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Converting the Cynics

Why you shouldn't shy away from engaging with the most vocal skeptics in the room

About a decade ago, I was the president of a local chapter for my college alumni club. Every so often, we'd bring together fellow alums for a networking happy hour, a panel discussion on the state of the industry, or another social event.

As an entirely volunteer-run group, we were always hurting for more on-the-ground support at events and on our working board of directors, which meant we were nearly always scouting for additional recruits.

I did my best to meet as many people as possible. You'd typically always see the usual crowd of fresh-out-of-college graduates, the ones still too-eager to impress the visiting professors with their latest real-world accomplishments. But every once in awhile someone would show up for the very first time.

"What brought you here today?" I remember asking one woman, who had graduated something like 20 years before my time.

"I haven't been to one of these in so long, I thought it was just about time to come back."

"That's nice," I invited.

"To be honest," she interjected, "I think what's going on is just terrible. Zero engaged with seasoned alumni like me, I only ever hear from the school when they want my money."

"I know what you mean..."

"And too many happy hours! Is that really the best way to forge smart, intellectual connections among our peers? It's almost as if you don't care at all about getting to know people of my generation. Between that and all the sweeping fundraisers, leadership changes, and complete abandonment of journalistic integrity, I've just about had it."

I looked at her thoughtfully for a minute.

"Would you consider joining our board?"

She was taken aback by the request. "You don't want a grouchy old lady like me," she protested.

"Yes," I insisted. "We do."

I introduced her to several of my peers on the board and she joined us about a month later.

Flash forward back to this summer. I attended an alumni event for the the first time in a really long time. I showed up, a little bit annoyed, a little bit curious. Guess who I ran into?

"Do you remember me?" she asked, gleefully? "Remember how I was the one who complained so much and then you got me to join the board all those years ago?"

"How could I forget?" I smiled.

All these years later, and she's still one of the most actively involved board members to date.

That's why I love converting the cynics. Most of the time, their cynicism comes from a place of perverted passion. If you can tap into them in just the right way, they'll bring it back. And they'll be the ones who keep showing up, even 10 years later.

Converting the Cynics (image source: DALL-E)

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