Most of us don’t hate selling because we’re bad at it. We hate selling because we believe a handful of myths that make selling into something manipulative, transactional, and bad.

What follows are some of the most common myths about selling – and what actually works instead.

Myth 1: Build It and They Will Come

I remember hearing this quote when I started my first internet business in the industry that would come to be called dropshipping. I thought that if I just built an internet business, people would buy my product.

I built an online store in 2009. I created a custom website, designed a logo, registered the business, bought inventory, and wrote a 40-page business plan.

Unfortunately, I didn’t evaluate if people wanted to buy the DVDs I was selling, or if they would buy them on the Internet!

I sold nothing for six weeks. Then, I was sent a cease and desist letter by a lawyer and was scared out of business.

The best product in the world goes nowhere without promotion.

Myth 2: If You’re Good, People Will Notice

There’s no denying being good is important! It is necessary, but not sufficient.

The mistake many bootstrapped entrepreneurs make – and that I made in that first dropshipping business – is assuming being good will get you noticed.

What’s required is enough promotion that people will notice, enough of a flywheel that people want to share about your thing.

Myth 3: Business = Sales

We mistakenly believe business exists to make money. Actually, the function of a business is to solve a problem.

Every business exists to solve a specific problem:

• ​Robin’s Cafe provides coffee, quick food, and somewhere to sit.
• ​Responsive Conference helps people learn to build better organizations. It provides hope, new ideas, and community.
• ​Zander Media helps big companies tell their stories.
• Snafu helps non-salespeople speak up and ask for what they want.

But in order to solve a problem, the business also has to communicate about that solution. That’s sales.

You cannot build a successful business by offering a solution that nobody receives.

Myth 4: Always Be Closing

When we think of selling, what usually comes to mind is Glengarry Glen Ross or The Wolf of Wall Street.

That “always-be-closing” ethos has given salesmen a bad name. When we push to close a deal, we limit the opportunity and alienate people, especially in the long-term.

The goal of a great non-sales seller is not to get everyone to say yes, but to create as many opportunities as possible. In short, to be as useful to people as possible – and occasionally to ask, “Would you like to buy my stuff?”

Don’t always be closing. Instead, always be helpful and occasionally ask if they’d like to buy what you have to sell.

Myth 5: Just Use Pressure

When I was 10 years old, two Mormon missionaries came to my house. They asked me about my faith, and when I said that I was an atheist, they told me that I was going to go to hell.

Not only did I not change my mind at that moment, but for the thirty years since I’ve had a chip on my shoulder about Mormon missionaries.

Pressure doesn’t work, and particularly not in the long term.

Myth 6: Selling Requires Persuading People

Years ago, when I was working alongside the Persuasive Technology Lab at Stanford, BJ Fogg told me not to try to persuade the unpersuadable, but to find what people I was talking to already wanted and make it easier for them to say “yes.”

That idea informs everything I do.

Successful salespeople don’t do anything to anybody else.

Trying to get someone to do something is counterproductive. We are all great at sensing ulterior motives – and avoiding them.

Instead, selling is about helping people, being useful, and being of service. Selling is about helping people make a decision they already want to make.

Myth 7: Sales Is Manipulation

Manipulation is trying to get people to do things that they do not want to do.

Selling, by contrast, is inviting somebody to do something – including buying something – that they believe they want and will benefit them.

Selling also means trusting that they know what’s best for themselves.

Selling and persuasion aren’t inherently good or bad. It is how they are used that determines their worth.

Whenever we approach selling with an eye towards helping people, we rarely go wrong.

Myth 8: It Isn’t a Popularity Contest

When I graduated high school, my mother told me that everything was going to get better from here. She explained that unlike middle school, where I was bullied, or high school, where I felt alone, life after high school wasn’t a popularity contest.

My mother, bless her, was wrong.

In business and in life, being liked by a lot of people is a competitive advantage.

Your product has to be at least as good as anybody else – and ideally much better. But if you know lots of people and are liked by many of them, you’ll do well.

Conversely, if you are unknown or unheard – no matter how good your product or service may be – it is very hard to succeed.

Myth 9: You Have to Be Loud, Brash, and Gregarious

There’s a stereotype of salesmen as loud, brash, and gregarious. That you have to talk to lots of people and charm them.

That’s one way to do it, certainly. But selling is actually much simpler than that.

I was discussing with Snafu Conference speaker David Shackelford over the weekend, sales is very simple:

• Figure out who your customer is.
• Determine what they need.
• Figure out how to meet their need.
• Communicate that you’re able to do so.

It doesn’t matter if you are loud or quiet; persuasive or inquiring. You just have to follow those four steps.

Myth 10: Nice Guys Finish Last

There’s a common misconception that in order to get ahead you have to be willing to play rough.

