by Berend Booms, Associate Editor, Future of Assets

In my role, I spend a considerable amount of time writing, reflecting, and trying to make sense of the shifts we are seeing across asset-intensive industries. In doing so, I have come to realize that whatever clarity I am able to bring to my own thinking is rarely created in isolation. It is shaped, refined, and often challenged by the ideas and perspectives of others. Reading, more than anything else, has become one of the most important ways for me to continue learning, to expose myself to different ways of thinking, and to deepen my understanding of a space that is evolving faster than any single perspective can keep up with.

There are a few sources and platforms that I find myself returning to consistently, not just because of what they say, but because of how they say it. Today, I would like to highlight one such platform: Jon Mortensen’s excellent Substack “The Asset Management Guy”. I always enjoy Jon’s content, he has a clarity and sharpness that makes complex ideas feel accessible without ever oversimplifying them. A recent piece of his that I find particularly intriguing is the article “The art of the dumb question”. It has quietly lingered in my mind for a good number of days, and today I finally decided to write about it.

From both an editorial and a content perspective, it is the kind of writing I admire deeply, because it manages to be both practical and thought-provoking at the same time. What resonated most with me is Jon’s observation that asking so-called dumb questions can be one of the most effective ways to challenge authority without triggering defensiveness, because it invites explanation rather than confrontation.

The Questions That Stay With You

This made me think of all the times I have asked a question and instantly regretted doing so. Those moments often come back to me later, and end up with me endlessly replaying the conversation in my head, wondering how I navigated the conversation so poorly. For a long time, I found those moments difficult to let go of. I would overanalyze them, and quietly resolve to avoid putting myself in that position again. What I did not realize at the time is that in trying to avoid asking the wrong question, I was also holding myself back from asking the right ones.

Looking back at my own journey into asset management, where I am at now has in large part been shaped by asking questions I would now consider to be very basic. Coming into this space without a traditional technical background or education meant that I was often the least technically knowledgeable person in the room. While that can be a very uncomfortable position if you allow it to be, it also had a huge upside. I had the freedom to ask questions that others no longer thought to ask.

I remember asking a technician once why he filled out an ‘X’ in so many data entry fields. He responded that this was the fastest way to fill the mandatory fields, and the system would not let him continue otherwise. He simply had too many balls to juggle to take data entry seriously. My honest question addressed a deeper underlying issue than the technician not filling out data; because if he had been doing this for a while, why had no one downstream, who depended on that data, raised the issue earlier?

This is not limited to operational contexts; I have seen the same dynamic in transformation work as well. In a previous role, I was working on a big change management project in a global IT company. All of their processes were neatly documented, but the language used was really technical, full of jargon and very hard to digest. The majority of people I worked with were non-native speakers. During a team call, I asked if everyone understood these processes, as I had a hard time making sense of them myself. My question was followed with a brief silence, but it led to one of the most productive sessions in that project. Even if they do not always feel comfortable in the moment, these questions serve a good cause.

Questioning What Everyone Thinks They Know

Jon makes a point that I think is particularly relevant in our space, which is that so much of what “everyone knows” is built on assumptions that have simply gone unchallenged for long enough to feel like facts. In asset-intensive industries, where processes are often shaped by decades of experience, regulation, and legacy systems, those assumptions can run deep. They often go unquestioned because questioning them requires someone to step up and speak out.

This is where the so-called dumb question becomes incredibly powerful, because it creates a different kind of conversation. Instead of challenging a statement directly, which can trigger defensiveness, it invites explanation and conversation. It shifts the dynamic from debate to exploration, and in doing so, it often unveils insights that would otherwise remain below the surface.

Many of the discussions I have around digital transformation and the role of new technologies benefit from this vantage point. It is very easy to talk about predictive maintenance, AI, or connected assets at a conceptual level, and to assume a shared understanding of what those terms mean in practice. But when you ask a simple question like “what problem are we actually trying to solve here”, or “how will this change the way someone does their job tomorrow morning”, the conversation often shifts to become more grounded and more honest.

Asking open questions allows you to gently steer the conversation without ever positioning yourself in opposition. Asking a genuine question can be very disarming, lowering the natural resistance people feel when their ideas are challenged directly. In that sense, asking a question can be one of the most effective ways to influence direction, precisely because it does not feel like influence at all.

Getting Comfortable With Discomfort

Admittedly, none of this removes the discomfort entirely; there are still moments where a question lands awkwardly, or where you realize mid-sentence that you are poking at something that others may consider obvious. I still reflect on how conversations went and conclude that I could have composed myself better, or perhaps not asked any questions at all. The difference is that I no longer see those moments as something to avoid, but as part of the process of learning and creating a better understanding. For every question that feels misplaced, there are others that unlock understanding, challenge assumptions, or create space for someone else to admit that they were wondering the same thing.

That last point is really important: asking a question does not just serve your own learning, it often gives others permission to engage more openly as well. I have found that in business and other professional settings, there is an unspoken pressure to keep up appearances. I am absolutely complicit in signaling understanding even when things are not entirely clear. One honest question can shift that dynamic, making it acceptable to step out of that pattern and have a more meaningful conversation.

The Future Is Based On Better Questions

The idea I have in mind for what we are building with Future of Assets is very aligned to this idea. This platform is not about presenting polished answers or reinforcing established narratives. It is meant to be a space for conversations that help us better understand the challenges and opportunities in front of us. This naturally requires a willingness to ask questions, even if those questions are uncomfortable, incomplete, or lacking an obvious answer. Progress in this space is rarely driven by having all the answers upfront. It is driven by curiosity, by the willingness to explore, and by the ability to look at familiar problems from a slightly different angle.

Jon’s blog is a great reminder that the questions you hesitate to ask are often the ones worth asking; they do not have to be perfectly phrased or offer immediate insights, as long as they help create movement, open up conversations, challenge assumptions, and ultimately help us get closer to understanding what really matters. And perhaps that is the real shift we need to embrace: not striving to always have the right answers, but becoming more comfortable asking the questions that move us closer to them.