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The Design Loft · Jul 3, 2026

Better Questions for Better Designs

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Cameron Norman · The Design Loft

Asking better questions is part of good design work.

And by good design, I mean creating products, services, and programs that are effective, attractive, and easy to use.

Yet, the mere asking of questions requires a space and time that’s not always available, or rather, it requires its own set of design conditions. That’s what we’re going to look at in this issue.

Research is a fundamental component of designing for health (or anything), as it ensures that the frame we use fits, and that the problem or situation we’re looking to address is actually the one that is contributing to our need for something different.

This past week I hosted the first in a series of six webinars on design for health in the age of complexity. (If you’re interested in the schedule and joining in on a future one, register here). The focus for the first event was on asking better questions.

Some of what was discussed was profiled in two previous editions of The Design Loft, with an emphasis on asking:

What are you trying to improve?

Who are trying to improve it for?

At the core of our first session was the role of questions and how better questioning can lead to insights. We covered some examples of how question-asking can lead to exploring some of the fundamental assumptions we bring to a situation and the possibilities that the answers enkindle.

What we didn’t get time to cover, was that asking questions is, in it’s own way, a process that requires some design work. Freedom to question, time to explore, and space to reflect all require some form of intentional action in our systems, whether those are organizations, networks, homes or otherwise.

It’s easy to suggest that we ought to ask better questions and give ourselves space to reflect upon what we see and do. But ask any leader, clinician, or caregiver and you’ll find that the time, care, and attention necessary to do this well is often lacking because of the demands of the system that they are in. That system — the clinic, the hospital, or the home-life demands, all bring with it continued demands, expectations, and norms.

We won’t cover all of these in this post, rather we’ll look at some of what we know about healthy question-asking conditions, drawing on the work of Warren Berger and others, who have looked at the role of question-asking and how it leads to better (more useful) answers.

Setting the stage for people to feel safe that they can ask questions, take (and make) space to question things is critical. Amy Edmonson’s work on psychological safety is of critical importance here. Edmonson, and others, have argued that there must be a culture where people can fail, share disagreements, ask questions of the process, and consider alternatives without fear of repraisal.

This also means creating a culture where people can be emotionally honest, which is another key factor in shaping design and critical inquiry.

Learning fails in poor systems. We often speak of learning, but to learn means to be open to new thinking and have a means to ask questions that can generate that new thinking.

As I noted on Censemaking, there are multiple issues we face with learning: 1) metrics that are poorly synced with outcomes, 2) an ingrained fear of failure, 3) credentials (and false attribution of skills based on them), 4) no pathways for knowledge to move, and 5) poor systems in place.

These also mean including slack time / “why” space, where there is a release from the pressure to “execute”. At it’s most innovative, Google instituted it’s 20% time policy, where employees were encouraged to develop projects adjacent to their work.

Creating cross-disciplinary spaces for conversations and collaboration. The work on Team Science is one example of where disciplinary transcendence in collaborative environments can yield better questions. This builds on what Berger found about the “beginner’s mind” that comes when we release the ‘expert trap’ that comes with experience in one area, yet might be limiting in others.

Warren Berger has a list of four questions that he suggests asking to help you ask better questions as part of a personal practice:

These are the kind of questions that can immediately bring you new ways to explore things.

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The final set of conditions are ones we’ll be exploring much more in depth in future posts. Setting up the conditions as an organization to structure, reward, support, and facilitate questioning and creativity is part of what the next session our Summer Series will cover.

Developmental Evaluation (DE) is a method of bringing together inquiry and questioning to the organization. To undertake DE in practice requires organizational changes that allow people to explore, sit, and make sense of what they see and provides a means to work with it.

Is your senior leadership on board with asking questions? Do you set aside time in key meetings or gatherings for question-making? Are there moments and systems to help you make sense of complexity when you encounter it (versus just trying to push through it).

Ask better questions and you can find your way to better design options.

Maybe ask yourself: how can I build a practice in my organization to consider the kind of question-asking and culture of inquiry that’s needed to innovate?

Stay tuned for more coming in the weeks ahead. In the meantime, join in our the summer series or check out the links here to find more about how you can innovate and design better for health.

If I can be of help, also reach out > https://linktr.ee/censemaking

Photo by Red Zeppelin on Unsplash

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