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.
3 Things I’ve Loved This Week
Quote I’m Considering
"Your success in life will be largely determined by your ability to speak, your ability to write, and the quality of your ideas. In that order."
-Patrick Winston, MIT professor of computer science
Shoulder Bag I’m Loving
Carhartt Cargo Series Waist Pack
I’m an unapologetic fan of the Carhartt brand. I have two pairs of their classic Double-Front Dungaree pants that have withstood daily use for a decade, and another pair that I’ve used regularly for the last five years.
But I recently started looking at other items in their collection, including this Carhartt Cargo Series Waist Pack. I wear it diagonally across my chest or across my back, and particularly like it when I’m traveling internationally and don’t want to carry a full backpack for the day.
Book I’ve Loved
Molly's Game: From Hollywood’s Elite, to Wall Street’s Billionaire Boys Club, My High-Stakes Adventure in the World of Underground Poker by Molly Bloom
I’ve just finished Molly Bloom’s memoir Molly’s Game. I’d seen the hit movie (by the same name), but after listening to a recent interview with Molly on the All-In podcast, I was curious to learn more.
Her memoir is as much of a page-turner as the movie is riveting – and goes into considerably more detail about the world of poker, and the human psychology that made what she did possible.
The memoir is a reminder that when you sell to multiple stakeholders you can build a much more robust business – and also that cash businesses are just plain hard.
Want more?
My book Responsive is only $0.99 for Cyber Monday!
If you’re building a company or want to improve your company’s culture, read Responsive: What It Takes to Create a Thriving Organization.
The Snafu Conference is an immersive 1-day experience about authentic selling in a chaotic world. The summit will take place on March 5, 2026 at the Oakland Museum of California. Ticket prices go up on December 15, so get yours now!
Responsive Conference is coming back in 2026! Our theme is "attention & work." We'll be looking at how our attention shapes our work – and our lives. Ticket prices go up December 15, so don't wait!
Until next week,
Robin
