The Senior Leader Who Never Asked Questions
He was talented, prepared, and highly accomplished — a senior leader at a major financial services firm. His team executed flawlessly on whatever he told them to do. His peers respected his competence. And yet, something was missing.
People found him difficult to connect with.
His team never surfaced problems until they turned into crises.
His colleagues rarely sought him out.
After weeks of observing how he actually operated, one pattern stood out above everything else: **he led with answers, not questions.**
He was so focused on proving how smart he was that he had almost completely stopped asking them. In his drive to demonstrate competence, he had unintentionally shut down the very information flow he needed most.
This pattern is far more common than most professionals want to admit.
Why Most People Don’t Ask Enough Questions
Harvard Business School research and multiple studies have shown that people dramatically underestimate how much asking good questions improves likability, builds stronger relationships, and unlocks critical information. Yet most professionals — especially high-achievers — ask far too few questions, and when they do, they often stop at the surface.
In preparation for this article, I spoke with several outstanding journalists and producers who have turned the art of asking questions into a professional superpower:
- **Kendall Green**, reporter at FOX 5 New York
- **India Wright**, nine-time Sports Emmy-nominated features producer at NFL Media
- **Krysia Lenzo**, journalist and anchor at Newsmax
- **Katerina Parent**, Associate Producer at E! News
Here’s what they do that most leaders and professionals never practice:
1. Come without the answer already prepared
The best journalists walk into conversations genuinely curious, not hunting for quotes that fit a pre-written story. India Wright begins her process with deep research — not to confirm her narrative, but to understand the terrain well enough to ask about what she *doesn’t* know yet.
Most professionals do the opposite. They’ve already written the story in their heads and ask questions designed to collect evidence that supports it. That approach kills discovery.
2. Ask curious, open-ended questions
Leading questions (the ones that contain their own answer) destroy the quality of information you receive. Skilled questioners strip them out entirely.
Instead of asking, “Don’t you think this is a problem?” they ask, “Walk me through how you arrived at that decision.”
Replace statements disguised as questions with genuine invitations to explain reasoning. The difference in the depth of responses is dramatic.
3. Follow the answer, not your next question
The real gold rarely comes in the first response. It emerges in the second or third layer — if you’re willing to follow where the conversation actually wants to go.
India Wright’s favorite story wasn’t about a superstar athlete. It was about a relatively unknown woman who became the first to earn a college football scholarship as a non-kicker. That story only surfaced because Wright stayed open, listened intently, and followed the thread instead of sticking to a script.
4. Use silence as a tool
After asking a question, count to five in your head before speaking again. Most people rush to fill the silence because it feels uncomfortable. Journalists know better. The information that comes *after* the pause is often more honest, more nuanced, and more valuable than the polished first answer.
5. Make honesty feel safe
Build rapport and a genuine human connection before asking anything difficult. Make people feel seen and heard first. As Kendall Green learned early in his career, making someone feel comfortable and valued opens the door to truths they rarely share.
6. Ask on behalf of someone else
Shift your mindset: you’re not asking questions to look smart. You’re asking on behalf of your team, your stakeholders, your customers, or your audience. That small reframe removes ego and dramatically improves the quality of your questions.
My client eventually changed one thing: he started showing up with more questions than answers. Within three months, his team began bringing him problems early, his peers started seeking him out, and his relationships noticeably improved.
Nothing else in his approach had changed — only the quality and quantity of his questions.
In journalism, asking great questions *is* the job. In most other professions, we treat it as a minor supporting act.
That single shift in perspective might be one of the highest-leverage changes any leader can make.
Because the quality of what you discover is almost always a direct reflection of the quality of how you ask.
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