The attitude required for sales

In my early twenties, I ran a business working with children with autism.

Autistic kids often lack the social standards that we take for granted. They rely on their felt-sense of those around them – their intuitive feel for the attitudes held by others – in place of social niceties.

We all sense other people’s attitudes, whether we realize it or not. And these attitudes shape how we behave.

The same attitude that I learned working with special needs kids is useful in persuasion. You can sell a car through pressure and pushiness; I can motivate a child through judgment and shame. But it is more effective to show up loving, curious, and present, and invite towards what you want from there.

About the attitude

An inviting attitude is more effective than one that is demanding and judgmental.

This is the same attitude that great parents have with their kids, great leaders have with their teams, and great salespeople have with their clients. It has three parts:


Successful selling starts with generosity.

When you show up compassionate and loving, you are more compelling and better able to foster connection.

This loving attitude provides your prospective client the rare opportunity to see themself, and their situation, with love and compassion. It builds rapport.

So, before you try to sell your product or persuade someone of your belief, take a moment to connect with them.


In working with kids with autism, the first skill I learned to practice was presence – following them into their world, instead of insisting that they join my own.

And this ability, to be present with yourself or someone else, is equally valuable in sales.

You won’t be 100% present. But when you get distracted, returning to your client, and the connection you’re building.


Acceptance is often the most difficult part of a successful attitude in sales. As salespeople, we get attached to the outcome of a successful sale.

But when you don’t judge the decisions of the person that you are selling to – when you only want what is best for them – you create an environment where things are more likely to go your way.

Your presence closes deals

How you show up with a prospective customer will determine whether they buy.

Maintaining an attitude of enthusiasm, and not desperation. Keep your buyer’s best interest at heart and you have a much better chance of having things go your way.


Without prying, find out three personal details about your local barista.

Show up with interest and enthusiasm for who they are. Ask how long they’ve been working at the cafe. Find out what they’re aspirations are. Are they saving? Are they in school? Do they want to own their own cafe, someday?

Get to know them and find out personal details. If you’re uncomfortable asking, all the better. Practice the attitude.

In order to do that you’ll have to be curious, present, and non-judgmental.

Until next week,

Specialization is for insects

Selling is interesting to me because of who you become through learning to ask for what you want. And, like selling, there are a handful of important life skills that everyone should try.

While these activities are useful, they are also meta-skills, with application beyond the specific activities themselves.


Practice failing

Surfing comes with a lot of failure. You miss most of the waves that you try for. Failing to ask someone on a date or failing to sell your first product can feel mortifying – so much so that most people don’t try.

Practice failing by chasing waves.

You can’t fight the ocean

In a significant car crash, drunk drivers sometimes walk away uninjured because they don’t tense up. Don’t drive drunk or surf drunk, but that same quality of letting go is useful in the ocean.

When you get swept off your board and caught in the “washing machine” of rough surf, the only thing to do is to let go.

In business and in life, some things are outside of your control.


The ocean is vast. And there’s no better way to recognize your insignificance than by sitting on a surfboard.

When life feels overwhelming, it is useful to reflect how insignificant we all are. (And then get back to work!)

Several years ago, I wrote an article about learning to surf. You can read that here.

Brazilian jiu-jitsu

Physical chess

Chess trains you to think strategically and plan several steps ahead. Brazilian jiu jitsu does, too. While it doesn’t look like much to people with no experience, Brazilian jiu-jitsu is a good form of both physical and strategic training.


We’re all confronted with aggression. And there are times when being aggressive – going after what you want – is useful. It is helpful to not be intimidated by other people’s aggressive behavior, to channel your own and use it to your advantage.

Jiu-jitsu is a good way to practice channeling that aggression.

Every fight ends on the ground

The stereotype of a bar room brawl consisting of punching and kicking is more Hollywood than reality. There’s a common phrase in martial arts that every fight ends up on the ground. And since most fights end up on the ground, it is useful to know how to begin there.

Ask questions

Asking questions as thinking

I once heard Tony Robbins say, “Thinking is the process of asking and answering questions.” There are no right and wrong questions, but there are questions that are more useful for a specific outcome. In asking and answering questions, you train yourself to think more clearly.

Talking under pressure

Whether you are on a first date, applying for a job, or talking someone down off a bridge, it is useful to be able to talk persuasively under pressure.

The only way to train for this unpredictable environment is to practice. And the best time to practice thinking on your feet is before the stakes are high.

Job interviews

There’s no better training for a job interview than asking questions. Most people are passive participants in an interview process. If you’re able to turn the tables and make an interview interesting and informative for the person conducting the interview, you’re more likely to succeed.

Manage People


We think about leadership as a noun; something people are or aren’t. Actually, leadership is a verb; something to be practiced.

To manage people well you are, by definition, leading them. Learn to lead by practicing management.

Learning to follow

Following is as important as skill as leading. A good leader is also a good follower; they share power and allow other voices to be heard.

The goal of managing people is to help them learn and grow. In managing people, you have to listen, support, and follow their lead.

Practice taking action

Bystander apathy – the tendency for people to stand passively by on the assumption that someone else will take action – is insidious.

The best way to combat bystander apathy is to remember this tendency and take action.

The world needs more leaders; people willing to take courageous action.

Learn to sell


The definition of courage is taking action despite your fear or uncertainty.

Since most of us are afraid to ask people to buy what we’re selling, selling is an act of courage.


The world needs more people who are willing to advocate for what they believe, and able to do so in a way that brings other people along.

Sales is a way to practice advocating for what you believe and enrolling other people in those beliefs.

We need more sales people

Selling is a form of leadership. In asking somebody to purchase, you are asking them to buy into your beliefs, product, or service.

In a world that is increasingly fraught and divisive, selling brings people together.


What is a skill you already practice, which is a meta-learning skill?

Spend five minutes writing out the 3-5 secondary skills that your practice helps develop.

Just by writing out the benefits, you’ll be more aware of them.

Until next week,

Selling is a creative act

I was in Texas recently to help a client redefine their brand. My agency, Zander Media, was hired to learn about the client and help them distill a new organizing idea.

