Yesterday, I was at lunch at a popular local restaurant, and I observed a classic example of how salespeople can sell to younger buyers – or, more properly, how NOT to do it.  I observed two men walking in.  One appeared to be in his sixties, the other in his late 30s, both in embroidered company polo shirts from different companies (the uniform nowadays, it seems).  They were seated directly behind me, where I couldn’t help but overhear the conversation.  Immediately, I could tell it was a sales lunch.

The older man was the seller, and the younger man was the buyer.  And I could tell that the salesman was of the old-style “Good Time Charlie” type.  After they ordered drinks, the buyer asked, “So, you have a quote for me, right?”  And the GTC salesman said, “Yeah, we’ll get to that, but how about that Bobby Witt in the Home Run Derby?”  I’m not kidding.  The buyer asked for his price and he redirected to a sports conversation.  The buyer, being nice, said, “That was pretty awesome.  So were you able to get the specs I need?”  It got worse from there.

Here’s what was happening.  The salesman was selling in a style that has probably worked for him over the years – but has gotten obsolete in the last 5-10 years.  As I discussed in my Webinar, “From Hippies to Hipsters,” the Boomer generation typically builds business relationships based on personal aspects first, and segues that relationship to business needs later.  In other words, what the salesman was doing was probably the correct approach for a customer of his generation (although I’m finding that even Boomers are more interested to get down to business these days, for reasons I’ll discuss shortly). But the salesman had no idea how to sell to younger buyers.

Millennials and Generation Z’s tend to be much more protective of their time.  When in buying roles (or selling roles, for that matter), their impulse is to get business done FIRST.  They’re looking for a salesperson who can solve their problems and make their lives easier in a very time-efficient fashion.  If a salesperson is able to do that, THEN they get the opportunity to build a personal relationship and friendship.  In other words, the relationship dynamic is flipped on its head.

Why didn’t I mention Generation X?  Well, we tend to be fence straddlers between “personal first” and “business first,” and so we’re harder to generalize.  My own personal style has been more of the “business first” style, and for that reason, I identify well with the Millennials and Z’s.

One other aspect of this that is key is the concept of “work/life balance.”  That was a phrase that didn’t even come into popularity until the Gen-X’s were firmly entrenched into the workplace and into positions of authority.  Essentially, from Generation X forward, more and more people are identifying with the idea that “we work to live, we don’t live to work.”  In sales, this manifests itself into the concept that we need to get down to business NOW, because time I waste talking about baseball is time I have to spend later on catch-up work, and therefore time I don’t get to spend with my friends and family.

That’s where the Boomers reenter the conversation.  You see, many Boomers have watched us in the X, Millennial, and Z generations spending more time outside of work enjoying our lives and thinking, “Gee, I want some of that, too.”  In order to do it, they’ve reordered their business lives to get more done during the day.  Which means that, ironically, many Boomers are mirroring their younger counterparts’ buying styles.  Those Boomers don’t have a problem understanding how to sell to younger buyers.

One other thing to put in here is an acronym called NAXALT.  It means that:  Not All “X” (where “X” is whatever generalization you’re making) Are Like That.  Hence, there are Boomers who buy like Millennials, and there are Millennials who want to talk endlessly about football before they start talking business.  Your role is to figure out where your customers are, and meet them where they are.

Now, let’s go back to my lunchtime neighbors.  Good Time Charlie next invited the customer out to play golf on Friday, and the customer just laughed and said, “Man, if my boss thought I had enough time on my hands to play golf during a work day, I’d be fired!”  The conversation kept going in that vein, through drinks, through ordering lunch, and through eating.

Wanna know the saddest part?  The buyer wanted to buy.  I could tell.  He kept redirecting the conversation back to the quote, and buyers aren’t that insistent on knowing the price unless they are genuinely interested in buying.  But Good Time Charlie couldn’t see that there was a potential deal on the table.  Yes, I wanted very badly to turn around, tell them to pause the conversation, and quickly clue ol’ Charlie in.  But I didn’t.

I don’t know how the conversation ended.  I’m protective of my time, too, and I had a Coaching client that I needed to meet with.  What I do know is that, if Charlie made the sale, he did so in spite of himself.

What makes inter-generational selling so difficult is that sometimes, salespeople must go against their own type.  The buyer was trying to clue Charlie in that he wanted a business resolution.  My guess (because I’ve seen this many times) is that, had Charlie gone ahead and presented the quote over their iced teas, that by the time the sandwiches came, they would have been having an enthusiastic conversation about the Home Run Derby.  And both parties would have had the result and experience they wanted.

And now you’re thinking, “But Troy, you already said NAXALT, what if Charlie had gone business-first and his customer had been one of those exceptions?”  I have a simple answer.  Your customers will tell you where they want to be, and where the conversation needs to go.  Tune in.  What the buyer wanted from Charlie wasn’t a well-kept secret.  He was virtually slapping Charlie across the face.

And yes, younger salespeople can run into similar issues when selling to older salespeople, just in reverse.  My advice to you, when selling across generations, is a simple three-point plan:

1. Start your conversation with the general rules as your approach. In other words, if you’re selling to a Boomer, think “personal first.”  With X’s on down, think “business first.” (With Generation X, even though we straddle the fence, I suggest starting business-first because if you’re wrong, your course correction is easier.)
2. Ask a couple of “flicking the jab” questions to see how your buyer reacts. For instance, if you as a personally based question and your buyer seems impatient, flip over to business-first, or vice versa.
3. Adapt your own conversational approach to theirs. This might even mean having two separate questioning tracks prepared.  That’s okay – it’s better to have a “plan B” and not need it, than to need it and not have it.

Whether you’re a more seasoned salesperson trying to figure out how to sell to younger buyers, or a younger salesperson trying to sell to older buyers, inter-generational selling can be a challenge.  But it’s one that’s easily overcome; just remember to meet your buyers where they are.