Memorable Inquiries: Asking the Right Questions First

Yeah, I've been that person that raises my hand more than classmates or meeting attendees like to see. It used to bother me, my mother's voice in the back of my head telling me not to come off as a know it all or suck all of the time and attention from the room. But after a while, I saw it more as a part of the exchange with the teacher or the speaker. Perhaps it was the more I was on the other side of the discussions, I realized how valuable well thought out questions could be.

After speaking on a panel this past week, the moderator reflected to me, post session, how much she enjoyed my different perspective on the topic we had at hand. It's not the first time I've heard this. Similar sentiments have been shared in regards to the type of questions or hypotheticals I propose as well. Of course there's times when my inquiry or insight fall completely off mark, but even that tends to be something folks remember.

And it all got me thinking. How the heck did I get here? To being someone that will reach out at a moment's notice to ask "can we talk about xyz topic?" or the person who never hesitates to fill an awkward silence if it presents itself. Like the analytical mind I can be, I parsed out what made it work for me. The magic memorable sauce so to speak.

Here is it.

I ask questions that I already know what my answer would be.

I don't ask them out of self validation, I ask them because perhaps I've gotten stuck in my assessment and problem solving somewhere along the way, or because I'm hoping a diverse perspective may help pressure test or enhance my thought process, maybe I'll find a partner in the effort I'm focusing on.

Here's an example.

In 2024, I attended what's called the American College of Healthcare Executives annual Congress. Basically a huge conference attended by middle and executive leaders across hospitals, insurance, consulting, tech - all of the healthcare industries. On the last day of the conference, there's a half day to a full day that was set aside for the military and Veterans Affairs attendees. It was a highly supported event by leadership and allowed for a few hundred folks to get together with senior leadership for a symposium of our own. That year, the sessions had really stoked a fire in me that we could do so much better. Having taken over Enterprise Risk Management for the whole org, I was seeing so many problems and so few effective solutions, something not unexpected for an organization the size of VA, but still, something we should always be working on.

The Undersecretary for Health, our equivalent of a CEO, was Dr. Shareef Elnahal. He was actually younger than me and one of the better speakers and presenters. We hadn't worked closely together but would cross paths over that following year until his departure with our new administration. He held time for questions after his overview, and, of course, I decided to take a shot at a possibly tricky question.

"How can we better understand the needs of medical centers as central office programs? To move from putting fires out to putting up smoke detectors, to truly meet the needs in being less reactive and more proactive?" Someone clapped, then a few others.

Dr. Elnahal paused and said "I'd like to hear your thoughts on what you'd do."

I was ready. I'd been stewing over this since the problem first arose. So I pitched the very general idea. I stated we needed to sunset metrics, we needed to push back on the idea of following everything under the sun, that we needed to assess what site visits were necessary and what were already being done by other groups, and that we needed to work together and ask the hospitals to be patient with us and trust us."

No concrete solution by any means, but, sprinkling in a few tangible examples helped my proposition. When I was done, the claps were louder this time. Dr. Elnahal supplemented my response and afterwards, a set of hospital leaders and corporate leaders approached me and thanked me for raising the concern.

Anyone who's work love language is words of affirmation, you know darn well I was riding high the rest of that day. I never did get the chance to make the bigger wave of change that I wanted, but I at least threw the pebble in the pond. The ripple was started and, if ever given the chance, I'd prob jump back in and try to pick up where I left off.

Dr. Elnahal, most of the senior leadership team and I have all moved on since the start of 2025. Continuing our efforts to improve health care delivery for veterans and others through different pathways. But I still ask the question. How can we do "different"? Not better, not faster, not smarter, but differently.

When I interview people on the podcast, I think of questions that I truly want to know the answers to, like absorbing their knowledge over the course of that 60 minutes into the sponge of my mind. And I think of questions that I would want to be asked if I was in their shoes. I ask the question they might be afraid is coming, along with one I know they'll breathe a sigh of relief over.

There's a quote by Claude Levi-Strauss "The wise man doesn't give the right answers, he poses the right questions."

Maybe that's why I got into this line of work, looking at risk and consequence, assessing outcomes and diving into root causes. I know, in many cases, I may never find a true answer, however, at some point, I may have exhausted all of the questions I can. At least, for now.

So next time, I challenge you to stand up and ask a question. Don't worry if it's silly or if someone will grumble that you're extending the class or the lecture. Ask it with curiosity and hope. Know that whatever preconceived answer you have may not match their response and accept that the differences are what ultimate expand our knowledge and our chances of change. Welcome being asked questions that are uncomfortable, that you feel you don't know the "right" answer for, and strive to inject your passion into all that you do.

That's how you become memorable. Not because you aced an answer - something that really only you may know - but because you had the most thought provoking inquiry in the first place. That is the thing that everyone can truly appreciate.