Why We Hate Salespeople
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?
3 Things I’ve Loved This Week
TV Series I’ve Binged:
Andor
I'm trying to give up television. As I did with alcohol in 2021 and ice cream this last year, I would like to get to a place where I don't watch screens except for work.
In the meantime, though, my fiancée and I binge-watched Andor, which is an exceptional series.
I’d listened to this conversation between New York Times columnist Ross Douthat and Andor’s showrunner Tony Gilroy, so I was expecting fascism that felt hyper-liberal or somehow out of step with the original Star Wars.
Instead, I found characters I could love and the single best antagonist I’ve seen on screen in a decade. (Dedra Meero, a zealous and ambitious officer, is an incredible character that I loved to hate.)
Across two seasons, Andor contains innumerable heists, and I’m a sucker for anything heist.
Video I’m Revisiting
DIY Guide to Filming
Zander Media made this DIY video during Covid, when interviews were moving online and everyone wanted us to edit Zoom video.
We made this PDF Guide, and then the video itself, to help people use their smartphones better.
It has also become a sales tool, because it shows prospective buyers what they could do themselves and highlights the difference our work can make.
Podcast I’m Listening to
Tristan Harris on Diary of a CEO
I’ve tracked the work of Tristan Harris since before his documentary The Social Dilemma.
Though we haven’t met, we both worked with BJ Fogg, back when his lab was called the Persuasive Technology Lab at Stanford.
This two-hour interview is worth listening to. It outlines the alarmist case for the future of AI, which I believe.
As Miki Jackson articulated in our recent podcast, while AI companies want us to believe that this future is inevitable, it isn’t.
Want more?
The next How to Sell Yourself workshop series begins January 2026. This is a different approach to selling for people who aren't quite comfortable selling themselves - yet!
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
