When I first moved to San Francisco, I worked as a personal trainer in gyms. Gyms are intense sales environments. The folks at the front desk are trying to close new members, and personal trainers prowl the gym in search of new clients and the “packages” they’re hoping to sell.

I got a job working at World’s Gym, a bodybuilder’s gym in the Potrero Neighborhood. Every Saturday mornin,g professional bodybuilders would oil up and flex in front of the mirrors. I taught step aerobics. Those 5 AM classes were the only part of the job I got paid for. The rest was “eat what you kill.”

After about two weeks, the manager of the gym got angry with me because I didn’t have any clients. He gave me an ultimatum: close a client today, or don’t come back.

It was already a sales-heavy environment; this pressure made it insurmountable. I didn’t sell any new clients and was fired the following day.

I left World’s Gym, and without quotas hanging over me, something shifted. The first client I ever landed came not from a sales script, but from walking out of a contact improvisation dance jam onto the street and noticing a woman holding her knee in pain. As a runner, I was intimately familiar with knee pain. I walked over – not as a salesperson, not even consciously as a trainer – but as someone who had been where she was.

“Hey, I’ve had a bunch of knee pain,” I said. “I’m a personal trainer. Would you like me to give you a free session and see if I might be able to help?”

She said yes. The next day, she came to my house, and that free session turned into a working relationship that lasted six years, three days a week. I earned tens of thousands of dollars in lifetime value from a single moment of noticing someone else’s need and offering help.

My second client arrived just as strangely. I was driving my parents’ Toyota pickup down Valencia Street in the Mission when I saw a man hunched over on the sidewalk, holding his lower back. Without thinking, I stopped the truck in the middle of the road, jumped out, and approached him, “You look like you’re in pain. I’m a personal trainer. I might be able to help. Do you want to talk more?”

We ended up working together for three years. I didn’t give him a pitch. I didn’t have a package prepared. I wasn’t even trying to land a client. I was responding to someone in pain, and I had a possible solution.

Those stories sound bold in hindsight; dramatic, even. Who jumps out of a truck in traffic to approach a stranger on the street? They sound like courageous examples of proactive outreach. Or what Internet marketers would call “lead generation.” But I wasn’t approaching strangers out of a desire to do business or to fill a quota, but because I sincerely wanted to help.

At World’s Gym, when I was told I had to close clients or be fired, I froze. But with that pressure removed, I was able to ask people if they wanted help that I was prepared to offer.

In last week’s “How to Sell Yourself” workshop, I shared that I’ve never been good at “closing” – at trying to pressure or persuade a prospective client into buying anything. I avoid closing in favor of asking, “Would you like what I have to offer?” and making it easy for them to say “yes.” Those early experiences as a personal trainer showed me that the most transformative opportunities don’t begin with a close, but with an invitation.

Homework: Approach a Stranger

This week’s homework is about practicing connection without pressure – strengthening the muscle that makes asking possible.

Approach a stranger. Not from a place of asking for anything, and especially not in an attempt to close. Leave off your agenda. Don’t try to sell. Instead, just say hello to someone. Maybe ask their name. If you’re feeling bold, compliment them – their clothing, eyes, or hair.

So much of getting comfortable asking someone for something comes from a place of authentic human connection. The pressure to get your way is antithetical to simple human connection.

Focus on the connection, not the close.

A few weeks ago, I spent several hours with my friend Michael, a ghostwriter who helps authors clarify their ideas. One of the fun tasks he gave me out of our time together was to list my Commandments for Reluctant Sales.

The argument behind Snafu is that the very things that make us reluctant salespeople are actually superpowers that make us great. What, then, are those attributes?

Thou shalt not use force

I first heard the phrase “Don’t use force” from Doug Kirkpatrick, who I wrote about in Responsive: What it Takes to Create a Thriving Organization. It is one of the two principles of the Morning Star Company, an entirely self-managed tomato manufacturing company.

“Don’t use force” describes my approach to learning. I’ve learned the best – and accomplished the most – when I don’t use force. (Incidentally, all my best personal relationships embody this principle.)

Stereotypical salespeople are pushy. They use pressure to prioritize what they want even over what’s best for prospective customers. When we don’t use pressure, we are embodying the first and most important commandment of a reluctant salesperson.

Thou shalt be of service

I have been enamored of Danny Meyer, the famous restaurateur behind Union Square Café, Eleven Madison Park, and the Shake Shack empire for more than a decade. He coined the term “enlightened hospitality” in the 1980s to describe businesses that prioritize their employees, even over their customers.

I tried to apply this principle at Robin’s Café by showing up in service to my employees. By creating a culture of service for my employees, my hope was that they would then show up in service to our customers.

When we show up in service of something greater than ourselves, sales happen naturally as a result.

Thou shalt lead with curiosity

For many years, I ran a business helping children with autism.

Autistic children often lack the social standards that we take for granted. The only way to work with those kids was by being completely curious about their experience – even when you don’t know what their experience is.

When you are even more interested in the best interests of another person than you are in getting what you want, you are more likely to get what you want.

