The Art of Asking Open-Ended Questions

Early in my career as a legal practitioner, during cross-examination, I asked a witness, “You were not there that night, were you?”

The witness replied, “No, I was not.” I attempted to recover by asking, “Could you tell us where you were?” but I realized my error immediately, even before I looked at my principal.

The problem? My question told the witness and everyone in the room the answer I wanted to hear. In law, it is called a leading question. In the workplace, it is called a closed-ended question or, better yet, a technique to confirm my own assumption.

Why Open-Ended Questions Matter

Just as in legal cases, in investigations, and leadership conversations overall, the goal isn’t to control the narrative; it’s to understand it.

Open-ended questions invite people to share their experience in their own words. They can reveal context, emotion, and nuance that closed questions can never capture. A yes/no question limits the truth. An open question invites it. This is especially critical in sensitive investigations involving harassment, discrimination, or misconduct, where emotional safety and psychological insight are paramount.

Let's compare these questions in practice.

CLOSED “Did your manager yell at you?”

OPEN “Can you walk me through what happened during that meeting with your manager?”

CLOSED “Were you angry?”

OPEN “How were you feeling at that moment?”

CLOSED “Was this the first time?”

OPEN “Tell me about any other times something similar happened.”

Notice how the CLOSED question seeks confirmation, and the OPEN question allows room for detail and perspective.

What Investigators Can Learn from Shoan v. Attorney General of Canada 2016

In Shoan v. Attorney General of Canada, a workplace harassment investigation was dismissed because it was conducted in an improper, impartial manner, based on claims by the respondent, Mr. Shoan, that the investigator was biased. The Court examined whether the investigator had approached the matter with a closed mind, effectively predetermining the outcome. The Court concluded that the investigator had indeed failed to maintain the necessary openness and impartiality. What’s most instructive is how the Court reached that conclusion by closely analyzing both the investigator’s conduct during the process and the language used in the investigation report.

The takeaway for investigators is clear: it’s not enough to be open-minded; your actions, tone, and written findings must also demonstrate that impartiality. Perception matters as much as intent, and a well-documented, neutral approach is your best safeguard against allegations of bias, and that starts with how you craft your questions.

Crafting Effective Open-Ended Questions

To avoid the appearance of bias and pre-determination, every step of the investigation must comply with procedural fairness, including the questions asked of all the parties and witnesses. I have outlined a simple framework supported with examples that I use and coach my clients on:

  1. Start broad, then narrow. Begin with context (“These are the issues that have been brought forward. I want to hear your side of the story; can you walk me through what happened?”) before digging into specifics.

  2. Use neutral language. Avoid words that imply judgment or disbelief, e.g., “Why didn’t you report this sooner?”, “Are you sure that’s what happened?”, “So you’re saying he actually said that?”.

  3. Pausing is valuable. Silence is your ally. Allow others time to think; avoid rushing to fill the silence.

  4. Follow the thread. When someone mentions a detail in passing, explore it gently: “You said you felt uncomfortable, can you tell me more about that?”, “You mentioned there was a meeting that day. What was discussed in that meeting?” Use soft leads like Use soft lead-ins like: “You mentioned…”, “Help me understand…”, “Can you tell me more about…”, “What happened right before/after…”

  5. Stay curious, not certain. The best investigators aren’t trying to prove something; they’re trying to understand everything. For example, suppose a manager files a complaint claiming an employee was “rude and insubordinate,” rather than accepting that label. In that case, the investigator can meet with the employee and ask, “How do you usually communicate with your manager?” and “How do you think your tone was perceived?” This technique can reveal whether the employee is rude, whether both parties have different communication styles, and whether the tension stems from misunderstanding rather than defiance.

Call to Action

One of the worst situations for an investigator to find themselves in is to realize too late that they’ve drawn conclusions before gathering all the facts.

It happens subtly, a tone in someone’s voice, a personal bias, or an assumption that “this sounds familiar.” But once your mind closes, every question, every interpretation, and every written word starts to lean in one direction. That’s why good investigators constantly check themselves and their biases. Remaining open-minded isn’t just a best practice; it’s what keeps the process fair. When people feel the outcome has already been decided, even the truth no longer matters.

As an experienced Employment Relations and Human Resources Consultant, I specialize in conducting thorough, unbiased investigations that support both organizational integrity and employee trust.

For a confidential discussion or to learn more about how I can assist your organization, please contact me at: hrsupport@reliablehrm.org

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Setting the tone for a Safe Workplace Investigation Interview