When You Need to Sell, Stop Pitching

A couple of months ago, I managed to have a CEO leave a comment on one of my pieces. This wasn't just any CEO. It was a CEO whose company and work I'd admired. I'd been trying to connect for weeks, if not months. So, I was pretty psyched. I thought maybe I'd finally overcome the hurdle to a relationship I wanted and, potentially, a chance to learn awesome stuff one on one.

For the first couple of messages we sent back and forth, I felt like Riff from West Side Story, singing a message to myself -- just play it cool. I didn't want to mess things up by coming on too strong too quickly, so I took time before each response to think about how my words might come across. The CEO asked some questions and seemed genuinely interested in the topic of my piece.

Then it happened.

The CEO mentioned a new investment.

I should definitely consider this investment.

Did I want more information? It was legit. I should invest.

From that point on, everything was the investment. Pressure. Insistence.

I felt like somehow I'd teleported into some alternate dimension where survival meant beating off pushy car salespeople with a stick.

I sighed.

I politely thanked the CEO for inviting me and told them I wasn't in a position to invest.

Was I sure? They could send me more information. No trouble.

Oh. I was sure.

I was also sure I no longer wanted to deal with this CEO.

The conversation fizzled over the day. Perhaps I should have been more patient, but I didn't try to reengage.

Setting expectations

Three words sum up everything about why the experience was so icky for me.

Bait and switch.

I started to engage with the CEO believing we were going to have a genuine conversation about something I cared about. I'd been made to feel for a moment that the CEO and I were on the same page about the issue and that we might have a fruitful and stimulating discussion about it. I'd expected them to listen to me but, because of their experience and standing, to also perhaps offer some wiser insights and counsel. I was so excited at the prospect of insight and counsel!

My expectation, based on the initial way the CEO reached out, was to build a relationship, not to be sold to or pushed into something.

The abrupt pivot toward the CEO's opportunity, however, left me feeling like their initial engagement had just been a ruse. Perhaps if they'd merely mentioned their investment offer to me in passing instead of insisting that it become the new conversation focus, it might have come across differently. As it was, I left feeling deflated, naive, and guilty for my own disillusionment. It felt worse than interacting with a pushy car salesperson, because at least with a pushy car salesperson, you know the intent out of the gate is to sell cars.

Validate first, offer second

There's a valuable lesson in this experience for others who, like me, are still making their way and building careers -- not everyone you laud is worth the laud. Don't let yourself be so starstruck that you forget that those you look up to can suffer from misjudgment.

Focusing on the leadership aspects, though, having written for professionals for years, I'd like to think that I understand how difficult it is for high-level leaders to turn off their business brains. After so many hours looking toward the bottom line and searching for every possible way to convert someone into a customer, shutoff of the sales compulsion isn't going to happen easily. I can be a little forgiving to the CEO I dealt with because of that.

But if I could tell leaders anything based on what happened, it would be to think about how those without your clout are going to perceive and hope in you. In connecting with you -- you, with everything you've done and accomplished -- average Johns and Janes see possibility for themselves. That doesn't mean you can't tell them about an option eventually. It just means they want validation first and offers second. If you flip the order, you don't just risk the loss of the sale and make them feel like a number. You make them lose the sense that good, caring people can reach down from the top to listen and help them get closer to their own dreams.

And that's devastating.

Don't take your authority as blind license to keep filling your cup

If you are privileged enough through merit, luck, hard work, or all three, to find yourself with younger, less experienced people eager to interact with you, don't take it for granted. When you need to sell, stop pitching. By giving yourself, the sale will happen on its own.

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