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ATD Blog

5 Reasons Why You Need to Lead With Audacious Questions

Wednesday, August 21, 2019

“The smart ones ask when they don’t know. And sometimes when they do.” —Malcolm Forbes

No one wants to look stupid, naive, or as if they do not know what they are doing, which is why so many of us are reticent about asking questions. Whether your leadership style is servant, democratic, or visionary, it’s grounded in a secret element: curiosity. If we just begin practicing and embracing inquiry-based leadership, then we can build more robust leadership styles. In the process, we will become cognizant about the ways we frame questions.

Ray Dalio, the CEO of investment banking firm Bridgewater, is an example of a leader who lives by the principle to lead with questions. At Bridgewater, all conversations are recorded—that’s right, audio recorded. Dalio’s rationale for this policy is doing so will reduce opportunity for office politics and spin. He wants to encourage people to thoughtfully and honestly say what they think and ask what they want to understand.

In a 2014 interview at a New York Times conference, Dalio asked, “Don’t you want to know if people disagree with you and what they think about you?” He also asserted that “mistakes are good things.” In his view, by surrounding himself with thought-diverse individuals, he secures more insights about a topic. And in his business of trading, the more perspective he has on a market opportunity, the more informed he will be to make the best decision.

Dalio goes so far as to say it is unethical not to engage in critical thought and inquiry during meetings and conversations. By building an organizational culture of radical transparency, he wants Bridgewater to be a place of “meaningful work and meaningful relationships, through radical truth and radical transparency.”

While you may not go so far as having audio recording equipment in every room of your office, you can lead with questions to craft radical transparency. In A More Beautiful Question, Warren Berger made the astute point that asking questions is a way of thinking. Yes, in the short-term, questions may reveal your ignorance on a particular matter; however, leading with curiosity opens everyone to new perspectives. We must keep in mind that invention precedes innovation.

The best way to help your team become more inventive is to inspire them with questions that require them to look at their work in new ways. Ask about your hiring practices. Ask how long certain traditions have been around and why you still do them. Ask junior level and newer hires their opinions about a strategic decision. Getting fresh perspectives can help shift paradigms and lead to exciting discoveries.


Here are five benefits to practicing inquiry-based leadership and why that style is game-changing for your organizational culture and your bottom line:

1. Inquiry-based leadership democratizes your organizational culture. Inquiry-based leadership requires thought diversity from people with different skill sets, mindsets, ethnicity, gender, and age. Thought diversity leads to more vibrant and dynamic organizations that can anticipate change by identifying multiple scenarios.

2. You become more accessible as a leader. Curiosity is the precursor to empathy. You must first want to understand “Why?” or ask “How?” before empathy can be cultivated. Empathic leaders create empathic organizations. Empathic organizations start with their end-users, delivering what the market needs, not what the company likes.

3. Asking questions is fun. There is no wrong question. That reality helps people to connect once they see that no one is taking themselves too seriously. Bringing joy into a work environment adds to productivity.


4. You gain so much more than you give. You are guaranteed to get better at asking questions over time. Each time you open yourself up to not knowing, the added value to what you understand and want to explore further can be priceless.

5. The more audacious the better. In work environments and competitive landscapes with increasing ambiguity, asking big questions serves as a manner of wayfinding and sensemaking through the muck. For example, there’s a major difference in between the question, “What are our goals?” versus “What may our post-mortem read?”

Ultimately, inquiry-based leadership helps you develop hindsight, insight, and foresight—which are fundamental to strategy—in these ways:

  • Hindsight—Why have we done things the way we have done them? How have we done things? Where did it all start? Make time to do a physical show-and-tell of your company’s past attempts.
  • Insight—What’s working well now; what’s breaking down? Who is it benefiting? Who could we be learning from?
  • Foresight—What are multiple, possible audacious futures that could play out? What would they look like? Pay attention to trends.

As a wise person once told me that you can tell a lot about a person by the quality of the questions they ask. We are only as good as the questions we ask, so start developing some great ones!

About the Author

Natalie Nixon,Ph.D., is a strategy, foresight, and innovation expert. As president and founder of Figure 8 Thinking, she advises leaders on unique approaches for process transformation and leveraging creativity as an innovation resource to more rapidly achieve priority business goals. Natalie does this by applying her background in cultural anthropology, fashion, and service design. Natalie is also a published author, global speaker represented by BigSpeak, regular columnist for, and lecturer at The University of Pennsylvania.

1 Comment
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When I was leading an ambulance service, I always had employees come to me and say "This may be a dumb question, but....". I always told them I'd rather answer the same "dumb" question 100 times than have one person not understand. I always questioned those above and around me, and I encouraged each person working for me to do the same. Like Mr. Dalio, I believe that an idea can't truly be tested unless it is questioned- and through questioning the truth / reason is revealed.
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