As originally published in Canadian Defence Review magazine.
Some topics don’t disappear because someone decides they should. They simply fade. A question is raised, there is a pause, and the conversation moves on.
These are rarely minor issues. More often, they’re the topics that matter most. They create uncertainty or don’t fit neatly with accepted explanations. Raising them makes people uncomfortable. Many organizations, especially large ones, are not designed to deal with that feeling.
Plato once suggested that asking the right question is usually more important than finding the right answer. In institutional settings, however, we often behave as though the opposite is true. Questions are valuable only if they can be answered quickly, resolved cleanly, and translated into certainty. The result is predictable. The most important questions are often the ones most likely to be softened, postponed, or quietly set aside.
The challenge is how quickly intent is assumed. Questions are not always heard as questions. They’re sometimes received as criticism, advocacy, or dissatisfaction, even when they’re meant to create positive change. Once that happens, discussion stop being neutral and becomes personal, whether that was intended or not.
I’ve learned this through experience. There have been moments when my focus on analysis or problem-solving moved faster than my awareness of how exposed people might feel when certain issues are raised. What seemed like a straightforward assessment meant to add value landed differently. Not angrily. Just…unfortunately.
Those moments are easy to miss if you are not paying attention. The pause lingers. Someone changes the subject. The energy shifts. The meeting continues. Only later does it become clear that the issue itself wasn’t the problem. It was how it was introduced.
Although this pattern exists in many sectors, it’s especially familiar in defence. Defence organizations are built around caution for good reasons. Mistakes have real consequences. Accountability lasts. Decisions are revisited. Over time, this creates cultures that value certainty, continuity, and disciplined process. None of this is accidental.
At the same time, these habits can make open inquiry harder. Admitting past mistakes can feel risky when responsibility doesn’t fade. Procurement processes often continue because stopping them introduces a different kind of uncertainty. These are not flaws. They are defaults.
Industry faces similar pressures. When companies depend on a small customer base, thin margins, and a competitive bidding environment, caution is encouraged. Questions that might complicate a proposal or strain a relationship are often softened or postponed. Sometimes they’re only raised after decisions have already been made, often to the detriment of the relationship.
Over time, certain subjects acquire a reputation. Everyone knows they exist, yet few people want to address them directly. Silence becomes the safer option. Not because people lack insight or commitment, but because the system quietly rewards caution.
What rarely helps is arriving with fully formed answers, frameworks, or solutions. Certainty, especially from outside, often hardens positions rather than opening discussion. When progress does happen, it usually starts in a less satisfying place: with careful, incomplete and sometimes uncomfortable questions.
When asked the right way, questions change the tone of a conversation. They slow things down. They allow people to think instead of defend. They create room for leaders to work through implications on their own terms. In this sense, inquiry becomes a way of managing risk rather than creating it.
Working this way takes discipline. It means resisting the urge to sound certain, allowing conversations to unfold and sitting with discomfort longer than feels natural. This is not always easy, particularly in organizations where momentum itself can feel reassuring. Yet, activity should not be mistaken for progress, and timeliness should not be confused with plans.
Avoiding difficult questions carries costs that are easy to overlook. Decision quality suffers. Risks build quietly. Dependencies become harder to change. Organizations move forward with confidence while rarely pausing to ask whether their direction and intention still align.
This does not mean every sensitive issue should be discussed publicly or resolved quickly. Some require discretion. Others need time. The challenge is knowing the difference between productive inquiry and unnecessary noise. Trouble begins when avoidance becomes routine and discomfort becomes a reason to stop thinking.
Healthy organizations are not those that eliminate unease. They’re the ones that can work with it. Silence can feel stabilizing in the short term but over time it usually has the opposite effect.
Long before modern organizations worried about governance frameworks or procurement cycles, philosophers understood the power of careful questioning. Socrates did not persuade by offering answers. He created space for understanding to emerge.
The challenge facing the defence sector today is not a lack of expertise or commitment. It’s learning how to ask difficult questions without treating them as acts of dissent and learning to recognize discomfort not as a signal to stop, but as an indication that something worth examining has been reached.
