How My Mentor Led Me To Become the Question Queen

Dave was the most influential mentor in my professional career, hands down. Needing money for Christmas presents, I signed on for just a few weeks at a temp agency, placed as an administrative assistant at a large corporation. I had no intentions of working for Corporate America, ever. This was just temporary. I didn’t know at the time, how much my soon-to-be-boss would influence my career trajectory. Every few days during my short assignment, he would say to me, “You know Kathy, this is a full-time job that you can apply for, if you want.”

I would aggressively answer, “Thanks but no thanks.” What I didn’t know, is he saw something in me that was different. What I didn’t know, is he had gone through 23 assistants in his career, so knew when he found a good one. Since I kept saying no, he raised the bar on our equally-matched stubbornness by taking a different route: he asked two other assistants in our department to talk me into applying for the position.

I said yes. That began my corporate career over 20 years ago. I learned so much from Dave for the five years that we worked together. I observed him like a hawk, as he managed “up” to our CEO, managed “down” to his staff of up to 5,000, and managed “across” to his peer group, whom he needed to sell his ideas to and gain partnership.

Since I handled his day-to-day work life, I got comfortable asking him all sorts of bold questions to learn the lay of the land in this odd corporate world. After all, I had no interest in a long-term corporate gig, so I didn’t hold up my guard:

• “Why do you speak extra quiet during your leadership meetings? You normally talk a lot louder.
• Why are you flying to Connecticut for that [issue]? I thought you said you didn’t have much expertise in [subject matter at hand]?
• Why did you put John in charge of [division]? What do you see in him?
• Why are you investing time in leadership training for your team? They are so busy already…”

To not let me take the easy route, he would fire questions right back. “Why do you think I’m doing that?” Or, “Take a look at this [problem to solve]. What do you think I should do here?”  I had no idea that I was developing a skillset for critical thinking, question by question.

Dave finally kicked me out of the nest, by convincing a small part of me that I can do more. I can be a leader. I do have something to contribute. I met Dave for lunch just once after his retirement, during the early years when I still carried unsure wings. I remember asking him meekly, “How can I find a mentor?” I was really hoping he would mentor me from retirement to guide my new fledgling career. I was disappointed in his response. He gave me a vague, disinterested answer, something like, “Just get really good at asking questions, Kathy.”

Fine. In my stubbornness, I’ve taken his advice, trying to prove him wrong. The funny thing is, asking really good questions has taught me my most invaluable lessons. Along the way, it’s helped our team solve problems and projects achieve success.

And, as you anticipate, the best questions are always the most basic.

I’ll never forget the first time I took the risk of asking a basic question. I was running projects for a marketing team. With my crackled voice and heart pounding, I said, “Can you please explain what you mean by [fancy marketing word]?” Do you know what happened? I found out others had the same question, but were too scared to ask. After the meeting, the project sponsor pulled me aside, and said “Thank you so much for asking that question. I was really lost.”

With that reward, I kept asking questions.

Just a couple of years ago, I was leading an onsite session to uncover the unique value of a new clinical platform, so that we could develop supporting analytics and the storyline to share with customers. Of the 12 people in the room, I was the least formally educated with my meager bachelor’s degree. I was surrounded by big titles, fancy words and expensive watches.

Two hours into the six-hour meeting, we had a great conversation going. We were whiteboarding. We had product owners nodding their heads. We had two Really Big Titles really going at it, weaving together sentences they understood, using fancy words like “propensity to engage,” “algorithms” and “health continuum.”

The problem? I was lost. And, I was the one accountable for the meeting outcomes. So, I took a risk. I interrupted the Really Big Titles.

What was the best way to get their ivy-league attention?  Digging up my courage, I said, “You know, I am a farm girl. I am not a clinical expert. Pretend it is my first day of employment here, and please explain it to me, from the top.”

I immediately had their FULL attention. Challenge accepted.

They would talk for a few minutes, and I would interrupt and repeat back what I thought I heard. “So, what you are telling me is x, y, z….” and the first few times, they said, “No, not at all. What we meant was a, b, c…”

You know what happened? We finally made progress. They got better at explaining it, sometimes finding flaws in their own logic. Our whiteboarding turned into something that everyone understood. Those who were once sitting silent at the table turned on their light bulbs and chimed in with their own courageous questions. And that was when we moved from “just having a conversation” to achieving our meeting’s outcome.

This scenario happened on year 17 of my 20-year career. It still takes courage to ask questions, but that day taught me that I have to trust my instincts. If you’ve ever had a meeting with me, you know that I am not scared to ask questions if its warranted. They won’t waste our time.

Thank you, Dave, for all of the lessons you gifted me, and especially this quiet one of questions. The moral of this story? Don’t be afraid to become a Question Queen or King. It can be out loud in front of your peer group, or silently, asking questions to your own heart. Yes, it will draw upon your courage, and the rewards will exhilaratingly keep you on the edge of your seat.