Thou shalt have boundaries

One of the reasons many of us are reluctant salespeople is an absence of boundaries.

Boundaries can be as simple as time-boxing meetings, arriving on time, or discussing what you are going to discuss in advance. Boundaries can also be as nuanced as not negotiating past your comfort or saying “no” to a sale when you don’t think your offer is a good fit.

When you know what you’re willing to do – and what you’re not willing to do – it is much easier to be curious, show up in service, avoid force, and make clear asks.

Thou shalt ask boldly and without apology

Asking is the most difficult part of selling for reluctant salespeople. In our nervousness to do well or not cause offense, we ask hesitantly, apologize, or just don’t ask at all.

The simplest way to ask boldly without hesitation is to believe that the other person can – and will – decide what’s best for them. The person you are talking to is their own best expert.

There is no such thing as “taking advantage” of someone else when you don’t use force, try to help them, and trust that they will decide for themselves.

Thou shalt tell them stories

Humans are constantly telling stories. The stories we tell ourselves become how we think of ourselves and the stories we tell others shape those relationships. The first step to telling a good story is to recognize that you already are.

The best stories have four parts: a beginning, middle, and end, and something unexpected. This “turning” or moment of surprise helps make the story memorable.

Finally, practice the stories you frequently tell. Notice what lands, improve your delivery, timing, and affect.

Everyone likes a good story, so get better at telling them.

Thou shalt practice incrementally

Bruce Lee said: “I fear not the man who has practiced 10,000 kicks once, but I fear the man who has practiced one kick 10,000 times.”

Selling is a craft. Like great athletes and artists, salespeople improve through practice, reflection, and feedback. It is the small refinements, consistent practice, and feedback that create mastery.

Improving at sales is a matter of practice and incremental improvement. The key isn’t to be perfect at each iteration but to put in the repetitions which will help you to improve.

Thou shalt celebrate small wins

Acknowledging wins isn’t self-indulgent; it’s essential to creating lasting change.

BJ Fogg argues that there are two necessary steps to adopt a new habit: making the habit tiny and celebration. When we celebrate our successes, we create a positive association with the behavior, and when we make those behaviors so small that they feel almost inevitable, they are easier to do.

The same holds true for selling.

Celebrate any success; not just a closed sale, but the tiny steps along the way. Thus, you become better at the habit of selling.

Thou shalt accept rejection (and move on quickly)

For most reluctant salespeople, it is the fear of rejection – even more than rejection itself – that limits success.

Get to know your prospect and their needs as quickly as possible. There are eight billion people in the world. If the person you are talking to is not a good fit, somebody else will be!

Great selling means getting rejected and knowing when to move on.

Thou shalt maintain flexible goals

When I worked with autistic kids, I found that most parents would see incremental progress and then get fixated on that issue continuing to improve. The more fixated these parents would become on their child’s speech clarifying or digestion improving, the less creative they’d become.

People who want something, who are very driven toward an outcome that they are seeking, often get fixated on the specific outcome.

You can want a specific sale or objective a lot, but never lose sight of other beneficial outcomes.

Thou shalt know thy purpose

Purpose is at the core of sales and persuasion.

Whether launching a product, pitching an investor, or trying to be taken seriously at work, having a clear purpose helps you get over rejection and continue to improve.

The most influential people have a clear sense of purpose.

In last week’s How To Sell Yourself workshop, one participant admitted he sometimes asks too many questions. He gets so caught in curiosity that he “gives away all his marbles” before ever making the ask. Another participant shared the opposite pattern: she avoids asking questions because she’s afraid of what the answers might reveal – especially when she’s afraid the prospect isn’t a fit.

Both patterns are a form of resistance. Whether we over-ask or under-ask, we’re avoiding the discomfort of discovering the truth.

The conversation inspired me to write an article about questions – why they matter, the different types of questions, and which to use when.

Why Questions Matter

There are several different kinds of questions, and the kind you choose determines the outcome — in sales, in conflict, and in life.

Asking questions demonstrates authentic curiosity about the customer, which allows you to build rapport and an emotional connection. And in asking questions you’re able to get to the heart of the customer’s issue.

Ask Questions as Training for Real Life

One of the most important interpersonal skills anyone can practice is the ability to ask questions. Whether you’re gathering information, selling, coaching, interviewing, or navigating a hard conversation, asking questions trains many other essential human skills.

How Questions Sharpen Your Thinking

There are no inherently right or wrong questions – only questions that are more or less useful depending on the outcome you want. Asking better questions improves your ability to listen, connect, persuade, and think clearly.

High-Pressure Conversations

Any situation that matters – a first date, sales call, job interview, or giving feedback to a colleague – brings uncertainty. Important moments require the ability to think while under pressure.

Most people become passive in high-stakes situations. They respond reactively or expect the other party to lead. But if you can stay curious and ask thoughtful questions, you change the dynamic. You become an active participant instead of someone being carried along by circumstances.

