The Questions I Keep Coming Back To

What HR, analytics, public speaking, motherhood, and AI have taught me about the value of asking the obvious.

Last night, as I was trying to fall asleep, my mind wandered to a rather unexpected topic. I started thinking about all the different roles I've played throughout my life and career, and how some of the same lessons seem to follow me everywhere.

I've spent time working in Human Resources, interviewing candidates and navigating conversations about people and careers. I've built dashboards, worked with business leaders to understand their challenges, spoken at conferences, and taught classrooms full of people eager to learn something new. And somewhere along the way, I became a mom to two sets of twin boys, which has given me an entirely different education in communication, negotiation, and patience.

These roles don't necessarily have much in common on paper. Yet, as I thought about the experiences that have shaped how I approach problems and interact with people, I kept coming back to a few surprisingly simple habits.

I certainly don't have everything figured out. If anything, the longer I've worked and the older my boys get, the more I realize how much I still have to learn. But I've noticed that some of the things that have served me best aren't technical skills, complicated strategies, or anything particularly groundbreaking. They're often the little things that are so obvious we forget to do them.

And perhaps the biggest one is simply being willing to ask the question.

Don't Be Afraid to Ask the Obvious

Early in my career, when I worked in Human Resources, I spent a considerable amount of time interviewing candidates. Over time, I developed a habit of starting interviews with something that might seem a little silly.

Before diving into someone's experience, I would briefly review the job description and the requirements of the position. Then I'd ask, "Before we get started, based on what I've just shared, does this sound like a good fit for you?"

You would think the answer would always be yes. After all, they applied for the job, scheduled an interview, and showed up ready to talk about their qualifications. Surely they knew what they were interviewing for.

You might be surprised how often the response started with, "Well, yes, but..."

And that but was often where the most interesting part of the conversation began.

Sometimes there was a misunderstanding about the responsibilities. Other times, the candidate had different expectations about the position, or there was a requirement that didn't quite align with their experience or interests. It didn't necessarily mean they weren't a good candidate, but it gave us an opportunity to talk about those differences before spending the next hour discussing a role that might not have been what they expected.

It was such a simple question, but it taught me something I've carried into almost every role since. Just because something seems obvious doesn't mean everyone is operating with the same understanding. I've been on both sides of that realization more times than I can count.

I think we're sometimes hesitant to ask questions that feel too basic, especially in professional settings. Nobody wants to be the person asking something everyone else supposedly already knows. But I've found that those questions are often the ones that uncover the most important information.

The What Behind the Why

Fast-forward to my career in analytics, where I've found myself applying that same habit in a completely different setting.

When someone approaches me with a request for a dashboard, there's usually a conversation about what they want to see. We discuss metrics, filters, charts, business objectives, and all the other details that go into building something useful. And while those conversations are important, there's one question I've learned to ask that can completely change the direction of a project.

"If I build exactly what you're asking for, what happens next?"

What will you do with the information? What decisions will you make? Who else needs it, and what are they going to do with it?

It's a question that seems almost too obvious to ask. Surely, if someone is requesting a dashboard, they already know what they're going to do with it. But I've learned that understanding why someone wants something doesn't always tell you how they intend to use it.

Imagine building a beautiful, interactive dashboard with all the requested metrics, filters, and visualizations, only to discover that the next step in the process is for someone to export the data and send it to a third party.

Wait a minute. We're building a dashboard so someone can extract the data?

That changes things.

Maybe a dashboard isn't the best solution. Maybe what we really need is a structured dataset or an automated process. And if a third party is ultimately going to use the information, perhaps we should have a conversation with them before we decide what to build.

This is what I think of as finding the what behind the why. We're often encouraged to ask why, and I absolutely believe in understanding the purpose behind a request. But I've learned that asking what happens next can be just as important. It helps uncover the requirements that nobody thought to mention because they seemed obvious or simply weren't part of the original conversation.

I've also learned that asking these questions isn't about challenging someone's knowledge or suggesting they don't know what they need. It's about understanding enough of the bigger picture to be genuinely helpful. I would much rather spend a little extra time having those conversations than build something that technically meets every requirement but doesn't actually support the way people need to work.

And yes, sometimes the answer really is that they need a dashboard. That's great, too. At least now we understand why we're building it and what success should look like.

What Kind of Brother Do We Want to Be Today?

Of course, some of my most memorable lessons in communication haven't happened in an office or a conference room. They've happened at home.

As a mom of two sets of twin boys, our house is rarely quiet. There are four personalities, four opinions, and plenty of opportunities for disagreements. If you've ever spent time around siblings, you know that sometimes an argument can erupt over something that seemed completely insignificant just moments earlier.

My husband and I are raising our boys with a set of core values and beliefs that we hope will stay with them as they grow. We talk about kindness, love, compassion, and how we treat the people around us. But knowing those values and remembering to practice them when your brother has just done something to annoy you are two very different things.

One of my favorite questions to ask when the boys are arguing is, "What kind of brother do we want to be today?"

