How asking better questions can strengthen your influence, accelerate your learning, and create opportunities for career advancement.
I was at an event today at Chicago's 1871, a center for entrepreneurship and innovation, and during the discussion, speaker Clarence Bethea hit home on what I believe is one of the most important skills for founders: curiosity.
I don't think this is exclusive to founders.
In fact, I believe curiosity is one of the most valuable—and often underestimated—skills we can develop throughout our careers. Entrepreneurs need curiosity to uncover problems worth solving, challenge assumptions, understand customers, and identify opportunities that others may overlook. But so do managers, analysts, educators, researchers, consultants, and professionals at every career stage.
And one of the most powerful ways we demonstrate curiosity is remarkably simple.
We ask questions.
I've been thinking about this for years. In fact, I recently revisited an article I wrote early in the development of Archer Career Partners in 2017 about the role of asking questions in professional advancement. Reading it again in 2026, I found myself thinking about how much more important this skill has become. We work in an environment where information is readily available, AI can produce answers in seconds, and the pace of change makes it increasingly difficult to rely exclusively on what we already know.
But having access to answers is not the same as knowing what to ask. The ability to ask thoughtful questions is becoming a defining professional skill.
Are Your Questions Helping or Limiting Your Career?
Years ago, I was leading a workshop for MBA students and alumni called Advancing Your Career Internally. We were discussing the importance of building relationships with senior colleagues and increasing visibility within an organization.
I asked participants a straightforward question:
"What do you talk about when you have conversations with more senior colleagues?"
One participant responded that they regularly asked questions about projects, information they needed, and how to complete their work. Initially, I was pleased. Building relationships and seeking information are important professional behaviors. But as we continued the discussion, I began to wonder whether the types of questions this person was asking might actually be reinforcing their position as a junior employee rather than helping colleagues recognize their potential for advancement.
That observation stayed with me.
We frequently tell students and early-career professionals that there are no dumb questions. I agree with the intention behind that statement. People should feel comfortable asking for clarification, seeking support, and acknowledging what they don't know. But I also believe something else is true. Different types of questions accomplish different things. Some questions help us obtain information. Others demonstrate preparation, judgment, strategic thinking, or leadership potential.
The challenge is knowing when and how to use each one.
As professionals grow, the questions they ask should evolve alongside their responsibilities and capabilities.
6 to Use Questions to Advance Your Career
Over time, I've come to think about question-asking through six distinct purposes. Each serves a valuable role, and together they provide a framework for becoming a more thoughtful, influential, and effective professional.
1. Ask Questions to Get Information
This is the most familiar type of question. We need facts, instructions, data, clarification, and context to complete our work.
Examples include:
What is the deadline for this project?
Where can I find the most recent financial results?
Who is responsible for approving this decision?
What are the client's requirements?
Which system should we use for this task?
These questions are necessary at every career level. They demonstrate diligence, attention to detail, and a willingness to seek accurate information rather than make assumptions. However, if these are the only questions you ask, you may inadvertently communicate that your primary contribution is executing assigned work. The career advancement opportunity: Move beyond gathering information to understanding what the information means.
Instead of asking only, "What were our sales results last quarter?" consider adding:
"What factors contributed to the change in sales, and what might that tell us about our priorities for next quarter?"
The second question creates an opportunity for a more strategic conversation. Both questions are valuable. They simply accomplish different things.
2. Ask Questions to Get Direction
There will always be situations when we need guidance. Perhaps we're facing an unfamiliar assignment, navigating organizational complexity, or making a decision with consequences beyond our immediate responsibilities. The question is not whether we should ask for direction. It's how we approach the conversation.
Consider the difference between these two questions.
Approach A: "What should I do?"
Approach B: "I've considered two approaches to this project. I'm leaning toward the second because it would reduce implementation time, although it may create some additional cost. Do you see any risks or considerations I might be overlooking?"
Both seek guidance. But the second approach also demonstrates independent thinking, preparation, and an understanding of trade-offs. It tells the other person that you've invested time in evaluating the situation and are seeking their perspective to improve your judgment. I often encourage professionals to bring a recommendation, not just a problem, when they have enough information to formulate one.
Of course, there are times when you genuinely don't know where to begin. Asking for help early is far better than proceeding in the wrong direction. The goal isn't to pretend you have all the answers. It's to demonstrate increasing ownership of your work.
3. Ask Questions to Get Advice
One of the most rewarding aspects of my career has been the opportunity to work with individuals who have experiences, perspectives, and expertise different from my own. I regularly seek advice from people I respect. That hasn't changed as my career has progressed. If anything, I've become more appreciative of how much I can learn from others. The best advice-seeking conversations usually begin with thoughtful preparation.
For example:
"I'm considering expanding our work into a new market. I've identified a few potential opportunities, but I'm concerned about how to prioritize our resources. Given your experience, what factors would you evaluate before moving forward?"
This kind of question opens the door to meaningful discussion. It also creates an opportunity to build a relationship rather than simply complete a transaction. Importantly, advice doesn't have to flow from senior professionals to junior colleagues.
