How To Overcome Uncertainty And Deliver Genuine Behavioural Change In Organisations With Sam Conniff

Uncertainty is a fact of life, and you will have faced it at some point in your personal life or career. Yet it doesn’t have to be a permanent state of being if you understand the underlying reasons behind the feeling and the behaviours that uncertainty brings.

Author, public speaker and facilitator Sam Conniff has dedicated his life to untangling the complexities of uncertainty. In this thought-provoking interview, we discuss the neuroscience behind how to adapt in situations when you won’t ever have all the answers, the importance of his latest book, The Uncertainty Toolkit, and how workshops can be designed to implement genuine behavioural change.

What uncertain moments from your earlier life led you to do the things you do, like write Be More Pirate and found initiatives like Livity and Digify Africa?

Uncertainty has been the defining feature of my career, long before it became something I studied or spoke about.

Early on, I found myself repeatedly in situations where the “right” path either did not exist or felt deeply wrong. I did well in conventional systems, but I was restless inside them. I could see talent, energy, and intelligence being wasted by rigid rules, outdated hierarchies, and a quiet fear of doing things differently. I did not yet have language for it, but I could feel the cost of certainty when it was mistaken for safety.

The moment that really set everything in motion was leaving a secure, successful role without a clear plan for what came next. On paper, it made no sense. Internally, it felt unavoidable. That period was uncomfortable, financially risky, and emotionally exposing. But it forced me to confront something fundamental. When people are pushed into uncertainty, they do not just lose confidence. They lose permission. Permission to act, to experiment, to trust their judgement.

That insight became the foundation for everything that followed.

Be More Pirate came from researching people and movements who had operated in uncertainty without waiting for permission. Pirates, activists, social entrepreneurs, and rule breakers were not reckless. They were highly adaptive. They understood which rules mattered, which ones did not, and how to move forward without guarantees. Writing the book was less about rebellion and more about reclaiming agency in uncertain systems.

Livity and Digify Africa came from the same place, but applied practically. I saw young people full of potential who were locked out of opportunity not because of ability, but because systems could not adapt quickly enough. Rather than waiting for policy change or perfect funding, we built programmes inside uncertainty. We tested, iterated, learned, and scaled while things were still messy. That messiness was not a flaw. It was the point.

Looking back, the common thread is not confidence or courage. It is tolerance. Learning to stay present, creative, and purposeful when outcomes are unclear. That is what I now help organisations and leaders build. Not certainty, but the psychological capacity to act well without it. 

Your focus on taking lessons from historical periods like the Golden Age of Piracy resonates with me, as I find a lot of use from ancient wisdom.

Is there any other historical periods you feel like people can learn a lot from, whether from a leadership perspective or a training programme perspective?

Absolutely. I am less interested in history as nostalgia and more in history as a stress test for human behaviour.

The periods I find most useful are not the ones that look impressive in hindsight, but the ones shaped by volatility, weak institutions, and rapid change. That is where human behaviour becomes visible, because certainty is stripped away.

One example is the early Enlightenment. Not the polished version we teach now, but the messy transition period where old religious and political certainties were breaking down, and new ways of thinking had not yet stabilised. What stands out is not individual genius, but the rise of informal networks, salons, letters, and shared experimentation. Progress did not come from top-down training. It came from peer learning, debate, disagreement, and the freedom to test ideas publicly. From a leadership and learning perspective, that is a powerful reminder that capability grows through conversation and permission, not just instruction.

Another rich period is the early industrial revolution. It is often framed as a story of machines, but it was really a story about humans having to relearn how to work, lead, and collaborate at speed. Traditional apprenticeships broke down. Roles changed faster than training systems could keep up. The organisations that adapted best were not the ones with the most control, but the ones that invested in adaptability, trust, and shared purpose. That has direct parallels with how AI and automation are reshaping work now.

