Questioning in 2025

Do You Know It All, Like Me?

Yep, I tend to lead most conversations with what I know—or what I’ve convinced myself I know. Over time, I’ve become the person others count on for answers, and somewhere along the way, I started believing I had them all.

I confess: I am a know-it-all.

So, when I began this year searching for a word to define my growth, I did what any self-proclaimed wordsmith would do—I asked myself, what could possibly be left for me to learn?

I reflected deeply. The word that kept coming to me wasn’t faith, love, or devotion. It was something I needed to embrace, to live with less angst and more confidence, with less fear and more trust.

The irony? As someone people turn to for meaning, words, and ideas, I rarely stop to ask. I had developed a false narrative that knowing was more valuable than wondering.

And there it was. The word I needed.

Question.

The Practice of Asking More Questions

This isn’t a one-and-done shift. Learning to question takes practice. It takes reflection. And it takes humility.

Three steps to start:

1. Confess to not knowing it all. (Take it from me—this is tough.)

2. Commit to making questions a regular part of your conversations.

3. Cultivate questions that trigger both answers and new questions.

   
   

Then go deeper.

My Forbes colleague Pia Lauritzen describes the power of questions beautifully in the “Great Questions Report” she wrote in collaboration with her colleagues at Qvest:

"Unlike answers, questions can be invitations to join a conversation about something we have in common. And when we react spontaneously with ‘Great question,’ it is either because something resonates with us or because someone (typically the person asking the question) makes us feel called upon. This ability to connect people with each other and commit them to a shared purpose is the essence of the power of questions.”

How beautiful is that? A well-asked question doesn’t just extract information; it calls someone in.

The Paradox of Mastering Questions

Here’s where it gets interesting. Once you begin to master the art of questioning, you also have to learn when not to ask.

Some conversations don’t require questions at all. They require presence, common ground, and stillness.

Think about these moments:

• When someone is grieving. They don’t need solutions; they need space to feel heard. The best response isn’t a question—it’s presence.

• When a team is facing a tough decision. Sometimes, asking too many questions creates doubt instead of clarity. Instead, silence can be the most powerful tool.

• When a friend or colleague is celebrating. There’s a temptation to ask, How did you pull that off? What’s next? but sometimes, it’s best to just let them bask in their moment and show them you see them.

Four months into this journey, I can tell you it’s hard.

I often catch myself having not asked a question after a conversation rather than in it. But I trust that leaning into this practice will raise my self-awareness and make this one of the most transformative years (for me) yet.

In closing, I’ll leave you with the very thing I’m learning to embrace:

Do you feel called upon to begin something new?