October 28, 2020

Selling and my pal Gil Gunderson

Selling and my pal Gil Gunderson

If you’ve ever watched The Simpsons, you’ll have more than likely developed an affinity for one of the characters. Some people go for the main characters like Homer or Marge, while others are drawn to less obvious choices. For me, there is only one choice - Gilbert Gunderson. Usually just Gil, sometimes Ol’ Gil - and, always utterly desperate.

He shows up in one shape or form in over 70 of the shows 639 episodes. I’ll be honest, that’s a lot more than I thought. Gil is your classic overly anxious salesperson. The particular sales role changes from episode-to-episode, but there’s always a need to close the sale. It’s little surprise that he’s my favourite character as he’s the animated embodiment of Jack Lemmon’s character Shelley Levenne from the movie Glengarry Glen Ross. If you haven’t watched it, I thoroughly recommend it.

Here’s a bit of Gil in action -

I like Gil for another reason. I can relate to him. I have, at various stages of my life, been a salesman. I sold newspaper advertising for The Sunday Times and I sold outdoor advertising for Viacom Outdoor. Selling any form of advertising is tough and, I’m not ashamed to admit that at times I was a Gil clone. I was nervous. I was desperate. I tried too hard.

Over the last 6 years, as the owner of my own business, I’ve had to sell my services. The legacy of a less than stellar career in sales and the burden of responsibility for selling my wares, has weighed heavily on me. It’s been a cause of a lot of anxiety. A lot of it stems from my own lack of confidence, not in my ability to deliver my services, but in my ability to sell. During my career I’ve attended three different sales courses. I’ve also read a lot about sales and generally tried to up my selling game. The sum of all of that advice has largely been ignored.

A major breakthrough in my sales thinking came from my first sale in the business. It was February 2015 and I had my first ever meeting with a prospective client. I was nervous. We had a great conversation and they shared their problem. I shared some advice of how they could do what they needed without me. Then, they asked me for a proposal. I sent it. They hired me. And, just like that, I was in business. The lesson from that moment was, that actually, there’s very little selling that’s ever done. It’s a philosophy that I’ve carried forward. I don’t have ‘sales meetings’, I have conversations. If over the course of that conversation someone thinks I can help them, then they’ll ask me to do just that. In the vast majority of cases that means going away and creating a proposal and sending it to them.

Even then though, I had a tendency to be ‘persistent’ with my follow-ups. Now, in sales, you’re taught that the ‘follow-up’ is an absolutely essential part of the process. You’re taught to be tenacious, consistent and relentless until you have a decision. I applied a ‘three strikes’ approach.

  • Strike 1 - The proposal is sent.
  • Strike 2 - I follow-up
  • Strike 3 - I follow-up… again.

That was my logic and I said that I wouldn’t continue to follow-up as it looks, you know, desperately desperate. Here’s the thing though - in many case I absolutely was DESPERATE. So, I kept on following-up. I’ve only had two moments where the response has made me cringe.

“Yes, we got all your emails, we’re very busy with other priorities right now. If we decide to go ahead, we’ll get back to you.”

It’s a polite but clear passive-aggressive message that essentially says - ‘fuck off’.

The universal truth of buying, now more so than ever, is that we don’t like being sold to. The converse is, in most cases at least, we do like buying stuff.

After that response and one or two like it, I realised something incredibly important. It’s either important to them or it isn’t. From that point on, the tone of ‘Strike 3’ changed to a message that basically said, ‘if you need me, you know where I am’. It was liberating to take back control and to mentally move on.

This year, I’ve simplified the process even further. I send the proposal and a week or two later, I send an email that says, ‘if you’ve got any questions, just let me know’. That’s it. With that 2nd email, my job is done.

This week a new sale was confirmed that proves my point. I had a conversation with this organisation in June. They asked for a proposal which I sent the week later. I followed up in late July. The sale was confirmed in late October. It came as a nice surprise, as I’d genuinely forgotten about it. For me, that’s a real mental breakthrough. I now realise more than ever that if someone wants to work with me, it’ll happen.

My former sales managers and sales trainers would tell me that this approach is wrong. They’d argue that ‘I’m leaving money on the table’. They’d urge me to reconsider and remind me that sometimes people just forget. I’d politely tell them that I can’t be sold on their way of selling.

My way might not be conventional, but it works for me. If it didn’t, I wouldn’t be in business today. And, even more importantly, it works in a way that causes me the least amount of stress and anxiety. I am not sharing any of this as part of some revolutionary selling counter-culture. And, I am absolutely not looking to shame anyone that sells differently to my approach. While I don’t advocate my approach, I do advocate finding your own way.

It’s taken me the best part of 27 years to get to this stage, but the destination is great and the long journey, despite the odd pothole, was well worth it.