I got my first sales job at 16.

It was an uphill struggle at first, but the moment I made my first sale, I was hooked.

The excitement of the hunt, the nerve-wracking adrenaline rush of the close and the elation when the client says yes.

It’s a high that never gets old, and other than university and a brief stint in banking and real estate (kill me), I’ve worked in sales my entire adult life.

Perhaps the most important lesson I’ve learned is that you always need to be moving forward. 

Selling is a painful business.

The highs are stratospheric and the lows are canyon-like.

And what better way to illustrate exactly that, but with a story.

So gather around the bon-fire ladies and gentleman – it’s story time.

It’s time for the story of the most painful sale I ever lost.

What happened was this:

A colleague of mine had booked a meeting with a person in my territory, and so had handed off the lead to me. He’d booked the meeting and gotten an initial idea of what the client was looking for. The first thing I noticed about this particular lead, was that it was a solid potential client, but the person the meeting had been booked with was not far enough up in the system to be considered a decision maker. At best he could influence the sale, but the signature on the dotted line (and the money) had to come from someone else.

Armed with this knowledge, I called the client and introduced myself, as well as told him why I was taking over, and that we should set up a meeting to explore his needs, in order to see if there might be a basis for doing business together (note: I didn’t ask him for a coffee meeting, or a touch base meeting – it was very clear to everyone, that this was a business meeting). This made him feel important and included in the process, which in turn made it easier for me to get to the true decision maker, as we’re about to see.

Before the first meeting I reached out to him over the phone, rekindled the conversation about the high-level goals he was aiming to achieve (as he saw it) and asked him what the biggest challenges were to achieving these goals as he saw them.

Now – I know that you might think to yourself why in the world would I do this, with a person who is not a decision maker? 

The reason is that I had a strong inkling that he would be involved in the decision on some level, and might be crucial to execution later on, and so I would shoot myself in the foot, if I failed to establish trust with him.

So I did.

I spend that extra time building trust, because I knew that it would benefit everyone involved further down the line.

Once he told me his goals and challenges, it quickly became clear that they were operational – and I needed to get into the strategic side of things (because that’s where the money is). But instead of going over his head, or asking him if I could talk to his boss – both of which would have been self-defeating, I asked how do you usually make these kinds of decisions here? 

His answer?

Oh, we need to talk to Bob who is the head of commercial. 


And if we want to give ourselves the best shot at resolving the issues you mentioned earlier, how do we best approach him in your view?

Now we’re together – in the same boat, working the problem.

That’s easy, I’ll just explain what we’ve talked about, and set up a meeting between the three of us. 

Here’s where I knew I needed to watch out, because if I let him take the lead on this, then there was going to be a 100% chance that he’d misrepresent our conversation – not out of any ill will, but simply because he’s never going to know what I’m trying to communicate in the same level of detail, that I will – so I needed to make sure that I would talk to Bob first.

Again – I had to be careful so as not to step on his toes.

So I said:

You know in order to save you the time and effort (client benefit), how about you let Bob know I’ll give him a call, and I’ll set up the meeting between us, when it fits all of us?

I kept the ball in my court, while signaling that I’m working on his behalf, and he just needs to take care of his own business – in other words, a I took on the role of partner he could trust.

Solid. I’ll let him know you give him a call. 

So I call Bob and give him an outline of what we’ve discussed so far, and that I’m interested to learn about his agenda, as well as the challenges that he sees.

Within two minutes we agree on a time and date for our meeting.

I follow the same recipe as before – only this time we quickly get to talking about what they’re looking to do. They are in the market for the service we provide, and it’s essentially a beauty contest between us and a competitor.

So then, we transition into talking about how he prefers to roll this out in his organization, which pitfalls to avoid, and I position myself in relation to our competition in a straight-forward and easy-to-understand manner. Everyone is on board, and it’s clear that we’re the preferred choice.

So I go back and design the solution, based on what we’ve discussed, take it back and give them the presentation of a lifetime.

In Bob’s words; another masterful presentation – you really hit everything we’ve talked about on the head

At this point I’m thinking I’m golden- there is no way I’m going to lose this one…

Bob calls me up a week later and lets me know they went with the competitor.


I’m outraged. I have no idea what I did wrong, and Bob doesn’t really offer much feedback other than his higher-ups had decided they liked the other guys better, because they’d previously worked with them.

I hung up, and hung my head for a little bit.

That one hurt like a son of bitch.

I’d done everything right…

Hadn’t I?

Then I started reflecting on the process.


No one said anything about higher-ups.

But then again I hadn’t asked.

I’d taken for granted that because Bob was head of commercial, that he’d be the one making the call.

But at the end of the day, everybody has a boss to please.

Looking back on my presentation as well I couldn’t help but feel, that although they’d praised me for it – something was missing.

And the more I thought about it, the more I realized that it had been me presenting to them.

We hadn’t hashed things out together. I hadn’t involved them in the creation of the solution.

At the end of the day, all I had done was tell them how was going to solve their problem.

In other words I was the hero of the story, and they were merely bystanders, when in truth it should have been the other way around.

What this painful experience taught me is that: 

  • Never take for granted that you know the entire stakeholder landscape – and even if you think you know it, asking one more time doesn’t hurt
  • Design your solution to make your client the hero of their story – not the other way around

The value of these lessons learned turned out to be real, tangible and almost instantaneous…

But that’s a story for another time.

Until next time.



Share on facebook
Share on twitter
Share on linkedin