The Art of Asking Better Questions
Thoughtful questions deepen trust, reveal real needs, and spark introductions rooted in genuine opportunity.
Great networkers are great questioners. They resist the urge to fill the air with credentials and instead invite stories. Questions shift the spotlight from “me” to “us,” and that’s where collaboration lives. Ask better questions and you’ll learn where someone is headed—and how to walk with them a little farther.
Shift from job titles to momentum
Swap “What do you do?” for prompts that surface motion and obstacles:
- “What are you building this quarter?”
- “What’s working better than expected?”
- “What would make next month a win?”
Once you know what a “win” looks like to them—specific numbers, dates, or milestones—you can make introductions and share resources that directly move that goal.
Follow curiosity into specifics
- New product? “How did you validate demand?”
- Hiring struggle? “Which traits lead to success on your team?”
- Recent win? “What did you do differently this time?”
Specifics make the right introductions obvious.
Structure the conversation (funnel + boundaries)
Start broad, then narrow:
- Context: “How did you get into this work?”
- Current focus: “Where are you investing time right now?”
- Concrete ask: “What help would move the needle this month?”
Mirror boundaries by checking time and energy: “Is now a good time to dig into that?” Respect builds safety; safety invites honesty.
Listen to illuminate—not to respond
Listening is the second half of questioning. Reflect the essence:
“It sounds like the bottleneck is the handoff between marketing and sales.”
Reflection shows care and ensures accuracy. From there, ask permission to offer a connection or idea.
Try the two-minute inquiry drill
At L.E.N.S., we practice a simple exercise: one person shares a goal; the partner asks questions only—no advice—for two minutes. The result is striking: better questions surface better answers, and people often discover their own next step. Advice is easy; inquiry is a craft.
Turn questions into momentum
Carry one detail from the conversation into your follow-up and ask for a quick update in two weeks. Momentum accelerates when conversations don’t evaporate after the meeting. Your aim isn’t to interrogate; it’s to illuminate. When people feel seen, they invite you closer to the work that matters.
Question bank (steal and adapt)
- What constraint—if removed—would unlock growth this quarter?
- Which client is your best teacher right now, and why?
- What introduction would save you two weeks of trial and error?
- Where are you over-delivering, and where are you under-resourced?
- What have you tried that didn’t work, and what did it teach you?
- Who needs to say “yes” for this to succeed, and what do they value?
- What would make this project easier to measure—or celebrate?
Quick Boosters
- Pro tip: Before your next meeting, jot two specific questions or introductions you can offer—and one clear ask you’ll make.
- Practice: After each conversation, send a three-sentence follow-up: restate needs, offer one resource, propose a next step.
- Reminder: Clarity compounds. When your message is simple and specific, others can carry it farther for you.