The team and I had done a lot of preparation, but I was still nervous. We had promised the client a new organizing principle by the end of the day-long workshop!

I facilitated the workshop, we covered most of what we’d planned to discuss, and then – as if by magic – we found a new tagline that perfectly captured the company and brand.

Zander Media had been paid to deliver an outcome, and we did. But describing that day so clinically doesn’t do justice to the magic of that moment.

How to do creative work

As prospective salespeople we don’t generally regard ourselves as artists.

There are a lot of mundane tactics requited to sell. You have to source leads, make cold calls, and get comfortable asking for what you want.

But, at its most elegant selling, is a creative act. To sell your ideas is to channel something bigger than yourself for a cause that is more important than money.

Preparation is essential

The more thought and care that you put into a project, the more likely that project is going to be successful.

I spent a hundred hours conducting interviews and researching my client in advance. Expect to spend ten times as much time preparing as you do executing.

But preparation alone doesn’t equate to creating something from nothing.

The moment of execution

None of the preparation I did for our client would have mattered had we not delivered the workshop.

Place the phone call.
Send that email.
Step out on stage.

Don’t use preparation as a way to avoid the work that needs to be done. The pitch – any moment of execution – matters more.

Have a cause that’s more important

Have a cause greater than your own self-interest.

The cause doesn’t have to be grandiose. The world wasn’t immediately going to be altered through our client finding a new organizing idea.

But by harnessing that purpose, applying all of your preparation, and coordinating the time and effort of others, you may be able to create something bigger than any one person.

Creativity in sales

I’m fascinated by moments of peak performance in sales – when we outperform our own expectations.

And transforming sales from work into a creative habit takes practice.

But with enough preparation, a clear purpose, and an openness to the unexpected, your outcomes can be greater than the sum of those parts.


Today’s homework is to look for creativity in your daily work.

Instead of attempting to make your current sales efforts creative or cultivating an entirely new creative habit, look for creativity within your current habits.

What is something that you do every day that you can turn into a creative practice?

By practicing a creative habit, no matter how small it is or in what domain, you’ll be better at recognizing creativity elsewhere and when it really matters.

Until next week,

Why you should focus on a single customer

You’ve probably heard that you should focus on a specific type of customer or prospect.

I’ve always found this to be a struggle because I don’t want to work with just one type of client! I like a lot of people and want my business to serve a variety, as well.

Today’s article is about organizational burnout and the consequences of not serving a single client.

The consequences of high growth

My creative agency, Zander Media, took off in 2020. With a lot of companies in need of video production, we grew from one full-time employee to ten in less than two years.

Being an enthusiastic salesman, I said “yes” to every piece of inbound work. Zander Media produced scripted commercials, testimonials, animated videos, entirely new brands, and even a documentary.

Building the plane while flying it

As a ten person company delivering a wide variety of services, we tried to be everything for everybody. As a consequence, the team and I were perpetually stressed.

We were building the plane while flying it.

The benefits of a singular focus

What would have happened if we had only provided a single service?

I’d have had to turn down a lot of work. But the team would also have had time to learn the specifics of the tasks required.

We’d have gotten better at doing the specific things required for that kind of deliverable.

Burning out my team

At Zander Media, we had enough sales to keep the business going. We had an abundance of skilled employees. But we didn’t have enough time to learn how to do each job from scratch, which then led to an unsustainable working environment.

Trying to adapt to the needs of each new project took a toll and we lost several valuable employees.

Dissatisfied customers

There are a lot of unknowns when you try something for the first time.

It takes a lot more work to deliver a novel offering. Things are likely to go wrong and there’s a high likelihood of poor communication.

We were fortunate at Zander Media that many of our clients from that stressful era continue to work with us today. But I worked consecutive 80 hour weeks for two years to make it happen.

Without a specific focus, you are much more likely to lose repeat business, or lose your business entirely.

An efficient way to think of business

Think about your business as a manufacturing plant that produces a very specific type of widget.

While you probably don’t want to work on an assembly line, it’s a useful metaphor.

What’s the one thing that you or your business want to do exceptionally well? Focus there.


Who do you serve? Describe a single, unique customer. (It is okay if that ideal client changes in the future.)

Think of a single person in your life – someone you actually know – and write a few details about that person.

Their demographics:

Their psycho-graphics:

Practice getting very specific about the person you are selling to. Doing so will help you sell more sustainably.

Until next week,


How to sell video production

I sat down with a Snafu reader recently who runs a one-man video production company.

In the five years I’ve been building my own agency, Zander Media, we’ve been in the fortunate position of handling inbound work, not cold calling prospects. I still have a lot to learn about selling video production.

Today’s newsletter is for solo professionals interested in doing bigger budget work for high quality clients.

Got Milk?

I watched a MasterClass with Jeff Goodby and Rich Silverstein, the legendary founders of Goodby, Silverstein, and Partners. That’s the advertising agency behind such icon marketing as “Got Milk?” and the Budweiser frogs.

Jeff and Rich discussed how they go about getting new work for their now 40-year-old ad agency. Jeff (or maybe it was Rich) describes pretending to be a journalist and talking his way into a fancy car convention in order to meet with a marketing executive at BMW to make a pitch.

Even having built and grown a 300+ person institution for decades, these two founders are not above entry-level tactics in order to meet the person they are trying to pitch.

Prior to this interview, I’d have believed that leaders as savvy and experienced as Jeff Goodby and Rich Silverstein wouldn’t need to sneak into an event in order to sell to a new client. But it turns out that nobody is above selling, no matter how fancy their title or company.

This approach – going out and finding new clients – I’ll call hunting. The other approach – cultivating existing clients; generating goodwill and referrals – I’ll call farming.

We’ll tackle each in turn.


In order to hunt, you have to first know who you are trying to reach.

It wouldn’t have worked for Jeff and Rich to show up at a flea market and pitch their company. (Though I’m certain they’d have enjoyed that, too.)

They chose a very specific event, and one very specific attendee whom they were trying to reach. In short, they knew who they wanted to work with.

Most of us probably aren’t going to target the Head of Marketing for BMW North America, but we can target specific people.