I also take a lot from civil resistance movements. Whether it is the US civil rights movement, the Polish Solidarity movement, or parts of the suffragette movement, what fascinates me is how leadership functioned without formal authority. These movements had to train people psychologically, not just tactically. Participants had to manage fear, uncertainty, and social risk over long periods. That kind of training was embedded, lived, and reinforced daily, not delivered as a one-off intervention.

Across all of these periods, the lesson is the same. The most effective learning systems do not try to eliminate uncertainty. They help people function inside it. They build shared identity, moral clarity, and practical agency, so that action continues even when the path is unclear. That is as true now for organisations as it was then.

How did these experiences lead you to create Uncertainty Experts, and what ties do you feel the concept of uncertainty has with neuroscience?

Uncertainty Experts emerged when I realised that the problem I was circling was not cultural or strategic alone. It was biological.

Across all those historical periods and modern projects, I kept seeing the same pattern. People did not fail because they lacked skill, intelligence, or motivation. They struggled because uncertainty triggered a threat response in the body. Once that response was activated, even capable people defaulted to caution, compliance, or avoidance. Training would land intellectually, but behaviour would not change under pressure.

That gap between knowing and doing became impossible to ignore.

Uncertainty Experts was created to address that gap directly. Instead of asking people to think differently, we focused on helping them feel differently when certainty disappears. That shift only made sense once we rooted the work in neuroscience.

From a neurological perspective, uncertainty is processed as a prediction error. The brain is constantly forecasting what will happen next, and when those predictions break down, the nervous system treats it as potential danger. The amygdala becomes more active, stress hormones increase, and the prefrontal cortex, which supports planning, creativity, and decision-making, becomes less effective. In simple terms, uncertainty narrows thinking before people even realise it is happening.

Traditional training often works against this reality. It assumes that insight leads to behaviour change, when neuroscience shows that state comes first. If someone is physiologically braced, no amount of rational instruction will unlock experimentation, collaboration, or adaptive leadership.

Uncertainty Experts was designed as a psychological intervention, not a content programme. Through live experiments, embodied reflection, and measurable exercises, we help people recognise their own uncertainty response in real time and build tolerance for it. As tolerance increases, cognitive flexibility returns. People become more creative, more decisive, and more open, not because they are trying harder, but because their nervous system is no longer treating uncertainty as a threat.

That is the thread that connects pirates, social movements, and modern leadership. The people who function best in uncertain environments are not fearless or unusually confident. They have trained their nervous systems to stay regulated when the future is unclear. Uncertainty Experts exists to make that trainable, measurable, and practical at scale.

What do you feel are the characteristics of an effective workplace cultural change training programme, and how can those skills be implemented effectively?

The most important thing to say first is that effective cultural change training does not try to change culture directly. It changes behaviour under pressure. Culture shifts as a by-product.

From my experience, there are a few consistent characteristics that separate programmes that create lasting change from those that feel good in the room but fade quickly.

First, effective programmes work on psychological state, not just mindset. If a training session does not account for fear, threat, status anxiety, and uncertainty, it is working on the surface. People can agree with new values or behaviours intellectually, but if their nervous system defaults to protection when things get uncomfortable, the old culture will reassert itself. Programmes that last help people recognise and regulate their own responses in real time.

Second, they create lived experience, not just shared language. Culture does not change because people adopt new words. It changes when people have a felt experience that contradicts their existing assumptions. That is why experiments, simulations, and moments of safe discomfort matter so much. When someone experiences themselves behaving differently under uncertainty and surviving it, that learning sticks in a way no slide ever will.

Third, they focus on repeatable micro-behaviours. Big cultural ambitions often fail because they are too vague to act on. Effective programmes translate values into small, observable actions that people can practice immediately. Not “be more innovative,” but “run meetings where uncertainty is named out loud,” or “test ideas before seeking permission.” These behaviours become cultural signals that others can copy.

In terms of implementation, the key is reinforcement through the system, not reliance on individual willpower.

Skills need to be revisited, not just remembered. That means building in moments of reflection before and after key events, using managers as amplifiers rather than gatekeepers, and designing light-touch follow-ups that bring people back to the emotional experience of the training, not just the content.