Some of the most valuable insights I've received have come from students, early-career professionals, and people working in fields very different from my own. The key is to ask because you genuinely want to listen. Advice-seeking becomes far less effective when we've already made up our minds and are simply looking for someone to validate our position.
4. Ask Questions to Get Grounded
Throughout my years in management consulting, I frequently entered organizations where I needed to understand a business, its people, and its challenges quickly. Sometimes I had very little initial context. Yet I was expected to formulate recommendations that would create value.
One of the most important parts of that work was asking questions that helped me understand the broader environment.
Who are the key decision-makers?
What has the organization tried before?
Which initiatives have succeeded or failed?
What assumptions are influencing the current approach?
What obstacles might prevent a recommendation from being implemented?
And perhaps most importantly:
Why are things done this way?
That last question can be particularly powerful. We sometimes assume that an established process must exist for a good reason. Other times, we assume an inefficient process should be changed immediately. Both assumptions can be wrong. Asking questions helps us understand the history, constraints, relationships, and perspectives that shape decisions. It also builds credibility.
When people see that you're genuinely trying to understand their environment rather than immediately imposing your own solution, they're often more willing to engage with your ideas. This is especially important when you're trying to influence people over whom you have no formal authority. Before attempting to persuade someone, invest time in understanding their perspective.
Influence often begins with curiosity, not persuasion.
5. Ask Questions to Introduce Your Point of View
This may be the most overlooked opportunity for career advancement. Many professionals assume that demonstrating leadership potential requires making bold statements, confidently presenting recommendations, or consistently having the answers. Those capabilities certainly have value. But sometimes the most effective way to introduce an idea is to ask a thoughtful question.
Consider these examples:
"I wonder if we could automate portions of our monthly reporting process so the team could spend more time analyzing results?"
"Could we review our supplier relationships to identify opportunities for consolidation and cost savings?"
"Would a small pilot help us test this idea before committing to a full implementation?"
"What would happen if we approached this problem from the customer's perspective?"
"Could we use AI to reduce the administrative work involved in this process while maintaining appropriate human review?"
Each question introduces a potential opportunity. Rather than demanding agreement, it invites others to consider an alternative. That's powerful. Questions can encourage dialogue, surface concerns, and give colleagues an opportunity to contribute to the idea. They can also help professionals who may not yet have formal authority demonstrate strategic thinking.
Think back to the MBA workshop I mentioned earlier. When I asked participants how often they used their conversations with senior colleagues to introduce ideas or perspectives, relatively few indicated that this was something they regularly did. Many realized they were missing an opportunity. Their conversations were focused on getting information and direction rather than contributing ideas about the organization's future.
That doesn't mean every conversation with a senior leader should become an opportunity to pitch a new initiative.
But if your goal is career advancement, consider how frequently you're demonstrating the ability to think beyond your immediate assignments. Are you simply asking how to complete the work, or are you also asking how the work could be improved?
One important distinction: asking a question should not become a way to disguise a recommendation or avoid taking ownership of an idea. Sometimes the strongest approach is to state your perspective clearly and then invite discussion:
"I think we could improve the process through automation. What risks or opportunities do you see?"
That combination—an informed point of view followed by genuine curiosity—can be especially effective.
6. Ask Questions to Learn
My final category is perhaps the one I value most personally. Sometimes we ask questions for no immediate professional benefit. We ask because we're curious. We want to learn about another person, an unfamiliar subject, a different culture, a new technology, or an experience we haven't had ourselves. I find these conversations incredibly rewarding.
I have a vivid memory from my undergraduate years studying abroad in London. I was taking a course examining the emergence of Eastern Europe after Communist rule. One of my classmates was from the Czech Republic. We were studying historical and political changes that she and her family had experienced firsthand. What we were reading about in books and discussing in class was part of her lived experience.
After class, during dinners, tours of the city, or conversations over tea, I would ask questions. She shared stories and perspectives that brought the course material to life in ways no textbook could fully capture. And the learning went both ways.
She was eager to read and explore subjects that hadn't been readily accessible to her growing up. We discussed books, experiences, and ideas, each learning from the other's questions.
That experience has stayed with me. It reinforced something I believe deeply: Everyone we meet has something they can teach us, if we're curious enough to ask and willing to listen.
In a professional setting, this might mean asking a colleague about their career journey, learning how another department operates, or exploring why a customer sees a problem differently than we do. Not every question needs to lead to a decision, a promotion, or an immediate business outcome. Sometimes the value is simply developing a broader understanding of the world.
And that understanding may become extraordinarily valuable later.
Asking Good Questions Is a Skill We Can Teach
There's another dimension of question-asking that I think deserves more attention, especially from leaders, managers, educators, and mentors. People are sometimes afraid to ask questions. I've seen this with students and professionals throughout my career. They may worry about appearing unprepared, exposing a knowledge gap, challenging authority, or saying something that others will judge negatively.
Years ago, I was leading a Knowledge Management Center within a consulting organization. Part of my work involved onboarding new consultants and supporting professionals who were between client assignments. Every quarter, our team participated in an update with the Practice Director.
At the end of each meeting, he invited questions. And almost nobody asked any.
