What happens when individual wisdom meets organizational learning? (Part 1)

Laura Richards (Illuminary Perspectives) spends her days helping organizations build the capacity to learn while the work is happening, not after. Laura Hartley (Scintilla Centre) spends hers on the other side of that: helping changemakers gather the relational, emotional, and creative skills of transformation.

We kept running into the same gap from opposite directions. Laura H. would describe a client who’d done real, hard personal work and still felt swallowed by their organization within a month of walking back in the door. Laura R. would describe organizations that built entire learning systems that never actually changed how a room behaved. Same problem, different entry point.

So instead of resolving it into one tidy answer, we decided to write it out in the open - either questions, each answered independently, then responded to across the individual/organizational divide. It ran long enough that we’re splitting it into two posts.

The first post covers the terrain: what uncertainty actually is, what a sane relationships to it looks like, where adaptive capacity lives, and whether an organization can be wise at all. Laura H. works from the insight out - the individual, the story someone’s carrying. Laura R. worked from the outside in - the room, the structure, the pattern an organization falls into without meaning to.

Neither of us thinks the other’s answer is wrong. We think you need both. Where we agree, you’ll see it. Where we don’t quite land in the same place, that’s in here too.

Part 2 picks up where this one leaves off: why individual change doesn’t automatically become organizational change, how organizations actually learn, and what it takes to build the capacity for wisdom to stick.

What kind of uncertainty are we actually talking about?

Laura Richards: The organizations I work with are trying to shift systems, strengthen communities, and change policy. People don’t behave the way the model predicted. A funder’s priorities shift mid-grant. A partner organization reorganizes and your point of contact is suddenly gone. There’s rarely a single right answer sitting there waiting to be found. There’s a moving situation you’re trying to stay in relationship with.

So for me, uncertainty isn’t a stage before certainty. It’s the terrain itself.

I think we struggle here because we bring tools built for stable ground into places that keep shifting under our feet. We build detailed plans, dashboards, and theories of change like they’ll eliminate uncertainty if we’re just thorough enough. Those tools are useful. But only if we remember what they’re actually for: not maps that mark the destination, but instruments that help us tell where we are while we keep moving.

That reframes the question for me. Instead of “how do we reduce uncertainty,” I ask, “how do we get better at learning inside it?” That’s a different muscle. It means paying closer attention to what’s actually emerging instead of what we predicted would emerge, questioning our own assumptions on purpose, and treating course correction as normal rather than as a sign something went wrong.

Uncertainty isn’t the problem I’m trying to solve for with my clients. The real work is building their capacity to respond to it with some steadiness, instead of lurching from plan to plan every time the ground moves.

Laura Hartley: I so agree.

I also bring a macro lens to uncertainty to begin; we’re living in a world that is deeply uncertain right now. Where once there might have been a narrative of security - if you were fortunate enough to be born into certain countries, and you took the right steps, studied the right course, got the right job, followed the promotion, took the “sensible” steps - that things would work out; that story is no longer holding true.

We live in a world shaped by increasing conflict and violence, economic upheaval, climate change, AI, fraying democracy… uncertainty is the landscape now. The world will not look the same in 20 years as it does now, but not many of us have a clear picture of exactly how it might look. This can be both scary or liberating, depending on how we look at it.

This lens for uncertainty, as something generative as much as fearful, is really important: because often when we think of uncertainty, it’s framed in the light of a “problem” - something tricky, something to manage or fix, something to “figure out.” We also frame uncertainty as being specific to a time, place, or challenge. We might be “uncertain” in deciding our next career steps, or navigating a messy conflict, or how to get where we want to be.

But uncertainty, in my opinion, isn’t so much of a “problem” to be solved, nor is it unique to a time or place (although, sometimes we feel its presence more than others). Rather uncertainty is a foundational reality of living.

If change is the underlying promise of life - and along with death (and taxes?), it is - then uncertainty has a foundation and role that means we are in constant relationship with it. The reality is much of the big “stuff” of life is and always will be uncertain:

• We don’t know when we our our loved ones will pass away.

• We can’t know at the beginning - or middle - of a relationship if it’s “forever.”

• We can plot our career as best we can, and still not predict the redundancy, the illness, the mid-life crisis, the market crash.

