When was the last time you asked a question that made the room go silent?
Asking insightful questions is one of the most undervalued — and impactful — career skills. It’s how you demonstrate judgment, strategic thinking, and influence without ever saying, “I’m smart.”
Most professionals believe influence comes from having answers. In reality, it comes from asking the right questions — the ones that make others pause and say, “That’s a good question.”
🧠 Why This Matters
Edgar Schein called this practice Humble Inquiry — the art of asking questions to which you don’t already know the answer. It’s not small talk. It’s not a tactic. It’s how leaders build trust, uncover truth, and create space for collaboration.
When you shift from telling to asking, people stop performing for you and start thinking with you.
🔑 Micro-Habits of Insightful Questioning
Here are five simple “Humble Inquiry” micro-habits you can start today:
1. Lead with curiosity, not certainty.
---> Replace “Why did you…” with “What led you to…?”
2. Be short and simple.
---> Ask one question at a time — and wait. (This one is tough for me as I habitually “tack questions”).
3. Lower your status to raise connection.
---> Say, “I could use your perspective here” instead of offering your opinion first.
4. Listen for learning, not rebuttal.
---> Don’t prepare your response while they’re talking.
5. Make it psychological safety in action.
---> When someone risks honesty, reward it with appreciation, not critique.
⚡The Real Power
Insightful questions signal humility — and humility earns access.
---> Access to truth.
---> Access to trust.
---> Access to influence.
They turn conversations from “proving” to discovering. That’s where great leadership lives.
👇 Your Turn
When was the last time you asked a question that made your manager or peers pause and say,“That’s a good question”?
💥 Hi, if we haven’t met yet, I am Howard— an executive coach and former consulting leader who helps high-achieving professionals navigate what’s next. Blending coaching, consulting, and practical strategy, I take a “no script” approach—start broad, get tactical fast, and focus on what moves careers and organizations forward.
If you liked this post and want to see more insights on leadership, growth, and navigating change with purpose: Connect with me