Sales is like dating…or is it?

Lindsay Lackner
4 min readFeb 19, 2017

Originally published on authenticsales.com

I started my career in Sales, like many people, in an Inside Sales role. My job was to call on small industrial accounts and try to sell them over the phone. Needless to say, I didn’t ‘love’ this first role. To make matters worse more interesting, I was reporting into the manager of our industrial division, a man who’d been with the company for 20+ years.

Now don’t get me wrong, Martin was great. He cut his teeth in Sales and had worked his way through many other divisions of the company. A very direct man with an uncanny ability to make his reps squirm. He was dedicated and intent on teaching us newbies the ropes above all else in terms of the sales pipeline process.

Every week I’d drag my heels down the hall to Martin’s office for my pipeline review, anticipating my impending doom. I’d hesitantly knock on his door, hoping that he’d double-booked me or had to run out to an important call (he never did either…). I’d plunk myself down in front of his desk with my shoulders rounded and my head hung, and limp-ly hand him my call summary sheet for the week listing my conversion rates.

With Martin, you never quite knew if you were doing well or poorly but Martin was a great coach. He taught me about discipline, consistency and most importantly resilience. He taught me that sales process is extremely important to your success and that it can be taught (and learned). However, on one particular day, Martin took it upon himself to draw a comparison for me in the hopes that it would help improve my spirit. “Lindsay, Sales is like dating. You’re going to get a lot of No’s to get to a ‘Yes’.” Martin was very pleased with his new metaphor and pretty soon it started taking on a life of its own. “Lindsay, Sales is like dating. You’ve got to experiment a little to see what pick-up line works best.” “Sales is like dating. You can’t expect to close every deal.”

Finally, a few months down the road, when I’d developed enough of a thick skin and worked through my battle fatigue from cold calling, I got up the chutzpah to challenge Martin on his coaching technique. At this point, I’d also had a few wins under my belt, but most of my success had come from leads from our Distributors or expanding current customer business. In his office for my weekly pipeline review, Martin started into another one of his dating metaphors “Lindsay, Sales is like dating. You have to ask a lot of people to the prom before one will accept.” I straightened up in my chair, looked him straight in the eye and said, “Martin, that has NEVER been MY experience with dating! People ask ME out!”.

The lesson here is that not every sales job is the same and managers…not every sales analogy is applicable (but they often make great stories…). In the end, I had to grit my teeth and make the calls, refine my approach and build a tougher skin. I got an early taste of rejection in a part of our business with very low risk of doing any lasting damage. I learned how to be resilient and not take things personally, although this really is something I still struggle with to this day. I learned how to quickly and concisely summarize our offer and always ask for the business. While I never ‘excelled’ at phone selling, my experience in inside sales served me well in my future roles.

As I moved on in my career I realized that key account management and enterprise selling was more aligned with my personal style. Looking back, I wouldn’t pass on this experience, no matter how painful I found it at the time. But unfortunately, I think experiences like this are often the reason young people ‘opt-out’ of sales and thus forgo a potentially very rewarding career in sales. So if you find yourself in a situation like this I have two pieces of advice 1) be grateful for what you’re learning, just because something is difficult does not mean it isn’t valuable and 2) nothing is permanent, there are other opportunities that your selling style may be more suited to just around the corner.

So is sales like dating? Yeah, I think it is, but only in the sense that the style and experience are different for everybody!

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Lindsay Lackner

Authentic Sales speaker, The Sales Graze curator, Sales & marketing professional, avid reader, photography enthusiast and poorly-behaved-dog owner...