Small Questions, Big Leadership

July 1, 2025

by Stephen T. Messenger

We are in positions of leadership to plan appropriately and solve problems. This charge is often easy to forget when the volume of small questions becomes overwhelming and all land in our lap. Multiple people asking the same questions can get frustrating, but it’s important to welcome those questions instead of expecting others to know every detail of what we’re thinking.

By listening to and answering these questions as they arise, we can both build confidence in our leadership and show people they’re valued. That lesson hit home for me just last week when I found myself navigating this very issue on two fronts: one leading an event at work and one volunteering at church.

I was in oversight of a large project at the Army War College. We, and especially the fantastic planners of the event, worked tirelessly for ten months to ensure smooth execution—and it was. But like every complicated project, there were countless questions from people that we’ve already answered through many emails, planning events, shared drive documents, and conversations.

Yet, the questions kept coming and were often asked while interrupting important events. It was easy to get frustrated by these distractions, and honestly, I was a little bit.

At the same time, I was volunteering at a Church Vacation Bible School each night. On the second day, I found myself doing the same thing that frustrated me with my people. I asked the leader, Elizabeth, a question that she already put out in an email I hadn’t read. After she cheerily answered it, I mentioned I’m running a project at work where people ask me little questions all the time, and I know her frustration.

Without missing a beat, she said: “Oh no, it’s great! That’s what I’m here for.” What a gracious response to someone in the organization. This simple, cheerful example of leadership helped me reframe my attitude towards questions at work the rest of the week.

Welcome the Problems

As Colin Powell famously said, “The day the soldiers stop bringing you their problems is the day you stopped leading them. They have either lost confidence that you can help them or concluded that you do not care. Either case is a failure of leadership.”

His words ring true across every stage of life. I saw this as a child and again as a teenager. At the first sign of blood, I remember running to my parents for help, knowing they would stop everything to assist. I knew they could help, they wanted to help, and they would help in the future.

As a teenager, I remember asking a baseball coach to help with a small scrape. He dismissed it immediately and told me to get back on the field. I didn’t come back to him for help the next time.

There’s a quote often attributed to Gandhi: “Your beliefs become your thoughts, Your thoughts become your words, Your words become your actions, Your actions become your habits, Your habits become your values, Your values become your destiny.” Every time we help someone in thoughts, words, and deeds, it becomes habit to them, and they know we’re on their side. Each question matters. Each answer matters more.

Building Confidence

The more patience we have in answering questions and fixing small things, the more confidence our people have in us. Four ways to do this are to show appreciation, follow through, eliminate judgment, and be decisive.

First, we should always default to gratitude. People show up to work every day looking to do a good job. People asking us questions is usually about them trying to understand and be better. Our church director did such a great job smiling and thanking people when they asked, including me.

Second, follow through on any commitments. A trusted leader is a credible leader. If we say we’re going to send an email, fix something, or figure out the answer, that should be the first thing on our to-do list.

Third, it’s our job to remove all judgement from the question. Sure, they may have all the information buried in their email, and we told them four times already, but it’s okay to tell them again and get them moving.

Finally, make a decision. When asked, it’s important to tell them the answer and have them execute. If we don’t know, quickly find out. We must quickly solve problems and launch people out to do great things, while we move to the next event.

Building Care

Once we’ve built confidence, the next layer is care. The second part of Colin Powell’s quote is to ensure they know how valued they are. We do that by showing empathy, being approachable, and recognizing contributions.

First, people ask questions because they’re confused. This is natural in big events—there’s a lot going on! We need to acknowledge that we may not have communicated clearly or put the information out. A little empathy goes a long way.

Second, as we’re moving around the event to check progress, it’s important to reach out to people, ask how things are going, and ask if they have any questions. We need leadership that wants to help and is looking to decrease ambiguity.

Lastly, appreciation is a superpower. The more we use those two coveted words, “thank you,” the more people feel valued and recognized. We’re not the only person working hard out there. It takes all of us rowing in the same direction. Our job is to appreciate the effort.

Accountability Matters

As a side note, we also need people to be prepared, study their profession, and come ready to execute. Little things will always slip, and that’s okay. But it’s also important that we hold people accountable when they’re simply not prepared.

We can create a shared sense of accountability by laying out clear expectations from the beginning, obtaining commitment in those tasks, and holding people to the standard. This creates an environment of shared goals and team dedication.

Bring Us Your Problems

When confidence, care, and accountability are in balance, problems become progress. When people are asking questions, it shows they care. We shouldn’t be frustrated like I was but instead emulate the Vacation Bible School Director who welcomed questions and happily solved problems.

Next time we get asked a question, let’s not consider it an interruption, but an opportunity to make things better.

Click here to sign up for The Maximum Standard’s weekly email where you’ll get a leadership vignette delivered for free every Tuesday morning! 

We’re always looking for authors. We coach first time authors (and anyone) through the writing process if you need a little help. It’s worth taking the first step and showing interest.

This website is a personal blog and all writings, podcasts, opinions, and posts are the authors’ own and do not represent the views of the United States Army nor any other organization. Podcast music credit in this audio file is to: “Alex Productions – Legends” is under a Creative Commons license (CC BY 3.0).    / @alexproductionsnocopyright