Great questions have the power to build immediate connections and deeper relationships in our personal and business lives. A common thread with people that ask great questions is they spend more time listening than talking. I was recently interviewed by Patrick O’Shaughnessy and the last question he always asks his guests is: What is the kindest thing anyone has ever done for you? It’s such a great final question because it ends the podcast with a spirit of kindness and gratitude which humanizes the guest.
As a full-time microcap investor, I talk to a lot of management teams. What you ask, how you ask it, and when you ask it, can mean the difference between acquiring useful differential insights or just wasting time. Chip Maloney wrote a great article on – The Art of Interviewing Management.
Power Questions by Andrew Sobel and Jerold Panas is an excellent book that highlights over 300 essential questions that can lead to deeper meaningful answers. In each short chapter, they highlight a question(s) using their real life professional experiences consulting with hundreds of management teams. They go into detail on 44 of these questions and give a list of 293 more in the back to use in different situations.
Quite often I’ve been on the phone with a CEO or management team and you can sense they want to say more. A simple question the authors talk about which I’d like to use more effectively is “Can you tell me more?” Or when someone is complaining about someone and you need to refocus them on fixing the problem, “What do you wish they would do more of?”
Let me give you an example of a bad question [the authors agree] to ask in a first-time meeting with management:
“What Keeps You Up At Night?”
Early in my investing career I used to ask this question, until one day I asked it to an executive and he replied, “Son, do you expect me to tell you the truth? I don’t even know you”.
He was right. It was a stupid question to ask him, and I immediately took it out of my question set. Don’t expect a personal and real answer from a person you don’t have a personal and real relationship with. “What keeps you up at night?” is an impersonal lazy question to ask someone you barely know.
The first step to asking great questions is listening more and talking less. Power questions can be very potent and influential. Add them to your life.
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