##### The art of asking better questions begins with finding words for what bothers you For my writing in 2026, I want to apply some changes to my Notefields publication. I enjoyed the high pace I developed last year and I want to go further in this direction. But I also realised I only could achieve about 3x more output in the 2nd half of 2025 compared to previous years by investing a significant bit of my resources into this kind of writing. I can not invest that much in the long run, hence I need to review my way of writing things here. To focus the scope of Notefields, I want to focus my writing in this mode on **questions**. Questions want to be answered. Questions connect thinking to a purpose. They create a pull of relevance, around traps of procrastination, right into rabbit holes of serendipitous value. Questions create momentum.[^1] Going forward I want to tackle ONE question at a time. I don’t expect I will have answered a question every time I finish a piece, but at least I should have developed my understanding far enough to come up with a better question for the next piece. Recognizing the questions I keep asking myself and then address them one at a time in my writing seems like a good enough scope to test it in the first quarter of 2026. This approach puts a lot of weight on the initial questions that trigger my writing. That’s why I started wondering: what makes a good question? How can I ask myself **better** questions? I read a bit in ["A More Beautiful Question" by Warren Berger](https://www.amazon.de/-/en/Warren-Berger-ebook/dp/B00GC53AG8). It oozes of 2010s Silicon Valley kool-aid, yet I could draw some good insights from it. The framework is centered around a philosophy I like: asking "ambitious yet actionable" questions.[^2] Considering the questions I ask myself, this seemed a promising way to go. Berger further proposes to categorize questions into three archetypes: WHY-Questions, WHAT-IF-Questions, and HOW-Questions.[^3] These are like developmental stages in a sensemaking process, sitting on top of each other: - You start with the "**Why?"** (of course, its a Silicon Valley book). Any line of questioning should start with clarifying motivation and context. Gaining an understanding of "Why" helps to deconstruct the initial problem statement, to challenge the briefing.[^4] - When the Why is clarified, you should move on to thinking about possibilities. So next up is "**What if?"**. By asking "What if?" you create a hypothesis, asking "What if X was the case?". Investigating possibilities allows interesting things to emerge and it creates the stage for probing things with the following question. - Next up is the "**How?**" stage. This is about practical impact. After you created a bunch of possibilities and scenarios, it is now about finding ways to apply some of it in reality and learn something from the feedback.[^5] These ideas seem decent enough to give them a try. But thinking further about it, I thought something is missing. Because: how do you come up with a "Why" question in the first place? I think in the beginning, there should be a hunch. Something that is nagging me, something I cannot let go of. It’s a preverbal notion, an embodied idea, something that is just not yet ready to fully put into words. Being able to name the thing that bothers me is a first step of understanding and it is when the medium of writing offers unrivaled benefits. A hunch is ready to be investigated further when I can put it into words, when I understand what my yet unexpressed ruminations are about. Thats why expressing a hunch may be considered a "**What?**" question. If I am able to provide some initial answers, this can be the starting point of a chain of sensemaking. My personal four-phase model of questioning now looks like this: 1) **What?** *What is the thing that keeps nagging me?* 2) **Why?** *Why does this concern me?* or *Why is this the case?* 3) **What if?** *What if the thing would be different?* 4) **How?** *How can I try to change something about it?* I tend to be impatient with my writing because I always want to move on with my thinking. I sometimes get frustrated with myself, when old writing unforgivingly uncovers that mental breakthroughs from the day before have been circulating in my notes for years without moving much. This impatience led me to skip steps in the above arc of Sensemaking. But rushing Sensemaking fires back, it’s accumulating epistemic debt that will haunt me later. I have experienced how this feels: - If you investigate a Why question without a well established hunch, you end up with lifeless academic pieces of writing. Unfortunately this is the kind of "serious" writing I know (and have produced myself) in the space of Design Criticism. While trying to sound professional by keeping out the personal motivation (thats where the hunch should be). This creates boring writing without enough stakes involved. - Working on What-if questions without having answered the Why before ends up in shallow speculation. I have seen this in ideation sessions when people start to push out ideas without understanding the texture of a problem. Very often, you come up with things that seem innovative in a narrow context like a workshop or a social media post. But this stuff does not create lasting impact. Its merely good enough to make the "Future" section of an automotive trade fair look innovative for visitors passing by. - Investigating How questions of implementation without having worked on a What-if before is a classic case of stubborn bad engineering. People receive a spec and execute it the way they have always done it because they want to avoid criticism, because they don’t want to face the discomfort of going new ways. The web is full of instrumental pieces answering how to fix problems nobody cares about. You can find plenty of advice for asking better questions on the tactical level. Avoiding ambiguous terms and value judgments, making questions falsifiable, and so on. All of that is nice. But I think it’s much more interesting to look at questions from an upstream perspective.[^6] Where am I located with a certain topic in a process of understanding? Am I still figuring out **what** I am actually thinking about? Am I trying to understand **why** something is like it is? Or am I wondering **what if** something about the thing would change? Or am I already trying to understand **how** I can do something with the thing I figured out? To make this more practical, let’s apply my extended 4-stage framework of questioning myself to the way I arrived at this piece: - While I was writing Notefields essays at the end of last year, I felt a growing unease that the effort I invested to write at this frequency would not be sustainable. At some point, I could point the finger to my unease and I had to address it. I had answered the question of "***What** is concerning me with this mode of writing?"