sales

Here’s a thing that happens to me all the time: I’m facilitating a meeting with a team of executives and they’re discussing a complex part of their business. I pause to ask a “dumb” question. (The ability to ask questions like that is one of the perks of being an outsider looking in at an organization.)

Instead of getting an articulate answer to my "dumb" question, I get blank stares. People blush and clear their throats. Why? Because the question that seemed so dumb to me is one none of them actually knows the answer to. And it's not because they're not smart enough; it's because they've simply never thought to ask.

Why are we afraid to ask questions?

Part of why I love my job is that I’m paid to ask questions. Asking lies at the heart of facilitation. A great question is often the fastest path to an answer or a cool discovery.

Maybe you're afraid you'll look incompetent. But asking questions is often the smartest move you can make.

But so many people fear asking questions. If you're one of them, there could be lots of underlying reasons keeping you from asking the questions that would help you make progress. Maybe you're afraid you'll seem incompetent, or that you're unable to figure things out for yourself. Maybe you're worried that you'll slow the work down, or that you're making an unreasonable demand on someone else's time or energy.

My goal today is to convince you that asking questions, and asking them well, is often the smartest move you can make. Questions, when you ask them strategically, have the power to connect you, expand ideas and thinking, and grow and develop your capabilities.

How asking great questions at work can help your career

Let’s talk about what a great question can do for you and how you might benefit from the asking.

Asking questions can further your great idea

You want to show up as a genius at work. Who doesn't want to be the hero, right?

The key is to strike a balance between showing a point of view and having a sense of curiosity.

But that natural desire to be the ua-competent one has its drawbacks. It can mean that when there’s a problem to be solved or a challenge to be met, you want to be the one with the answers, not the questions. But sometimes asking the right question is just the thing to sharpen and shape your idea.

The key is to strike a balance between showing a point of view and having a sense of curiosity. Let’s say you’ve noticed that sales on a particular product line are down. You’ve got some ideas on how to tweak that product to help make it shine again. But before you unleash your own brilliance on the world, pause to consider that maybe a small tweak from a colleague could make your idea even better.

Start a conversation with a coworker or your boss. You might begin with:

I’d love to experiment with adding X feature to Y product. How do you think customers would respond? And what suggestions do you have?

This approach showcases your idea but also invites people to weigh in. You’re not just asking for approval. Instead, you’re genuinely seeking input. And their ideas may just put the finishing touches on yours.

Asking questions can trigger a connection

Maintaining connections—to a community, to a purpose—is a hot topic. And asking questions can be a simple way to keep connection at the forefront.

I’m not talking about the “how are you?” or “what’s new?” moments. They may be punctuated with question marks, but they’re really just conversational hygiene. I’m talking about questions of substance; the kind intended to open discussion.

A question that drives connection needs to meet a few criteria in my book.

• It's authentic. Ask a question that doesn't come with a scripted answer like "I'm fine" or "Nothing much." Seek a real response.
• It's open. Great questions invite a range of possible answers beyond yes, no, right, wrong, up, or down.
• It taps curiosity. Consider who you're striving to connect with. Where do they put their energy? How can you tap into their passions and interests with a targeted question?

A friend of mine, a marketing professional, lost his job a few months ago. He’s been struggling and he’s turned inward.

I want to make sure he continues to feel connected, both to me and to his own sense of competence. So, every few weeks. I reach out with a marketing question. It may be about an experiment I want to run in my own business, or for an opinion on a topical article I’ve read. 

My question to him is always genuine—I do want to tap into his wisdom. But I’m being intentional in using the question as a way to keep a connection alive. It always sparks a conversation, and I know it’s helping him hang tight in this challenging season.

Asking questions can provide a new direction

Sometimes it’s not that you don’t know something or can’t figure it out, it’s just that you’ve been spinning on it for a while and you need to break that spin cycle.

Recently, I was designing a program for a leadership team striving to work more collaboratively with each other. The program would have two components. The first was education about what strategic collaboration looks like and some general practices for doing it well. The other was a facilitated discussion to help the team identify where things were breaking down and propose strategies and solutions to move them forward.

Asking for a push doesn’t mean you’ve failed to deliver. It means you’re wise enough to see the potential of adding wisdom on top of your own.

This is my jam. My bread and butter. (I’ve got to stop writing just before lunch).

But in designing the program, I got stuck at one point. I couldn’t figure out how to transition between the two pieces and I was banging my head against a wall.

I finally decided to phone a friend, another experienced facilitator. I asked how she would approach the program challenges. And in that moment, if I’m honest, I felt a bit of shame. Why couldn’t I just figure this one out?

But it turns out, talking it through with her helped me have a breakthrough. She didn’t give me the answer, but she pushed my thinking in a direction I hadn't even considered.

I had to get over this idea that my expertise wasn’t enough. 

Asking for a push doesn’t mean you’ve failed to deliver. It means you’re wise enough to see the potential of adding wisdom on top of your own.

Asking a question can challenge or develop someone 

There’s this thing I do sometimes when I’m running a meeting. I’ll pose a question to someone specific—not because I don’t know the answer, but because I see an opportunity to shine the spotlight on them.

Allowing someone else to showcase their thinking, their courage, or just their willingness to think out loud can be an incredible gift.

Maybe the team has gotten stuck somewhere. They ask me what they should do. While I’m always happy to offer a point of view, if I know someone else on that team who can respond in a way that demonstrates their expertise or creativity, I’ll ask them the question.

Allowing someone else to showcase their thinking, their courage, or just their willingness to think out loud can be an incredible gift. It helps them to grow. It also demonstrates your own capability as a leader and someone worth following. 

And there you have my thoughts on the power of great questions. Are there other scenarios in which you’ve used questions to move you forward? (You see what I did there? An open question coming from my genuine curiosity!) I’d love to hear how you’ve asked a question that pushed you over the finish line.