Choose a single, specific person you’d like to work with. Go hunting for them. You can always expand your audience later on.

Identify the work you want to do

When my ideal customer sees an example of our work, they should be able to say “That looks like a Zander video!”

A video production company that does this especially well is Sandwich Video. Sandwich explainer videos are recognizable on sight – the bright colors, lighthearted demeanor, and the presence of their founder and CEO in each video.

What do you and your work stand for?

That mission statement might evolve over time, but you need a singular focus in order to be recognized and to stand out to your preferred customers.

Where to find your customers

Once you know who you are trying to reach and the type of work you want to do, you need to find the customers who want that work done. There are infinite numbers of ways of doing this, so here are just a few of my favorites…

Asking for connections

Asking for help from connections has been the most impactful approach I’ve found to date for building any kind of business.

I wrote an article on “How to sell with no network or connections” about selling tickets to my annual Responsive Conference.. Also, watch this video about how I went from selling $1,000 scopes of work to $100,000 scopes of work in just a couple of years at Zander Media.

Asking for help goes a long way!


Since 2014, I’ve run more than a hundred events on behavior change and the future of work.

If I’m not organizing an event myself, I try to set myself up to be an authority – by speaking, working at the event, or otherwise coming into contact with as many people as possible under favorable conditions.

Consider even just organizing a dinner or an un-conference targeted at the people you are trying to reach.

LinkedIn Sales Navigator

There are a wide variety of digital tools that provide you easy access to people, including LinkedIn Sales Navigator.

Most of the people you cold email won’t want to hear from you, so you’ll have to get over your reticence for contacting people who might not be interested. But LinkedIn Sales Navigator, and tools like it, allow you to reach out directly to the people you’re trying to contact.

Cold calling

The most extreme version of this approach is cold calling people directly, or even knocking on doors.

While you are likely to get a lot of “No, thank yous” in response, cold calling prospects is also the avenue that most sales people avoid or use poorly.

Most of us are scared of rejection and will go to great lengths to avoid asking people for what we want – and those who do use this approach rarely do so with finesse.

If you’re going to cold call people or knock on doors, use it as practice honing and refining your pitch, instead of actively trying to close a deal with every call.


Farming is reminding your current and former clients that you exist, up-selling, and cultivating raving fans who will recommend you to their friends and colleagues.

Do great work

The first principle of farming is that you have to do great work. This is a good principle of business in general because without great work, the best marketing and sales in the world will just reveal that you have a terrible product all the quicker!

Promote your work

You should always be striving to improve the quality of your work – both in your delivery of the work and in how you communicate about it to your customer.

Doing great work that nobody knows about is doing a disservice to your potential future customers!

Ask for referrals

Anytime, you deliver work for a customer, asking for referrals.

When a client walks away satisfied with the work you have delivered, it isn’t enough to just anticipate or expect that they will recommend you in the future. As we know, most people are bad at selling, and referring work is a form of sales.

Towards the end of an engagement, schedule 30 minutes with your client and tell them that part of your business revolves around people – like them – referring clients to your business.

Keep in touch

The best referral system in the world doesn’t matter if you are not then top of mind for your customer. They need to be thinking about you at the appropriate time in order to hire you again or refer you to a likely connection.

My preferred mechanism for keeping in contact is an email newsletter, because everybody uses email. But this can also be through consistent social media, contact, videos, or even a text base platform.

The key is to remain top of mind, so that your clients think of you at the right moment.

Surprise and delight

Look for ways to surprise and delight your clients.

At the end of every year, I receive a handful of care packages from customers and clients, all with varying degrees of thoughtfulness and care. This is the same principle behind the ubiquitous startup branded hoodie and other swag.

But surprise and delight can be more nuanced. What’s a little thing at the right time that can encourage or delight your customer?

A get well card for a sick child. A sports jersey to their favorite team. Thoughtful gestures that take time and consideration can have an impact for years.


It’s easy to get overwhelmed by the number of things that can be done to improve your business.

The only recourse is to take one small step today every day towards one of the objectives, and focus on that goal every day until it has been improved.

Your homework is to pick a specific tactic from this list and write out the incremental steps towards its improvement.

What are a few small steps which will improve your client’s experience?

Until next week,

What’s in their best interest?

I recently started dating somebody new. She’s a fellow athlete, owns her own business and I’m quite excited. Unfortunately, it’s unclear if she’s available for the kind of relationship that I want.

The solution is to want what is best for the other person, even over what you want for yourself. And this is true whether you are selling a product, hiring an employee, or dating someone new!

It is hard to want what’s best for the other person while still advocating for your desired outcomes. Here are some things that can help…

Generate goodwill

I use the example of the Santa in the Miracle on 34th Street to depict the benefits of a well-executed sale.

In the movie, the department store Santa sends eager customers to a different department store because that store has exactly the right product for that customer.

The store manager is furious that Santa is sending people elsewhere – until he sees that customers are returning and buying more, because of the goodwill that Santa has generated.

In business, and in life, positive word of mouth can determine success. When you do the right thing, you’re more likely to succeed.

Don’t be too eager

I first learned to negotiate in the busy marketplaces of Oaxaca, Mexico as a child. I went back to Oaxaca with my family this winter and one thing I wanted to buy was a new leather belt.

I found a local market and one leather seller, who had a wide assortment of beautiful leather goods.

I began the process of negotiating for the belt I liked. The stall purveyor was polite, and completely unattached. When I returned hours or days later, she showed no sign of recognizing me.

She wasn’t pushy, but she had clear boundaries on price. And between the dozens of people passing her stall, she also didn’t have a lot of time to spare for one customer who wasn’t in a hurry to buy.

That stall owner didn’t have my best interest in mind. She wanted to make a sale! But she also wasn’t pushy.

And that freedom gave her a lot of flexibility when it came to making a successful sale.

As a result of her non-urgent attitude, I not only did buy a belt from her – I purchased two. I left satisfied and will refer other people to her in the future.

Maintain clear boundaries

One of the things that I loved about the leather goods seller is that she had clear boundaries. She did not need me to buy but was happy to entertain some amount of bargaining if I showed up in good faith. On an early visit, I proposed a price that was laughably low. She declined and moved on to another customer.

