How To Kick Ass And Take Names In Your Sales Job


I used to train at a gym by my hometown. There was this guy there, Scott, that I used to bullshit with here and there. Nothing too deep, just the usual gym banter.

“What are you training today?” “Chest, you?” “I got Back.” “Nice.”

That kind of thing. Anyway, at some point in the not too distant future, while tending bar at a restaurant called Damon’s, I ran into Scott. I was running a drink into the dining room for a server, when I noticed he was sitting down in a corner booth with his family.

I stopped and said hello, shook his hand, and got introduced to his family as Chris, a guy from the gym. Then I told them that if they needed anything at all, to let me know.

I may not have known it at the moment, but that was my first real sales situation. I did two very basic things that day. I went out of my way to say hello. And even though I wasn’t serving their table personally, I wanted to make sure they had a great experience.

One week later, I was walking to my car after a workout, when Scott came running after me and called my name. He said, “So, what the hell are you up to? What do you do again?”

I told him how I was working for a start-up, for free, and that my loans would be coming through soon, so it was time to get some real work. He offered me a job on the spot.

I ended up working for Scott for five years.

Scott became a mentor to me. When it comes to sales, he’s in Cooperstown. He’s Muhammad Ali. But he’s also just a great fucking dude.

He also has tattoos all over and rocks a cutoff at the gym; he doesn’t always look like the owner of a successful steel company. It would have been easy to be short with him and selfishly avoid conversation. But I didn’t. I was nice, like I try to be to everyone. Most importantly, I was myself.

I’m particularly proud of that story because in this day and age, it’s becoming increasingly difficult to get a job like that. The old fashioned way.

I’m getting way off topic here but I also think we’re getting to a point in business where a plain resume will never get you the job you want. It’s more important than ever to stand out.

And another quick note about that story: before I interviewed formally, Scott invited me to dinner at Red the Steakhouse with the rest of the sales team. It was a great tactic. He got to see me in a relaxed, yet professional state. And at the same time sell me on the team and company.

It was the best steak of my life, in the best restaurant I’d ever set foot in. I was sold; completely intoxicated by the idea of working for this company.

So, all that said, here are what I consider to be the most important sales skills I’ve learned:

Be yourself, because you’re always selling.

People can smell a fraud like Cinnabon at the airport. Also, people like to deal with people they like. And most people don’t like fakes. It’s pretty straightforward.

Don’t be afraid to deliver the bad news.

This is huge for me because I hate confrontation. Hate it. I used to lie to customers when I screwed up and it only made it worse. I’d tell people that the lead-time would be one week when I knew it would be a month. Then after a month, I’d make up an excuse and then tell another lie.

You have no idea how many times I’ve had a screaming client ask for a manager. Needless to say I don’t do that anymore. It’s not under-promise, over-deliver bullshit. It’s called being fucking real.

Trust me, tell them the truth and do it now.

Be a great story-teller.

Again, people like to deal with people they like. That’s why it’s so important to be confident and tell a story. If you stutter or sound nervous, they’ll think you don’t know what the hell you’re talking about, or worse, they will think you’re lying. The second that becomes the perception, you’re dead.

Being able to tell a story is a good life skill to have. If you can walk up to a guy or girl at a bar and make them laugh or entertain them with a good story, you’re golden, Pony Boy.

Be persistent.

There was a study that showed that people give up after the fifth contact with a prospect. The thing is, those prospects would have bought from them after the seventh contact. Hang in there and be persistent.

I’ve had so many situations where after finalizing a deal, people have thanked me for staying on them. These days, in a world where people wear busy like a badge of honor, a person who effectively follows up is virtually taking a to-do off of their client’s plate. It can really be an advantage.

But always read the situation; you don’t want to be annoying either.

Here’s a cheesy bonus tip: If you are being annoying, fall on the sword: “Hey, it’s me again, that pain in the ass from XYZ Co.” I know, I know. But trust me, it works. You’ll get a laugh every time.

Don’t let the highs get you too high; don’t let the lows get you too low.

Another mentor of mine – Marc – told me this when I first started out in sales. I’m a high anxiety dude and tend to get way down on myself when things aren’t going well at work. And when things are going well, I get super amped up about it.

I think it’s great to celebrate your wins and you should always learn from your loses. But it’s so, so important to try your best to remain as Stoic as possible.

Relax and do the work, the sales will come.