All Dressed Up and Nowhere To Go

Many years ago, I arranged a meeting with my CEO (we’ll call him Terry) to meet a new major donor prospect (let’s call him Joey).  Prospect Joey and his family were known to me (from a previous organization) and agreed to hear about the new cause I was representing.

CEO Terry had a strict rule when meeting with major donors (whether prospective or active):  always wear a tie and sports jacket. 

For this meeting, however, I assured Terry that we did not need to wear a sports jacket and tie.  I knew Joey well, having interacted with him and his family many times.  I understood the prudence of dressing professionally, however I knew it was a misplaced tactic with Joey.

On the day of the meeting I arrived early to greet Joey.  Terry arrived right on time wearing, wait for it, a three-piece black suit with a tie and matching pocket square!  I briefly introduced them, then Terry launched into a solid 73 minutes telling about our cause. 

All dressed up and nowhere to go.

I was heartsick.  After Terry departed, Joey looked at me and made this request: “Please don’t ever do that to me again.”  Yes Joey, and I’m very sorry.

Now, Terry is an easy target in this story.  He made several mistakes.  But here’s the mistake I made.  Although I knew Joey well, I did not prepare CEO Terry sufficiently to set him up for success.

Terry and I had only been working together a few short months. I assumed he would accept my advice on appropriate attire for the meeting.  I knew Terry was long winded, especially when nervous, yet I didn’t cue him on the most effective way to engage with Joey.

So, what do you do when you have a CEO who does not accept your counsel on dress, posture, loquaciousness, etc.?  Here’s my best suggestion:  You kindly prepare the donor prospect for the eccentricities of your brilliant CEO.  

It was clear to Joey that I failed to do my part in helping this meeting be a win.  Joey didn’t say to me, “Man,Terry really missed the mark by showing up in a suit.  Then he talked for 73 minutes straight and didn’t ask anything about me”.  Instead, Joey simply said, “Please don’t ever do that to me again”.  Message received, my friend.  Message received.

Here’s how I might have changed the outcome - just a brief conversation with Joey to cover a few essentials:

• CEO Terry is going to dress to the nines.  It’s his strict discipline in these scenarios.
• CEO Terry is going to talk a lot.  I’ll do my best to facilitate some interaction.  But this is going to be a bit of a firehose.
• The cause we’re representing is worth it.  I hope you will trust me in taking this step to meet with Terry.  He’s a brilliant guy and what he lacks in emotional intelligence is made up in strategic skill and economic ability.

Joey might have said, “Great, ok, I’ll give you 30 minutes.”  I would have said, “Wonderful, thank you. I’ll set up the meeting.

And I probably would have worn my favorite tie.

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Blessings,