Why Middle-Aged-Men Are Such Lousy Sales Prospects

I know that I'm going to be in for a tough time as soon as I realize the a potential customer is a middle-aged guy.
Why Middle-Aged-Men Are Such Lousy Sales Prospects
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Entrepreneur Leadership Network VIP
President of The Marks Group
6 min read
Opinions expressed by Entrepreneur contributors are their own.

The other day I was responding to a prospective customer who inquired about our products online. The minute he answered the phone I knew I was in trouble: he is a middle aged man. Middle aged men tend to be lousy customers. I know this. I'm a middle-aged man.

Am I generalizing? Absolutely not.

Every man in business has a similar arc. In their 20's and 30's they're eager, full of energy and willing to do whatever's necessary to conquer the world of opportunities and riches which lays before them. By the time they hit their forties they've become either settled or unsettled with the professional life they have chosen. They know they have limited time left, and maybe no time at all, for making any drastic changes. By the time they get to their fifties -- middle aged -- it all comes to a head.

When you're in your fifties you've either reached a happy or an unhappy place in your business life. You've been in the working world for 30 years. You've seen it all. Maybe you've prospered but, other than a fortunate few, probably not as much as you would have hoped. You're not a professional baseball player like you dreamed. You certainly never expected your body to be as depleted, or your belly as bloated, as it is.

Related: At What Age Do Our Intellectual Abilities Peak?

You've been lied to countless times. You've had many disappointments. You've lost deals. You've been stiffed by deadbeats. You’ve had vendors not meet their commitments and partners bail at the last minute. You've had trusted and loyal employees who turned out to be not so trustworthy and loyal. You're more-than-just-a-little angry at the world. You've taken your share of crap, but you know you've got to slog through at least another 10 years before you can (hopefully) retire and enjoy the finer things.

So now you're going to take these years of baggage and take it out on...me. I know this as soon as I realize that a potential customer is a middle aged guy. I also know that I'm going to be in for a tough time.

That's because most of the middle aged business guys I know are still operating like they did 20 years ago. They like to talk too much, tell stories and share their "wisdom." They’ve learned their lessons about business, technology, people and products back in the day and they still think those same lessons apply today. People still like to drink beer at lunch, right? They still use Windows 95, right? They appreciate a good phone call over an email, right? Things may have moved on but many of my middle aged customers tend to cling to an earlier time. Why? Weariness. Laziness. Complacency. It took too long for them to learn what they learned and they just don't want to learn something new.

Related: How Older Entrepreneurs Can Turn Age to Their Advantage

And besides...they're middle aged, right? They've been around the block, right? They've seen it all and done it all. They're geniuses (at least in their own minds) and many that I speak to won't hesitate to remind you of that. I get the pleasure of hearing it all.

"I want you to know right away that I understand all about this stuff," the guy on the phone announced to me as soon as we started to talk about the software my company sells. "I sold mainframes for IBM, OK?" Maybe wisdom does come with years, but does a 57-year-old guy know everything there is? Is there nothing more to be learned? I'm a 53-year-old guy and I can assure you that I’m just as ignorant about most things as I was in my twenties. I just wish that guy on the phone would admit the same.

The reality is that most of the middle aged business men I meet are tired, impatient, oftentimes angry and mostly frustrated. They complain about millennials. They rail against liberals. They mostly watch cable news. They long to golf in Arizona or go to their vacation homes in Florida. They reminisce at Jimmy Buffett and Rolling Stones' concerts. They refuse to understand why their gender-inappropriate comments aren’t acceptable today. They still read newspapers, wear cargo shorts and listen to sports radio. They have never used Uber, subscribed to a podcast or posted a photo on Instagram. They count Ronald Reagan, Jack Welch and Cal Ripken among their heroes and still don't trust Jimmy Carter or vegans. They vividly remember Nixon, the Vietnam War, OPEC and the Miracle Mets of '69.

Related: What Is the Ideal Age to Be An Entrepreneur?

In business, they've paid too much rent and overpaid for too many products over the years. They hate China, paid time off for new parents (“we didn’t get that in my day!”), government regulations and taxes. They would love to sell their businesses if they could, but they either run a company in a place where no one wants to move to or can't find a buyer willing to pay the price they think they deserve. And their kids? Feh…they just want to smoke weed and work for Google.

So how to deal with a middle aged man who's a prospective customer? One option I always consider is just hanging up the phone. But look: a sale’s a sale, right? So here’s what I do.

I’m respectful. I’m admiring. I’m empathetic. I keep my opinions to myself and become either a liberal or a conservative depending on who I’m speaking to. I take a deep breath and set aside the extra time because I know I’ll be subject to stories, complaints and some timeless, brilliant wisdom. Eventually he'll run out of gas and give in to my sales pitch. And I’ve learned that if I’m courteous, friendly and -- most importantly -- deferential enough I’ve got a good shot at winning him over.

I should know, right? I’m that middle aged guy.

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