’d ever been able to accomplish before. It was a very Responsive.org dichotomy; a tension between traditional bureaucracy and rapid innovation.

Over the course of a few weeks, I realized that AI wasn’t just another important topic, like blockchain, social media, or the Internet. It is much bigger.

Most nights after dinner, my girlfriend and I sit in the sauna. Invariably our conversation turns to AI.

My girlfriend is a data scientist, and has taken the rise of AI for granted for many years. She believes that in the next 18 months we’ll see widespread use of Zoom AI avatars. This led into a conversation about what humans would do instead when our AI avatars take our meetings. And, as someone who talks to people for a living, I’m really not sure.

My only solace is that humans are slow to adapt.

QR codes were developed in 1994, but it wasn’t until the Covid-19 pandemic that we got comfortable ordering food from a QR code taped to a table. And given the option, most of us still prefer a server. Even when we can chat with an AI doctor online, we’ll likely still want to be able to meet with a human doctor, in person.

As the rate of change continues to accelerate, some things are going to be slowed down by humans’ own inertia.

This brings me to a personal decision. I’m doubling down on those things that AI is going to have the most difficulty replacing.

• In-person meetings – even over the convenience of Zoom.
• Educating and selling in-person – instead of through email exchanges.
• In-person gathering – like those that happen at Responsive Conference.

Each of us is going to need to reinvent ourselves over the next decade. The most important skill is going to be adaptability and reinvention.

Today, I’m still taking a majority of my meetings on Zoom. But I’m beginning to default to in-person meetings because they’re harder to replace.

To adapt, we need to lean into work AI can’t easily replicate. But what that work is, I’m not sure.

Last week, I taught the first workshop in a series about selling – because knowing how to influence and persuade are essential skills for navigating chaotic times. I brought together a handful of friends and taught one of the most overlooked elements of selling: being of service.

When we think “sales”, we think of a car salesman trying to persuade you that his junker is just what your family needs. We’ve all received a call from a telemarketer who won’t take no for an answer. That kind of selling gives sales a bad name.

But there’s a growing group of salespeople who are goodhearted, aligned with their audience, and want to create wins for everyone involved. These people know that great selling is about service, not manipulation.

A groundswell

There’s a quiet groundswell of people reclaiming selling.

A son supporting his mother through a cancer diagnosis. A single parent who is struggling, valiantly, to get her daughter to bed on time. A first-time entrepreneur trying to get the world to hear about his new offering.

People taking risks, stepping out on their own, and advocating for what they believe in. This is the approach to selling that we need. And one of the best illustrations of sales as service comes from an unlikely source, a classic movie about Santa Claus.

A Christmas miracle

The example I often give to describe sales as service is the Santa from the 1947 movie “Miracle on 34th Street.” In the movie, an alcoholic Santa Claus is hired to give out candy canes and sell goods for a local Macy’s department store.

The Santa – apparently not caring very much about the job description of “sell things to customers” – answers customers’ questions honestly when they ask him where to buy products that his store doesn’t have in stock. He sends them across the street to the competition!

When the department store manager finds out, he’s furious. How dare this washed out Santa Claus send customers elsewhere, instead of just redirecting them to a different product that they already sell? Until customers begin to return en masse, praising Santa’s good advice and expressing their undying gratitude and loyalty to his store, for guiding them so well.

The department store manager does an about-face, celebrating Santa’s ingenuity.

Enlightened hospitality

Even though we’ve never met, one of my early mentors was restaurateur Danny Meyer, whose thoughtful approach to service has reshaped the hospitality industry.

Danny is the founder of the New York institution Union Square Cafe, and went on to build a variety of other famous restaurants, including Eleven Maddison Park and the global Shake Shack chain.

His approach, often referred to as “Enlightened Hospitality,” emphasizes the importance of caring for employees first, then guests, and then the broader community. If we support our employees, they’ll serve our customers, and the rest will follow.

Inspired by Danny, I designed Robin’s Café to prioritize employees, creating an employee and service-focused environment.

In service to our employees

When I opened Robin’s Café, it was with the clear intention to open a coffee shop in service to our employees who, in turn, would provide great service for our customers.

One night, about six months into running my old restaurant, I came in at closing to pick up some paperwork. The employee who was closing the cafe for the night, turned to me and said, “Robin this is the single best job I have ever had. Thank you for this opportunity.”

This employee worked irregular hours in a small café, serving hundreds of customers every day with no guaranteed minimum of hours. To hear this from him reminded me – and reminds me still – of the reason Danny’s “Enlightened Hospitality” matters. It creates environments in which people will do their best work.

Serving multiple stakeholders

The most skin-crawling sales people sell exclusively for their own betterment. They only serve themselves. A successful salesperson has to at least serve two stakeholders – the salesperson and the customer.

But a sales person who serves a multitude of stakeholders is more likely to succeed. There are more parties invested in their success!

Robin’s Cafe served 5 different stakeholders:

• Employees: in creating a fulfilling, supportive workplace
• Investors: return on investment and pride in supporting a meaningful venture
• Landlord: a vibrant, community-oriented tenant
• Customers: a welcoming, enjoyable “third place,” in addition to good food
• Me: a meaningful, rewarding endeavor, both financially and emotionally

Once you have identified the different parties that benefit from your efforts, it is helpful to delineate how each one benefits from your selling.

Service is selling

When we think of restaurants, we don’t usually think first of a sales environment. But they are.

When the server asks if you’d like dessert after a meal or the sommelier asks if you’d like another bottle of wine with dinner, they are upselling – encouraging you to purchase a more expensive menu item than the one you’d intended to buy.

But what restaurants do differently is sell through the act of serving their customers. By being of service and providing an exceptional experience, they’re creating an environment that we, as patrons, are pleased to pay for.

Whether you’re selling a product, an idea, or simply persuading a friend, selling is about genuine service. When you serve, you don’t just sell. You also create lasting value for everyone.