Thinking on Your Feet

High-stress conversations are unpredictable. Someone says something surprising and emotions get involved.

You have to respond in real time.

The only way to train for this is to practice before the stakes are high. Asking questions builds the habit of staying calm when it matters.

Practice Before the Moment

We all face pivotal conversations. Instead of waiting for the critical moment to arrive, you can practice the skill of asking questions every day. This might mean:

• asking a friend one more follow-up question
• pausing to clarify someone’s intention
• checking in during a difficult conversation
• being curious instead of defensive

These small practices prepare you for the moments when the pressure is real.

The Different Kinds of Questions

There are several different types of questions, and each serves a different purpose.

Blaming questions

These are the most common — usually asked in frustration: “Why did you do that!?” When used intentionally, blame can motivate action, but more often these questions land as an attack and create distance.

Manipulative questions

These are the pushy, sales-adjacent questions everyone dislikes. They steer someone toward a predetermined answer and usually feel transactional.

Research questions

These are questions that accelerate learning. By asking an expert specific questions about their discipline, you dramatically increase your speed of learning.

Consulting questions

These assume you’re the expert and help the other person see the problem the way you see it. They’re directive and designed to move someone toward your conclusion.

Leading questions

These guide someone toward an insight, a storyline, or an emotional shift. They’re useful for teaching, storytelling, and persuasion — especially when they contain an unexpected twist.

Connecting questions

These presume the other person is their own expert. They create space for introspection and help someone articulate what they think or feel. They’re the least common, and the most powerful for building trust.

Each of these types of questions has an appropriate context. Even blaming and manipulative questions can be useful. But each type shapes the relationship differently – and some build connection while others break it.

Know Your Intentions

It’s important to know your intentions before beginning to ask questions, and to leverage your intention to ask the right kinds. All too often, we are attached to a specific outcome – closing a sale, getting what we want from a family member, achieving our desired ends. That desperation is perceived as pushy and a lack of consideration.

If you are feeling urgency, stop. That urgency, which comes across as pressure, will ultimately not serve you or your desired outcome.

Regardless of what you are selling, or the knowledge that you have, your intention should be to help the person you’re talking to. If, through the course of discovery, you find yourself thinking that what you are selling is not a good fit for the person you are talking to, explain “I don’t think this is a good fit for you.”

Thank them for their time and move on.

Being clear about your intentions means that people are more likely to come back later and the goodwill you generate by being so straightforward outweighs the loss of a sale.

Putting It All Together

In order to sell anything – an idea, a changed behavior, or a product – you must first understand the other person’s challenge. But you also have to know your own intentions.

I once heard Tony Robbins say thinking is the process of asking and answering questions. As we learn to ask more refined questions, our thinking improves. By asking more questions, you train yourself to think more clearly, understand your intention, and get better at asking the right questions.

I’ve never compiled a gift guide before, but with the holidays around the corner and two years of “3 Things I’ve Loved” in the Snafu newsletter, I thought I’d give it a try!

Best Mechanical Pencil: Pentel GraphGear 500 Mechanical Drafting Pencil​

I’ve been using the same mechanical pencil since high school. They used to cost $40, but have substantially decreased in price in recent years. Now that my fiancée has begun borrowing (read: stealing) mine, I find myself ordering more and keeping them stashed around the house.

Best Marker: Paper Mate Flair Pen, 0.7 mm Medium Tip​

I take a lot of physical notes. Even though my Zoom calls are recorded with Fathom, and I keep my To-Dos in Asana, I think better when jotting down ideas on note cards. For that purpose, I love these markers and keep a box on my desk.

Voice Dictation: ​Wispr Flow​

I’ve tested voice-to-text dictation apps since Dragon Dictate came out in the late 1990s. None have worked well enough for daily writing until a friend recommended Wispr Flow. After a week of testing, it’s easily the best voice-to-text app I’ve ever tried.

Best Green Tea: Numi Organic Gunpowder Green Tea​

Sadly, I’ve stopped drinking my beloved pu-erh in favor of green tea. I’m sure I’ll return to it, but the unknown quality of the tea (there are concerns about buying tea from unknown origins in China) combined with a deep dive into my gut health has led me to drink only green tea for my daily caffeine. For that, I love this bulk gunpowder green tea from Numi.

Best Gut Aid: Seed​

Speaking of gut health, I’ve continued to enjoy Seed DS-01, since first starting to use it daily early this year. I’m intrigued by the science behind their product, and have also heard a lot of good reports from friends who’ve tried the supplement.

Best email tool: ​Superhuman​

I don’t love paying for email, but Superhuman is an email app that I can’t live without. It really does save me a lot of time managing my inbox – their promise – and continually reminds me that there are a lot of behavioral cues that can (and probably should) be built into any technology.

Best newsletters (besides Snafu, obviously)

• ​5-Bullet Friday – I’ve never been disappointed by Tim Ferriss’ five recommendations each week. His weekly 5 inspired me to include my “Three Things I’ve Loved” in each Snafu newsletter.
• ​Ryan Holiday’s Reading List – I’ve been on Ryan’s reading list since 2010, and read hundreds of books he’s recommended. He’s never steered me wrong.