Don’t get me wrong. I am all for ambition and pig-headedness; for chasing what you want and running through walls in order to get it. But it’s also incorrect that assholes finish first and nice guys finish last.

While it might look that way at the beginning of the race, jerks always get what’s coming to them.

The difference is that nice people tend to be much quieter about it.

I’m not here to tell you that life is fair. It certainly hasn’t been my experience that just by being nice you will get ahead.

But when you are nice, do well by other people, build relationships for longer, and are still determined and hardworking towards the outcomes that you want, you’ll go much further. You’ll also have a better time along the way.

At the end of the year, I thought it would be fun to review some of my favorite books from the last year.

​A Fever in the Heartland: The Ku Klux Klan’s Plot to Take Over America, and the Woman Who Stopped Them by Timothy Egan
When I feel overwhelmed by the state of the world, I turn to history. I find it helps to remember that humans have been through – if not this, then something like it – before.

I was shocked to learn about the rapid growth of the KKK through the 1920s, and the book helped me understand the rise of white nationalism in the U.S. today.

​Good, Reasonable People: The Psychology Behind America’s Dangerous Divide by Keith Payne
My friend Marie wrote the following blurb about this book:

There is much to be learned in considering how people with actually similar goals or core ideas can end up in wildly opposing camps based on how they communicate those ideas. And while I’m certainly not advocating for bringing more politics into the workplace, what’s happening politically in the US remains a pretty big elephant in the room these days.
​
I recently read Good, Reasonable People: The Psychology Behind America’s Dangerous Divide by Keith Payne, a social scientist who studies polarization. There are numerous ways we can consider how to best influence those around us—and Payne’s book adds a great deal of understanding around the psychology of how people on all sides of an issue rationalize their ideas. A worthwhile read as you consider your strategic communication skills!
​The Haves and Have-Yachts: Dispatches on the Ultrarich by Evan Osnos
I stumbled on this collection of essays on Spotify while waiting for a flight, and enjoyed it as a somewhat mindless summer read.

The author, a New Yorker journalist, published these as a series of essays about wealth, inequality, and the lifestyles of the ultrarich.

I particularly enjoyed Chapter 2, which is all about super yachts and Chapter 3, which is about booking famous artists for private parties.

​Abundance by Ezra Klein and Derek Thompson
I’ve been listening to Ezra Klein’s podcast for the last couple of years, and I think it is among the best contemporary podcasts today.

Ezra’s new book Abundance puts the challenges facing the political left in America into perspective, issuing a call to arms that we must build – more affordable housing, more public works, and more energy solutions – if we want to thrive

​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!

​Barnum: An American Life by Robert Wilson
I’ve always known of P.T. Barnum, but never knew much about his life. It turns out the phrase “There’s a sucker born every minute!” is misattributed to him!

Barnum was a hustler and a showman – and quite an incredible character. There’s a lot to learn about showmanship and self-promotion from his example.

​How to Sell Anything to Anybody​ by Joe Girard
Joe Girard holds a Guinness Book of World Record for most cars sold.

The book is written in plain language, and shares Joe’s journey into sales, the belief that anyone can learn to sell, and how to do it.

Where a lot of books about sales are technical, describe complex systems, or site a lot of research, this book is humble, approachable, and legitimately fun to read.

​Boyd: The Fighter Pilot Who Changed the Art of War​ by Robert Coram
This book follows the life of John Boyd, one of the most unsung heroes in American military history.

Even more than his impact on plane design or military strategy, Boyd sacrificed career advancement to push against military bureaucracy and a sense that we do things a certain way because “that’s how it has always been done.”

​Atomic Habits by James Clear
​Tiny Habits by BJ Fogg
Anytime I feel the need to reassess my routines, I pick these two books up. Both copies are well-worn. Sometimes just the reminder to leave my running shoes out where I can see them, or to celebrate tiny successes to reinforce a habit, is enough for me to get back on track.

​The Comfort Crisis by Michael Easter
I’d heard the name Michael Easter, but never sat down to read one of his books until recently. I’ve been listening to both The Comfort Crisis, which put Easter on the map, and Embrace Discomfort, which consists of a series of interviews with people who’ve intentionally chosen challenge over convenience.

​The Sovereign Child: How a Forgotten Philosophy Can Liberate Kids and Their Parents​ by Aaron Stupple
I stumbled on this book earlier this week on X/Twitter, and it fits with a lot of my approaches to working with children, back to when I worked with kids with autism.

The basic premise is that children ought to be treated with the same respect as adults. Let kids figure things out for themselves. Or in the words of The Morning Star Company, which I wrote about in my book ​Responsive​ – don’t use force.

I won’t give my future kids unlimited junk food and unlimited screen time, but I agree with a lot of the ideas in the book.

