Is it just me, or are we having more town hall meetings because of COVID? In a recent Townhall meeting, I was reminiscing about my early career Townhall meetings.  Let me set the stage, I was young and ambitious, and I would ask that one question that would put me on the fast track to the executive suite.   I had no idea what I wanted or where I was going, but I knew I wanted to get noticed.

To get noticed, I would think about all the problems in my job and how the CEO could fix them.  Then I would ask a great question or what I thought was a great question. Generally, it was something like this "We have lost some important clients or employees, etc., how can you fix this."  What is funny is I expected the CEO to think, "What a great idea, I never thought about that." Instead, however, they probably thought, "what a stupid question," but said, "That is an excellent question. We know this is an issue and are working to fix it." Most CEOs have surprisingly high EQ, so you might get the answer you were looking for but not a positive impression.

What is funny is I was thinking that by solving my problems, the CEO would solve his problems.  I failed to realize that at the time that the CEO's problems were not mine.  I most likely just made him defensive by asking a question that assumed he was ignorant.  [Facepalm]

Fast forward a couple of years of asking dumb questions, and my perspective started to change. I was working in a small department of a billion-dollar company, and the CEO showed up to talk with a fortune 500 client that my department serviced. Since the CEO was in town, she graciously agreed to meet with our small team. Most of us were truly happy to have her speak with our group and were equally disappointed that the CEO could not solve our department's problems.  

One of my coworkers brought this up, and I ran the math and divided our department's revenue by the companies ($2m/$2b). We were a small fraction of business. Our CEO was not here to see us but to meet with the Fortune 500 CEO across the street. So how do you ask good questions when your problems are not the CEO's problems?

It is surprisingly simple.  Present the problem in a way that allows the CEO to share their perspective and experience.

"We have had a lot of attrition. What are you planning on doing to fix this?" Becomes "We have had a lot of attrition, and I am sure you have experienced this in your career.  What have you seen work and not work?"  

"We are working extra just get stuff done, what plans do you have to rectify this" Becomes "Given our current labor constraints, I am sure you have had seasons in your career where you have felt overworked, what did that teach you, and how will that guide you now."  

This subtle shift in question might not give you the answers you want, but they will give you insight into the leader's perspective.  And most importantly, you will have more of a chance to be noticed because you asked for advice vs. venting.

Five tips for asking good questions  

  1. The Executive is human, and their focus is on the meeting and getting their point across. Do you like when your meetings get hijacked?
  2. Ask for advice, not for their plan to fix your problem.
  3. If your question sounds like a complaint, don't ask it, rework it and then ask.
  4. Use "I" statements. For example, "Recently, I have felt like we have had too much change."
  5. Ask "How" questions and not "Why" questions. How questions lead to solutions and why question only questions the past and a lot of times don't have a good answer