Life is inherently built on uncertainty - and in many ways this is what gives it its meaning. I also think when we start to see uncertainty with a different lens, we already have different names for it, including adventure.

LR: That macros lens explains something I notice at the practical level as well: why no methodology was ever going to out-plan this. If uncertainty is baked into the biggest things in life (who we lose, whether a relationship holds, what the market does to a career), then no dashboard was ever competing with certainty. It was only ever competing with denial. That reframes by own work a little: the plans and theories of change I build with clients aren’t failing to eliminate uncertainty. They were never supposed to. Once I see it at your scale, the client-level version stops looking like a limitation of the tools and starts looking like the correctly sized response to something genuinely uncertain all the way down.

What does a same response to uncertainty look like?

Laura Richards: Here’s what I notice: the more uncertain things get, the tighter organizations grip. More plans, more dashboards, more metrics, more evidence that we’re “on track.” I get the impulse…gripping tighter feels responsible. But grip doesn’t reduce uncertainty. It just makes you feel better about the uncertainty that’s still there. The actual sane move is the opposite of grip: curiosity.

Curiosity is what lest you keep functioning without already knowing the answer. It’s not naive optimism, and it’s not the passive “let’s wait and see” that starts to look a lot like avoiding a decision. It’s active - you keep paying attention, keep asking what’s happening compared to what you expected, and you let that attention change what you do next. Certainty forecloses. Curiosity keeps the door open.

In practice, curiosity is built out of small, unglamorous moves. Before I ask a client “did you hit the target?,” I ask, “what we we noticing?” That one substitution changes the whole conversation, because it invites people to make observations instead of defending a number. I treat a plan as a hypothesis, not a promise, so a plan not working out isn’t a failure to explain away; it’s data. I treat an evaluation as a source of ongoing questioning rather than a verdict, something you argue with instead of something that closes the conversation.

None of that means abandoning rigor. You still make the call with the best information you’ve got. You just hold it loosely enough to change course when Tuesday’s information contradicts Monday’s plan. And you treat needing to change course as a sign the curiosity worked, not a sign the plan failed.

Here’s why I call this sane rather than just nice: uncertainty doesn’t go away because you gripped harder. Certainty was never actually on the table. The organizations that hold up under uncertainty are the ones that stayed curious enough to notice what was actually happening, instead of what they’d already decided should be happening. Curiosity was the only real option the whole time. It just doesn’t feel like one because it asks you to sit in not-knowing on purpose, in public, in front of your board or leadership.

Laura Hartley: As individuals encountering uncertainty, we often respond by trying to control, mitigate, or de-risk the situation. We want to make sure we make “the right decisions,” pause until we have “more information” or delay starting until we “feel ready.”

We do this in the hopes that we’ll be more safe amidst the uncertainty. Uncertainty comes with the unknown - with risk, with fear, with the potential for things to go in a direction we may not want. But in trying to respond to uncertainty with the methods of “monoculture” - control, fix, eradicate, ensure, holding tightly and rigidly - then we miss both the possibility, and the transformative potential, that uncertainty actually holds.

If we consider uncertainty to be a teacher, it works on us in three ways.

First, it allows us to build the emotional and moral musculature that reshapes the world. Without uncertainty, risk would not exist. Without risk, no courage, no vulnerability, no deep and radical acts of love. And all three of these - along with compassion and empathy - help form the emotional architecture we need to be drivers of a just world.

Secondly, uncertainty helps us understand our place in the relationship of things. We are not controllers or Gods, and while we may be able to steward and care for life, uncertainty keeps us humble, and reminds us we’re not at the centre of it. Uncertainty, with its inherent partner risk, also creates the conditions for us to be present, to make meaning, to sense and wayfind our way forward into the world. A risk-free, certain world has no need for these skills, all of which are at the heart of being human, and what make adventure.

Third - and this is particularly important when we’re considering a sane response to uncertainty - is it allows us to develop our creative musculature. Contrary to how we often feel when we meet uncertainty, it can contain as much potential and possibility as it does what we fear. Uncertainty is uncertainty - so what if things worked out? What if you got really creative with the raw materials in front of you? What if you could be led by something other than past data? What if all the scarcity of options you see was actually an invitation to create something new?

