I piss people off. I piss people off because I’m curious. I like ideas. I like intractable problems. I like to make people think. I like asking the tough questions. You know, the questions which need answering if you are going to go forward, make progress. I like questions which dig deep into people’s motivations.
Kathy and I attended a dinner party over the holidays. It included three couples plus our host. The condo was decorated beautifully. The spirit of Christmas and family was everywhere, as was evidenced by the photos and keepsakes. It was a warm and inviting environment.
Over dinner we all shared what we did for a living. Our host was in real estate. The husband of our friends in the building was retired from the JAG unit of the Air Force. The couple we had just met included a husband who is a retired serial entrepreneur and a wife who leads the regional office of a large wealth management firm.
Why Would He Work for You?
The wealth manager was very interested in what I do as an angel investor. She asked lots of questions and really got me talking about myself, my investments and my family. Then she said, “I would like to connect you to a former entrepreneur who works with me. I think you’ll have a lot in common.”
I asked, “You say he was an entrepreneur.”
She said “Yes. He was very successful. He built a software business in the healthcare market and had a large exit.”
“Now he works for your wealth management company?” I asked.
She answered “Yes. And he is doing an incredible job for us. I am not asking you to meet with him so he can sell you on becoming a client.”
“I’m not concerned about that. But I am curious as to why he would take the job to do business development for your firm,” I replied.
She said, “Why wouldn’t he work for us?”
I said, “Because he is independently wealthy and comes from the software business. It doesn’t make sense to me. That’s why I am curious to know why he joined you. What’s in it for him? How does it fit into his plan?”
She said, “You are asking me his motivation for taking the job.”
“That’s right,” I said.
She said, “You should ask him.”
I said “Since you hired him, you must have been curious about his motivation yourself. You had to know this before you offered him the position. So why did he join you?”
“That is not for me to share with you. If you meet with him, you can ask him yourself,” she responded.
At this point, the tension was so high someone else stepped in to change the subject. I wanted to know this guy’s motivation, and so I was going to keep asking. She was dug in and pissed at me. So much for my dinner party questioning etiquette.
This conversation really bothered me. In reflecting on the conversation, I wondered what I could have done differently. I became so focused on wanting to know the answer to my question, everyone else at the party disappeared. It was me and her. I was going to get an answer, but she wasn’t going to give it to me.
A Few Months Later
A couple of months later, I was at a lunch meeting with a Venture Capitalist friend. He asked me about my investment portfolio. He zeroed in on one of my investments and said he knew someone who might be able to help me.
Guess what? It was the husband of this lady I verbally sparred with at the dinner party.
I told him the story of the dinner conversation. He laughed and said he is personal friends with the guy I was interested in. He said his friend took the job with the wealth management firm to build his network with wealthy individuals and families. He figured he could do a good job for the wealth management firm, get paid an attractive salary and build a new network, all while determining his next steps in life.
I said, “That totally makes sense to me.” I finally got my question answered.
Now I ask myself, “Was being abrasive worth it?”