Sales Is Like Dating—In Sickness and in Health

This is the fourth installment in a four-part series on how sales is like dating (or, er, other forms of care-giving).

February 22, 2023

By Adam Rosa

I was sick last week. The kind of sick where you reach out to loved ones, tell them you love them just in case. Make a lot of promises about how you’ll never take good health for granted, and then once you feel an ounce of normal again, forget all the promises and swear it wasn’t that bad.

It’s the month for love blogs, and we are sticking with the theme until we can’t stick anymore. (Which is next week because love only exists in February.) But for this blog, we forgo romance for a different love. The love of family and mothers. What do we do when a loved one (or a deal) gets sick?

LUNCHABLES AND CARTOONS

A deal may get “sick” if there is a new roadblock; possibly the prospect has slowed down their interest, but it’s still there. Maybe the company is undergoing changes so the legal team is pushing down harder. The initial budget may have unexpectedly changed. These things happen, but just as we don’t leave our kids to their own devices when they have a cold, we shouldn’t leave deals just because they get a tiny hiccup.

When I was young (and maybe, possibly, definitely even now) when I was sick, I always enjoyed two things until health came back to me: Lunchables and Sunday Cartoons (even when it wasn’t Sunday). Without fail, my mother, no matter how much work she had, no matter how tired or busy she was with my three siblings and her full-time job, made sure if I was sick, I got my Lunchables and that the TV was on the right channel.

Am I saying to get your prospect Lunchables and invite them over for cartoons if things get off track? Of course not. (Unless I’m your prospect, in which case that would work.) What I am saying is, when times are tough, you must be willing to ask and find out how your prospect likes to heal. How do they like to be treated?

When a deal gets sick, make it great for your prospect. Treat them wonderfully, be willing to go the extra step despite your full-time job and four kids and dog who admittedly is the best-behaved kid. Be willing to accommodate meetings and check-ins, and do temperature checks. If they notice that even when things are rocky, you are nothing but a solid rock, they will remember those moments and know that deals with you never go sour, they only get better with the challenges. They will close the deal and likely want even more deals with you when applicable. Be like my mother and buy some Lunchables.

FEVERS AND COLD SHOWERS

The worst symptom I could have as a kid was a fever. My mom believed that a hot shower would make my temperature go up, so it was always lukewarm showers when I had a fever, which to me felt like frostbite was only moments away. She swears they were lukewarm. I still swear they were frigid.

But here comes perhaps the most important part of when a deal gets sick. Doing what may make the prospect uncomfortable—what you know is good for them if the deal is going to get better.

We all hate medicine, cold showers, and the Red Sox. But we must do what we must do to stay healthy and not root for the worst franchise in all of sports. When a deal gets sick, there is only one purpose in staying with it—to help it get better. If it’s dead, it’s dust, and that’s when you walk away (hopefully this is where deals and love are not the same).

Sometimes you must give your prospect their medicine, the part of sickness that isn’t all Lunchables and cartoons, and it goes like this: Making sure the deal is still worth your time by asking the uncomfortable questions. Which leads us to perhaps my favorite question I have learned to ask in my time with Maestro: Earlier you were very excited to get this solution in place, what has changed?

BOOM! MAESTRO! BOLD! Wowza!

Some of you may be thinking, isn’t that an obvious thing to ask? Well, I ask you, isn’t medicine obvious to take? Just because it’s obvious doesn’t make it easy, and a lot of sales professionals struggle with a question like that. They beat around the bush, try to hide the medicine in juice or dessert, but sometimes you simply need to give the medicine. Sometimes you need to bathe in the Arctic.

BACK TO FULL HEALTH

I finished my medicine, the fever went down, and the fake cough can only work so many times; eventually, it was time to go back to school. Likewise, with a deal, you need to be able to recognize when it’s time to go back to school, time to get back on track to close your deal.

One thing not to do is panic. Imagine if you were sick, and the first day your mom checked in on you once. Then four days later, she is checking in every five minutes. It would give you a panic attack! You’d be certain something is wrong, and that surely you are dying. The same goes for deals. If you touch base once a week at the top of the funnel, checking in twice a day later on comes across as desperate, like something is wrong, and it’s enough to make any prospect worry or see you as suddenly pushy.

And this is exactly why it’s important to stay consistent with your checks from start to finish, and not be worried about frequent touches at the beginning. 24/48/72 hours between touches, even at the top of the funnel, is good. It lets people know that is the norm, and they aren’t going to panic when you do that toward the end of the deal.

If you spend your “sick” time accommodating, giving medicine, and being bold, but the prospect isn’t healing, it’s a sign something bigger exists. Sometimes you need to realize when a deal simply isn’t under your wheelhouse of cures and, for your benefit and your prospect’s, you need to let them go.

Love is tricky. We never want to admit when a loved one may leave us, we always want to believe they will get better, but sometimes that simply is not the case. But by treating the sick with what they need, handing them their medicine of boldness, and showering them with Popeye and Scooby-Doo, more often than not we can get a deal that was once healthy back on track to prime stature and a close.

Show us some love. Reach out at mastery@maestrogroup.co to find out more about our live trainings and self-paced learning modules.