Best Gym Tool: Timebirds Timer – I’ve recommended the Timebirds Mini magnetic timer before. I use one anytime I’m working out, and keep another on my desk as a writing timer. They’re nearly indestructible, magnetic, rechargeable and keep you from using your phone as a timer at the gym.

Best multi-tool: Leatherman Wave​

I’ve owned and loved a Leatherman Wave for more than two decades. Now that I own a house, there are a lot of household projects that call for a multi-tool, and I keep my Leatherman handy.

Best knife: Kershaw Leek​

My everyday carry knife is the Kershaw Leek. It is small enough to be unobtrusive, handsome, and sturdy. I own several, and have used them for everything from opening mail to gutting fish.

Best Kitchen Knife: Victorinox Swiss Classic 8-Inch Chef’s Knife​
​This is the kitchen knife everyone should own. Don’t take my word for it. Just search “Victorinox Swiss Classic Chef’s Knife” and you’ll come to see why normal people love it and most chefs have it in their kit.

Best Finishing Salt: Maldon Sea Salt​

Everyone needs Maldon sea salt. It is the default sprinkling salt in fine dining, and I consider it a kitchen staple. Pro tip: buy the 20 oz. tub, and not the 8.5 oz. box.

Best Specialized Salt: Beautiful Briny Sea​

If you want something a bit more unusual, I discovered Beautiful Briny Sea back during the pandemic, and have used their salts regularly since. Based in Atlanta, Georgia, this little company makes a variety of salt blends. Their Sultan Papadopoulos Sea Salt remains my favorite – I use it on air fried chicken, in stir fry, on eggs, and just about anywhere else that occurs to me.

Best Supplements

Fish Oil: Nordic Naturals ProOmega, Lemon Flavor​

When I’m asked my favorite supplement, it’d be a hard choice between fish oil and magnesium. Most people are deficient in both! For fish oil, I like Nordic Naturals as a well-sourced, single-source fish oil that has the Omega-3s we need.

Magnesium: Doctor’s Best High Absorption Magnesium Glycinate Lysinate​

Humans used to get a lot more magnesium through our food, but there isn’t as much in the soil as there was pre-Industrial Revolution, and so we all need more magnesium. While a lot of people recommend magnesium citrate for sleep, I find this magnesium is excellent for the blend of recovery, sleep, and mood stabilization.

Best flashlight: ​Fenix PD36R Pro High Lumen Tactical Flashlight​

Whether I’m running in the dark or trying to find something in the closet, my iPhone light just doesn’t suffice. This tactical flashlight – highly recommended by a variety of reviewers – has been the best flashlight I’ve ever used.

Best Barefoot Shoes: Whitin​

Back in the early 2000s, I was one of those weirdos sporting toe shoes. These days, I prefer my barefoot shoes less ostentatious. The Whitin brand of barefoot shoes looks perfectly ordinary, cost $40, and last longer than many of the more expensive brands. I currently own three pairs.

​
​Best Cold Plunge: The Plunge​

This is the one item on my gift guide that’s more than $100. It is, in fact, in the range of $6000. But cold plunge is as hard to do as it is worth doing. While it is possible to make your own, anything that makes this already difficult task harder means that you’re less likely to do it.

I started the How to Sell Yourself cohort series when, independently and within weeks of each other, two friends asked me for advice and mentorship on self-promotion. I’m not an extraordinary salesman or self-promoter, so I declined “mentorship” but suggested we get on a Zoom call to discuss and share ideas about selling.

That single Zoom call led to more, and eventually to me compiling the curriculum for How to Sell Yourself. Since the beginning of the year, I’ve run two 10-week cohorts through the program.

We’re a few weeks into the current How to Sell Yourself cohort, and last week I changed the curriculum on the fly.

I start the workshop with a segment on “Sales as Service,” drawing on Danny Meyer’s reinvention of restaurant service with Setting the Table, Will Guidara’s recent sensation Unreasonable Hospitality, and my own restaurant experience.

I start with redefining sales as service because it’s an unusual place to start a discussion about selling. Service is the opposite of stereotypical selling and one of the big differentiators in how I approach sales.

The second week is about the attitude of a great salesperson, which I encourage everyone to define for themselves, but for me includes love, presence, and acceptance. Instead, we spent the second week of this cohort discussing habits and behavior change!

Behavior change applies to sales in two ways:

• Our own behavior – if we can develop better habits and change our behavior, we’ll learn faster and thus sell more.
• Others’ behavior – when we understand behavior change, we’re more likely to sell in ways conducive to getting what we want.

Every sale is an effort to change behavior – whether your customer’s or your own. Predominantly, though, I focused on habits and behavior change in order to help my students become better learners. As reluctant salespeople, we learn more quickly and are more likely to keep improving.