Know where your boundaries lie – the price of what you are selling; the amount of time you’re willing to spend.

It never helps to give more than you are comfortable with in the hope that the other person will come around. When you self-sacrifice, they won’t.

Invite, then leave it alone

Invite towards the outcome you want and then remain unattached to the outcome.

Invite someone on a date or ask them to buy what you are selling. Observe how they respond! And, if they don’t, that tells you everything you need to know.

It is too early yet to say where my new romance will go. But I’m reminded that when I don’t cling to a specific outcome, I’m more likely to get what I want.


What is an outcome that you are attached to?

It could be the specific outcome of a sale, but it might also be something much more personal.

Identify 1-2 real life examples where you are attached to things going a certain way. If you’d like, email me with your examples!

Then, practice, just for a minute, asking “What’s best for the other person?”

That simple question, asked with curiosity and not with a sense that you know better, will likely make things easier.

Until next week,

How to practice cold calling

Two friends of mine recently started a new business, which we’re affectionately calling BookBook.

It is a digital platform that allows users to display their favorite books.

The platform would display the spines of books, just like I do on my physical bookshelves. And the collections would only feature collections of books, like my favorite cookbooks or a list of what Tyler Cowen calls quake books.

Sourcing book spines turns out to be quite difficult. So I set out to phone book publishers in the attempt to find book spine designs for this project!

I took on this task of cold calling publishers because I love books, my friends are starting a company and I wanted to help. Really, though, I undertook this project to practice making cold calls.

Here are a few things I learned that will make your next cold calls easier.

Outline your pitch

The first step was to decide on my sales pitch.

I sat down with my friends and asked each of them to sell me on their startup. I recorded the audio of their sales pitches and took copious notes.

Then, I pitched my own version and asked for feedback.

We went back and forth like this until I had a rough script and was prepared to answer a variety of questions.

Outlining your pitch shouldn’t be complicated. Decide what you are going to ask for and write a rough script. Bullet points are fine! Consider getting some feedback

Then move on to the next step.

Set a deadline

Practice enough that you are ready to deliver your pitch, but don’t let practice get in the way of actually getting started.

Don’t use preparation as a form of resistance. And don’t forget Parkinson’s Law – work will expand to fill the time allotted for its completion.

I scheduled a day when I would start actually calling publishers. That deadline gave me a concrete window in which to practice.

Set a deadline and give yourself a limited amount of time to prepare.

Rehearse your pitch

My next step was to rehearse my pitch.

I booked time in my calendar, because, for me, if something isn’t in my calendar it doesn’t happen.

During those rehearsals, I reviewed my notes and recorded a voice memo of my new pitch. Then I listened back, took notes and tried it again.

Hard things often take less deliberate practice than we think. But you do have to show up and do the work!

Make some calls

The final, and most critical step, was to actually start calling publishers.

On the day I had set aside, I Googled book publisher phone numbers and called all six of the big book publishers.

It would have been more effective to locate phone numbers in advance, but fortunately book publishers are easily available online.

This is the most critical step, because without actually putting in this practice, outlining your pitch, deadlines, and rehearsal don’t have much impact!


In talking to representatives at all the big publishing houses, I learned that book spines are even harder to source than I’d thought!

So while I haven’t yet gotten access to book spines, I’m grateful to have taken on this small sales project as practice.

As people who have something to sell, we all want to be more comfortable talking to strangers. Likely the reason you don’t ask more often is that discomfort and your fear of rejection.

And the best way to overcome that discomfort is to practice.

Most of us are uncomfortable asking strangers for things. But through this project, I put in the practice and took an incremental step.


Cold calling is one of the scariest things most people do. But that’s because the steps are too big.

Get comfortable doing the uncomfortable thing when the stakes are low.

Today, pick up your phone and call one person spontaneously. Most people don’t use their phones for phone calls, so maybe that’s enough of a stretch.

If you do talk to people by phone, phone someone you don’t speak to regularly.

See if you can stretch beyond your comfort and phone when you’d ordinarily text, or to contact somebody you don’t normally talk to.

All the practice and rehearsal doesn’t matter if you never pick up the phone and call, so just get started.

Until next week,

How to get over rejection

I just read an interview in the New York Times about what it’s like to be a sociopath. The subject of the interview, Patric Gagne, is preparing to publish a book called Sociopath: A Memoir.

The article highlighted that I am not a sociopath because I care deeply — often too deeply — what other people think of me. Most of us do.

And caring too much about other people’s opinions limits us from doing scary things like asking for what we want.

Asking is hard

Asking for what you want can be really hard!

Let’s use a concrete example:

I would like to take you to lunch.
I know the best secret sandwich spot in Oakland.
And then finally the ask: Would you like to come with me?

Asking means risking being told “No.” Or worse yet, getting laughed at.

Asking is even harder when we’re trying to sell something $1000 tickets to my annual Responsive Conference.

I am confronted by insecurities like “What if they take offense to me asking?” or “What if they agree, but then hate the experience?”

Asking is scary because of the risk of rejection.

What is rejection?

When I compare myself to someone who actually doesn’t care what people think of her, like the author of Sociopath Patric Gagne, I have to define my terms.

What is rejection?

Rejection is caring about what people think, even if I shouldn’t. It means basing my decisions and actions on how I think someone else might respond.

Rejection is the fear that you are going to be judged, or worse yet, ostracized by your peers.

Throughout human evolution, getting ostracized meant likely death. Infants can’t survive without the support of their adult caregivers. Prehistoric humans couldn’t survive without the support of their community.

Today, we live in a world with eight billion people. Even if we were to get excommunicated (which isn’t likely to result from a single request), that probably wouldn’t mean the death that would for our prehistoric ancestors.

The world is a lot safer and more convenient than it was tens of thousands of years ago!

Motivated by the opinions of strangers

I can rationalize why I should care about the opinion of my best friend. If I acted in a way that a close friend found unacceptable, I’d like to know so that I could at least consider changing my behavior.

I’m also highly motivated by what my parents think of me. This is less appropriate, because, at 37-years-old, I’ve outgrown the need for their approval.