Measurement also matters. When organisations track shifts in confidence, tolerance, or behavioural response, rather than just satisfaction scores, they take cultural change seriously. What gets measured gets rehearsed.

Ultimately, the programmes that work treat culture as something that lives in bodies, habits, and interactions, not posters or principles. Implementation succeeds when training changes how people respond in the moments that actually matter.

Congratulations on your upcoming book, The Uncertainty Toolkit. What was the purpose of writing the book and what kind of lessons can people learn from reading it?

Thank you. The Uncertainty Toolkit came from a very practical frustration.

After years of running Uncertainty Experts with organisations around the world, I kept encountering the same pattern. People would leave sessions energised, with genuine insight and emotional shift, but then ask the same question: “What do I do when this shows up again on a Tuesday afternoon?” They were not asking for more theory. They were asking for something they could reach for in the moment uncertainty hit.

The purpose of the book was to bridge that gap.

I did not want to write a book about uncertainty. I wanted to create something people could use inside it. That meant translating neuroscience, behavioural science, and live experimental learning into simple, repeatable tools that work under pressure, not just in reflection.

The core lesson of the book is that uncertainty is not a problem to solve, but a condition to train for. Most people believe their reaction to uncertainty is fixed. It is not. With the right practices, people can increase their tolerance for uncertainty in the same way they build physical or emotional resilience. When that tolerance increases, better thinking follows naturally.

Readers learn how to recognise their own uncertainty response early, before it hijacks decision-making. They learn how to stabilise themselves physiologically, widen their attention, and regain agency when outcomes are unclear. Importantly, they also learn how uncertainty spreads socially, and how leaders can either amplify fear or create calm and clarity through small, deliberate behaviours.

The book is deliberately practical. Each tool is designed to be used in real situations: difficult conversations, moments of change, high-stakes decisions, and periods of ambiguity. It is not about becoming fearless or confident all the time. It is about becoming functional, creative, and humane when certainty is unavailable.

Ultimately, The Uncertainty Toolkit exists to help people stop waiting for clarity before they act, and to start building the psychological capacity to move forward well, even when the future remains unresolved.

What are your thoughts on how to create good psychological safety within organisations?

Psychological safety is one of the most overused and misunderstood ideas in organisational life.

At its core, psychological safety is not about comfort, harmony, or people feeling good all the time. It is about people believing they can take interpersonal risks without being punished or humiliated. That belief is fragile, and it is shaped far more by behaviour than by intention.

The biggest mistake organisations make is trying to create psychological safety through statements of values or top-down declarations. Safety is not something you announce. It is something people infer from what happens after they speak up, disagree, admit uncertainty, or make a mistake.

From a neuroscience perspective, safety is read through the nervous system before it is rationalised cognitively. People are constantly scanning for cues. Who gets interrupted. Who gets credit. How leaders respond to bad news. What happens when someone says “I don’t know.” These micro-moments matter more than any policy.

In practice, psychological safety is built through three consistent behaviours.

First, leaders must model uncertainty openly. When leaders admit what they do not know, change their mind publicly, or ask for help, they lower the perceived risk for everyone else. This is not vulnerability as performance. It is uncertainty handled competently and calmly.

Second, disagreement has to be normalised and protected. Teams that are psychologically safe are not conflict-free. They are conflict-capable. That means making dissent explicit, rewarding challenge, and separating disagreement from personal threat. If disagreement is only welcomed rhetorically, people will sense that immediately.

Third, consequences must align with messages. Nothing destroys psychological safety faster than saying “it’s safe to speak up” and then socially or professionally penalising the people who do. Consistency matters more than perfection. People watch patterns, not promises.

Importantly, psychological safety is not a permanent state. It fluctuates based on context, power dynamics, identity, and history. That is why it cannot be “rolled out” once and assumed to exist. It has to be continually rebuilt through everyday interactions.

The organisations that do this well understand that psychological safety is not soft. It is a performance enabler. When people feel safe enough to think out loud, challenge assumptions, and admit uncertainty early, errors are caught sooner, learning accelerates, and decision-making improves. Safety, paradoxically, is what allows people to take the risks that progress requires.

