The moments that matter most rarely come with perfect information. Leaders are often asked to make high-impact decisions with incomplete data, competing priorities, and little time to think. There is a lot of change in today’s environment, and leaders are under pressure to constantly pivot. McKinsey found that 82% of leaders say their organizations have had to undergo significant strategic or operational changes in the last two years to stay competitive. When facing change, some freeze, while others make bold moves that earn lasting trust. How can leaders prepare for so much complexity to make smart choices in such a volatile time? To answer that, this article draws from my conversations and interactions with six decision-making experts, including a former poker player turned strategist, a former FBI hostage negotiator, a focus expert, a culture-driven CEO, a disruption specialist, and a leadership futurist, to explore how better thinking leads to better leadership.
What Decision-Making Experts Teach Leaders About Risk
In high-pressure environments, leaders often hesitate to make bold decisions for fear of failure. But what if the real failure is avoiding the decision altogether? One essential leadership trait is learning how to evaluate risk without being paralyzed by it. When leaders judge success only by outcomes, they risk reinforcing flawed thinking. That is where a more probabilistic approach to decision-making becomes essential.
Annie Duke, a former professional poker player turned decision strategist, shared this insight with me in our conversation. She explained that smart decision-makers separate the quality of the decision from the result. In her words, “A bad outcome doesn’t mean you made a bad decision. It just means you were dealing with uncertainty.” That mental shift helps leaders embrace risk as a calculated part of progress rather than something to be avoided.
How Leaders Improve Decisions Through Tactical Conversations
Many leaders focus on presenting their ideas persuasively, but real power comes from listening. Decisions made without understanding the full picture often lead to resistance or unintended consequences. That is why effective leaders use questions to uncover insight and reduce defensiveness.
Chris Voss, former FBI hostage negotiator, discussed this with me when I interviewed him. He explained how tactical empathy and carefully calibrated questions allow people to feel heard, which builds trust and opens dialogue. “When people feel understood,” Voss said, “they’re more likely to offer the information that helps you make a better decision.” His techniques serve as a reminder that great decision-making often begins by slowing down and engaging more deeply.
Why Focus Is Essential For Leadership Decision-Making
The inability to concentrate is one of the most underestimated barriers to strong decision-making. Leaders who are constantly interrupted or emotionally triggered make more reactive choices. What appears to be a time-management issue is often a deeper challenge with focus and clarity.
Nir Eyal, author of Indistractable, talked with me about how leaders can regain control of their attention. He shared that distractions often arise when leaders try to avoid discomfort. “If you’re unsure, anxious, or overwhelmed,” he said, “you’re more likely to jump into busywork instead of doing the hard thinking.” The most effective leaders are the ones who make time to think, reflect, and choose with purpose.
How Psychological Safety Supports Leaders’ Stronger Decisions
Smart decisions rarely happen in isolation. They emerge from open dialogue, challenge, and collaboration. But none of that is possible if people are afraid to speak up. That is why psychological safety is foundational to good leadership.
In my conversation with Garry Ridge, former CEO of WD-40 Company, he described how he built a culture where learning was valued over perfection. Ridge told me, “We don’t talk about failure; we talk about learning moments.” That mindset reduced fear and encouraged experimentation. It also improved decision-making across the organization by making it safe for people to share information, challenge assumptions, and admit uncertainty.
How Leaders Benefit From Challenging Assumptions
Resilient decision-making requires a willingness to re-evaluate long-held beliefs. This is especially important in industries facing disruption, where the biggest threat may be assuming that what worked before will work again.
Being a member of Thinkers50 Radar, allows me to attend their London events. Another Thinkers50 member, Rita McGrath, spoke about strategic inflection points, the moments when an industry changes direction and past success can become a liability. McGrath emphasized the importance of constantly scanning the environment and not clinging too tightly to existing business models. Her work reinforces the idea that the best decisions are not just timely but also forward-looking.
How Self-Disruption Strengthens Leaders’ Decision-Making
The pressure to repeat past success often leads leaders to avoid change. But environments shift, markets evolve, and yesterday’s strategy may not work tomorrow. Leaders who excel under pressure are those willing to question their own assumptions before circumstances force them to do so.
Jay Samit, former vice chairman of Deloitte, former Executive Vice President at Sony, and author of Disrupt You!, told me that personal reinvention is often the key to professional resilience. “You either disrupt yourself,” he said, “or the world will do it for you.” Samit’s approach underscores that decision-making is about preparing yourself and your team to adapt in advance.
Why Decision-Making Is A Teachable Leadership Skill
One of the most dangerous myths in leadership is that good decision-makers are born, not made. In reality, every leader can improve with the right tools and habits. All of the experts I met with shared that decision-making can be learned. Effective leaders create space for deep thinking. They build teams where questions are welcome and feedback is safe. They resist the urge to act quickly just to appear decisive. Instead, they use reflection, structure, and collaboration to make choices that serve their teams and their missions. In uncertain times, decisions become even more visible. Every move sends a message. Leaders who understand that build better cultures. And in the long run, those are the leaders people trust, follow, and remember.
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