Worse, I’m motivated by the opinions of strangers. When I meet someone walking down the street, I wonder what they think about me.

Most of us are too busy judging ourselves through the eyes of strangers to pay close attention to what we want, recognize our fears and then ask for it.

I haven’t found a magic solution to not caring what people think of me, but here are some approaches to overcome the fear of rejection.

How to care just a bit less


We have a word for acting in the face of fear. That word is courage.

And most of us want to be more courageous.

A good way to practice being courageous is to practice asking for what you want. Incidentally, you’ll get better at asking!

Identify what you’re afraid of

The first step to overcoming your fear is to identify what it is that you are afraid of.

Fear is often an amorphous emotion that clouds even our ability to notice what it is that we’re afraid of.

First recognize that you are fearful and then identify the specific thing that you are afraid of.

The worst case scenario

When I opened up Robin’s Cafe in 2016, I did so with the knowledge that if it failed, I might end up $50,000 or more in debt.

The only way I was able to step into the unknown and open the cafe was to literally calculate how long it would take me at $15/hour (plus tips!) to earn back that $50,000.

Ask yourself “What’s the worst thing that could happen?” Write down a few of your answers.

Practice asking

Asking takes practice.

Just like anything else worth doing, learning to ask for what you want is a learned skill that you can improve with practice.

Unless you work on a sales team, you probably don’t have a lot of experience selling, asking or risking rejection.

Make facing rejection a deliberate skill you practice.


I’ve started a new practice this year of complimenting strangers on the street. Any time I walk by someone who’s clothing or style I admire, tell them so.

It seems like such a small thing – and it is – but I, for one, and most of us are hesitant even to pay a compliment.

For the next week, complement someone you see at least once a day on some element of their clothing or style. As you do so, notice your discomfort – and complement them anyway!

By the end of the week, you may find that you are less uncomfortable than initially.

The difference between marketing and sales

I taught a workshop a few weeks ago for a handful of entrepreneurs who wanted to get better at selling.

I asked attendees what they thought of when they heard the word “salesman.” I expected answers like used car salesmen and telemarketers, but instead attendees described the challenges of creating social media content.

I realized that most people don’t have a clear distinction between marketing and sales.

Marketing and sales both require:

Selling adds a few crucial steps including asking, “Would you like to buy my thing?”

What is marketing?

Marketing is storytelling. It is the stories we tell each other and about ourselves, which inspire toward a desired outcome.

When I was ten years old, my Dad and I read The Odyssey aloud together. The book was written two thousand years ago. Nonetheless, I vicariously experienced Odysseus’ ten-year journey home from the Trojan Way.

Marketing is using the story of Odysseus’ bravery, loyalty and pride to inspire the next generation to stand up for what they believe in and to lead.

Marketing consists of telling stories that are:

Marketing is the stories we tell about our work, or tell each other about the world around us.

What is sales?

The ask is the primary difference between marketing and sales.

Selling is attempting to persuade somebody to adopt a belief, asking to change their behavior, or inviting them to buy. Even the “Buy now” button at the end of an ad moves it into the category of sales.

Effective sales incorporates an ask after first delivering a story that is personal, relatable and inspiring.

After we finished reading The Odyssey together, my father asked if I’d like to run cross country. I’ve been an athlete, gymnast and runner ever since.

Good selling is about making an ask. Great selling is about making an ask that you’ve prepared for by telling a compelling story that pulls on emotions, aligns incentives, helps the other person become more of who they want to be.


What’s one thing you’re trying to sell?

Before you pitch, what’s a story that inspires the other person to become more of who they want to be?

Write out a couple of sentences about:

  1. What you have to sell.
  2. What you are selling will help your audience become more of who they want to be.
  3. A story that bridges that gap.

Send me an email with your answer to these questions!

Until next week,

The car salesman bias

Most consumers are leery of car salesmen. And that’s understandable because car sales usually means a lack of price transparency, a high price tag, and pressure.

As soon as I walk into a car dealership – and I’ve purchased more than my share of used cars! – my hackles rise up because I’m approached by salespeople looking for a fresh victim.

Attitude, first

Everything in sales comes down to the salesperson’s attitude.

Here are a few tips:

As a salesperson, your attitude matters more than anything else.

Be aware that the customer is likely to be skeptical and hold a “used car salesman” bias. Counter that narrative by being different from any other car salesperson the customer has met before.

Build community loyalty

Pressuring a customer to purchase can work in the short term. But it never results in long-term loyalty.

And since word of mouth referrals – people talking about you to their friends – is the ultimate mark of success in any business, a primary goal of your salespeople should be building loyalty within your local community.

This can mean the subcultures that each of your salespeople lives within – a neighborhood, the local recreation league, someone’s favorite coffee shop – and also your city itself.

People talk about their experiences. So it should be the job of each of your salespeople to create positive experiences and generate goodwill towards your business.

Become the mayor

You want your business to become the “mayor” of your city. When people think of your town, you are one of the first names that comes to mind.

This can either be you, as the owner of the business, or something that represents your business, like a mascot or the logo.

One way to approach this is to run for local office: city counsel, leader of the Parent’s Association, etc. But this can also be implied power.

Doing things that someone with deep ties to a community would do is a way to generate goodwill.

The value of cold call

Doubtless, you’ve already considered the benefit of having your salespeople make cold calls. But I think that the likelihood of actually selling cars by “dialing for dollars” is very low.

To do so a salesperson has to reach someone who is:

If any of these four aren’t true, then cold calling damages the reputation of your business.

Instead, I suggest cold calling for a completely different purpose. Teach your salespeople to make cold calls to collect information.

Here’s a script:

Hi there –

Do you mind if I take 3 minutes of your time?

I’m calling from your local BMW dealership 
but I am not calling you to try to sell a car. Instead, I’m just collecting some demographic information about local residents so that we can be a better part of this community.

Again, I’m not here to sell you a car. Do you mind if I ask you three brief questions?

If they respond in the affirmative, proceed:

Do you own a car? If so, what make and model?

What is your perception of BMW cars?

What is your perception of car dealerships?

