One Must-Read Article

7 Sins of Questioning (They’re Costing Your Company More Than You Think)

Updated February 2026 • Originally published July 2020

One of the costliest habits in a growing company has nothing to do with strategy, hiring, or product. It’s this: leaders obsess about getting better answers while spending almost no time learning to ask better questions.

I’ve seen this pattern repeatedly across growth companies. A founder walks into a quarterly planning session with the right instincts—and then asks questions that shut down the very people who could help. Not because they’re bad leaders, but because nobody taught them there’s a discipline to questioning.

David Marquet did the teaching. A former nuclear submarine commander, Wall Street Journal bestselling author, and Inc. Magazine Top 100 Leadership Speaker, Marquet wrote the book on how the words leaders choose either unlock or suffocate the intelligence around them. His “7 Sins of Questioning” framework from Leadership Is Language is one of the most practical leadership tools I’ve encountered.

The 7 Sins

1. Question stacking. “So, how much testing has been done? Do we have all the bugs identified? Are we good to go?” Asking the same question multiple ways overwhelms the listener and signals you’re not listening—you’re building a case. Ask one question, then stop.

2. Leading questions. “Have you thought about the needs of the client?” This comes from already thinking the other person is wrong. It’s a statement disguised as a question, and your team knows it.

3. “Why” questions. “Why would you want to do that?” This puts people on the defensive immediately and carries an implicit judgment. In a growth-stage company where you need problems surfaced early, “why” questions train people to stay quiet.

4. Dirty questions. “Do you have the courage to stand up to them?” Like a leading question’s subtler cousin—it doesn’t overtly say you’re wrong, but it carries a built-in bias and anticipates a particular answer.

5. Binary questions. “Are we good to launch?” Binary questions narrow responses to yes or no. If your VP of engineering has 14 concerns but you ask “are we ready?”, you’ve forced a complex situation into an oversimplified box.

6. Self-affirming questions. “We’re good to launch, right?” These are binary questions designed to coerce agreement on a decision you’ve already made. Particularly dangerous in founder-led companies where the power dynamic is already tilted.

7. Aggressive questioning. Jumping straight to “What should we do?” skips over the thinking work and pushes people to make future-facing assessments before they’ve processed the present situation.

7 Ways To Ask Better Questions

Marquet doesn’t just name the problems. Here are his seven shifts:

1. Instead of question stacking, try one and done. Ask a single, clear question. Silence after a question isn’t a vacuum to fill—it’s space for thinking.

2. Instead of a teaching moment, try a learning moment. If you already know the answer, you’re not asking—you’re testing. Genuine curiosity is what separates good leaders from smart ones.

3. Instead of a dirty question, try a clean question. Replace “Do you have the courage to push back?” with “How do you see this playing out?”

4. Instead of a binary question, start with “what” or “how.” “What would need to be true for us to feel confident about this launch?” gets you ten times more useful information than “are we ready?”

5. Instead of “why,” try “tell me more.” This removes the judgment and signals you want to understand their thinking, not cross-examine it.

6. Instead of self-affirming, try self-educating. “What am I not seeing?” is one of the most powerful questions a founder can ask.

7. Instead of jumping to the future, start with present, past, then future. Before “what should we do?”, ask “what are we seeing right now?” Context builds better decisions.

One More Thing: These Sins Apply to AI, Too

Every one of these sins shows up in how leaders interact with AI tools. Ask a leading question, get a leading answer. Binary prompts produce binary outputs. The companies getting the most out of AI aren’t the ones with the best tools—they’re the ones whose leaders know how to frame the right question.

Here’s My Take

Pick one sin this week—the one you recognize most in yourself—and try its alternative in your next meeting. You don’t need to overhaul how you communicate overnight. You just need to catch yourself once, and you’ll start noticing it everywhere.

Marquet’s Leadership Is Language remains one of the most useful books on leadership communication I’ve come across. If you haven’t read it, it’s worth your time.