From Checklist to Curiosity: How to Ask Better Questions

While the public was captivated by Enron’s extraordinary financial success, McLean, then a journalist at Fortune, dared to ask a seemingly simple question: “How exactly does Enron make its money?”

That simple question would help unravel the truth behind one of Wall Street’s most celebrated companies that eventually became a fraud case study. Rather than accepting the first overly technical response like other journalists, she asked for more. Jeffrey Skilling, Enron’s CEO, called her line of questioning “unethical.” Shortly after publishing, Skilling was in prison, while McLeans reporting received recognition, awards, and praise. 

Other journalists covered the company, but what made her work different? It wasn't that she asked more complicated questions, but rather simpler ones that readers could understand. And when the answers didn't add up, she kept asking for more. For internal auditors, her story raises an important question: How can we bring that same curiosity into our work to uncover more impactful insights, which leads to a more valuable audit?

1. Leave Your Ego at the Door

One of my favorite scenes in the movie Margin Call (2011) features John Tuld, played brilliantly by Jeremy Irons, sitting at a tense conference table as his firm's leadership confronts an enormous financial problem involving the volatility of the vast amount of mortgage-backed securities the firm holds.

In this scene, Peter Sullivan, a junior analyst played by Zachary Quinto, begins explaining how the firm's massive exposure to mortgage-backed securities could generate losses large enough to bankrupt the company. To better understand the problem, Tuld asks the junior analyst to explain it as though he were speaking to a “young child or a golden retriever.”

This scene has always stuck with me during interviews and walkthroughs. I often remind my clients that they are experts in their business, and I am here to learn. I encourage them to keep things simple so I can better understand their processes. As internal auditors, we understand risks, controls, and governance, but the people sitting across the table understand how things work. Sometimes, the best thing we can do is put aside our technical knowledge, listen, and let them explain. After all, our objective isn't to prove how much we know, but to understand the process and identify where things could go wrong.

2. Ask Open-Ended Questions and Actually Listen

Another journalist I admire is Jonathan Swan, who has a remarkable ability to ask direct questions, follow up when an answer doesn't make sense, and let silence fill the room. In an interview with former federal prosecutor Preet Bharara, Swan explained that silence is one of the most underused tools in journalism. Often the most interesting information comes when you simply stop talking and let the other person speak. When we interrupt management, we are not learning anything we do not already know.

In his Atlantic article, “Stop Trying to Ask Smart Questions,” journalist Derek Thompson reflects on how he spent years trying to ask sophisticated questions that demonstrated his knowledge, only to realize that simpler, open-ended questions often led to more meaningful conversations. As he put it, “Maybe the point of a good question is to arrive at a better question.”

This is something I try to remember during audit interviews and walkthroughs. Too often, we feel pressure to move from one prepared question to the next, rather than allowing the conversation to develop. Consider the difference between asking, "Do you have a documented review process?" and "Walk me through the last time that review identified a problem." The first question might get us a policy or a simple yes or no. The second allows us to understand how the process actually works. And when something doesn't add up, don't be afraid to ask another question or let a moment of silence encourage someone to elaborate.

3. Follow the Conversation, but Don't Forget the Evidence

Open-ended questions might uncover insights, but the evidence might point to a different conclusion. When performing interviews and walkthroughs, be cognizant of the number of biases that could be present.

Consider a routine walkthrough where management explains that a particular review occurs every month. Rather than simply requesting evidence of the review, we might ask what happens when the responsible employee is unavailable or when an exception is identified. Those follow-up questions could reveal a much different picture of how the control operates.

The Next Question Matters Most

The curiosity and thoughtful questioning I admire in journalism continue to shape how I approach internal auditing. Our work will always require structured testing, documentation, and sound methodology. But sometimes, our greatest insights come from looking beyond the checklist.

So, the next time you're conducting a walkthrough, take a moment to listen a little longer, challenge an assumption, or ask one more question. Some of the most valuable audit findings begin with questions we never planned to ask.