End the call by asking if they would like to be added to your free monthly newsletter, which is about the goings-on in your region. Thank them for their time, appreciate them for the time you’ve spent together and encourage them to reach out if you can help them in the future.

This approach will help your salespeople get better, spread the brand of your business, and generate future leads. The last question, What is your perception of car dealerships? will highlight for your salespeople the perception that they are having to combat to build customer loyalty in the region.

The prospect will be pleasantly surprised when the salesperson doesn’t try to sell them a car at the end of the call, thus ending on a positive note.

Hire great people

It goes without saying that you want to hire great salespeople. But instead of focusing solely on people who always hit sales quotas, hire people who add to the reputation of your company through goodwill and long term customer loyalty.

A great salesperson who also alienates customers or employees does more harm to your business.

Define what a great salesperson brings to your company, and don’t settle for less.

Company culture

We often overlook the importance of company culture in sales. After all, the purpose is to close more deals and make more money!

The cohesion of your sales team matters. One overly pushy salesperson can model for the rest of the team an approach that will alienate customers.

When we put a smiling face on what is actually an unhappy working environment, our customers can tell the difference. Similarly, customers know when a member of your team really, sincerely enjoys their job, and is excited to be a part of the company.

A culture that derides the worst performing salesperson or hazes newly incoming team members creates an environment that will, invariably, trickle out to the customer’s experience.

I’ve written a book about the importance of team culture, so start here.

A culture of feedback

One important aspect of company culture, particularly in sales, is creating a culture of feedback.

Sales teams often only provide feedback during the onboarding process of a new salesperson. But every salesperson – and everybody! – can benefit from feedback. And in a thriving company culture, every employee should want to.

Here are a few ways to incorporate feedback into the daily cadence of your company:

Be generous

One of the phrases least likely to be uttered about a typical salesperson is that they are generous.

The common perception is that a salesperson wants to take advantage of the customer. It is your responsibility to contradict this narrative by being incredibly generous with your time and effort on behalf of each customer that you work with.

As often as possible go to the extra effort with each person you come into contact with to help them – even if that help has nothing to do with the sale you are aiming for.

By being unexpectedly generous you foster long-term relationships and make it more likely that a customer will come back in the future.

Until next week,

The three pillars of selling

What do you think of when you hear the word “salesman?”

I think of the Wolf of Wall Street, the movie Glengarry Glen Ross or a used car salesman. My first thought is of someone who will stop at nothing to get what they want.

That’s unfortunate because we are selling to each other all the time – our ideas, our beliefs, our products.

But what are the core characteristics of selling? There are three:

Connection – form an authentic connection with the other person.

Story – tell a story that is authentic to you and resonates with the person you are selling to.

Ask – Invite powerfully towards the outcome that you want.

Authentic Connection

When I was five years old, my father had me plant pumpkin seeds to grow pumpkins for Halloween.

Together with a couple of neighborhood boys, I stood in the street, waved down cars and asked them if they’d like to buy my pumpkins.

Because, even then, I was a bit ridiculous, often I dressed in a full body scarecrow costume – passers by would speculate if I was a motion-activated robot – and would then tear off my costume to chase down cars.

That childlike enthusiasm to sell something that I’d worked hard to grow is authentic for me. I’m excitable and playful. That exuberance allowed me to connect with my customers.

Whenever you are selling – a product or an idea – look to share yourself with the person you are selling to. Be yourself and you’ll be more likely to create a real relationship with your customer.

That authentically connection is why, when I visit my hometown, I still get asked if Robin’s Pumpkin Patch is coming back next Halloween.

Tell Them Stories

When I started Robin’s Cafe, I’d lived in the neighborhood for a decade.

That period was a time of transition in the Mission District in San Francisco. There were new companies moving into the neighborhood and a lot of local residents were feeling displaced. But that gentrification also came with benefits.

What had historically been an unsafe neighborhood was becoming a thoroughfare. What had been a parking lot across the street was turned into a playground.

As somebody who had lived and worked in the neighborhood for a decade, I bridged the gap between longtime residents and newly incoming tech. workers.

By relating my story, and listening to the stories of my neighbors, I was able to sell the idea of Robin’s Cafe as a community space that served the needs of the neighborhood.

By relating your own personal experiences, and listening thoughtfully to the personal experiences of others, you create the trust and connection which ultimately leads to sales.

The Ask

This final step is the part of a sale that salespeople call “closing.” The moment when you ask your prospective client, “Would you like to buy my thing?”

But I think closing is the wrong word because it gets the incentives backwards.

The goal isn’t to close a deal at any cost. Pressuring your customer to close a deal is more likely to result in a dissatisfied customer and long-term ill will.

Instead, invite them – powerfully – towards the outcome that you believe is best for them, while knowing that they are ultimately responsible for making their own decision.

Selling something can be as simple as forming an authentic connection, telling your story and listening to the other person, and then asking the other person if they would like to buy what you are selling.

Until next week,

How to sell without a network or connections

In 2016, I was given an amazing opportunity to take ownership of a global community called

After running my first ever business event early in the year, I decided to create my first business conference, Responsive Conference, 9 months later.

I’m a circus performer. I had never attended a business conference, not to mention produced one, so that first year of selling tickets to Responsive Conference was a madhouse.

That was also the same year that I started Robin’s Cafe, so any moments that were not spent behind the counter, or hiring and firing baristas, I was on the phone with everybody I could think of asking for advice.

This distinction is key: I wasn’t trying to sell tickets to the conference at first. Instead, I asked for advice.

Ask for advice

I brought 275 people to Responsive Conference 2016 by asking people for advice. It is really that simple. I turned to the founders of, everybody who had come to my free event earlier in the year, and everyone else I could think of.

When you ask for advice, you create the opportunity for excitement and support from people who might not otherwise be open to purchasing. People get enthusiastic about your cause, regardless of whether they’re interested in spending money – or attend my conference.

By asking for advice, you create advocates who want to see you succeed.

Practice telling your story

One of the things that making those hundreds, even thousands, of calls in the first months of Responsive Conference gave me was practice telling my story.

I was new to By luck and good timing, I was able to bring together 150 people for a free event at the start of the year and there was a lot of interest in our topics. But I was no expert!