And while we live within a world in crisis, isn’t creating something new exactly what we need?

So a sane response to uncertainty is les about waiting for clarity, or trying to control the variables, or even surrendering our power and saying we’re helpless to the uncertainty of life; rather it’s about building our moral, emotional, and creative musculature to ensure we’re adequately equipped to navigate whatever arises.

LR: I like sitting with your “teacher” framing next to my “unglamorous. moves” one, because I think they’re the same muscle at two different weights. Asking “what are we noticing” instead of “did we hit our target” is a small, low-stakes rep. Nobody’s really at risk in that swap. But it’s rehearsal for exactly the courage you’re describing: sitting in not-knowing when the stakes are real and the board wants a number. I don’t think you get to the big, brave version of curiosity by deciding to be brave once. You get there by practicing the small version often enough that the nervous system doesn’t panic when the real one shows up.

LH: Yes, exactly! None of this - personal or organizational - is a one time thing. It’s the practice and the reps, even at micro-scales, that build what we’re talking about.

Where does adaptive capacity actually live?

Laura Richards: I don’t think it lives all the way inside individuals, and I don’t think it lives all the way inside org charts and processes either. It shows up in the space between people, which is a less satisfying answer than “it’s this specific thing,” but it’s the honest one.

Here’s what I mean concretely. Picture a project that just missed its number for the third month running. In one room, that news makes people go quiet, defend their piece of it, or wait for the leader to hand down a fix. In another room, the same news makes people lean in and get curious together - what did we miss, what are we noticing, does anyone have a theory nobody’s said out loud yet? Same event. Completely different capacity in the room. That difference isn’t sitting insight any one person’s skill set, and it isn’t written down in a process document anywhere. It’s in the relationship, in whether the room has practices treating a miss as information instead of a verdict.

That’s what I mean by adaptive capacity living between people rather than in them. It lives in the conversation where a team makes sense of something messy together. It lives in the two minutes at the start of a meeting set aside for “what’s surprising us lately.” It lives in whether someone can say “I’m not sure” or “I think I was wrong about this” and have that land as useful instead of risky. You can’t point to it on a org chart, and you can’t install it by sending one person to a training. You build it by practicing it together, our loud, often enough that it becomes how the room behaves by default.

Which is why I’ve come to think of this as relational work first. The processes matter. The individual skill-building matters. But the actual capacity gets built in the exchange between them…in the conversations, not the components.

Laura Hartley: I will second that it lives in the space between us, in the relationships we hold and practice. It’s the “what becomes possible when…” we live, act, and relate in certain ways. We are after all social creates, and even when we’re facing hard or messy situations as an individual, we are shaped by the relationships we hold, whether they be nourished and supportive or starved with criticism and judgement. The more we see these relationships - the thing that happens between us - as shaping our capacity to move forward, the more we also reshape the myth of hyper-individualism and meritocracy, and better create the conditions and cultures that are able to genuinely meet today’s challenges.

What I would say however, is that there are certain skills, practices, and conditions - as individuals - that allow us to better grow our adaptive capacity.

Because, yes, our adaptive capacity is us leaning into relationship and asking better questions of what we’re missing, what we’re noticing - particularly at an organizational level; but how do we do that without having built a degree of self awareness? Or vulnerability to share what’s actually going wrong, to risk the harsh perception of another? Or developed some degree of backbone and power to disagree, to offer a different perspective?

So while our adaptive capacity lives between us, in relational, collective work; it has foundations that we build as individuals in order to show up in a way that we can practice together.

Can an organization have wisdom?

Laura Richards: My first instinct is no. Wisdom feels like a human thing. It comes from lived experience, humility, the ability to hold two true things at once without collapsing into a single answer. An organization can’t do that. People do that.

But I keep coming back to this question because some organizations genuinely act wiser than others, and it’s not about who has better data or smarter people in the room. It’s that some organizations consistently create the conditions where good judgment shows up. They catch a problem while it’s still small. They let disagreement into the room instead of managing it out. They remember what went wrong three years ago instead of relearning it the hard way. They stay tethered to why they exist even when everything around them is changing.

