Sales Is Like Dating—Break Up with Hope

This is the third installment in a four-part series on how sales is like dating.

February 15, 2023

By Adam Rosa

Yesterday was Valentine’s Day. You may be wondering, does that mean they write these things the same day they post them? Are they allowed to speak about the past when really, it’s the future for them? Do I even understand what that means?

In actuality, I am writing this as you read it. Every Maestro blog is actually written personally catered to you; it’s why you find them so useful. *Cue the swinging pocket watch that makes you sleepy*

“These are so useful!”

So, for this week’s super-duper-ultra-awesome-useful-Valentine’s-Day-blog, and our series on dating—story time!

ROSE-COLORED FLAGS

In the month of love, and in the career of sales, it is especially prudent to know when to move on. From bad deals, dead deals, and that guy who keeps sending you dead roses because he thinks they are “unique.”

I have a friend named Esperanza. She was big on hope. Always hoped her dates would be better than they seemed. Always hoped things would work out even if she did the same things. Always hoped she would learn Spanish without taking any classes.

Her first hope is the key to speeding up deals. It’s seeing prospects as they are and dropping the bad ones.

Esperanza had the unfortunate problem of conflating kindness with passiveness. It is not kind to stay with someone in the hopes that they get better or because you want to ignore their flags. It only prolongs the inevitable and in fact often causes more harm. You (and Esperanza) can be kind and direct.

The same goes for sales. If a client is clearly not a good fit, but they show some interest, by not moving on you’re both wasting time. Don’t ignore obvious red flags just because they are interested, like if the company’s budget is far too small, if the person you’re in contact with clearly has no real decision power, if they still live with their parents.

The point of a first date is like a discovery call.

There’s a reason it’s not called a convincing call.

It’s about learning more about the prospect, seeing if they are a fit, and THEN using your prowess to show them why they are the fit you know they are. And not everyone is a fit. Not everyone is your true love. Accept that and move on when it’s clear from the jump. You’ll find your love and close other deals faster.

NEW DAY, SAME HEARTBREAKS

Esperanza’s real problem isn’t that she is full of hope (seriously, so full of it, it should have been her name or something). It’s that after her hope leads her down long and winding wastes of time, she does not change her process. She finds a man selling dead roses outside her local donut shop. He asks if she wants one, she says no thank you, then he asks if he can bring her one for their date. She’s hesitant because his shirt says, “Seriously, Esperanza, say no,” but she goes for it anyway.

Then she realizes he’s mean, unsanitary, and worst of all, does not floss! She wastes months hoping it will get better, but after a year, he still does not floss, and she runs away. Then a few months later, she’s back at the donut shop, and another guy is selling flowers and asks her out. With the same shirt!

We can’t fault her for the first time. We have all had relationships we hoped would simply work themselves out. We have all had deals we hoped would magically turn out ok. The potential payout was so large we ignored all the obvious dealbreakers. The client was so charming that we ignored that they were just being polite and didn’t want to hurt our feelings.

It happens to everyone, but it need not happen twice to anyone. Esperanza’s issue is she didn’t change the process. Find a new donut store, pick someone who likes living things, find someone with a different shirt. With the right process she will know she is true to herself and at the end of the day, you can do no more in love. Or sales.

The best sales professionals do the same. If you read Maestro, you’ve heard it before, but the best know that you can never think about the basics enough. Have a repeatable process. When a deal goes wrong, look at your process AND what the prospect said. Looking at one without the other does not help.

Looking at Dead-Rose-Man saying that he enjoys leaving food in his teeth for later is not enough on its own. Esperanza must look at how she reacted, and why she didn’t leave immediately. One without the other is only half the puzzle.

So, the next time a deal goes wrong, you are to do the following, to reinvigorate your life with some hope, and lessen the heartbreaks.

  • What did the prospect say about why they were unwilling or unable to complete the deal?
  • Where did that objection initially come up?
  • What was your reaction to the objection?

If the objection never came up, the deal may not have been done when you let it die. If it was dead, you missed asking the right questions earlier and should address where you missed them to save time in the future.

If the objection did come up, how did you handle it? Perhaps it’s not them, it’s you! What could you have done differently, said differently? Question tree it, find all the best responses, guess all the responses that may stem from that and see if any lead to the path you want.

If there simply is no good solution, perhaps it just was not a match, and your only issue was having a bit too much hope and missing when to leave. Your process and radar will be better next time.

NO HABLO SPANISH

If you recall Esperanza’s last hope, it was to learn Spanish without taking classes. If you have missed the running joke about Esperanza, you too should learn some Spanish.

The lessons here are quick and two-fold. The first is simple, there is no growth without work. Sometimes we forget that, but more often we simply misconstrue working with hope.

Wanting something is not enough. Want is not effort. Effort means working on open communication, listening, admitting when you’re wrong, and learning to solve problems by being honest together. When you work at all of that, your relationships grow and your sales do too, but you can’t simply hope.

The second is that Esperanza wants to learn Spanish because her name is a Spanish word, but actually she is of Moldovan descent. And she doesn’t know a single person who speaks Spanish. She keeps striving to be someone she is not.

If instead she practiced Romanian (the language in Moldova is not Moldovian, sorry), she would be able to speak to her family, have more relationships with people in her community, and an astrologist once told her she’d marry a man who speaks Romanian, so she would have her shot at love.

When you are who you are, when you sell the product you have to sell, when you are honest about what you can do with your product and skillset and are honest with yourself about whether a deal can work or not, the work you put in will yield far greater results.

You’ll have bigger deals, more deals, and maybe, just maybe, a Valentine who doesn’t try to give you a dozen dead roses.

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