By asking everyone I could think of for advice, I got a lot of practice telling the story of the ecosystem and why I wanted to create Responsive Conference.

Build a network

When you are beginning to sell something new, you probably don’t have a network or a reputation. But what you lack in network you can make up for in short calls with strangers.

Ask everyone you talk to refer you to three other people. Quite quickly, the size of your network grows!

It takes time and effort to take calls with so many people, but you’ll also go from no contacts to hundreds of potential prospects in a very short time.

The final step is to ask

The final phase of this saga, once you have enough experience telling your story and have built out a network, is to begin selling. Change your pitch from “Will you give me advice?” to “Would you be interested in purchasing a ticket?”

Several months into asking for advice, I’d talked with hundreds of people and generated a list of prospects in the thousands.

It takes courage to ask people to purchase. You can’t hide behind the “I’m just learning how to do this” anymore.

The final step is to muster up the courage and ask, “Would you like to buy?”

A word on authenticity

This approach to learning how to sell something new only works if you are sincerely interested in what people have to say.

If you go into an “advice call” with the desire to sell, the other party will know and be turned off by the experience.

Be humble, stay curious, and look to learn.


If you don’t need to, I don’t recommend spending hundreds of hours on the phone with strangers asking for advice. That said, the practice of building a network is incredibly valuable. This is the same process I use anytime I’m starting a new business or exploring a new opportunity.

Your homework is to call one person in the next two days and ask them for advice. The rules are simple:

And just like that, you’ve landed your first advocate.

Until next week,

How to tell a great story

I’ve told the story of starting Robin’s Cafe with no experience and selling it on Craigslist hundreds of times.

What’s funny is I’m actually most proud of the culture we built behind the counter, the amount of learning I went through in learning to operate the cafe, and the role the cafe played in creating community in that neighborhood.

But when I mention selling a restaurant on Craigslist, I invariably get a laugh. “Craigslist?” People ask, incredulous.

Stories are the reason people buy from us – our ideas, our services, even our avocado toast. In order to sell, you need to tell a great story.

Everything is storytelling

You are already telling stories all the time.

The stories we tell ourselves become how we think of ourselves and the stories we tell others define those relationships.

The first step to telling a good story is to recognize that you already are.


Take note of a story you’ve told recently. I like to do this during my morning journaling. Take two minutes to note down a story that you told someone yesterday.

See What Sticks

The parts of a story that matter the most to you aren’t necessarily the things that matter to your audience.

When it comes to Robin’s Cafe, I’m more proud of having opened up a restaurant in 3 weeks, but that tends to fall flat. I’m proud of the culture we had behind the counter, but without experiencing it, that’s not of great interest to the listener. The moment I get a chuckle is when I share that I sold the cafe on Craigslist.

You aren’t telling a story for yourself, but for the person you are talking to.


Look for reactions. Aspects of your story will land and other parts won’t. That’s useful information! Save the parts that illicit a reaction for your next telling.

Notice What Stories You Already Tell

In 2020, I moved into a house in the woods with my partner. Within a couple of weeks, my partner was parroting back to me a handful of stories that – apparently – I told all the time on Zoom. I hadn’t realized that I was repeating so many of the same stories on different calls!

Even if you aren’t aware of it yet, you are telling other people stories all the time. Pay attention to those stories, and use them as fodder as you refine your narrative.


When you are beginning to sell something new – as sophisticated as a new business or as simple as asking a friend to lunch – write down a list of possible stories that might help you accomplish your goal.

Refine and Hone Your Stories

We take for granted that a comic has to practice their jokes, or an athlete their sport, thousands of times for every single performance. It is less obvious that that storytelling, too, is a craft.

Every time you tell a story is a chance to iterate and improve your storytelling craft.


Try telling a story in a subtly different way. Add a new variation or detail, and notice how your audience reacts.

Emotion > Rationality

When we foster connection with another person, we create the opportunity for change.

Facts and figures are great, but they don’t accomplish much without the wrapper of a good story. To get someone even just to listen to your data, you have to form an emotional connection.

We like to tell ourselves that we are rational, but most of our behaviors come down to emotion.


As you head into your next meeting or difficult conversation with your spouse, ask yourself how you want them to feel.

We don’t get to control another person’s emotions, but just considering how you’d like for them to feel will influence how you show up and the course of the interaction.

A good story doesn’t guarantee in a successful sale, but without a good story your attempt to sell probably won’t work. Storytelling is necessary, but not sufficient.

Hone your storytelling skills, by noticing and improving the stories that you already tell, and you’ll be better able to move your audience – and your objectives – forward.

Why we’re afraid to ask

Last week, I wrapped up a two and a half million dollar fundraise!

That is, by far, the most money I have ever tried to raise. One of the issues I had to face was my fear of the close, of asking the question, “Would you like to invest?”

It is one thing to tell a good story, complete with compelling data. It is more difficult to ask someone to purchase what you are selling.

I can’t share the specifics of why, together with a few close friends, we were trying to raise the two and a half million dollars, but we were ultimately successful, even though the deal fell through.

As I went through the process, I wrote down reasons why I was afraid to make the final close and some strategies to address each of those fears.

Concern: Taking advantage of people

One of the most common concerns I hear about selling is the fear of taking advantage of your prospective customer.

Most people find coercive salesmen offensive. But there is a big difference between relying on pressure to close your deal, and never asking people to buy in the first place.

If I’d let my fear of taking advantage of someone stop me, I’d never have started Robin’s CafeResponsive Conference or Zander Media. More importantly, I wouldn’t have developed the courage that I’ve learned along the way.

Answer: They get to decide

Define what you mean by “taking advantage of people.”

Inherent in that phrase is the belief that you can force people to do things against their better judgment. And while I could, theoretically, use physical force or the threat of violence, the kind of gentle persuasion that I encourage is the furthest thing from that force.

Here’s my shortcut: If you are the kind of person worried about forcing or coercing someone, you don’t need to worry about taking advantage of your prospective customer.

The person you are talking to gets to decide what’s best for them. There is no such thing as “taking advantage of someone” when you don’t use force, believe that they are their own best expert and trust that they will decide for themselves.

