How to sell IT to a cranky millennial

I am regularly accused of not liking salespeople, sometimes by the salesperson I’m currently meeting with. I don’t think this is true, but I can understand why one might think it.

If I smell blood in the water – an obvious lie, hyperbole, arrogance, insincerity – I go for the jugular. An example must be made, a lesson taught. I don’t mean to be this way, it’s just something in the way I’m wired – a neurological pre-disposition to not suffering fools.

To be clear, my hostility is not directed at the person, but the role they are playing, in many cases, the role they have been taught to play.

Truth is, I’m fine with salespeople. At several points in my career, I’ve been one. I have stared into the abyss of constant rejection. I’ve felt the pressure and inadequacy. Sales can be miserable and, at times, soul crushing.

What I actually dislike is the Game of Sales, the wagon wheel ruts that so many salespeople fall into and never steer away from – the pitching, the talking in circles, the “I read it in a Zig Ziglar book” tactics, and oh-my-God, the presentations.

I reject the notion that this is the way it has to be, that this is just “how it is” and everyone needs to get on board, power through, and get comfortable with never saying what they mean in a sales meeting.

It can be different. It can be so much better and it all starts with one thing.

Ask questions, and listen

I’ve lost count of the number of salespeople who’ve told me “Our customers love us because we listen to them.” and then proceeded into a lengthy soliloquy about how awesome their company is.

They talk about partnerships and our future together, coming off like the psycho person who talks about marriage and kids on a first date.

If we’re meeting in person, they probably brought a PowerPoint deck with lots of slides showing awards and Gartner Magic Quadrant placement and some insufferably cliche mission statement.

Guess what? This might hurt a little, but your prospects don’t care who you are. If they agree to anything as the result of your pitching, most of the time it’s just to get you out of their office.

As for partnerships? If you’ve pitched a partnership at our first meeting, I don’t want it. I don’t even want to be your customer. Partnerships are forged and justified by time, information, and action. We have none of those things together. What you’re really asking for is un-earned, blind trust so you can sell me the moon with no questions asked. Sorry, but no.

Try this instead: Ask questions.

  • “What do you need?”
  • “What’s causing you guys the most heartburn right now?”
  • “Tell me about your business.”
  • “What’s the next six months look like? Where do you want to go with this stuff?”

And just keep asking questions. Hone in on the problems your product or service can help solve. Gather information so that the next time we meet, you actually have something worth presenting: how you can help, which is 1000x more important to a prospect than anything else you’ve told them.

Maybe the answers to your questions reveal that you can’t help. That’s a real thing, accept it. What you’re selling doesn’t work for everyone.

Instead of wasting time chasing the prospect with follow-up calls and e-mails, and driving them to never wanting anything from you even if you could help, how about you shake hands and move along to someone else you might actually be able to help?

This works. It absolutely works. I’ve sold way more by asking questions than I have by pitching and I’m a lot more receptive to salespeople when they approach me the same way.

One of the earliest big sales I closed still sticks with me, not because of the dollar amount, but because of what the customer told me and my business partner after we closed.

“Out of all the companies who came in here today, you’re the only ones that asked me what I needed.”

Image Credit: Elias Levy