How Organisations Learn, One Question at a Time

Following a single question from your notebook to the rooms where strategy is made

Dec 04, 2025

This article is a collaboration with Jason L Zimmerman. His publication 3Fold Outcomes unpacks why some strategies quietly succeed while the vast majority unravel.

You probably don’t control the strategy slides, the budget lines or the org chart. But you do control the questions you ask in the next meeting, the next 1:1, the next email you send. And those questions quietly decide whether your work is just execution — or whether it becomes a source of learning for you, your team and, eventually, your organisation.

Most companies say they want to be “learning organisations”. In practice, many of them run on a different fuel: directives, updates, and answers delivered as fast as possible. Work becomes a conveyor belt. Things move, but very little actually changes. The surprising thing is how small the shift can be when a different fuel starts to flow. One well‑placed question can slow the belt just enough for people to see what’s really happening — and once people see differently, they tend to act differently.

This is where you have more influence than you think. You don’t need permission to start asking questions that surface assumptions, clarify what you’re really trying to learn, or make it safer to say “we don’t know yet”. You can start at your own desk, in your own notebook, in the way you debrief your week. Over time, the questions you use privately have a habit of leaking into the conversations around you. Others pick them up, adapt them, and carry them into rooms you’re not in.

In this article, we’ll follow that journey. We’ll start with the questions you ask yourself, then look at how they change the texture of a team, and finally how they can spread into the wider system. Along the way, we’ll look at the conditions that either kill this kind of curiosity on contact or allow it to become quietly contagious. Because while you may not be able to redesign your company from scratch, you can absolutely change the local climate around you — one good question at a time.

Fancy a deep dive? Social scientists describe this as a threshold model of collective behaviour: each of us has a point at which seeing enough others ask different questions or frame problems differently makes it feel safe to do the same. Once enough thresholds are crossed, norms can tip quite quickly from silent.

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Act 1 – The Questions You Ask Yourself

Most shifts in culture start long before anyone names them. They begin in the quiet, unremarkable moments where you decide how to make sense of what just happened. That is where questions do their first, most invisible work.

Imagine a week where a project you care about is drifting. Stakeholders are slow to respond, priorities are colliding, and you’re caught in the middle. The default reaction is familiar: frustration, a mental list of people who “don’t get it”, maybe a late-night rant to a friend. In that mode, the question running in the background is usually something like, “Why is this so hard?” or “What’s wrong with them?” You may not say it out loud, but it quietly shapes how you feel and what you notice.

Now swap that question for another one: “What am I actually learning from this?” or “What would I like to understand better about how decisions are made here?” Nothing changes on the outside at first. The delays are still there, and the clashing priorities don’t magically resolve. But you start scanning the situation differently: you notice who responds quickly and who doesn’t; you see which arguments land in emails and which only work in a live conversation; you start collecting small fragments of pattern instead of only collecting evidence that you’re stuck.

That is the first act of contagion: a question changes what one person pays attention to. Before it travels anywhere else, it rewires the experience of work for the person using it.

To make the shift possible, you need some conditions at the individual level that effectively lower the friction:

A sliver of time to reflect, even if it’s five minutes at the end of the day.
A willingness to sit with “I don’t know yet” instead of demanding a neat story.
Permission – mainly from yourself – to treat frustration as data rather than as failure.

From the outside, this doesn’t look like culture change. It looks like someone scribbling in a notebook or staring out of the window on the commute home. But over weeks and months, those seemingly simple questions do something important: they give you language. When you’re clearer on what you’re trying to learn, it becomes much easier to bring that curiosity into the conversations around you.

Interested in exploring how this shift may happen in practice? Check our Jason’s article:

3Fold Outcomes

Part 3: How Microsoft Rewired Its Culture for Curiosity

At a Glance: When Satya Nadella became CEO in 2014, Microsoft was a paradox: profitable, yet paralyzed by internal rivalry. Rather than reorganize or mandate culture change, Nadella quietly redesigned how learning spread. He seeded empathy and curiosity through trusted relationships, repeated modeling, and shared ownership — conditions that mirror socio…

a month ago · 2 likes · Jason L Zimmerman

Act 2 – When Your Questions Escape Into The Team

At some point, the question that has lived mostly in your own head slips into the room. Maybe you’re in a recurring status meeting that always runs out of time, or a planning session where everyone is rushing to assign owners and deadlines. You feel the same pressure to “get through everything”. But now you’re carrying a different internal script.

Instead of jumping straight into updates, you say something like: “Before we dive into the tasks, can we spend a couple of minutes on what we’re actually trying to learn from this next phase?” Or, at the end of the discussion: “If we look back in a month, what will we wish we had paid attention to now?”

You haven’t criticised anyone. You haven’t derailed the agenda. You have simply placed a question in the middle of the table.

The first time, people may look at you blankly. Someone might offer a quick, tidy answer and try to move on. But often something else happens. One person adds a nuance: “I suppose we’re trying to learn whether this new segment even cares about this feature.” Another voices a concern: “I’m not sure we’ve thought about how this affects support.” The air shifts, just a little: the meeting is now not just about “Are we on track?”, but also about “Are we even tracking the right thing?”

This is where questions become social. For a question to be contagious at team level, a few things help:

It needs to be safe to answer and not single anyone out as the problem.
It needs to be simple enough to remember and repeat. No jargon or ‘cleverness’ required.
It needs to reliably highlight something useful, so that every time the team answers it, they see a bit more clearly.