*. My answer: Because it does not feel sustainable. - Then I started to investigate the Why. ***Why** does it seem like the effort is not sustainable for the long term?* And I realised that the implicit quality criteria I developed for this format, which was intended to be fast-paced writing, somehow creeped into the territory of perfectionism. Despite me starting with the intention of doing quantity-over-quality style writing, I ended up (not for the first time) being quality obsessed. - Then I wondered what I might change. *"**What** if I adapted the bloated implicit quality criteria for my Notefields publication and reframed them?"* In particular, what if I sharpened the writing to maintain a decent level of quality but within narrower scope? A bare minimum quality criteria, so lean I would reliably able to match it every week of writing in the long run. - ***How** could I refocus the quality criteria of my Notefields?* This made me realise I could go back to an idea I had some time ago: focus every piece on tackling one single question at a time. It is about *tackling* questions, not *answering* questions, because some good questions may never be answered. A reframed question is a valid result of this process. This is how I can ask myself better questions: **A good question provides direction for my current location in a process of understanding.** Some interesting follow-up territory to consider later: - How do questions chain across pieces? Several related questions might merge into a question on a higher level, like answering a number of "Whys" and ending up with one "What-if". - It may also be possible to sometimes skip phases entirely, formulating a hunch and jumping to what-if without formulating a Why. It’s likely this would cause some kind of problems, but it might be interesting to play around with it, see how this framework really holds up, see when it breaks and epistemic debt starts to pile up - Or I might be able to move the chain backwards: When stuck with an implementation question of What, it could be interesting to move backwards to creating What-if possibilities and so on I will use this framework for my next pieces of writing, to see what it can do for me. If I am able to produce decent quality pieces at a consistently high pace without being stopped down by perfectionism, it is a useful framework worth investigating further. I got the feeling this might do good things for me. Let’s start 2026 with a Hunch. [^1]: *Articulating a personal challenge in the form of a question has other benefits. It allows you to be bold and adventurous because anyone can question anything. You don’t have to be a recognized expert; you just have to be willing to say, /’m going to venture forth in the world with my question and see what I find. As you do this, you're in a strong position to build ideas and attract support. (...) All of this helps to build momentum. Questions (the right ones, anyway) are good at generating momentum, which is why changemakers so often use them as a starting point.* [[--A More Beautiful Question The Power of Inquiry to Spark Breakthrough Ideas (Warren Berger)#Questions generate momentum]] [^2]: *A beautiful question is an ambitious yet actionable question that can begin to shift the way we perceive or think about something—and that might serve as a catalyst to bring about change. [[--A More Beautiful Question The Power of Inquiry to Spark Breakthrough Ideas (Warren Berger)#Ask ambitious yet actionable questions]]* [^3]: This is the line from Berger that inspired these levels: *"Person encounters a situation that is less than ideal; asks Why. Person begins to come up with ideas for possible improvements/solutions—with such ideas usually surfacing in the form of What If possibilities. Person takes one of those possibilities and tries to implement it or make it real; this mostly involves figuring out How."* [[--A More Beautiful Question The Power of Inquiry to Spark Breakthrough Ideas (Warren Berger)#Why What If How Pattern]] [^4]: *This all comprises the first stage of innovative questioning— first confronting, formulating, and framing the initial question that articulates the challenge at hand, and trying to gain some understanding of context. I think of this as the Why stage, though not every question asked at this juncture has to begin with the word why. Still, this is the point at which one is apt to inquire: Why does a particular situation exist? * Why does it present a problem or create a need or opportunity, and for whom? Why has no one addressed this need or solved this problem before? Why do you personally (or your company, or organization) want to invest more time thinking about, and formulating questions around, this problem?* [[--A More Beautiful Question The Power of Inquiry to Spark Breakthrough Ideas (Warren Berger)#Good Questions start with why]] [^5]: *The How stace of questioning is where the rubber meets the road or, in Nanda’s case, the clock hits the floor. It’s the point at which things come together and then, more often than not, fall apart, repeatedly. Reality intrudes and nothing goes quite as planned. To say it’s the hard part of questioning is not to suggest it’s easy to challenge assumptions by asking Why, or to envision new possibilities by asking What If. Those require difficult backward steps and leaps of imagination. But How tends to be more of a slow and difficult march, marked by failures that are likely to be beneficial—but don’t necessarily seem that way at the time. * [[--A More Beautiful Question The Power of Inquiry to Spark Breakthrough Ideas (Warren Berger)#The How Stage forces ideas to meet reality]] [^6]: *We are rational, analytical creatures. Many jobs in the modern knowl- edge economy – from market research to academic enquiry, sales to medicine, journalism to coaching – depend on practitioners using analytical thinking techniques to solve problems. Solving problems has a powerful gravitational pull towards the tactical and away from the strategic. Yet analytical thinking is not the only form of thinking that is valuable in the workforce. Insightful thinking, where we join old and old together to make something new, to create a profound and useful new understanding of a person, issue, topic or thing, is also incredibly ‌valuable. The trouble is, with so many roles in so many career paths predicated and rewarded on the basis of solving problems, analytical thinking is our preferred way of thinking and so more practiced and more highly valued than insightful thinking. What this means is that our thinking – and our questions – get too tactical, too soon, and often stop when a workable (if unimaginative) solution is proposed. This approach misses a whole step.* [[--Asking Smarter Questions; How To Be An Agent Of Insight (Sam Knowles)#Questions tend to turn tactical too quickly favoring analytical over insightful thinking]]