Uncertainty is rising, and with it, the instinct to double down on what’s worked before. But what if that very instinct is what’s holding you, your team and your organisation back?
Think about this for a moment…
In March 2025, researchers Cameron Jones and Benjamin Bergen from the University of California published a preprint study demonstrating that OpenAI’s GPT-4.5 passed a rigorous three-party Turing test.
In this test, human participants engaged in simultaneous five-minute text conversations with both a human and an AI model without knowing which was which. GPT-4.5, when prompted to adopt a human-like persona, was judged to be human 73% of the time, significantly outperforming both other AI models and actual human participants in the study.
This study marked the first empirical evidence that a large language model had passed a standard version of the Turing test. That test was initially proposed by Alan Turing as a measure of a machine’s ability to imitate human conversational behaviour.
Importantly, the authors and commentators note that passing the Turing test does not necessarily imply true machine intelligence or consciousness but rather the AI’s ability to convincingly mimic human conversational traits, including imperfections and emotional nuance. It’s also worth noting that the study has not yet undergone peer review.
This research serves as a timely reminder that the ground is constantly shifting beneath your feet, and standing still is not a safe option.
Stability no longer equals predictability
Traditionally, organisational stability was equated with predictability. Boards and senior leaders rewarded predictability, and risk was something to be mitigated, if not avoided altogether. The aim was to minimise disruption, avoid mistakes and play it safe.
Yet today, that approach can corrode a company’s adaptability and future readiness. In fact, the more tightly leaders cling to certainty, the more fragile their organisations become.
As well, paradoxically, one of the most significant barriers is holding onto past success. When things are going well, there is little urgency to challenge the status quo.
I’ve seen many capable leaders pause, not because they lack courage, but because success made the need for change feel less urgent.
Influential leaders don’t wait. They challenge their assumptions while things are still working. They invest in experimentation during good times, not just in crisis.
Why? Because they recognise that waiting until a crisis hits can leave them and their organisation at a disadvantage. They challenge themselves to change before the operating environment forces them to do so.
Safe choices can make you more vulnerable
It seems logical that reducing risk increases safety. But avoiding risk often amplifies it.
Take status quo bias, for example, a cognitive shortcut that favours the familiar over the unknown. Leaders influenced by this bias may delay critical decisions, cling to outdated models, or overvalue past successes. In doing so, they fail to notice subtle shifts in the market, customer expectations, or internal culture until it’s too late.
Behavioural economist Daniel Kahneman observed that loss aversion leads people to overvalue what they currently have and undervalue potential gains. In today’s environment, this bias can blind leaders to opportunities and stall progress.
Risk aversion is deeply embedded in organisational cultures, and for good reason. That’s why learning to feel the fear and act anyway becomes essential. Neurologically, our brains are wired to prefer certainty. The amygdala, our brain’s fear centre, is quick to activate in the face of the unknown.
In the workplace, this instinct is reinforced by structures and incentives that reward caution and penalise failure. Over time, people learn that keeping their heads down and staying in their lane feels safer than sticking their necks out.
But all of that comes with consequences. A perfect example is Kodak, which famously invented the digital camera in 1975 but didn’t commercialise it. Why? They feared it would cannibalise their film business. Their efforts to preserve stability became their undoing.
Ask yourself: What assumptions are you holding onto because they once worked?
The hidden cost of certainty
Most leaders are trained to prize clarity and encouraged to make decisions with complete information.
Yet research suggests that people often feel more regret after missing out on uncertain opportunities than from taking risks that didn’t pan out. We are wired not just to fear failure, but to fear inaction in hindsight.
Similarly, when leaders equate certainty with competence, they can inadvertently create cultures that punish exploration and silence dissent. Over time, this approach fosters a sense of learned helplessness and disengagement. Teams disengage not because they’re under pressure, but because they feel powerless to change what matters.
Employees also disengage when innovation is low. Gartner’s Global Talent Monitor study (June 2024), as reported in the Australian Institute of Company Directors’ magazine, found that Australian employees feel uninspired by their leaders. Additionally, employee perceptions of the level of workplace innovation are at an all-time low of 14%.
It’s a great wake-up call that too much certainty can drain energy and initiative. A little ambiguity, when framed positively, can ignite curiosity and innovation.
