November 20, 2023 / Esther Choy


A critical piece of leadership communication is harnessing the power of crazy-good questions. 

While teaching in the Major Gifts Solicitation Strategy program at Northwestern University, I made two interesting observations about gift officers and their donors. First, it seemed that most gift officers found it challenging to recruit and maintain major gift donors. The second was that they knew their donors, but were missing out on a population of ultra-wealthy individuals who had the potential to be major gift donors. 

With these observations in mind and a new opportunity of extra time in the midst of a global pandemic, I decided to conduct an in-depth study of ultra-high net worth individuals in the United States and their relationship with philanthropy. 

I was a rookie in research, and this was my first time publishing a white paper. With a massive stroke of good luck, I got the New York Times to be interested in my research. Trying to contain my excitement, I kept calm on the phone when I got the call from the reporter. However, that excitement nearly turned into panic when he asked me his next question.

The reporter from The New York Times requested to speak with some of the individuals I had interviewed for their study. The problem? I had promised my sources anonymity and confidentiality. The predicament deepened when the journalist insisted that without these interviews, the story couldn’t proceed. 

Thankfully, I was able to arrange interviews with some of my sources, including Joe Pulizzi, who shared his experience with the reporter. I asked him how the interview went, and he shared that it went well, they had a lot in common, and the reporter sent him a photographer!

I thought, wait, why a photographer? To take your picture? But what about me – the study author?! 



When the issue came out, and the article was a very fair and thoughtful piece, it clicked. Me, the self-proclaimed storytelling expert, finally understood why the reporter insisted on talking to and photographing the subject matter rather than the study author. 

When there is a face to the case, (in this example a face of a person who embodies over a hundred-thousand ultra-wealthy individuals in the United States) all of a sudden there is a concrete, relevant, and relatable understanding of the subject that makes it more memorable. Including personal narratives and a photo in the story humanized the complex issue of philanthropy among the ultra-wealthy.

In working with many, many clients over the years, all of them have told me that no one comes up to them after a presentation and says, “that pivot table on slide 32 really hit home for me.” Rather, their audience remembers the story and the face on the case that provided an opportunity for human connection, even if they may not remember when or where exactly they heard the story.   

In connecting with an audience, emotion is key in storytelling. Stories, with their emotional depth and capacity for connection, have the power to inspire action and engagement. 

And what leads us to having a library of such compelling stories? I have clients who have often lamented, “but I don’t have any stories!” 

Everyone has stories. It’s how we mine and tell them that matters. 

The critical component is the ability to ask powerful questions, empowering your leadership communication along the way.

3 Ways Power Questions Can Enhance Your Leadership Communication:

1. Powerful questions enable you to collect stories that help your audience learn and gain understanding:

When we have data to share, whether it’s an abundance of research on wealthy individuals’ relationship with philanthropy, proof as to why we’re the ideal candidate for a position, or findings from analyzing and studying policy, we need to understand that our audience doesn’t share our expertise or understanding of that data. We need a coherent, compelling story to help bridge that gap and allow them to gain a better understanding.

And how do we find these compelling stories? By asking crazy-good questions. Crazy-good questions aren’t just any questions, but are powerful, thought-provoking, and allow people to respond with interesting stories. And after they share, you can reflect on the stories you heard, and decide whether you want to share it with others later (with permission, if the story is a personal one).

Story collecting can give you a full “story library” to peruse so that you can pick out the story that is best suited to each type of audience you want to persuade, all from simply changing the way you approach small talk.


2. Powerful questions foster connection with your audience:

Poet and civil rights activist Maya Angelou wisely shared, “I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.”

Imagine you’re in a conversation with someone at a conference when there’s a lull between presentations. They turn to you and, after you exchange introductions and position titles, they idly ask how you’re enjoying the conference, briefly glancing at their watch or phone as you respond. They may be polite and cordial, but you probably leave the conversation with the impression that they didn’t really get to know you or find what you said all that interesting. 

Now, let’s reimagine that conversation. You both introduce yourselves, share what you do, then they ask you, “What’s something about your job most people don’t understand?” As you share, they nod, smile, and you can tell they’re actively listening and remembering your response. It sparks a deeper conversation, and before you know it, the lapse in time between presentations has passed. 

You likely leave the second scenario feeling much different than you did in the first. You felt heard, understood, and like you walked away with a new connection to someone within your field. 

3. Powerful questions can change your environment:

Introducing compelling, thought-provoking questions into our work environment encourages a new way of thinking. Incorporating these questions so they are a part of your leadership communication to your team not only shows them you have a genuine interest in their perspectives and ideas, but also encourages them to respond in a different way. Powerful questions enable them to think critically and analyze situations from various angles that they may not have considered before. 

For example, at the culmination of a project, asking “What was successful?” elicits a very different response than asking, “What was the most surprising about this process? What was one challenge you faced– that you didn’t expect– and how did you overcome it?” In the first, we’re simply reaffirming what worked. In the second, we’re prompting deeper reflection with a likelier chance of sparking creativity and innovation, which could then scaffold the team to handle similar challenges in the future. And in all this, we can strengthen team dynamics and communication, and take our environment to a higher level of creativity and innovation.

Asking powerful questions is a key to leadership communication. They allow you to collect compelling stories, connect with your audience, and encourage innovation amongst your team. Download our complete list of crazy-good questions to start incorporating thought-provoking questions into your everyday conversations. 


Related Articles:

The Best Business Storytelling Questions to Build Relationships

Theranos: Four Questions to Evaluate a Business Story

Hook Your Audience’s Attention at Networking Events

How Do Leaders Communicate Complex Ideas? 3 Strategies To Engage Your Audience.

Esther Choy

Esther Choy founded Leadership Story Lab in 2010 to help others leverage the art of storytelling to create extraordinary opportunities.
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