Make the Ask, Take the Silence

It was intense. I was a new candidate and decided to test the adage:?“The first one to talk— loses.”

I found myself in front of a prospective political donor whom I had not met.?His volatility reminded me of Joe Pesci’s “Tommy” in Goodfellas.?I didn’t have anything to lose, so I decided after I gave my pitch and made my “ask” that I wouldn’t say another word until he gave me an answer.

By my way of thinking, there were three things he could say which would prompt a reply from me. They were “yes,” “no,” or “I’ll give you less.”?If I didn’t hear one of those, I was not going to say anything.

This sounded better in my mind than when I actually sat across from him in his office in the middle of his work day during time he was making in his schedule. After some chit-chat I came around to my pitch and then said:

“I wanted to ask if you’d be willing to contribute a thousand dollars to my campaign.” ?

— FULL STOP —

(A thousand dollars was the maximum allowable contribution almost 25 years ago and it meant something then.)

It got very quiet, very quickly, and he looked jarred, as if I had cheated him.?I had just slammed on the conversational brakes, and he had the expression of someone who had hit his head on the dashboard. Immediately, I second guessed myself. Who did I think I was, coming into this guy’s office, taking up his time by playing some game?

I was tempted to say “I know it’s a lot of money” or some filler which would undercut me but somehow I resisted.

After an uncomfortably long pause, he replied in disbelief:

“A THOUsand dollars ?!”, with emphasis on THOU.

That was a question, not an answer, so I stayed quiet.?He looked put-out as more time elapsed.

“That’s a lot of money!” he declared.

That was a statement, not an answer, so I stayed quiet.?I’m really uncomfortable now. ?

Tick.?

Tock.

“Let me get this right.” (This is never a good sign.)

?“You want me,” he continued with his thumb to his chest,?“to give you a grand?” he said snapping his index finger at me. His Chicago accent completely flattened out when saying the word “grand” with a hint of menace. ?I’m starting to free fall. ?

Tick.?

Tock.

“Why does a nice young guy with a cute family want to go to Congress? ?That place is a snake pit.”

Question and statement. Not an answer.?

He looked over my shoulder as if off in the distance, and I sat still as if the dentist was going to?drill.?His eyes suddenly focused on mine and, looking like a stone cold killer, he said:

“Okay.”

Whew!

In the years since, I’ve had thousands of fundraising conversations and raised tens of millions of dollars for my campaigns for office.?I developed a better handle on how to ask and became more comfortable with silence in conversation.

The principle applies whether raising money, making a pitch or asking for an order.?As the end of your Q2 approaches, give it a try:

1. Make the ask clearly without undercutting yourself.
2. Take the silence and give your interlocutor time to think and respond.
3. Measure the results.

Let me know how it goes in the comments below.