Concern: Using force and pressure

Inexperienced sales people don’t close a deal or make their ask because they are afraid to pressure their prospects. And the experience of being pressured by a salesperson is unpleasant.

I have built up a robust immune response to that kind of pressure. If someone pressures me, I leave, even if the pitch was something I’d otherwise have agreed to.

But as unpleasant as being pressured is, being a pushy salesperson yourself is more so. The fear of pressuring someone else can be so intense that that we don’t even try to sell.

Answer: Know your emotional state

To ensure that you aren’t using force or pressure, learn to assess your own emotional state. If you’re not sure how you are feeling, check in.

Pressure usually comes from the significance we’re placing on a specific sale. I don’t sell unless the thing I’m selling really matters to me. And if it matters that much, I can get attached to the outcome.

Any single sale isn’t worth the feeling of having pressured someone else.

Use that knowledge to let go of your own pressure. Know yourself and what you are feeling. Ensure that you aren’t feeling pressure. Then show up with your customer with the desire to help.

Concern: Rejection

I learned to juggle in high school, and eventually became quite good. Inherent in juggling is dropping balls, which we could call failing to juggle.

Inherent in asking people for things is being rejected, being told “no.” That’s a part of selling.

Getting turned down when something matters can be unpleasant, absolutely, but it can also be just another data point. As with dropped balls while juggling, get rejected is part of the process.

Answer: Rejection is less scary than you think

Oftentimes, our fear of rejection is the thing we’re actually scared of, even more than the declination itself.

In selling, a rejection means nothing about you. It is actually great because it provides you data about how to improve and the simple clarity to move on to your next prospect.

Since clear answers in life are pretty uncommon, a rejection is cause to thank your prospect for their clarity. They were able to give you a clear answer, which is a compliment to everyone involved.

Concern: Danger to your reputation

Another common fear is that asking people to buy your thing will endanger your reputation.

Sorry to break it to you, but people will judge you based on what you ask for, what you promise and what you deliver.

Answer: Sell things you are very confident in

The answer is to have the utmost confidence in what you are selling and then to be very honest about the the risks and benefits involved.


Next time you are on a sales call or ask a friend to lunch, notice what concerns come up for you. (I keep a pen and paper nearby to take notes.)

Take a few notes about how you are feeling. Afterward, come back to the specifics of the sale and evaluate your feelings.

Assess how you felt and why you felt that way. What were you believing about yourself and the other person?

The more practiced you become at identifying your concerns, and the more you explore them, the better you’ll be at addressing and avoiding those fears in the future.

Everything Is Sales & You’re Doing It Wrong

Everything in life is sales. From inviting your child to do her homework, to deciding where to go for dinner, to encouraging a colleague at work, the situations we encounter daily are filled with the dynamic of sales and persuasion. And, unfortunately, most of what you know about sales is wrong.

What is Sales?

My favorite example of sales comes from a scene from the classic Christmas movie Miracle on 34th Street.

In Miracle, the Macy’s department store Santa asks each child who sits on his lap what they want for Christmas. Santa then tells the family where they can purchase that toy at the best price, even if it means at a competing department store. At first, the store manager is outraged that Santa is supporting his competitors – until he sees enthusiastic customers returning to Macy’s because of the excellent customer service. The value to Macy’s of Santa’s recommendations is greater than the sale of a single children’s toy; it’s customer loyalty.

Sales is having a clear solution – a service, opportunity or opinion – that can help to solve somebody’s problem. Like Santa, good sales means aligning yourself with the interests of the person you are talking to, to discover if your solution is a good fit for them. If it is, invite them toward your solution, and if not, move on. 

How to Do It Wrong

Sales and persuasion are most often practiced with pressure and urgency.

Think of the reputation of a car salesman – pushy, fast-talking, deceptive. They aren’t considering what is best for the customer. They only want to sell a specific car at the best possible price. The result: nobody enjoys the experience and the customer won’t recommend that product or service in the future.

Pressure and urgency can work, but only in the short-term. They don’t increase trust or loyalty.

How to Do It Right

A Process of Discovery

Done well, sales and persuasion should be a process of discovery. Instead of using force, inquire about what your friend wants to eat for dinner. Get curious about why your colleague doesn’t want to do the work assigned to them.

When you start by asking questions about what someone is looking to solve – for themselves, their business, or their family – you’ll discover if what you are selling is a good fit for the other person.

People relate through the stories that you tell them, so share your experience, too. As I discussed in “Everything is Storytelling,” your story should be brief, personal and relatable. 

Useful Beliefs About Sales

Abundance – If the person you are talking to doesn’t want the solution you are offering, somebody else will. There are between 7 and 8 billion people in the world today. If the person you are talking to is not a good fit, move on.

Believe it – Believe in what you are selling. That doesn’t mean that it is valuable to every single prospective buyer, only they can tell you that. But believing that it is valuable in the world makes closing easier, genuine, and fun.

Decrease the stakes – There are very few game changing moments in life, and this specific sale isn’t likely to be one of them. Whether or not you make this sale today isn’t likely to matter over the course of your or your customer’s life.

Autonomy – Foster the belief that everybody knows what’s best for themselves. You aren’t trying to convince anyone, but rather inviting them to entertain if what you’re offering is a good fit for them.

Look for “What I’ve learned” – It is useful to hold that even if you don’t close a sale, you will have learned a lot along the way. This practice of iteration and repeated repetitions will make you better at closing future sales.

Put in the Reps

Improving at sales is a matter of practice and incremental improvement. Many of the most successful salespeople and deal makers in the world have practiced tens of thousands of times. Sales is as much a performance as trying out for a sport or auditioning for a play, and practice makes for consistency.

Your Attitude Closes Deals

Who you are and how you show up with a prospective customer is what will determine whether they buy. Who you are closes deals.

Maintain an attitude of enthusiasm and want what is best for the other person. You’ll have a better chance of having things go your way.

Next time you are debating with your spouse about the dishes, trying to get your child to do their homework, or asking an employee to fill out their hours, think of Santa, sitting in Macy’s department store, referring customers to the competition.

Until next time, Robin