How I Sold a $150,000 Deal in Two Months with No Sales Experience

Welcome back to our free, three-part series, Master the Sale (MTS). This is our third and final post of the series. If you missed out on the beginning, you can see part one here and part two here. Now let's jump right into it.

You've heard it before, maybe in romantic comedies or from some random chick on the subway, crying to her girlfriend about it (people in NYC have no sense of privacy. Crying, relieving yourself or fighting in public are all fair game).

Or what about when your girlfriend walks away in silence (or anger) because you didn't say the right thing.

Or when you said all the right things and the prospective client smiles and says no after you're three months into the deal (wtf!).

What is it that I'm talking about and why does it matter?


Connection is merely allowing the other person to feel seen, heard and understood (tweet that Webster).

Early on in my career, at 24 years of age, I began working with Seth Godin as VP of Partnerships for The Domino Project. I had no sales experience and not the faintest idea of what exactly  why we were partnering.

What got me my first and biggest sale of that gig was my ability to connect with my prospects and believe 200% in the work we were doing. Regardless of  my lack of experience, young age and even if I had the right answer at that exact moment, I was confident in our ability to serve whoever we worked with.

And it worked. But how?

Let's flash back to the fight you had with your last significant other.

You're staring at one another, both sides clear on how they feel and totally unsure of what the other person really wants. In fact, you're pretty certain you know what they want, but when you express what you're hearing from them, they disagree. There's a clear disconnect.

"No! It's like you don't even know me!"she screams.

Then you jump in, louder, angrier and let's be honest, hurt.

"Don't know you? Don't know you?! Are you serious? I know your menstraul cycle I know you so well! I take public shame by buying you super sized tampons in the grocery store, everyone staring at me like I'm some weirdo. What's he doing with super sized tampons, they wonder. I bring you to meet my mother and I even painted your toes that one time! And don't tell me they weren't cute, because those sparkles? They were fabulous!"

In a primitive roar, deep from the underbelly of the earth, she shouts in retaliation.

From what you recall, her head soon turns into a praying mantis that looks like its going to eat you (see image here) and you soon wake up to realize she stormed out, took the dog (you hated that dog anyways) and the left over pizza.

Wtf just happened you wonder?

We don't want our loved ones or our prospective customers to disappear, neither silently or in a heat of rage and yet, this happens all the time.

What you see here is two people who are clear on how they themselves feel, "certain" they know what the other wants and it's through these assumptions they guide the conversation.

These assumptions, if not tested and corrected along the way, are what lead to failing partnerships across the board.

If we dig deeper, I can show you what happens in the above scenario, which isn't so different than your sales conversations.

Why your conversations turn sour (or end mysteriously)

With your words and body language (which is based on your assumptions about the other person), you begin to challenge the person.

You escalate your energy.

You metaphorically chest bang your prospect.

By continuing with these assumptions, you find yourself in a perpetual state of chest banging.

Do you remember the movie A Night at the Roxbury with Will Farrell? Do you remember how they would essentially chest bang women as their way of dancing? If you need some refreshing of that infamous scene go here and fast forward to 1:31

Chest banging, like perpetual assumptions, gets your energy up and both parties on the edge of their seat. If done too much, both parties grow agitated.

They fidget in their chair and begin to stare through you in boredom. They begin to squint their eyes and cross and uncross their legs...  a sense of edginess enters the room.

You need to break the cycle and that doesn't come from more assumptions (a.k.a. chest banging).

Can you imagine how ridiculous that would be to continuously chest bang your prospects? #kindacrazy #dontdoit

Breaking the cycle comes from doing something entirely different.

It comes from sitting down on the floor suddenly.

Or whispering.

Or smiling in silence.

In the above example, our guy here took his significant others' objections personally. She made a claim he didn't know her.

He then escalated the situation by mirroring her actions, tone and demeanor and then went deeper down the rabbit hole by justifying himself. However, he didn't mirror them from a stance of empathy. but rather of defense and self-preservation.

Imagine if your prospect said,

"You know, your products are really expensive and don't compare to the quality of X brand."

What if you said in return,

"What the f$%^ are you talking about? We're the best! I know you better than you know yourself you idiot!"

That doesn't work, does it?

But what if you say something like,

"You know what, I can see why you think that. A few years ago, I would have agreed with you, but in the past 5 years we've invested heavily in developing our product. And I'd like you to give me a chance to demonstrate just how much we've improved. I promise I won't waste your time."


That guy is smooth. That guy gets girls and closes sales.

Which do you want to be?

Realize that in most cases, we want objections from our prospects. We want to figure out what works and doesn't work, but we want it before the point of explosion. Once we find what doesn't work, we change direction, we don't continue to chest bang.

We welcome low-level "conflict". It allows us to change course, discover what is really important to the person we're talking about and it also gives us the chance to share more information about our products, services and beliefs (why we're different).

Mark, the man in this example who I just now named, didn't guide the conflict though, he was merely an observer of an explosive situation and thus was not connected. The conversation dominated him, he lost control and the emotion knocked him on his ass.

Had he been connected to his partner, he would have seen the explosion coming rather than hiding from it. He could have changed course earlier and prevented a bad outcome.

Connection is merely allowing the other person to feel seen, heard and understood.

Most of us, though, are merely witnesses to our failures, not realizing that our lack of guidance is in fact what led to this disaster in the first place.

And our lack of guidance comes from an inability to see. Our GPS (i.e. connection) is all screwed up and thus we can't see clearly.

What could he have done differently?

Three things you (and Mark) can do to prevent losing a customer

1) When people say something you disagree with, don't escalate the situation. You can disagree with them and still not escalate the conversation. We covered that in part two of this series. You can see the full article here.

2) Test your assumptions. Assumptions are good to use when you want to better understand someone. You openly state them to hear if they agree or disagree with what you said. But if you don't do the work of clarifying early on if your assumptions are accurate, you could be killing your the deal.

Test early and test fast so you can better understand who you're speaking to and what they value. (Remember-- assumptions are good to make, but only if you test them. We talk about that in part one of this series.)

3) Aim to genuinely help the person you're speaking to, even if you feel they're wrong. This helps you take a proactive stance (and be better understood), rather than reacting defensively and losing a chance at truly seeing the other person.

This may mean your ego takes a back seat. It means you may be listening to rants and raves that seem irrelevant to you. It also may mean you don't "close the deal" on the spot. And that's ok.

This concludes the end of our free series, Master the Sale, but it's not the end of our journey.

I want to know what you found most valuable out of this series and meet you if I haven't already.

So get to it!

Introduce yourself in the comments below and tell me one thing you loved about this series.

I read every single comment and take your feedback to heart. And remember, this is a community here, a tribe if you will. So speak up and let your presence be known!

Looking for more free tutorials like this one? Sign up for our blog here and get exclusive content delivered to your inbox every week. We never, ever spam.

Until next time!