Even Great Salespeople Don’t Like Sales


Welcome to Snafu, a newsletter about authentic selling in a chaotic world.

Last weekend I went fly fishing in Montana with a group of friends — all of them in sales. One of them said something that stuck with me: the best salespeople don’t think of themselves as salespeople. This week’s essay is about what that means — and what the best salespeople do instead.

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Fly Fishing in Montana

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.


3 Things I’ve Loved This Week

Quote I’m considering

“All behavior makes sense with enough information.”

– Morgan Housel in The Art of Spending Money

Two new videos by Zander Media

OpenTent & Boulder JCC
OpenTent & JCC Denver

Over the summer, the Zander Media team went to Colorado to film two mini-documentaries with the Jewish Community Centers in Denver and Boulder.

Across several busy days, we filmed interviews and site-specific footage and created these testimonial videos for our client OpenTent.

Whether for Jewish Community Centers, YMCAs, or other community centers, spaces where people can gather are needed now more than ever.

Book I've just re-read

Starship Troopers by Robert Heinlein

It has been a decade since I read Starship Troopers by Robert Heinlein. I picked up the audiobook this week, and enjoyed it more than I’d remembered.

The book is based on the premise of a society where full citizenship, including the right to vote, is earned through federal service.

I’m always fascinated by Heinlein’s eclectic background, and the ways he experiments with different forms of government and societal organization in his books. Interestingly, the book also introduced the concept of powered armor suits.


Want more?

Snafu Conference 2026

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 October 31, so get yours now!

How to Sell Yourself workshop

The next How to Sell Yourself workshop series just kicked off this week with 12 people from all over the world. I'll be hosting another cohort beginning January 2026. This is a new approach to selling for people who aren't quite comfortable selling themselves - yet!

Responsive Conference 2026

Responsive Conference is coming back in 2026! Our theme is "the attention economy & work." We'll be looking at how our attention shapes our work, and our lives. Ticket prices go up October 31, so don't wait!

Until next week,
Robin

This newsletter is copyrighted by Responsive LLC. Commissions may be earned from the links above.

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