The Illusion of Certainty in Modern Leadership

Most leadership teams, most people for that matter are searching for something they rarely name out loud. A sense of certainty. A structure that will hold, even as the world around them shifts.

Some teams, some people freeze in the face of uncertainty and change - Others try to re-order their world to feel a sense of control. They reorganize, redesign or adopt new models and frameworks, often with real care and good intent. And beneath the surface quiet hope: if we get this right, things will stop feeling so uncertain. The future will be ok.

It doesn’t work that way.

Not because leaders are naïve, and not because the structures are poorly designed. But because the future has no interest in respecting our blueprints. 

The problem isn’t that leaders choose the wrong structure. The problem is that we tend to treat structures as conclusions rather than starting points. As answers, instead of hypotheses.

The Voltaire quote “Doubt is not a pleasant condition, but certainty is absurd” is a quote that indeed stands the test of time. Living long enough to see the American revolution and dying just before the revolution in his own country of France began his voice was central to the enlightenment era. It was a time that emphasized reason, individualism, and skepticism over tradition, superstition, and absolute authority. It was this time in history that promoting ideals like liberty and tolerance. It was a way of thinking that upended the structures that defined the world. And the ruptures that came as a result of new thinking would fundamentally change the world that came after.

In Mark Carney’s recent speech to the WEF he highlighted the need to let go of the past - “nostalgia is not a strategy”.

This is a call to action to face uncertainty by embracing and establishing comfort with doubt. To become pragmatic about the unknown instead of living within the lie that we can control the future.

Organizational leaders often live within that same lie - believing that a structure will ensure the future. Once a structure is in place, it quickly becomes part of how we explain the world. Roles solidify. Decision rights harden. Meetings get scheduled, metrics get set, and before long, questioning the structure itself feels disruptive rather than responsible. That’s not a failure of courage. It’s a very human response to uncertainty. 

Psychologists call it status quo bias - our tendency to stick with what exists, even when it’s no longer serving us - especially once our identity, credibility, and time are tied up in it.

We work with, and have worked with, many legacy companies. Companies that have been in business for more than 100 years. Established cultures are particularly susceptible to building structures that offer the veil of certainty.

And that the core problem - the lie of certainty turns off the wisdom of skepticism.

The result? Uncertainty and the unknown become taboo. Silence is often the choice when people see an issue emerging.

We’re at a point now where “start-up culture” itself is becoming a legacy culture of its own with expected norms, experiences and problems - but nobody is asking “Does this need to be the way it is?”

Add pressure, pace and the expectation that leaders should project confidence and suddenly the structure, the legacy, what feels certain isn’t just how work gets done - it’s personal.

This is what erodes adaptability.

The desire for certainty of outcome - when what we need to focus on is clarity in a process of continuous improvement, innovation and adaptability.

Change is certain - That's why leaders need to develop a capacity for change instead of the mastery of control.

Without the capacity for change - and mastery of how to lead others through it  people will shut off their best instincts. People notice friction long before their leaders do. They form workarounds, they sense decisions being made further and further from the work itself. But if the environment doesn’t welcome challenges, those signals stay private. And, by the time the structure is clearly “broken,” the organization has already been compensating for it for a long time.

This is why so many change efforts arrive late. Not because leaders weren’t smart enough to see the future, but because the system was designed for stability and certainty instead of being designed to adapt, welcome change and listen to doubt.

In my upcoming book, Leading Beyond Fear, I argue that the most resilient organizations aren’t the ones with the best answers - they’re the ones with the best questions. Not “Is this the right structure?” but “What assumptions is this structure built on, and how will we know when they’ve changed?”

That shift matters. Because people will only adapt the system when it’s safe to say, this isn’t working the way we hoped it would.

Research on psychological safety makes this painfully clear. Organizations don’t fail to adapt because they lack intelligence or effort. They fail because information doesn’t travel. Concerns get softened. Learning slows down - until it’s too late.

The leaders that build adaptable, effective and high performing cultures don’t implement rigid structures that never change. They build in humility. They assume their thinking will age. They expect the world to surprise them. They design for learning.

And this starts with intellectual humility - one of the most critical and essential qualities of the most effective leaders. Just like Voltaire, just like Mark Carney and it is an acceptance for things as they are with clear eyes that will help build the future rather than living within a lie of the past.

In adaptable systems, decisions aren’t sacred - they’re revisitable. There’s clarity about what can be adjusted and who has the authority to adjust it. But, there is an openness from that authority to hear what might not be working. There are regular moments to pause and ask what’s no longer true, not as an act of criticism, but of care.

You can see it in how leaders behave when reality pushes back. Instead of doubling down, they model what updating looks like. That was the right call then. This is what we’re seeing now. That single move gives everyone else permission to think, rather than defend.

And you can see it in how psychological safety functions as infrastructure rather than aspiration. Speaking up isn’t framed as bravery; it’s treated as part of the job. Noticing isn’t punished. Questioning isn’t personal.

If you’re designing - or redesigning - how your organization works, the most important question isn’t whether the structure will last. It’s where it’s allowed to bend.

What is already unknown? Where are people encouraged to surface tension early? How quickly does uncomfortable information reach the room where decisions are made? Are people rewarded for protecting the system, or for improving it?

The future doesn’t demand certainty. It demands adaptability - adaptability built first on curiosity.

The structures that survive aren’t the ones that resist change. They’re the ones that expect it, welcome it, and make room for people to keep learning as it unfolds - long after the org chart is printed and the ink has dried.