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 Responsive.org.

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 Responsive.org, 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 Responsive.org. 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