What are your thoughts on concepts like wellbeing washing when a company may use wellbeing initiatives and programmes as a tick box exercise?

Do you feel there is any specific education that can be done to reduce this challenge?

Wellbeing washing happens when organisations treat wellbeing as an accessory rather than a responsibility.

It usually shows up when initiatives are designed to signal care without changing the conditions that cause distress in the first place. Mindfulness apps rolled out alongside impossible workloads. Resilience training delivered without addressing chronic uncertainty, poor leadership behaviour, or lack of autonomy. None of this is malicious. It is often well-intentioned. But intention does not equal impact.

The underlying issue is a category error. Wellbeing is framed as an individual problem to be managed, rather than a systemic experience to be shaped. When that happens, training becomes a tick box because it is disconnected from power, incentives, and everyday decision-making.

From a neuroscience and behavioural perspective, this is predictable. You cannot regulate people into wellbeing if the environment keeps triggering threat. The nervous system does not distinguish between a breathing exercise and a manager who routinely undermines you in meetings. One will always outweigh the other.

That is why education is critical, but not in the form of more wellbeing content.

The most useful education focuses on helping leaders understand how human systems actually work. How uncertainty, workload, ambiguity, and social threat affect cognition, behaviour, and health. Once leaders grasp that wellbeing is shaped by design choices, not just personal habits, responsibility shifts naturally.

There is also a need to educate organisations on the difference between support and substitution. Wellbeing initiatives should support people within challenging systems, not substitute for fixing those systems. A simple test is to ask: if this programme disappeared tomorrow, would the underlying causes of stress still exist? If the answer is yes, the work is incomplete.

The organisations that avoid wellbeing washing treat wellbeing as an outcome, not a programme. They look at decision rights, clarity, psychological safety, recovery time, and how uncertainty is communicated. Training then focuses on building leadership capability in those areas, rather than offering wellbeing as a bolt-on.

Ultimately, reducing wellbeing washing requires a shift in honesty. A willingness to say, “This is how work currently feels,” before asking people to cope better with it. When that honesty is present, wellbeing initiatives stop being performative and start becoming meaningful.

In relation to the topic of uncertainty, what is your perspective on AI as a force for good or bad?

I am instinctively wary of framing AI as either a force for good or a force for bad, because that framing itself is a human attempt to regain certainty.

AI is an amplifier, not an originator. It magnifies whatever psychological, cultural, and organisational dynamics already exist. In environments that are thoughtful, humane, and reflective, AI can reduce friction, expand creativity, and free people to focus on work that actually requires judgment and care. In environments driven by fear, speed, and control, it will do the opposite, accelerating anxiety, dehumanisation, and poor decision-making.

From an uncertainty perspective, what matters most is not what AI can do, but how people respond to the uncertainty it creates.

AI introduces a sustained prediction error. Roles are less stable. Expertise feels less secure. The future of work is harder to narrate cleanly. For many people, that triggers the same threat responses we see in any period of rapid change: defensiveness, overconfidence, disengagement, or blind adoption. None of those responses are about AI itself. They are about tolerance for uncertainty.

This is where the real risk lies. Organisations that use AI as a substitute for thinking, leadership, or responsibility will create fragile systems and brittle cultures. Organisations that use AI as a tool inside a psychologically safe, uncertainty-literate environment will likely see the benefits people hope for.

There is also a quieter danger that concerns me more than job displacement. AI can reduce our tolerance for not knowing. If every ambiguity is immediately filled, summarised, or resolved for us, we risk losing the cognitive and emotional muscles required to sit with complexity, doubt, and disagreement. That capacity is foundational to good judgement, ethics, and leadership.

Used well, AI can support human capability. Used badly, it can erode it.

So my position is neither optimistic nor pessimistic. It is conditional. AI will be a force for good in proportion to how well individuals and organisations understand their own psychological responses to uncertainty. Without that awareness, the technology will move faster than our ability to use it wisely.