Asking Questions and Why it Really Matters

We’ve all been there. Sitting in a meeting, a boardroom, or even across the table from someone we admire, and we feel the hesitation rise. There’s a point to be made, a question to ask, or a challenge to raise—but something stops us.

For so many women—even accomplished, senior leaders—there are moments where the instinct to speak is drowned out by an inner voice. “Is it the right time? Am I overreacting? Will this make things awkward?” And then, the moment passes, and with it, the opportunity to make an impact.

The truth is, it’s not just junior professionals who experience this. I’ve spoken to women leading organizations, sitting on boards, and running entire divisions who share that even they have held back in critical moments. Myself included.

The Boardroom Moment

I’ll never forget a discussion in a board meeting where everything seemed like a fait accompli. The decision appeared to be made, and the room had moved on. But something about it didn’t sit right with me. I knew the issue needed to be challenged—it was too important to let slide.

My gut told me to speak, but I felt the hesitation: “Am I reading the room wrong? What if I derail the discussion? Is this the right moment to push back?”

Finally, I leaned in and said my piece. The ensuing discussion? Uncomfortable. There were moments where you could feel the tension. And yes, those moments still feel hard, even after years of experience.

But here’s the thing: letting that discomfort hang, sitting with it, and seeing the conversation shift is how you build your muscle for the next moment. By the end of that meeting, the decision had evolved into something stronger—more inclusive, more thoughtful, and more aligned with the organization’s goals.

If I hadn’t spoken up, I’d have carried the frustration with me. Instead, I left the room knowing I had done the right thing, not just for myself, but for the outcomes that mattered.

Why Do We Hold Back?

Research shared by Claudia Hammond, suggests that women were two-and-a-half times less likely than men to ask a questions in public. Holding back from fear of not feeling clever enough or worried that we misunderstood the content. This doesn't hold true across all areas. Recent research from Berkeley Haas Professor Laura Kray, shows that women now report negotiating their salaries more often than men, but they get turned down more often.  Hmmm. I might sit with that one for a bit.

Years of social conditioning coupled with the fact that women are often penalized for assertiveness in the workplace and it's no wonder we hesitate before speaking. 

And yet, we know that speaking up—whether it’s asking a question, voicing a concern, or challenging a decision—is crucial to driving change and creating impact. 

The Growth Is in the Asking

If you’ve ever regretted staying silent, you’re not alone. But here’s the good news: every time you push through that hesitation and speak up, you’re building a habit. You’re proving to yourself that your voice deserves to be heard.

Here’s what I’ve learned:

• The discomfort doesn’t go away, but you get better at managing it. Sitting in those moments of tension builds resilience.
• Asking questions is about more than clarity—it’s about visibility. Every question shows your engagement and positions you as someone who thinks critically.
• Advocating for yourself and others is a skill, not a personality trait. You can learn it, practice it, and get better at it.

A Challenge for Next Time

The next time you feel that hesitation creeping in, I challenge you to ask the question. Raise the point. Challenge the assumption. Let the discomfort come, and then let it pass.

Because the truth is, the best leaders aren’t the ones who avoid discomfort—they’re the ones who lean into it. And every time you do, you’re not just building your own leadership; you’re modeling it for others.

If this resonated with you, I’d love to hear your thoughts—or the moments when you’ve pushed through hesitation and spoken up. What happened? What did you learn?