Asking thoughtful questions at the right time, in the best order, can help us make more informed investment decisions during uncertain times, when it matters most to our clients and their portfolios. Continuing from where we left off in ““Exploring the Art of Questionology in the Research Process,” this article focuses on mechanics and best practices for how to ask better questions.

What research exists on how to ask questions? What can we learn from other inquisitive disciplines about the type, tone, sequence, and framing of questions to enhance information-gathering techniques? I spoke with an investigative journalist and a litigation lawyer—seasoned fact-finding professionals—to find out.

Preparation: What do you need to know?

Read annual reports, transcripts, and industry reports and follow competitors. Research a company well to determine the areas where you require more information.

Decision sciences company, Mu Sigma, offers the following guide to choosing questions based on conversation goals¹:

• Funneling questions delve deeper into a subject “to understand how an answer was derived, to challenge assumptions, and to understand the root causes of problems.” What qualities does the new CEO bring to the company that are necessary for it to regain leadership in its markets?
• Adjoining questions explore a subject to broaden our understanding of it. How could this technology apply to a different industry?
• Elevating questions zoom out to raise broader issues and the bigger picture. What geopolitical trends should we be concerned about?
• Clarifying questions zero in to better understand what was said and uncover the intent behind it. Could you explain what you meant by that?

Figure 1¹:

Pohlmann, Tom, and Neethi Mary Thomas. “Relearning the Art of Asking Questions.” Harvard Business Review Article, March 27, 2015. https://hbr.org/2015/03/relearning-the-art-of-asking-questions

However, preparing for an information-gathering interview is more than just making a list of the questions you plan to ask.

Even more importantly, being well-prepared allows you to listen actively during the conversation, probe with follow-up questions, and confidently go off-script when necessary. These follow-up questions require minimal preparation but are especially powerful, as researchers at Harvard have found¹. They signal to your conversation partner that you are listening, care about their input, and want to know more. Experts emphasize that the skill of listening cannot be overstated—it helps you follow tangents, uncover unexpected insights, and spot issues that need addressing. Consider your conversation like a map: follow lines of thought with follow-up questions to reach a deeper understanding. Sometimes, you may even know more than the person you’re interviewing, so listening closely ensures the conversation remains honest and productive.

Sequence can be subjective: What are some best practices?

According to researcher Alison Wood Brooks, the optimal order of your questions depends on the circumstances². If the encounter is tense, asking the toughest question first may make later questions feel less intrusive. For relationship-building, start with less sensitive questions and escalate gradually.

Another suggestion from the professionals I spoke with was to begin by summarizing what you know. Then ask, can you help me understand xyz? This approach builds trust and encourages openness, the same way asking questions in a casual tone will³.