Ask yourself: Are you rewarding certainty or curiosity in your team?
The antidote is uncomfortable risk-taking
Influential leaders accept that the path to long-term organisational resilience is not paved with risk aversion; instead, it’s built on informed, intentional, and sometimes uncomfortable risk-taking.
Wise risk-taking is essential for resilience, innovation, and long-term viability. As McKinsey notes, the organisations that emerged strongest from previous crises were those that moved early, decisively and proactively, even before the whole picture was clear.
Taking risks isn’t gambling with your or your organisation’s future. It means being willing to act with intention and foresight, even when outcomes are uncertain. And yet, risk-taking is often romanticised as an act of bravery. A bold leap. A maverick move.
But wise risk-taking is deeply strategic. It demands rigorous thinking, systems awareness, and emotional regulation. Strategic risks are informed, calculated, and aligned with long-term goals. They are grounded in the question: What’s the upside if we do this, and what’s the cost if we don’t?
For example, Adobe’s bold pivot from selling boxed software to a subscription-based model offers a robust illustration. At the time, critics questioned the logic. But the decision allowed Adobe to become more agile, more attuned to customer needs, and better positioned for market shifts. It was a strategic risk that ultimately created a more resilient enterprise.
Your Leadership Imperative
Risk-taking requires self-leadership because resilient organisations are built by resilient people. Leaders who strengthen their own capacity for adaptation, recovery, and sensemaking are better equipped to support others through uncertainty.
This includes developing what psychologist Susan David calls emotional agility, the ability to manage one’s inner world with curiosity and compassion, rather than avoidance or rigidity.
It also means engaging in sensemaking practices that help you spot emerging patterns and signals across the system.
Ask yourself: How are you strengthening your own resilience so you can better lead through uncertainty and take wise risks?
Notice the slow-burning risks
When leaders consider risk, they often focus on external threats, such as competitors, economic downturns, and disruptive technologies. However, some of the most dangerous risks are internal and cultural.
For example, a reluctance to challenge assumptions, a fear of telling the truth to those in power, and an environment where failure is quietly punished.
These are the slow-burning risks that hollow out an organisation from within. And they rarely show up on a traditional risk register.
The countermeasure? Influential leaders who create space for dissent actively seek out edge perspectives and reward intelligent failure. These leaders treat discomfort not as a sign of danger, but as a signal of growth.
To do this successfully, you will want to manage the tension between accountability and safety. You don’t lower the bar on performance; you raise the level of trust. You set clear expectations, offer feedback consistently, and celebrate learning, even when outcomes fall short.
Ask yourself: Are there slow-burning cultural risks in your team?
Building comfort with discomfort
In risk-embracing organisations, failure is not feared but metabolised. The best teams ask, “What can we learn?” rather than “Who is to blame?”
Pre-mortems, where teams imagine why a project might fail before it begins, can be used to proactively identify and mitigate risk. This shifts the mindset from perfectionism to experimentation.
Additionally, processes such as scenario planning and risk-reward matrices play a critical role. They slow down impulsive thinking and create space for sensemaking. Frameworks such as the Cynefin model help you distinguish between complex and complicated situations, allowing you to calibrate your decisions accordingly.
Such tools foster better questions, deeper analysis, and, ultimately, smarter bets. They also encourage reflection on how different types of risk (i.e. financial, reputational, operational, technological, etc) interact and accumulate.
Leading for the long game
Risk-taking, when aligned and intentional, strengthens your leadership, team and organisation.
In a world that rewards agility over rigidity, leaders who embrace risk as a pathway to resilience are the ones who will shape the future, not just survive it.
In the words of management guru Peter Drucker, “People who don’t take risks generally make about two big mistakes a year. People who do take risks generally make about two big mistakes a year.”
His words remind us that making mistakes is inevitable, so avoiding risks does not eliminate errors. The question is not whether you will make mistakes, but whether you will make them in the service of wise and sustainable progress.
Step ahead, step up as an influential leader. Because in times of change, the riskiest move is standing still.
Getting you ready for tomorrow, today®
Award-winning author and global workplace expert, Dr Michelle Gibbings, helps leaders, teams and organisations unlock strategic influence to accelerate progress.