BL&T No. 199: Going Deeper with Generative Questions

This post originally appeared in my weekly newsletter, BL&T (Borrowed, Learned, & Thought). Subscribe

Borrowed

"The skill of the coach is the art of questioning. Asking incisive questions forces people to think, to discover, to search.

Larry Bossidy, Ram Charan, Charles Burck in "Execution: The Discipline of Getting Things Done" [Book]

Learned

I recently discovered actor Jon Bernthal's podcast, REAL ONES, with an episode featuring Larry Hagner, founder of The Dad Edge. Hagner discussed a small yet impactful shift in how we engage with others through our questions that hit home for me.

The core idea is what he calls generative questions. Often, we ask questions like "How was your day?" out of good intentions but typically yield surface-level responses like "Okay." I bet many of us can relate to this exchange as teenagers, much to the dismay of our parents. "Okay" or "Fine" are great ways to kill a conversation, which can be frustrating, but the response isn't the problem—it's the question.

Hagner suggests reframing our questions to engage more deeply and encourage meaningful reflection, such as:

"What was the highlight of your day?"
"What was your biggest challenge today?"
"What did you learn from today’s low points?"

During a recent dinner with one of our partners, I experimented with this concept. They asked me how everything was going and my mind started racing—where do I start? I opted to go surface-level with my response but then remembered Hagner's concept and shared it. We ended up reframing our conversation using generative questions—the quality of our discussion immediately deepened, uncovering new commonalities and insights among everyone at the table.

I find this method to be an invaluable tool for us as collaborators, managers, mentors, and service providers, prompting us to think more about the purpose behind our questions and what dialogue we hope to create.

Here’s how we might rethink some of our routine check-ins:

Client Check-In:

Instead of "What are your goals for the rest of this year?" ask "If there was one thing you could accomplish by year-end, what would it be?"

Team Meetings:

Replace "How is everyone doing today?" with "What is everyone most excited or concerned about this week?"

Project Collaboration:

Rather than "Are you feeling okay about the upcoming website launch?", probe with "What is your top 1-2 concerns about the launch, and how can we address them together?"

At home, my wife Dana and I have had some great conversations by rethinking how we talk about our days. It's just a matter of reminding ourselves to keep it in practice!

As a new Dad, I'm excited to keep this in my back pocket for when my 10-month-old son Mylo finds his voice and starts sharing his own stories. For now, I can only wonder what he might tell me about his favorite moment at daycare.