Project Description

I was 22 the first time I tried to bribe my way into a bar to cut a line. It was the saddest, most pathetic sale I ever attempted. I was going to school in Boston at the time and was well aware that line-cutting bribery was a common occurrence in the scene, but I had missed out on some of the details. Apparently walking up to the bouncer, holding out money in plain view, and begging to get in wasn’t really the way to go.

Clearly, I wasn’t much of a sales expert starting out. Few entrepreneurs are. But until you have the funds to hire a sales team, you’ll have to learn how to sell yourself — and fast.

In those early days, it’s all about the impressions you make. A generic copy-paste cold email will get you about as far as waving money at a bouncer. In most cases, I could probably even identify the software program companies use to knock on my door (nonstop) with cold emails. What I’m suggesting is a more personalized approach, which some might call consultative selling.

So how do you get away from the scattershot, spray-and-pray sales technique and position yourself as a trusted authority? Here are three strategies to get you started:

  • 1. Ask better questions.

    When Jon Vroman, author of “The Front Row Factor,” taught active listening, he would focus on asking questions that people have never been asked before. One of his favorite questions was, “What is something you wish people asked you more often?” When the person responded, Jon would always say, “I have a follow-up question.” And he’d ask that exact question back to them.

    It was such a fantastic, memorable act, and it fits in well with consultative selling. You might need to tailor them to the industry a bit, but here are the three questions I strongly recommend for any aspiring salesperson:

    “What is your No. 1 priority over the next [X] months?”
    “What is unique about the situation you’re in right now?”
    “If you could be, do, or have anything over the next X months, what would you be, do, or have?”
    Everybody thinks their situations are so different, but they’re wrong. Though the cast of characters is always unique, possible problems are finite. Oftentimes, what keeps people from making a decision or moving forward in a sales call is a feeling that this uniqueness is misunderstood by the people doing the selling. Getting out in front of that uniqueness is so powerful and will help you reach the more productive part of the conversation.

  • 2. Curate intelligent content.

    To be worth a person’s time, you have to become a source of really good information. This doesn’t mean endless self-promotion. If you write (or film, or record) something that’s relevant, of course you should send it out to people you think it would help. But oftentimes, leaders are readers. And in our reading, we tend to hoard information when we should share it.

    One of my favorite techniques lately is the classic “read this, thought of you,” approach. Rather than the shotgun work of sharing on social media, this is about reading something very specific and then passing it on to the person you think it could help the most.

    Recently, we hired a young actress for one of our shoots, and it was obvious that she was dead set on pursuing acting as a full-time career. But I stumbled across her IMDb profile, and it was grossly incomplete. So I found some content about how to make a kick-butt IMDb profile and sent it her way. Within a few seconds, I received an outpouring of thanks for helping her out. This just goes to show how the simplest gesture — helping someone else reach her goals using content — can go a long way toward building a relationship that could help you make sales down the line.

  • 3. Practice making first impressions.

    It’s easy to make a bad first impression. People can sense your energy, size you up and judge you within the first 10 seconds of meeting you. Whether it’s via cold email, digital chat or in-person meeting, you can always be working on your first impressions. You have to discern how people are feeling when you meet them, and then you have to try new approaches until you learn what works for you.

    Consider my first attempt at bar bribery. Once I overcame the total humiliation, fear and dorkiness I felt after that encounter, I gave it another go. Several years later, I was trying to impress a friend at one of the most prestigious pubs in Boston (during playoff season). I walked up to the bouncer and had this exchange:

    “Hey! I don’t believe we’ve met before. I’m Mike.”

    “Hey, what’s up.”

    “Well, now that we’re best friends, how much is it going to cost us to not wait in line?”

    He told me an amount, and I asked whether it was OK if I gave him a little more than that. He laughed, and soon thereafter (with a handshake and a bro hug), we found ourselves inside. First impressions matter.

    I’ve come a long way, and while present-day me cringes at the thought of bribing my way into bars, I’ve become conscientious about how I’m treating people in our first meeting. By practicing every day — in the checkout line, in the elevator, at the bank — you can notice how your interactions make other people feel and how you contribute to raising positivity in those around you.

    Become a skilled practitioner of first impressions and great questions as well as a repository of helpful content for your network, and you’ll find that the whole sales thing gets a lot easier — and faster. Business decisions are made by people, and people appreciate a more personalized, empathetic and thoughtful approach.