When those conditions are there, people will start to reuse the question. You hear a colleague say, at the next meeting, “Can we start with what we’re trying to learn here?” Someone else borrows it for a 1:1. In retrospectives or after-action reviews, it becomes a ritual. At that point, the question is no longer yours: it belongs to the team. And as it circulates, the question often changes shape. People adapt it to their language, their role, their risks. That evolution is a signal that the environment has been shifting through a process of repeat exposures: a team that once defaulted to execution is beginning to treat the work as something to learn from, not just deliver.

Of course, this can be shut down. If leaders respond defensively – “We don’t have time for philosophy, just get on with it” – the question dies on contact. If every meeting is packed so tightly that there’s no air for reflection, new habits can never take hold. But in teams where there is even a modest amount of psychological safety and a few minutes of slack, good questions tend to stick because they offer just enough relief and clarity that people are glad to see them again.

Act 3 – When Questions Cross The Boundaries of The System

The most interesting moment is when a question you helped seed shows up in a room you don’t control.

Picture a cross-functional steering group or leadership review. People are discussing a major initiative. The slides are polished and everyone feels under pressure to commit. In many organisations, these moments are dominated by declarations: “We will deliver X by Y.” “We are confident this will drive Z.” The goal is to look certain.

Now imagine someone at that table – maybe your manager, maybe a peer from another function – says, “Before we sign this off, can we be explicit about what we’re trying to learn from this in the next quarter?” Or, “What would we need to see in three months to know this isn’t working the way we hoped?”

It is the same kind of question you started with at your desk. But the stakes are very different! Here, it changes not only how a single team plans its week, but how the organisation treats uncertainty: instead of pretending that the future is fully knowable, the group names its assumptions and clarifies what will be measured, what will be watched and what might trigger a change of course.

Moments like this spread because multiple people, across different corners of the organisation, keep naming the same uncertainty, which in turn builds momentum. As we have explored above, most people won’t shift their behaviour on a single exposure, but they often will when they hear the same invitation from several trusted voices.

That is what it looks like when questions begin to operate at system level. They become part of the interface between strategy and reality. For that to happen, the conditions have to widen:

Leaders need to react well when someone asks a question that uncovers risks or doubts. Thanking the question, exploring it and acting on what it uncovers sends a strong signal.
Information has to be able to move. If insights from the front line can’t travel upwards – or if they are sanitised beyond recognition – then learning just doesn’t happen.
Incentives need to reward early course-correction, not just hitting the original target at any cost. Otherwise, there is no upside to asking the uncomfortable question.

So, even though you may not sit in those rooms yet, you can still influence what reaches them. When you turn your own frustrations into questions, and those questions into small team rituals, you are increasing the chances that someone, somewhere, will carry a clearer question into a bigger conversation.

Culture change often gets described in sweeping terms: new values, new strategies, new operating models. But under the hood, the day-to-day reality is far more granular: it is the accumulation of moments where someone decides to ask, rather than assume, to inquire, rather than instruct. From your vantage point “inside the machinery”, that is not out of reach.

Making It Practical When You Don’t Run The Place

Before we finish, it’s worth making this as concrete as possible. In simple terms, what do you actually do on Monday?

A useful way to think about it is in three small moves that mirror the three acts.

🔎 First, choose a question you will use as a private lens for a while.

Something simple, like “What did I learn from today that I don’t want to forget?” or “What am I really trying to understand about how this place works?” Commit to asking it at the end of the day or the end of the week. Write the answers down somewhere you’ll see them again. This is about training your attention so that work becomes raw material for learning rather than just something to get through.

💬 Second, introduce a question into one conversation you already influence.

That might be a regular team meeting, a 1:1 with a colleague or a project check-in. You don’t need a grand redesign of the agenda. You just need a small wedge of time where the group is invited to think out loud.

For example: “Before we wrap up, what did we learn this week that should change how we approach next week?” or “Is there anything we’re assuming here that we haven’t tested?” The goal isn’t to impress anyone, but to make it a little easier, and a little more normal, to talk about learning in the middle of the work.

🛫 Third, let one question travel a step further than usual.

When you notice a pattern or a frustration, resist the temptation to turn it into a complaint. Turn it into a question and send it where it might do some good. Questions tend to move fastest through relationships where trust already exists. So if you want a question to travel, aim it toward the people whose voices carry weight in the spaces you can’t reach. Influence is often informal, and learning follows those paths.

For example, you might go to someone with influence in the area you have in mind and ask: “We’re seeing a lot of rework when requirements change late in the process. What are we actually trying to learn from these pilots, and how could we see that earlier?” Or: “From where we sit, it looks as if initiative A and initiative B are pulling in different directions. Is there a way to make the trade-offs more explicit?” As you’d expect, you won’t always get the response you hope for. But you are increasing the chances that your question will be considered by someone in a different through a learning lens.

None of these moves require a new job title. They don’t depend on an off-site or a big announcement about culture. They are small, repeatable ways of adjusting the climate in your own corner of the system. Over time, they create the conditions in which questions can spread: people expect them, they see that they lead somewhere useful and they feel a little braver offering their own.

If enough people do that in enough places, the organisation begins to behave differently, even if nobody can quite pinpoint when the shift began. That’s the power of questions used consistently from your vantage point on the ground, which is not out of reach. It all starts by changing how you think about your own week. You end up, almost without noticing, shifting your habits and helping the whole system learn a little faster.

The Art of Asking Questions

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