​The Metabolic Approach to Cancer by Nasha Winters and Jess Higgins Kelley
I’ve been reading a lot about cancer since my best friend was diagnosed with breast cancer in 2022.

​The Metabolic Approach to Cancer is the most approachable book I’ve read about this atypical approach, which I believe will be the future of cancer treatment.

For more technical reading, the go-to book is Cancer as a Metabolic Disease by Thomas Seyfried.

​​The Education of a Coroner: Lessons in Investigating Death​ by John Bateson
The book is about Ken Holmes, who worked in the Marin County Coroner’s Office for thirty-six years, starting as a death investigator and ending as the three-term, elected coroner.

I started reading the book because I recently purchased a home in Marin County, which the book describes as “a study in contradictions.”

The book jacket reads:

Its natural beauty attracts celebrity residents and thousands of visitors every year, yet the county also is home to San Quentin Prison, one of the oldest and largest penitentiaries in the United States. Marin ranks in the top one percent of counties nationwide in terms of affluence and overall health, yet it is far above the norm in drug overdoses and alcoholism, not to mention the large percentage of suicides that occur on the Golden Gate Bridge.
I knew nothing about the work of a coroner when I started, but am fascinated by human anatomy and love Marin County, so this book was a perfect balance across them.

Fair warning: a few of the stories from Holmes’ 36 years investigating death are grisly.

​The Knowledge: How to Rebuild Civilization in the Aftermath of a Cataclysm​ by Lewis Dartnell
Hopefully, civilization doesn’t collapse and you never need to rebuild basic technologies from the ground up. But just in case, The Knowledge should be required reading for pretty much everyone.

The Knowledge contains the information you need to survive in the immediate aftermath of a catastrophe. The book is a step-by-step guide to building a windmill to generate power and grind flour, re-create an internal combustion engine, put together a microscope, get metals out of rock, and produce food.

It is an incredible primer for how things work, and a fun read. I keep a copy in my emergency kit.

​Tomorrow, and Tomorrow, and Tomorrow by Gabrielle Zevin
This novel was ranked one of the New York Times’s 100 Best Books of the 21st Century. It is lovely, and completely absorbing. The less said the better, but if you must, here’s the description:

On a bitter-cold day, in the December of his junior year at Harvard, Sam Masur exits a subway car and sees, amid the hordes of people waiting on the platform, Sadie Green. He calls her name. For a moment, she pretends she hasn’t heard him, but then, she turns, and a game begins: a legendary collaboration that will launch them to stardom. These friends, intimates since childhood, borrow money, beg favors, and, before even graduating college, they have created their first blockbuster, Ichigo.
​
Overnight, the world is theirs. Spanning thirty years, from Cambridge, Massachusetts, to Venice Beach, California, Gabrielle Zevin’s Tomorrow, and Tomorrow, and Tomorrow examines the multifarious nature of identity, disability, failure, the redemptive possibilities in play, and above all, our need to connect: to be loved and to love.
​Lock In by John Scalzi
Narrated by Will Wheaton, Lock In is the first in a series about a fictional disease that leaves one percent of the human population “locked in,” fully awake and aware, but unable to move or respond to stimuli.

This story examines how humanity might respond, and follows the story of two FBI agents investigating a murder.

Alongside others of John Scalzi’s books, including Fuzzy Nation and Agent to the Stars, this book is worth the listen.

Years ago, when I was working alongside the Persuasive Technology Lab at Stanford, BJ Fogg told me not to try to persuade the unpersuadable, but to find what people want and make it easier for them to say “yes.”

I’ve carried that with me ever since, and it informs a lot of the work that I do.

I picked up Tim Ferriss’ The 4-Hour Chef recently, perhaps my favorite of his books because it is a book about learning. It is the least well-performing of Tim’s books, and I began to think about why.

The 4-Hour Chef‘s main argument is that non-cooks can learn how to cook. It teaches the principles of meta-learning through the metaphor of teaching people how to cook.

The problem is that non-cooks do not want to learn how to cook! I enjoy cookbooks. Most people do not. Non-cooks aren’t likely to pick up a cookbook – even if it would enable them to make better food.

The argument behind the Snafu newsletter and my upcoming Snafu Conference is that non-salespeople already possess the skills needed to sell, get more work, and advocate for themselves.

We’re already doing non-sales selling every day.

But the problem here, too, is that non-salespeople don’t want to be salespeople. The cultural stereotype of a salesperson is bad. Anyone who does not consider themselves a salesperson likely avoids sales because of the stigma associated with the stereotype.

My task with Snafu, then, is not to persuade non-salespeople how to sell, but rather how to harness skills they already have and apply those to non-sales selling.