I asked cohort members to watch this TEDx talk by Stanford behavior designer BJ Fogg. BJ articulates the two things necessary to adopt a new habit:

• Make the habit tiny
• Celebrate your successes

(Now, if only change were as easy as that sounds…)

Make It Tiny

Common advice about habits is that if you want to run more, leave your running shoes out ahead of time. That makes it easier to start by changing the environment around the desired behavior, but it doesn’t make the success of the habit smaller. What if we called success just stepping outside the door? Or running just the length of the block? What if success was sending one email?

There are always ways to set your objectives smaller. This isn’t a lack of ambition. Doing so makes success easier, and thus easier to repeat.

Celebrate Your Successes

I’ve written previously on the unexpected benefits of celebration. BJ describes a handful of different celebrations like doing a little dance or pumping your fist in the air. Celebration is uncomfortable; we have a cultural bias towards self-critique.

As with dog clicker training, the key is that your celebration has to immediately follow your behavior. You don’t trigger the dopamine of positive reinforcement if you wait a few hours and reward yourself with a nice dessert.

Tiny Habits of a Great Salesperson

I left it to my cohort members to apply these two principles of behavior change to their own work in sales, but here are a few suggestions:

Make It Tiny:

Most reluctant salespeople don’t sell because they make their metric of success too big. While selling rewards persistence, most people define success to mean something so far from where they are that they never get started.

Instead, tiny selling can mean:

• Make one clean ask per week.
• Write one short email.
• Send one “thank-you” note or follow-up after a conversation.

Celebrate:

Traditional salespeople are actually quite good at celebrating. At Zander Media, we have a Slack channel that notifies my team when we sell a ticket to Responsive Conference.

The problem is that most sales teams celebrate only a successful sale or meeting their quotas – not the small steps along the way.

Instead, celebrate the little things:

• Physically celebrate (smile, exhale, fist pump) after every phone call.
• Pat yourself on the back after a single difficult client conversation.
• Say out loud, “That was a good ask!” every time you ask for anything.

One of my students, an HR executive-turned-coach, shared that she’s begun celebrating herself after meetings where her only focus is on helping the person she’s with – even if they don’t turn out to be a good fit for her practice. She found herself enjoying meetings, as a result.

As an added benefit to the practice of celebrating, the group now sweetly celebrates others throughout our Zoom with fist pumps and rocketship emojis.

Behavior Change – and Sales

Across the 100 or so books I’ve read about sales and persuasion, there isn’t much about about habits and behavior change. That’s an oversight.

I’m coming to believe that anytime anyone is teaching anything, they ought to start with a segment or two about learning. When we can help people become better learners, they’ll learn more of what they’re there to practice.

This last week was the first time I’ve applied two principles of behavior change to the topic of sales, and this article just scratches the surface. But, at a minimum, anytime we make our habits smaller and celebrate successes, we’re more likely to succeed.

A few months ago, I started collecting Snafu articles into categories, and was surprised by how many taught the tactics of doing something very specific: fasting, buying a used car, raising a puppy, or buying a house.

None of these experiments was a sure thing. In fact, nearly all of them began with the same phrase: “This might work.”

That phrase is the title of my new book. It’s an invitation.

We’re living in a dichotomous era – of unprecedented change and uncertainty. Of leaders promising guaranteed outcomes and “ten steps to anything.”

This Might Work is a record of experiments – of trying things without knowing how they’ll turn out, and what I’ve learned along the way.

Each essay began as an attempt to figure something out: how to tell a great story, how to curate a conference, how to change someone you love.

The through line isn’t expertise – it’s curiosity.

If there’s one thing I’ve learned from them, it’s that progress begins when we stop waiting for certainty. This Might Work is my attempt to compile those lessons in one place – and to invite you to try your own. Because the only way to know if something will work is to start.

Download “This Might Work” here for free:

https://download.filekitcdn.com/d/c7gqh8rbyNUQGR6tynkbna/nYxsYdXjpap6yAD8osSsPb

I went on a fly fishing trip last weekend in Montana with several work colleagues.

When it comes to fishing, I’m a bit out of my element. A trail run through the mountains, a mountain to climb, snowshoeing, or a ski resort – these are all outdoor adventures I know well. But fishing is entirely new to me. Fortunately, two of our party were avid fly fishermen and eager to teach me.

I ended up catching one fish (it was two feet long, I promise), but that’s scarcely relevant. I do understand why people fall in love with fishing. It’s quiet, peaceful, meditative – and a really deep rabbit hole.

Where in the river the fish are. The time of day and year; so many factors determine whether the fish are biting. How you throw the line matters, as well as where it is in the water. Whether your bait is underwater or floats on the surface. I could write an article on “A Beginner’s Guide to Fly fishing” just from the single day I spent on the river.

On the first day in Montana we took a boat down the Madison River and my friends gave me pointers. It helped, of course, that our guide was endlessly patient, rowed our boat, and replaced my flies anytime I got my line tangled in the trees! (As with learning anything, it helps to have someone else take care of the more tedious parts.)

Sitting on a boat on the river, casting and recasting my line – while trying not to get distracted by the bald eagle overhead and the snow-capped mountains in the background – was not a bad way to spend the day.

