Influence Change by Asking, “How and Why?”
Leading with curiosity: How asking strategic questions drives change and influence in any environment.
I grew up in a time and place when children were expected to be seen and not heard. Both of my parents were Marines, and asking questions could easily be considered questioning authority—with disastrous results for the asker (me). But I was lucky. Dad was a master strategist—he had to be, given that he was punching above his weight to snag my mom. At work, he leveraged his strategic curiosity and tactical skills to make necessary mid-course corrections because he understood his missions and ultimate goals—not just a small part of them. My mom grew up helping to run a Louisiana household with her 14 siblings, and in her career, she held her own in one of the most male-dominated environments imaginable. Both of my parents knew how to think and work with limited means, information, and resources. Fortunately, by the time I came along and began asking questions, they had found ways to pass those crucial skills—and many others—down to me.
All children ask, “How?” and “Why?” Most parents, however, have a limit to how many times they’ll answer before getting annoyed. My parents were no exception, even if their limit was closer to zero or one. So, I learned to choose my questions carefully. There was no asking just for the sake of asking, and no wasting questions that could be answered with a simple yes or no. I soon discovered that questions likely to spark longer conversations or more elaborate answers were the most valuable—they offered greater opportunities for connection and understanding. I learned about timing and tone (the hard way), delivery (from a safe distance was best), and how to read an audience effectively. I also learned that the only acceptable response to questions involving knuckle sandwiches or turning the car around was always, “No, sir/ma’am!” But I digress.
Many people grow out of asking “why” and “how.” They begin to believe that asking questions or admitting uncertainty signifies weakness or incompetence. Some even refuse to acknowledge that they don’t know something, preferring silence—or worse, making things up. I disagree. Learning to ask means learning to think. Learning to think prepares one to deal with the unexpected and to react optimally rather than habitually. I contend that active curiosity is one of the most effective ways to develop critical thinking skills, and I’m glad to say I never grew out of the habit of asking.
Admittedly, my first questions now are not always spoken; sometimes, my first response in a situation is to take a few deep breaths. This practice has served me well. It allows others space to ask their own questions—and perhaps enjoy a bit of schadenfreude from the relative safety of sitting behind the driver when your younger sibling asks, “Are we there yet?” for the third time while within grabbing range. It also gives me time for a rich inner monologue as I explore what I really want or need to know, and how best to ask before speaking aloud. This is generally wise, because having grown up on military bases, my inner monologue tends to be more direct—and more profane—than most people would appreciate. “How #$%&^ stupid are you?” and “Are you *&$^#% kidding me?” have no empirically correct answers, so they’re best left unspoken.
That said, curiosity does not grant anyone permission to arrive unprepared, be rude, or skip basic research. Contrary to what kind teachers may have told you, there are stupid questions—or, at least, questions that make you seem stupid (see “sibling schadenfreude”). And no one, including your boss or coworkers, wants to be disrespected or peppered with questions you should already know the answers to. Add “grumpy” to that mix, and you have a recipe for trouble. However, I have found that leading with curiosity has been one of the strongest tools in my professional toolbox—whether teaching, negotiating, solving problems, improving processes, having difficult conversations, or bringing order to chaos. If strategic questions are tools in that toolbox, then tactical information is the best weapon in my arsenal.
My current role involves leading a team that facilitates legal actions for over 20 programs regulated by Broward County’s Public Works and Environmental Services Department. Broward County, Florida, is home to more than 2 million residents and attracts over 14 million visitors each year. Our regulatory programs protect people, air, land, and water across 1,200 square miles—encompassing 31 municipalities, 24 miles of beaches, 266 linear miles of canals, and 790 square miles of conservation areas. Every day, our people and our environment face new challenges, and the solutions that worked yesterday may no longer apply today. Nearly all external customers who interact with my team have violated rules or regulations, while internal customers expect us to find a clear, reasonable path to compliance (see earlier reference to “bringing order to chaos”). Leading with curiosity and active listening is the only way to find common ground and mutual understanding.
Compliance is ultimately a far more important goal than levying penalties—but penalties must still be paid. When those in regulated industries internalize the “why” and “how,” they’re more likely to comply and take ownership of their actions. By examining problems, processes, and conflicts, understanding why certain practices exist naturally leads to solutions for how they can be improved. Whether the program involves childcare licensing, auto body repair, medical transport, vehicles for hire, air quality, manatee protection, domestic wastewater, hazardous materials, wetlands, or waste regulation, it’s always essential to understand why the violation occurred, why it shouldn’t have, how respondents can come into compliance, how they can prevent recurrence, and how they can make amends.
Helping people understand why something is a problem and how it affects everyone gives them ownership of both the purpose and the process. When time and energy are invested in exploring their “why” (purpose) and “how” (application), those in regulated industries become far more motivated to make informed, ethical decisions in the future. No one likes a repeat offender, and none of us likes repeating our mistakes. My team works hard to ensure that even negative experiences become opportunities for learning and growth. As any good teacher knows, understanding why students are learning and how they learn best allows the message to be tailored for maximum impact. Without using “why” and “how,” this task becomes needlessly complicated—and this holds true for everyone: our children, our staff, our customers, our coworkers, our bosses, our families, and anyone we engage with.
So, why am I using so many words? Why should you care? How does this affect you? (And yes, do some of those “other crucial skills” from paragraph one involve throat punches or eye gouging? DEFINITELY!) But again, I digress. I say all of that to deliver this one message: DON’T STOP ASKING.
Yes, some of your questions will be ignored. Yes, you may endure random, mind-numbing acts of hepeating and mansplaining—so much mansplaining! And yes, you may have to know and do more than your male counterparts to earn the same credibility. It’s not fair, but it’s the result of not having a consistent voice in conversations and decisions. None of that will change unless you understand the why (reasons) and how (methods) well enough to influence meaningful change. To be part of those conversations, you must enter them strategically. Unless the phrase “watch this” immediately precedes the question, you probably already know to ask “why” and “how” if someone asks where the Band-Aids are. Odds are, you’ll grab more than just the box.
Unfortunately, in the workplace, when faced with challenges, many people ask these “why/how” questions only internally—if at all. Instead, they watch, clean up, or suffer through chaos that could have been avoided simply by asking strategic questions. We hold back because we’ve been conditioned to stay quiet, because we’re afraid, or because it feels easier to do than to question. But when we’re brave enough to lead with curiosity, we engage. We learn—and eventually, we teach. We give others the chance to share their passions, expertise, and perspectives. We invite dialogue, build inclusion, and expand understanding. Through that process, we recognize our own value, knowledge, and strategic insight.
That interaction opens doors of communication and paves the way for critical thinking and positive change.
Why are we doing this? How can we do it better?
By asking these questions, we demonstrate our value to key processes—whether by avoiding calamity or knowing when to bring the entire first-aid kit. This strategic approach helps everyone distinguish between the symptoms and sources of a problem, especially when more than a Band-Aid fix is required. That’s how curiosity influences change.
It’s not always easy. Sometimes people don’t like being questioned. It can be challenging to find your voice—and even harder to know how and when to use it. It takes practice. Nearly 60 years in, I’m still not always successful, and it can still be maddeningly frustrating. Do I occasionally want to resort to a throat punch? Absolutely (I am my mother’s daughter). But even the aftermath of chaos can provide an opportunity to ask the right questions and prevent future mistakes. So keep asking. Strategic questions lead to tactical answers—and as my father taught me, when people realize you have answers, punching above your weight is just another way to influence change.
You’ve had the tools since childhood. HOW will YOU use them to enter the next conversation strategically?