I have to admit, I sometimes find their reactions pretty funny. The question tends to interrupt whatever argument is happening, at least long enough for them to think about it. Usually, the answers are some combination of kind, loving, or compassionate.

My next question is, "Okay, then how should we act? What should we do next?"

What I appreciate about this approach is that I'm not necessarily telling them what to do. They already know the kind of brother they want to be. I'm just asking them to think about whether their actions are lining up with those values.

Does it work every time? Absolutely not. They're kids, and they're brothers. Sometimes we're right back to arguing five minutes later. But I like to think that each of those little conversations gives them another opportunity to practice thinking about their choices and how those choices affect someone else.

And somewhere in the middle of all the noise and chaos of raising four boys, I've realized that this isn't so different from the conversations I have at work.

Sometimes people don't need us to tell them what the answer is. They need a question that helps them stop, reflect, and think through what they already know.

The Things We Forget When We Know Too Much

Another place I've noticed this habit showing up is in public speaking and teaching.

I've had the opportunity to speak at conferences, lead trainings, and share what I've learned with audiences of different sizes and backgrounds. And one thing I try to keep in mind is how easy it can be to forget what it feels like to be new to something.

When you've spent years working with a particular technology, subject, or process, certain concepts become second nature. You develop your own vocabulary, make connections almost automatically, and sometimes forget how much context you've accumulated along the way.

But the person sitting in the audience may be hearing those concepts for the very first time.

I've found that taking the time to establish a little common ground can make a big difference. Sometimes that means explaining something that feels incredibly basic. Other times, it's asking a question to understand where people are starting from or finding a more relatable way to describe a complicated idea.

I don't always get that balance right. There have certainly been times when I've explained something and realized afterward that I assumed too much background knowledge. But those experiences have reinforced something I keep coming back to: knowing a subject and helping someone else understand it are two very different skills.

When I'm presenting, I try to remind myself that the goal isn't to demonstrate everything I know. It's to share something in a way that makes sense to the people who have taken the time to listen.

And Now, We're Working With AI

As I was thinking through all of this, I couldn't help but connect these lessons to how quickly AI is changing the way we work.

It's fascinating to me that after years of learning how important it is to ask thoughtful questions, we're entering a time when we can ask a technology to build dashboards, write code, summarize information, create content, and help solve problems in seconds.

And yet, I keep finding myself coming back to the same questions I've asked throughout my career.

What are we actually trying to accomplish? Are we making assumptions? What information is missing? What happens next? And perhaps most importantly, does the answer we're getting actually make sense?

One of the things I find both exciting and a little concerning about AI is how quickly it can produce something that looks finished. A polished response, a working application, or a beautiful visualization can appear almost instantly. It's tempting to see that result and move on, particularly when it looks convincing.

But I've learned throughout my analytics career that a beautiful solution isn't necessarily the right solution. And just because an AI-generated answer sounds confident doesn't mean it's accurate.

I also find myself thinking about how much context matters. When I ask AI to help me with something, the quality of the result often depends on how well I've explained what I'm trying to accomplish. Sometimes I realize that I left out information I assumed was understood. Other times, I discover that I hadn't fully thought through what I wanted in the first place.

Sound familiar?

It's not all that different from sitting across from a candidate in an interview or meeting with a stakeholder about a dashboard. The tools are different, but the importance of being clear about expectations, questioning assumptions, and understanding the intended outcome hasn't gone away.

If anything, I wonder whether these habits will become even more important as the technology continues to improve. When it's easier than ever to produce an answer or build a solution, taking the time to understand whether it's the right answer or solution becomes a different kind of challenge.

I don't think that means everyone needs to become an AI expert. But I do think there's something valuable about bringing our own experiences, judgment, and curiosity into the way we use these tools. AI can help us do some remarkable things, but it doesn't eliminate our responsibility to think critically about what we're asking it to do or what we choose to do with the results.

A Few Things I Keep Coming Back To

The more I reflected on these experiences, the more I realized that three ideas seem to connect many of them: courage, curiosity, and communication.

It takes a little courage to ask a question that might seem obvious, especially when you're worried everyone else already knows the answer. Curiosity is what makes you want to understand what lies beyond the initial request or response. And communication is what helps turn those conversations into shared understanding, whether you're working with a stakeholder, standing in front of an audience, or talking with your children.

I don't think these are revolutionary concepts, and I'm certainly not suggesting I've mastered any of them. They're simply things I've learned to appreciate through different experiences, and things I continue to work on myself.

What I find interesting is how often the same lessons show up in places I wouldn't necessarily expect. A question I learned to ask while interviewing candidates turns out to be useful when building dashboards. A conversation with my boys reminds me of something I've encountered in leadership. And now, many of those same habits are helping me navigate a technology that barely resembles the tools I used when I started my career.

I have no idea what the next chapter of my career will look like or how much the world around us will continue to change. But I suspect I'll keep coming back to these same habits, learning from the times they work and probably learning even more from the times they don't.

And I'll keep asking the obvious questions. Because I've learned that sometimes they're the ones most worth asking.