Whether with Snafu, The 4-Hour Chef, or any other efforts of persuasion, the goal should be to help people do what they already want to do. Make it easier for your audience to say “yes.”

It is that simple – and also that difficult.

The reason we don’t like salespeople is they don’t respect our boundaries. When a telemarketer continues to say, “This will only take one minute,” after we’ve already said it’s not a good time, they are disrespecting our boundaries.

The Rocket Ship VC Story

A venture capital firm reached out to us at Zander Media last year. One of their companies was making rocket ship engines, and they wanted our help making a documentary about those engines.

By way of example, they shared a National Geographic video. It was a 45-minute film about rocket ships with more than 15 million views. It probably cost $10 million to produce.

I told this story during last week’s How to Sell Yourself workshop. Our topic was boundaries—everything from simple timekeeping to saying no to work.

When the VC called, I asked them why they needed a video about the rocket ship engine company. They explained that there were three financiers in New York City, and the company needed one of them to write a check for the startup. The video was the tool the startup hoped to share to persuade those financiers that the project was viable.

After asking more questions, I told them—bluntly—that they didn’t need a video.

They needed to sit down with the financiers for dinner. To wine-and-dine them. To have a lot of very personal conversations in carefully curated contexts. They should know the names of the children of those financiers.

Because they were raising tens of millions of dollars for this company from one of three investors, this was as personal a sale as it gets.

Of course, I would have loved to tackle a multi-million dollar film project telling the story behind a rocket ship engine company. But I would rather be historically correct than sell work that isn’t in the best interests of either party. We never worked with that company.

What Sleazy Sales Gets Wrong

Sleazy salespeople don’t consider whether the thing they’re selling is actually a good fit.

We all sense it when a used car salesman is asking just enough questions to know how expensive a car they should show you. They’re never going to not show you a car or recommend something they don’t stock.

Instead, act from integrity: don’t use force, keep your commitments, and act from a place of service.

What Boundaries Actually Look Like

Boundaries can be as simple as setting expectations at the beginning of a meeting, arriving on time, or discussing what you say you are going to discuss. They can also be more nuanced: doing what you say you’re going to do, not negotiating past your comfort, or saying “no” to a sale because you don’t think your offer is a good fit.

One of the simplest boundaries is time. At the start of a conversation, name the time, confirm that it still works, and say how long you expect you’ll need.

This can be as simple as, “We’re scheduled for 30 minutes. Does now still work for you?”

Checking in reminds the other person they have agency, and it puts the responsibility on you, as the salesperson, to hold the container.

Pushy sellers ignore the other person’s convenience. Respectful sellers make it explicit.

Most salespeople run over. They say, “This will just take a minute,” right after someone has said it’s not a good time. That’s a boundary violation.

I call this “timeboxing.” Do what you said you would do: start on time, end on time, follow up as agreed.

None of this is fancy, but it’s rare enough that people notice. When you manage time well, you don’t need pressure. The respect does the selling for you.

Ending Early Builds Trust

Ending early is one of the most underused tools in sales. If you tell someone a meeting will take fifteen minutes, keep it under fifteen—and if you can, end two minutes early. Giving someone back time is a tangible demonstration of respect. It says, “I meant what I said,” and “I’m not going to take more than I asked for.”

Pushy sales stretches time. Service-oriented sales protects it. When I end a call early, I’ll often say, “I think we’re complete—does that feel true for you?” That reinforces that the container matters more than squeezing in one more point. Ironically, this is often when people ask to continue.

Ending early shows that you’re not trying to extract value. Over time, those small acts of integrity compound into credibility.

Being Useful Without the Sale

Look for a way to help, no matter what. Be like Santa Claus in Miracle on 34th Street, and look to support the person you’re talking to even if it’s out of the scope of the solution you’re selling.

What can you give them? How can you leave them with something that isn’t your sale?

Clear Boundaries Close Sales

A circumstance similar to the Rocket Ship VC happened this month.

The preeminent leadership development program in Silicon Valley reached out to Zander Media for help telling their story.

As I often do, I shared our DIY Video. It’s a cute video that demonstrates our capabilities while teaching the viewer how to make a great video on a smartphone. It makes explicit the fact that they don’t need us.

The leadership development company hired us on the spot – and we filmed together last week. Now we’re in conversation to do a larger project together in 2026, as well.

When you show up in service, the other party notices—and comes back for more.

Homework: Name the Container

At the beginning of your next five sales-adjacent conversations—calls, meetings, DMs, even emails – explicitly name:

• The length of time
• What you plan to cover

Example:

“I have us down for 20 minutes. My goal is to understand X and see if it makes sense to continue.”

You are responsible for holding the container.

No “one last thing” at the end.

How did naming the container change how I showed up?

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.

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​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