Pitching like a pro

You'd think after a spectacularly unsuccessful career in advertising/TV/publishing and film, and at the ripe old age of 44, I'd be good at pitching ideas. But the truth is I suck.

It wasn't until recently that I have discovered, as in so many things, that I had been doing it all wrong.  And I didn't know that until my wife purchased me a yearly subscription to the Masterclass series.

Recently, I started taking classes with Daniel Pink, a NY Times Bestseller and former speechwriter for Al Gore, who discusses, quite elegantly and rigorously, the basics of salesmanship. Again, you'd think I'd know a little about that stuff but it turns out I know more about HVAC repair. And I know nothing about HVAC repair.

I'm halfway through his course and stumbled upon a 25 minute treatise on pitching ideas. As I mentioned on a podcast last week, I had the good fortune of walking into so many business pitches with the likes of Lee Clow and Steve Hayden. 

The way they command a room is simply masterful. As such my partners and I rarely had to do any actual convincing. We simply had to be jovial and enthusiastic. And we had to hit our punchlines and crescendos the right way. It worked.

But there were many, many more instances when we were not accompanied by these ad legends. And our schtick often fell flat. Followed by excessive drinking and even more excessive self loathing.

Well, as they say, recognizing the problem is half the solution. Other solutions, proffered up by Mr. Pink, who eschews the notion of a vaudevillian song and dance, include starting each pitch with a question as opposed to a declarative statement. This was put to great use by Ronald Reagan of all people, who in 1980, asked, "Are you better off today than you were 4 years ago?"

The question invites collaboration, which has always been a dirty word in my book. But now I'm burning that book and trying new things.

Another winning technique suggested by Mr. Pink is the rhyming scheme. Turns out our brains are hardwired for this. And its visceral nature pays dividends. Think back to the OJ Simpson trial and the remarkable effectiveness of, "If the glove does not fit, you must acquit."

At the end of the class, Mr. Pink addresses the changing landscape of advertising and how so many of our interactions no longer happen on TV or in print but come via email. 

And as someone who is unashamedly paying bills and putting food on my table thanks to this medium, my ears and note-taking pen perked up. Because our success in this arena depends on one thing...

Winning email subject lines -- and lets face it these are like headlines from a different era -- rest on two pillars:

1. Utility

2. Curiosity

With so many emails filling our mailboxes everyday, the trick is to blend the two in a way that makes that itchy finger on the mouse make the click. 

I'm getting better at it. But I want to get great. Because if I can, who knows maybe I can stick around the ad thing for another twenty years and retire at 64. 

Wish me luck.