Dear Quota Team,

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I’ve been in sales for several years, but only recently got into selling “big ticket” items. I went from car sales to being a manufacturer rep for a heavy equipment distributor, and have an assigned territory that I took over from a guy who retired.  
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I’ve closed a few deals so far. Nothing huge, but enough to get my feet wet and give management the confidence that I can get the job done. I believe in myself and after working in car sales for almost two years, it feels good to be treated better by customers and by my employer.
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Here’s what I’m wondering about. I have a potentially huge deal in the works. It would mean a six-figure commission (just from this one deal). I know how important it is, so I’ve gone above and beyond to make this customer happy. I’ve taken him to steak dinners, brought him donuts and coffee every time we’ve had a meeting, and even convinced my boss, who is pretty tight with cash, to pay for Suns tickets. But he keeps pushing his buying timeline further and further out, and gets vague whenever I try to pin him down on hard dates and commitments.
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My question is this: when should I give up and let it go? I know what it’s like to get strung along by someone, but in car sales it’s a bit different, because there’s always another customer right around the corner, whereas in this business, there aren’t as many potential customers, especially ones that can make your whole year in one pop. When do I just call it a day? Appreciate any advice you might have.
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Confused in Arizona

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Dear Confused

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We actually happen to be in the market for some heavy equipment… and we really like steak dinners. Let’s meet up at Ruth’s Chris to discuss!
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All kidding aside, the situation you’re facing isn’t unusual. Sales reps are constantly afraid of losing out on big, seemingly once-in-a-lifetime deals, so much so that they might ignore all the other opportunities that come and go.
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There’s even a scientific term for it: loss aversion. It’s the tendency to prefer avoiding losses to acquiring equivalent gains. Some studies have even suggested that losses are twice as powerful, psychologically, as equivalent gains.
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As to your question, the fact that this prospect is vague when you try to pin him down isn’t a great sign, but it doesn’t mean that the deal can’t or won’t happen. But if he knows that every time you show up, you’re bringing delicious steaks or fresh donuts or NBA tickets, then he’s definitely going to agree to as many meetings as you want.
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Here’s what we would do: ask him point blank whether he’s ready to sign a purchase order or put down a deposit. Don’t let him squirm out of it. If the answer is no, you should stop giving him freebies and focus on looking for new business (which you should have been doing all along, by the way), and check in with him once a week.
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You’ve already gone above and beyond to endear yourself to this person and to build rapport. If he’s a buyer, then he needs to buy. Otherwise, he’s just in it for the ribeye.