Even Great Salespeople

Everyone in our party was in sales. Whether an entrepreneur like me who sells to clients, someone managing a startup’s sales team, or as a relationship-driven salesman for an enterprise company, all of us are in sales.

As we were waiting to board our plane, I got to chatting about the Snafu Conference. One of our party said that the best salespeople don’t think of themselves as salespeople. He went on: “We are relationship builders, community builders. What we do is provide value. But we don’t consider ourselves salesmen.”

The best salespeople don’t call themselves salespeople because the word doesn’t describe the way they operate. It turns out that even salesmen don’t care much for salesmen!

Why We Avoid The Label “Salesman”

As I discussed in The Taboo of Sales, just the term “selling” feels manipulative or self-serving. We associate sales with greed, pressure, and rejection.

No one wants to be perceived as a persistent telemarketer among their friends!

There’s cultural shame around sales, even among people who are good at building a network and at persuasion. And understandably so: humans are hardwired to avoid rejection because rejection from the tribe meant death to prehistoric humans. As a species, we crave the approval and support of our peers.

But this results in the ironic twist that while everyone is selling something – ideas, trust, reputation or their love of fly fishing – even the best salespeople resist the identity.

Great Sales Isn’t About Force

As my friend pointed out at the airport, great salespeople bring value to other people. My friends who brought me fly fishing shared with me their love of the sport. I went to Montana! I saw a bald eagle! I caught a fish!

Those friends invited me to join them, encouraged me to try. They provided enough support that I learned something new.

They weren’t trying to win. They didn’t waste breath on why I should enjoy fishing. They just gave me an experience that would – they hoped – show me why they love it.

Great sales is voluntary. It respects the other person’s agency. Had my friends kept saying “See! See! This is why fishing is great!” or had they used pressure, I would have walked away.

Great sales replaces force with service and connection.

What Great Sales Looks Like

My friend didn’t have time to elaborate on what great salespeople do because we were boarding the plane. But I thought about it a lot on the plane ride home. Here are a few of my ideas.

Great Salespeople Are Empathetic

Empathy means the ability to understand the feelings of another. I always think it’s useful to define empathy in contrast to sympathy, which means to feel pity or sorrow for someone else’s misfortune.

Great salespeople pay enough attention that they can relate to or understand what another person is feeling.

Great Salespeople Provide Value

The trip to Montana was orchestrated by my friend Jesse. He planned out where we would fish, where we would stay, and even some local live music on our last night in town.

Providing value is a much-overused concept – especially when you listen to Internet marketers. Everyone’s advice is “provide more value.”

What does that mean, especially when it comes to selling?

I think providing value means trying to help people. We never get to control if we are actually being helpful, but the effort of trying is often enough.

Great Salespeople Connect

I recently got engaged, and two men in our party have been married for years. Throughout the trip, they shared specifics from their marriages that related to my own inexperience.

There’s a delicate balance between offering advice without being condescending. They did an excellent job and only offered feedback when I asked.

When we walked by a jewelry store, and I mentioned the challenges of sourcing an engagement ring, they shared their experiences. When I mentioned that my partner would like a gift from the trip, they offered sage advice on what to bring home.

Great salespeople connect with where someone else is.

Great Salespeople Listen

Jesse spoke at Responsive Conference 2025, and is excited for the Snafu Conference in 2026. While we waited for the rest of our party one morning, he asked questions and listened closely to my thoughts about who the Snafu Conference is for, why I’ve gone to the trouble to start an entirely new conference, and what I’m hoping to accomplish as a result.

At the end of the conversation, we had several new ideas for Snafu and how the conference might benefit his community, which could benefit us both.

He listened carefully and thoughtfully to what I had to say. Great salespeople listen before anything else.

Great Salespeople Have Good Timing

One of our party had taken the entire week in Montana, and I asked him how that influenced his day job and client relationships. He shared that closing clients on a project came down to timing, and that he’s learned over twenty years in the industry that timing is everything.

In a two-minute discussion, he outlined how clients will always take the time they need to make a purchasing decision. They can’t be rushed. I’ve experienced the same with selling tickets to Responsive Conference. No matter what I do, 50% of attendees always want to purchase in the last few weeks.

In taking time off, my friend wasn’t sacrificing relationships with those clients. Instead, he was giving his clients the space they needed to make their purchasing decision.

Great salespeople have good timing. They know when to follow up. They also know when to give space and let someone take time to make a final decision.

Great Salespeople Say No

One member of our party does a lot of paid sponsorship, and sponsored Responsive Conference 2024. They didn’t sponsor Responsive Conference 2025 because they didn’t find the return on investment sufficient. In short, they said “No” to sponsoring the conference for a second year.

Great salespeople know when to say no – to opportunities and to clients who aren’t a good fit. They can be relentless chasing the right opportunities, but only by first saying no to things that aren’t good for their business.

Great Salespeople Help People

There was a pool table at our Airbnb, and while I’ve played pool before, I’m a long way from being a pool shark. After dinner, the four of us teamed up and played five games of pool. (Of course, my team won.)

