I have lived on both lawns.

The lawn where you’re terrible at sales and dread every slow-ticking moment of the workday and the lawn where you excel at sales and every day feels like a Hallmark movie moment. From experience, I can confidently say, the latter is better.

Hi, I’m a career salesperson who has gone from hating everything about sales and transformed into a person who gets a big dumb first-day-of-school smile when reflecting on my career.

I believe that Sales has that wonderfully frustrating mix of being simple and challenging at the same time. It takes you on a rollercoaster of emotions from on top of the world highs, to I can’t-believe-this-shit-is-happening lows. It’s fast, furious, and you get out of it what you put into it.

When I first started in sales, I would devour books looking for any edge I could get. As a sales veteran who scrapped his knees enough times to find consistent success, I’d like to share the advice I wish I had when I started.

Read on to learn three tips that you can use to increase your chances of making a sell that aren’t discussed enough in books.

Make Your Prospect Laugh

The best lesson I have ever learned about understanding people and influencing a room was taught by someone who wasn’t in sales. In fact, the person who taught me the lesson worked a job that I would argue is the opposite of sales… he was a cop, and he was also my father. As a law enforcement officer, my dad has been in very tense situations, anything from domestic abuse to murder scenes. As you can imagine, showing up to these moments tensions are high, and the room for error is low.

What my father does in those situations to calm people down is a genius move that completely melts the walls of tension. What’s his move? He makes people laugh and lighten up, so they lower their guard. This tactic applies well to sales.

It only takes walking into one lobby or dialing someone who is busy to know that salespeople and sales calls aren’t always received as “Oh joy, someone is here to sell me something.” Instead, salespeople are usually met with eye-rolls, tension, and annoyance. An easy way to quickly lower voltage is to make your prospect laugh. You can accomplish this with a well-timed one-liner, a witty observation, and a general sense of humor. I have tested this theory out on 100’s of people from all walks of life in different positions… It works. This tactic will help you to come off as a real human and immediately lower your prospect’s wall.

Please know this: I’m not saying to go to your prospect’s office and deliver a tight five minute set like a stand-up comedian. I’m saying be professional, carry your importance but try to find a way to make your prospect laugh or lighten up. Anytime you can make someone smile, their guards will be lower and help them listen to you.

Don’t Try to be Mr. / Mrs. Perfect

As a new salesperson, I wanted to be Mr. Perfect. I wanted to be the guy who looked spick and span, knew what to say, and could handle any objection. I was so business-focused that I didn’t allow any room for my authentic personality. Instead, I was a walking brochure throwing up boring kill them with times-new-roman font typed information. Consequently, I wasn’t a good salesperson.

One lesson I learned in sales is that many people like you for who you are and not for who you’re trying to be. Again, let that sink in. People tend to like you better for who you really are, opposed to who you aren’t. In simplest terms, don’t be fake. Be the real you, even on the job.

Be the person who gets excited when your sports team wins. The person who can joke about gardening and all the hassles involved. The person that can poke fun at working from home during COVID. Typically the more vulnerable you can be with who you are, then it’s easier for people to relate to you. Being an excellent communicator is all about being relatable, and as a salesperson, your goal is to relate with people. Nobody can connect to a perfect person because perfect people don’t exist.

What this means in application is when you’re meeting your prospects, be sure to let your real personality shine through. Do you like sports? Talk about that. Do you like movies? Talk about that. Do you like _____. Talk about that. Often times in meetings, you can get clues to what your hobbies your prospect may like by looking at their desk or doing proper research about them online. Should you share a similar interest, mention that, and that way, you and your prospect can quickly find common ground, and you can go from being a stranger to becoming a friend.

Again, please has tact. Don’t show up and only talk about yourself and what you like. Instead, be calm and professional but point out a few things you notice or might have in common when an opportunity arises. Should that lead to a side conversation, then have it, then get back on track. Suppose you’re into developing a long-term relationship with your client. In that case, sooner or later, it’s in your best interest to be a real person and not another annoying salesperson.

Focus on Being a friend

Pretend you’re on a first date. You shower, use that one hair spray that smells bad, call your Uber to go to the restaurant, and finally meet your date & ten minutes in say they ask you for marriage. What the fuck ? How fast would you be leaving that date? Pretty damn fast.

Sales is a lot like dating, in the aspect of you meet a lot of people and you decide if you’re a good fit for each other. Many poor salespeople pull a Drake and go from zero to 100 real quick without seeing if what you’re selling is a good fit. This tactic of going for the sale without knowing anything about who you’re selling to comes across as desperate and uncaring, especially if the call is completely cold. Instead, focus on the long term game with the strategy of coming off more as a friend than as a salesperson. Ask how your prospect is doing, make them laugh, find out what they care about, take them to lunch, get to know them. Doing these every day, easy thing makes all the difference in the long term relationship with your customer.

At the end of the day, if you and your competitor are selling the same product and the prospect likes you better, you’re more likely to win the business. So it’s in your best interest to be friendly.

Now I would be remised not to say, in sales, you need to ask: ask for the appointment, ask for the sale, ask for the referral, but before you ask, it won’t hurt you to focus on being a friend. This mental shift will serve you in the long run.

Bonus: Selling Is Asking.

Many people think sales are like show and tell, but it’s really asking, listening, and telling. The great salespeople don’t really do much talking when they’re in sales mode. Instead, they ask their prospects diagnosing questions to see what problems they are currently having so they can recommend a solution.

This sounds like: Tell me about ______, How is _____ affecting you? What would be your ideal solution? How are you currently doing _____? Have you considered this? What would fixing ____ mean to you?

Think of sales as a game of Clue. The more questions you ask, the easier it will be for you to solve the mystery. So ask questions, and sleuth together your solution.

Please like, comment, share and tell me what you think. What tip helped you the most? How do you sell anything (ideas, writing, suggestions to try a new restaurant)