Asking Better Questions

Part of my job is meeting with management teams from publicly traded companies to evaluate their corporate strategy. I love my job, because I’m constantly learning, contextualizing, and evaluating. I don’t love that it forces me to make decisions without complete information, sometimes the truth of obfuscated, and making mistakes is costly, but part of the job.

It was a tough week at work and busy one at home. As I was packing myself up to go home Wednesday night I said to my associate, “I hope nothing bad happens tomorrow.” It was an admission of submission to the pounding I had taken on a number of fronts and maybe my bone tired body talking. Thursday was a better day. I was wrapping up my week as we are currently on our way to my cousin’s wedding in North Carolina.

Yesterday included two management meetings. At the end of the second one, the CFO said, “You ask really great questions, but even more you turn my answers around on me to get to what you want to know.” I totally blushed. First, it was a really nice complement. Second, it validate something I’ve been working on. He went on to say, “How do you do it?” I didn’t want to go into an in-depth explanation of how I have been practicing asking questions that get to the meat of the issue.

My response, “I have to give a lot of credit to my five-year old. He loves to give one word answers and try to evade my questions. It is a daily practice that helps me sharpen my skills at getting to the real answers.” We both laughed about it and he joked, “Your kids aren’t going to like you when they are teenagers.”

Probably true, but I hope that no matter how annoyed they are with my nosiness they will know that I’m interested in them. I hope they can recognize my exculpatory questions as me caring about what is going on in their lives. I hope my questions remind them that they can come talk to me about anything, even when I’m not asking the questions.

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2 thoughts on “Asking Better Questions

    • Some of my favorites right now at home:
      What is going really well at work/school/volunteering/home?
      How are you feeling about [something that is really important to the person – a project or the like]?
      What made you laugh today?
      What has been making you feel lonely or unworthy? What can I do to help change that?
      What happened today that was totally unexpected?
      What did you enjoy doing most today?
      What are you looking forward to most this week?

      At work, I try to implement a strategy where we get “off script.” You know how you end up in a meeting and the message triangle/talking points are so strictly adhered to… one of the things that I’ve had success in is asking questions about what others are doing well or poorly. In talking about things that others are doing well, there gets an avenue to talk about what the person/organization can do or system in place to make progress toward the same outcome or learn that it isn’t a desired outcome for them. If it is something someone else is doing poorly, I find we can talk about why it is a threat within their own business and how they guard against it. I also employ a technique where I ask for more and more detail when there are too many generalizations. The opposite sometimes works as well when someone uses so much detail to try and obfuscate (I often find that an overwhelming amount of detail is a sign of a lie) coming back with, “How would you boil this down and explain it to your mother?” Once the playing field is leveled, you can start directing the questions to an area you want to go. Ultimately, I think my “secret” is being curious and not being afraid to ask stupid questions. It’s always the simple questions that end up being the zingers.

      Liked by 1 person

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