My partner owns a pool table, and spent much of the games giving me pointers. He saw that I was interested and offered to help.

Great salespeople help people do more of what they already want to do!

You’re Not Alone In Avoiding The Label

I had a great time in Montana, and am tempted to make a very regular habit of fly fishing in the future. But more than the joys of spending several days in the mountains, or even in learning something new that I’d previously known nothing about, I learned something new about selling.

If you don’t think of yourself as a salesperson, you’re in good company! Most of the best salespeople don’t, either. They just do things that help people, and sometimes collect money in return.

The title doesn’t matter; the behavior does.

Whenever I curate a conference, I think about how people are feeling when they arrive and how they are feeling when they walk away.

When it came to Responsive Conference 2025, most people – regardless of political ideology – were coming in with some degree of apprehension. Whether anxious about politics, AI, or the accelerating rate of change in the world, most people I talked to throughout 2025 were nervous. The next question was to decide how I wanted them to feel at the end.

My word was “excited.” I wanted them to feel excited for their ability to contribute. Hopeful. Ready to roll up their sleeves. My work was to curate an experience that helped people move from apprehensive to excited through the course of the 2-day conference.

I wrote a few weeks ago about my concerns that people were having too good an experience, and the accompanying need to let go of the outcome. The outcome that I curated – almost without knowing it – revolved around purpose.

Simone Stolzoff debuted a new talk based on his forthcoming book How to Not Know. Many attendees came up to me afterwards and talked about how much his talk on uncertainty shaped their experience of the conference. I loved the stories he told about choreographer Twyla Tharp, whose book The Creative Habit is a must-read.

On Day 1, I facilitated A Funder’s Fishbowl with three venture capitalists about investing in startups amidst uncertainty. Perhaps the highest praise I received about that session was each of the VCs approaching me afterwards to share that they intend to use the fishbowl format in the future.

My former boss Vivienne Ming opened on Day 2 with a talk about How to Robot-Proof Your Kids – about how technology can make us better humans (and not replace us). As always happens, Vivienne’s talk ended with a long line of people who want to ask her questions and share ideas. Vivienne’s got “riz.“

I got on stage alongside Suzy Welch, author of Becoming You, and entrepreneur Shelby Wolpa, for a session on values and purpose in an age of AI. Suzy said that most people don’t even know what their values are. As a professor of management practice at NYU Stern School of Business who has studied values for decades, Suzy pointed out that values determine much of our lives, but aren’t taught, or well understood.

To close the conference, Eldra Jackson III brought the audience to tears with a talk about the importance of maintaining our humanity amidst constant change. Eldra was incarcerated for two decades and has dedicated his life to helping people inside the penitentiary system get and stay out. He brought gravitas and provided a perfect end to the show.

As we’ve collected feedback from attendees over the month since, conducted our internal After-Action Review, and considered what we want to do differently at Responsive Conference 2026, I’ve had no regrets. That was new to me.

Ten years ago, producing Responsive Conference was about logistics, ambition, and survival. This year’s conference was fundamentally different. I was calmer and well-resourced. The shift I experienced mirrors my attendees’ experience: moving from apprehension to excitement.

I wasn’t just running a conference. This year, I knew why it existed. That clarity wasn’t only professional – it came from the alignment in my personal life (I’m newly engaged. I bought a house. I’m happier than I’ve ever been.) And when purpose aligns across personal and professional work, execution is much easier. I’ve gone through the same transformation – from apprehension to clarity of purpose.

Attendees arrived at Responsive Conference anxious about politics, AI, and the pace of change. Through talks, workshops, un-conferences, and plenty of time to reflect (and play with animals), they rediscovered what they care about and what they can control. The conference itself was a live demonstration of moving from uncertainty to purpose.

The experience of Responsive Conference – or any great event – isn’t just about content. It’s about remembering why we do what we do, and how to do it better. Without purpose, everything is difficult. With purpose, everything gets easier. The antidote to chaos is purpose.

My mother has been a practicing artist for fifty years. She makes mezzotints, which are something of a lost art. Her curriculum vitae is impressive and her work has been presented in some of the most famous museums in the world.

But my mother lacks salesmanship: the ability to promote herself, share her story, and get people to buy her work.

She is a reluctant salesperson – and she isn’t alone. Most of us have some fear of self-promotion.

We fear rejection, or what people will say about us when we promote our work. We don’t want to be seen as selfish or self-serving.

Part of this is cultural. We’re taught to value generosity and service. Most of us are not raised with an emphasis on self-advocacy. We associate selling with the threat to belonging within our community, to being authentically known, even to being loved.

The cultural taboo

There are only a few cultural taboos – of which sex, death, and money are the most significant. Our boundaries around taboo topics have shifted and the Overton window continues to expand. Once-private, shame-filled topics are now more openly discussed, but sales still carries a charge.