I found this interesting because I knew many of our junior consultants were ambitious, thoughtful, and eager to learn. When I spoke privately with several of them, they explained that they weren't sure what to ask. They also worried about sounding uninformed in front of senior leadership. Yet they valued the opportunity to hear directly from the Practice Director.
So we tried something different.
Inspired by an approach shared by a colleague at another organization, I organized a discussion about asking questions. I encouraged each consultant to develop one or two questions they might ask during the next quarterly session. Together, we reviewed them.
We considered which questions were relevant to the broader audience, which might be difficult to answer without advance preparation, and which could be interpreted as unnecessarily critical in that setting. We also discussed how to frame questions that invited meaningful responses.
At the next quarterly meeting, the consultants participated. They asked thoughtful questions and engaged with the Practice Director. Afterward, several told me how pleased they were with the interaction. They felt more confident. They believed their contributions were valuable. And they had developed a skill they could continue applying.
That experience reinforced an important lesson for me.
Sometimes we have to teach the professional behaviors we want to see. We can't simply tell people to be curious, speak up, think strategically, or demonstrate leadership. We need to help them understand what those behaviors look like in practice.
Leaders can encourage stronger questions by making room for them, acknowledging thoughtful contributions, and responding with respect—even when the questions challenge existing assumptions. And we should remember that developing confidence doesn't mean every question needs to be perfectly formulated.
A workplace where people are afraid to ask basic questions is not likely to be one where they're comfortable challenging complex ideas.
Curiosity in the Age of AI
As I reflect on this topic in 2026, I can't ignore the role of artificial intelligence. AI has made it remarkably easy to obtain information, generate ideas, summarize research, and explore unfamiliar topics. But the quality of what we gain from these tools depends heavily on the questions we ask, the context we provide, and our ability to evaluate the responses.
Consider the difference between asking an AI tool:
"How can I improve my career?"
And asking:
"I'm an early-career financial analyst with three years of experience. I'd like to move toward a strategic finance role over the next two years. What skills should I prioritize, what experiences could I pursue in my current organization, and what questions should I ask senior finance leaders to better understand that career path?"
The second question provides context, identifies a goal, and invites more actionable analysis. The same principle applies to our conversations with people. Better questions help us move beyond surface-level information toward deeper understanding.
But there's another consideration. AI can generate answers, yet we remain responsible for assessing whether those answers are accurate, appropriate, and useful. That requires critical thinking, sound judgment, and the willingness to ask follow-up questions.
What assumptions are behind this recommendation?
What information might be missing?
What alternative explanations should I consider?
What would change my conclusion?
These are questions that help us use technology more effectively. And they're equally valuable when evaluating a recommendation from a colleague, manager, consultant, or other expert. In an increasingly AI-enabled workplace, curiosity and critical thinking are complementary skills.
The value isn't simply in getting an answer faster.
It's in knowing whether we're solving the right problem.
A Practical Challenge: Upgrade Your Questions
Here's an exercise I encourage you to try during the coming week. Pay attention to the questions you ask during meetings, conversations with colleagues, and discussions with your manager.
At the end of the day, reflect on three things.
First, consider the purpose of your questions. Were you primarily seeking information or direction? Did you ask for advice, explore context, introduce a point of view, or pursue something you were curious about? You don't need to use every category every day. But notice whether you're relying almost exclusively on one or two.
Second, consider the opportunities you may have missed. Was there a moment when you could have asked a follow-up question? Could you have introduced an idea, explored an assumption, or invited someone to share a different perspective?
Third, identify one question you could ask differently next time. For example:
Instead of asking:
"What should I do next?"
Try:
"I'm considering these two approaches. Which factors would you prioritize in deciding between them?"
Instead of asking:
"Why are we using this process?"
Try:
"What led us to adopt this approach, and are those considerations still relevant today?"
Instead of asking:
"Can we use AI for this?"
Try:
"Which parts of this workflow require human judgment, and which repetitive tasks might benefit from AI assistance?"
Small changes in how we frame questions can lead to more productive conversations. Over time, they can also change how others experience working with us.
Curiosity Is More Than a Founder Skill
That brings me back to Clarence Bethea and the conversation at 1871. Founders need curiosity because they're constantly navigating uncertainty. They have to understand problems, test assumptions, discover opportunities, and learn from people whose experiences may be very different from their own.
But these aren't exclusively entrepreneurial responsibilities.
They're essential capabilities for anyone who wants to grow professionally, contribute meaningful ideas, and navigate an evolving workplace.
Curiosity helps us learn. Questions help us put that curiosity into action. And thoughtful questions can help others recognize not only what we know today, but also how we think, how we approach problems, and what we might be capable of contributing tomorrow.
That's what makes question-asking such a powerful career development tool. It helps us move from simply completing tasks to understanding the bigger picture. From seeking direction to demonstrating judgment. From receiving ideas to contributing them. And from relying on what we already know to continuously expanding what we can learn.
As you think about your own professional growth, I encourage you to consider one final question:
Are you asking the right questions, in the right way, to create the opportunities you want?
Because sometimes, the question you ask is just as important as the answer you receive.
Dream Big and Take the Chance to Advance.