Sales tips from a guy who hates to sell. You gotta believe.


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I used to see a career coach who told me that in order to get to where I wanted to be, I had to start from the bottom.

While I waited for folks to get on board and agree that I was the greatest thing since sliced bread – and pay me handsomely for my opinions and presence – I had to get a job.

And since I was transitioning from law to tech, I should use my gift of gab in an area that he thought would be a natural fit: sales.

The thing about his advice, while 100% accurate – I can sell – was the fact that I hate selling.

Well hate may be a bit strong.

I dislike it greatly.

And it’s not the act of selling that I dislike. I am a hunter.

It’s the things I have to sell that I generally dislike.

It wasn’t always this way.

When I was in high school I worked at Macy’s in the ladies shoe department as a shoe salesman.

Selling was a cinch.

To be clear, shoes sell themselves to women.

All I did was shuttle different sizes back and forth from the stock room until my client decided which pair (or pairs as was often the case) she wanted.

I’d ring her up, bag her goodies and she was off to shop some more, or to her car with the balance of her shopping spree.

Sure, I was masterful at upselling.

Transitioning a patron from a low priced item, say some 9 West black slingback pumps, to a higher prices one, like an elegant pair of Via Spiga heels that just arrived, was my forte.

But for the most part, I didn’t have to hard sell (or upsell) anyone.

Fast forward to 2008, the heyday of mobile marketing and SMS, when I worked for one of the three largest mobile aggregators selling mobile marketing to brands eager to get into texting.

The services sold themselves, and I simply guided green content creators through the short code acquisition mobile marketing campaign activation wireless carrier gauntlet.

In the process of demonstrating my expertise, I also upsold premium services and our platform, which allowed brands to publish their own compliant mobile ready campaigns.

As a captive audience, who had already taken the plunge to embrace the brave new world of mobile, selling (and upselling) was like shooting fish in a barrel.

But here is where my love affair with selling abruptly turned for the worse.

You see, my third sales or “business development” role was with an app development firm.

It was here that I understood that sales was not for me.

While I fully believed in the future of mobile, and was prepared to assail anyone who would listen with the wonders of developing mobile applications with us, my heart wasn’t in it.

I didn’t believe what I was selling.

Or rather, the thing that I was selling didn’t sell itself.

As a salesman, you can sell anything.

If you’ve got a silver tongue (as I did) a freezing man will buy ice from you.

And if you’ve got something that sells itself (or you believe that you do), the world is your oyster.

You can flit in and out of offices, meetings, conferences and presentations with a self assuredness that allows you to throw caution to the wind.

I’ve got it, you want it. Now, what will you pay me for it?

Selling was simple.

As was prospecting.

Lead generation was never an issue as we were on the leading edge of new technology.

Apps were everything.

Simply say the word “apps” and folks were rapt with attention.

And I sold lots of apps.

But then the company didn’t deliver.

Project after project became trapped in a bottleneck.

Features that were sold as standard became “premium” or required “custom development,” and I started to see the wizard’s cape showing behind the screen.

And that was it. I learned that I wasn’t built to sell just anything.

Actually, what I really learned was that I excelled at selling what I believed in.

Before the veil was pulled back, I would have sold anything to anyone.

After I saw the wizard, I became increasingly selective about what I’d co-sign, pitch or promote.

This isn’t really a “proper” tips post, but to stay true to it’s title, here are a few tips for being better at sales.

  1. If you need a script, don’t sell it. If you need a guide to sell, it’s not for you.
  2. If you wouldn’t buy it, don’t sell it. It’s hard pushing something you wouldn’t take/use yourself.
  3. If you agree with buyers’ objections, don’t sell it. When you find yourself agreeing with all the objections a potential buyer has for not buying in, you shouldn’t be selling it in the first place.

In the final analysis that’s the key: sell only what you believe in.

Because then selling comes naturally.

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