So maybe organizational wisdom isn’t a trait an organization has. Maybe it’s closer to a pattern. Something that shows up when people bring their individual judgment into a shared process that helps the group notice things, make sense of them, and respond together.

If that’s right, then wisdom isn’t sitting in the strategic plan or the year-end evaluation report. It shows up in the conversation a team has when the plan stops matching reality and someone’s willing to say so out loud.

That’s why I keep pushing on this question. It means wisdom isn’t only an individual gift some leaders have and other’s don’t. It can be something a group builds together through what they pay attention to, how they make meaning of it, and what they’re willing to change because of it.

Laura Hartley: I agree. Wisdom is, in my opinion, a human thing. I say this because wisdom is a living thing. Wisdom is never static or fixed; if it was, it could be packaged and taught in a neat curriculum, a skill we could build or contained wholly in a book you could read. Rather wisdom is contextual, it’s adaptive, and it’s developed less through rote learning, and more our experiences, reflections, and perceptions.

And yet - I also think that an organization can hold wisdom, and I also see it as being able to act wisely; which are two distinct things.

On the idea of holding wisdom, this one I have a few caveats around; first, I see this is less about an organization holding wisdom, and more about the possibility and potential that a collective holds wisdom.

After all, wisdom never belongs to just an individual. Wisdom often contains universal through; something almost all of us can relate to, understand, benefit from or make sense of. Wisdom has historically also been shared and passed down through collective culture; through myth, storytelling, folklore, parables, song, dancing, communities of practice, and common expressions.

Wisdom is also lived and experiential. Because when we try to contain wisdom, to codify it and control it, it becomes doctrine. It loses its meaning and magic, it is no longer alive and it can no longer be felt.

This is one of the challenges an organization or collective (even a religion!) has in holding wisdom; that is must create the conditions for it to be alive as practice, as a felt experience, as a permission, and as a guardrail for those who exist within it. The moment it becomes a mission or values set that has no felt connection to the every day work of team members, or it becomes a story of this is what happens here, rather than this is what’s possible here, wisdom disappears.

But I think beyond the idea of holding wisdom, what I think almost any organization can do is act wisely. Acting wisely is not the same thing as holding or embodying wisdom; rather it’s a skill set we can develop that allows us to move in the direction of sanity.

As a skillset, this includes things like:

• Intentional pausing, allowing space for us to listen to what else might be happening beyond the noise, to other sources of information (from our bodies to community stories; our world is full of data we’re akin to miss in favor of numbers and spreadsheets).

• Asking better questions: what are we missing? What might be possible if…?

• Encouraging a diverse range of voices, mimicking the wisdom, and diversity of nature.

• If long-haul work is the goal, not putting all our eggs in one basket; having a variety of methods, tools, or revenue streams.

• Journeying together, e.g., decisions less driven by a single leader and followed by all, but shared and sensed together.

LR: The distinction between holding wisdom and acting wisely is doing real work for me. It’s sharper than what I had. But it also puts a mirror up on my own answer that I want to sit with honestly. I build standing questions into meetings on purpose, on a schedule, because that’s how a room learns to ask them without needing a “wise person” present. But you’re naming exactly the risk in that: the moment a practice becomes routine, does it start turning into the mission statement version of itself - technically still there, no longer alive? I don’t have a clean answer. My best guess is the schedule is what makes the practice show up, and the honesty in the room is what keeps it from calcifying into doctrine. But I think you’re right that those are two different things, and a lot of organizations get the first one and quietly lose the second.

LH: I think there’s something deeper here for us to explore at some point between routine and practice; because practice is part of how we become wise, and it’ show we become better learner, evaluators, and sensemakers. Routine isn’t necessarily a problem either, when it just means we engage with a practice on a regular basis and show up for it. But there’s something - a willingness, an aliveness, an openness - that needs to stay with the practice so that it’s not asking the questions for the sake of it, and instead staying with them because they offer us something.

That’s where the terrain sits: uncertainty as a permanent condition, curiosity as the sane response to it, capacity as something built between people rather than stored inside them. The obvious next question is the harder one: if that’s all true, why doesn’t it stick? Why does someone who’s genuinely done the work still walk back into a room that swallows it whole?

That’s Part 2.