The taboo of sales exists for good reason. From LinkedIn cold pitches to multi-level marketing schemes, there are lots of examples of sales gone wrong. Given the choice, most of us would rather discuss death over dinner than ask someone to buy our work.

The paradox

The irony is that the taboo of sales blinds us to how deeply human persuasion really is. Even though we stigmatize selling, everyone does it daily.

Daniel Pink argues in To Sell Is Human that most people aren’t in direct sales. Instead, Pink describes “non-sales selling” as any activity that requires persuasion and influence. When you convince your team to try a new process, or ask your partner where to go for dinner, you’re selling.

We pretend selling is something only other people do – even while we are all constantly selling.

The cost of a taboo

When we avoid selling, we also avoid clarity. We don’t acknowledge what we want and don’t ask for it.

Meanwhile, a small subset of people do the opposite. These are the salespeople who ask – obnoxiously, incessantly, and without apology.

When we avoid sales, we avoid the clean embodiment of an inherently human behavior.

Redefining the act

The solution isn’t to sell harder but to redefine what selling means. Done well, selling isn’t about convincing. It’s about being clear what’s true for you and inviting others to see that, too.

As my mother begins to tell her story — to share why she fell in love with mezzotints and what they reveal about the world — people won’t just buy her art. They’ll buy into her love for it, as well.
​
Sales isn’t something we avoid by pretending it doesn’t exist. When we refuse to speak up, we’re just leaving room for someone else to fill the silence – someone louder, less careful, and perhaps even less honest.

Homework

The sales taboo dissolves the moment we treat sales as service. Sales is a way of being honest about what we want to give and what we need in return.

Make one offer this week. Not a pitch. Not a plea. Just one clean, explicit offer for something you believe in. Say what it is. Name your price. And then stop talking.

The night before Day 2 of Responsive Conference, I spent an hour agonizing over how enthusiastic everyone was. I was worried the conference hadn’t struck the right balance of existential dread and optimism for the future – given that I feel a fair bit of existential dread myself!

But after stressing over my attendees’ experience for an hour, I looked back at the agenda I’d curated for Day 2 – starting with my old boss Vivienne Ming and ending with Eldra Jackson III – and realized that the program I’d created would provide attendees the experience I wanted them to have: real, raw, but not pessimistic.

One of the things I like most about live events – whether as an MC, speaker, or athlete – is that once the show begins, we have to let go of the outcome. As much as we’ve practiced our lines, rehearsed our talks, or reviewed our notes, once the show begins, there’s nothing to do but continue.

One of my early teachers, Feldenkrais-disciple Anat Baniel, described this idea as “flexible goals.” In the subsequent eight years I spent working with autistic kids, maintaining flexible goals was the only path forward! A myopic focus on hypothetical outcomes, like “I want my child to be neurotypical,” would impede progress.

Maintaining flexible goals, or letting go of the outcome, doesn’t mean that you don’t have an outcome in mind. When I am trying to sell tickets to Responsive Conference or a client on behalf of Zander Media, I want them to buy! But that’s only one of a handful of goals I hold simultaneously – including to be of service. Maybe there is someone I can introduce, a book I’ve read, or something else that would make a difference in their lives.

Let go of the outcome

Anytime I find myself feeling urgency or anxiety, I remind myself “Let go of the outcome.”

In the case of my attendees’ experience of Responsive Conference Day 2, the solution was simple. I’d already curated an excellent experience that didn’t shy away from difficult topics. From our opening and closing keynotes to topics ranging from AI to politics to the Safari animals who joined us at lunch, the experience of Day 2 provided my attendees with a rich and varied experience. I’d already done the hundreds of hours of preparation necessary. All I had to do was let them enjoy the experience.

Letting go of the outcome is a mental act. It is more about coming up with a half dozen ways in which other outcomes – in addition to your goal – could be just as good.

In the case of Responsive Conference 2025, if my attendees have too good an experience, is that a bad thing? So, they feel optimistic leaving the conference – and only afterwards are confronted by the realities of our rapidly changing world. There’s nothing wrong with providing a bit of escapism.

But if I’m trying to sell something specific or my mortgage depends on a certain level of earnings, it can be difficult to stay flexible. I have to deliberately make a list of alternative outcomes:

• If someone doesn’t buy from me, they’re looking out for their best interests.
• Maybe I haven’t done enough preparation? Maybe I’m not telling a compelling story?
• Or perhaps what I’m selling doesn’t fill a pre-existing need.

In the months leading up to Responsive Conference 2025, one reminder I had to give myself was to “Be less entitled.” As salespeople, we are not entitled to someone else’s attention – not to mention their money! If I was asking for help from colleagues to promote the conference, it was my responsibility to make it easy for them to promote. And when someone bought a ticket, take a moment to celebrate that small victory – instead of immediately calculating how much farther I still had to go.

↓

Homework

What are you trying to accomplish? List out 5 alternatives, beyond your primary objective.

Even with your primary objective in mind, can you make one of these secondary goals as big or bigger than the first? Can you want more for the person you’re talking to than for yourself?

It helps to write out then goals, and then write an explanation for each.