Strategic Choices: Advice from 6 Decision-Making Experts for Leaders
Life's most crucial moments rarely come with a complete blueprint. Leaders often find themselves in high-pressure situations, poised to make significant decisions with inadequate data, multiple priorities, and little time to breathe. Change is a constant in today's world, and leaders are under regular pressure to adapt swiftly. according to McKinsey, 82% of leaders admit their organizations have undergone radical strategic or operational transformations in the past two years, just to stay competitive. When faced with change, some leaders crumble, while others step up and make bold moves that earn trust. But how can they prepare for such complexity to make astute choices in these tumultuous times? Let'
us delve deeper with six decision-making experts, including a former poker player turned strategist, a seasoned FBI hostage negotiator, a focus aficionado, a CEO with a culture-oriented mindset, a disruptor at heart, and a futurist, to shed light on the art of better thinking and the enchantment of better leadership.
Taking Risks in High-Pressure Situations

Many leaders freeze at the thought of making bold decisions due to the fear of failure. Yet, what if the true failure lies in not making a decision? The key lies in learning to evaluate risk without letting it paralyze you. Success should not solely be defined by outcomes; instead, a more probabilistic approach to decision-making comes into play.
Annie Duke, a former professional poker player turned decision strategist, shared her insight in our conversation. She emphasized that smart decision-makers separate the quality of the decision from its result. As she puts it, "A bad outcome does not imply a poor decision. It merely indicates dealing with uncertainty." This mental shift helps leaders view risk as part of progress rather than something to avoid.

Improving Decisions Through Tactical Conversations
convincing pitch, the real power lies not in persuasive speech but in listening. Decisions made without understanding the entire picture inevitably lead to resistance or undesired consequences. That's where effective leaders use questions to uncover insights and reduce defensiveness.
Chris Voss, a former FBI hostage negotiator, discussed this with me. He explained how tactical empathy and finely calibrated questions allow people to feel heard, increasing trust and fostering open dialogue. "When people feel understood," Voss said, "they're more likely to share the information that assists in making a better decision." Voss's techniques remind us that effective decision-making often begins by slowing down and engaging more profoundly.
The Importance of Focus in Decision-Making
Being unable to concentrate is one of the most overlooked barriers to powerful decision-making. Leaders who are constantly interrupted or emotionally triggered tend to make more reactive choices. What appears to be a time-management issue is often a deeper struggle with focus and clarity.
Nir Eyal, author of Indistractable, spoke to me about how leaders can regain control of their attention. He highlighted that distractions usually emerge as leaders attempt to avoid discomfort. "If you're uncertain, anxious, or overwhelmed," he said, "you're more likely to engage in busywork instead of engaging in thoughtful contemplation." The greatest leaders make time to think, reflect, and deliberate with purpose.
How Psychological Safety Empowers Leaders' Stronger Decisions
Smart decisions seldom occur in isolation. They emerge from open dialogue, challenge, and collaboration. However, none of that is feasible if people are afraid to express their opinions. A foundation of psychological safety is essential for good leadership.
In my conversation with Garry Ridge, former CEO of WD-40 Company, he described how he cultivated a culture where learning was valued over perfection. Ridge shared, "We don't focus on failure; we focus on learning opportunities." This mindset diminished fear and encouraged experimentation, improving decision-making throughout the organization by making it safe for people to share information, question assumptions, and admit uncertainties.
Challenging Assumptions for Resilient Decision-Making
Reliable decision-making necessitates a willingness to reconsider long-held beliefs, especially in industries undergoing disruption. The gravest risk may be clinging to outdated beliefs.
At a Thinkers50 event, Rita McGrath, another Thinkers50 member, spoke about strategic inflection points – moments when an industry transitions direction, and past success can turn into a hindrance. McGrath underscores the importance of constantly scanning the environment, and not holding too tightly onto existing business models. Her work reinforces the notion that effective decisions are not solely about timing but also being forward-thinking.
Self-Disruption Strengthens Leaders' Decision-Making
The urge to replicate past success often prompts leaders to shun change. However, the environment alters, markets evolve, and yesterday's strategy might not be effective tomorrow. Leaders who excel under pressure are those eager to question their assumptions before circumstances force them to do so.
Jay Samit, former vice chairman of Deloitte, former EVP at Sony, and author of Disrupt You!, told me that self-disruption is often the key to professional resilience. "You either disrupt yourself," he said, "or the world will do it for you." Samit's approach emphasizes that decision-making centers around preparing yourself and your team to adapt in advance.
Decision-Making as a Teachable Leadership Skill
Perhaps the most hazardous myth in leadership is that excellent decision-makers are born, not made. The truth is that every leader can enhance their decision-making abilities with the right tools and strategies. All of the experts I spoke with agreed that decision-making is teachable. Effective leaders make space for thoughtful deliberation, foster inquisitive environments, and inspire constructive criticism. They resist the impulse to act swiftly just to seem decisive. Instead, they employ reflection, structure, and collaboration to make selections that serve their teams and their missions. In volatile times, decisions become even more consequential. Every action sends a message. Leaders who grasp this essence construct better cultures. Ultimately, those are the leaders people trust, follow, and remember.
Enrichment Data:- Embracing VUCA leadership involves recognizing the nature of uncertainty, developing strategies to adapt to it effectively[1]- Employing the concept of optionality in decision-making helps navigate unpredictability, maintaining flexibility, and preparing for various scenarios[3]- Quantifying both the likelihood and consequences of uncertain events helps leaders prioritize risks more effectively[4]- Encouraging continuous learning and investing in cutting-edge technology enables leaders to adapt to complex environments[5]- A multi-faceted approach blending robust quantitative frameworks with agile, intuitive decision-making assists leaders in navigating volatile market environments effectively[5]- Moving from reactive to proactive management of volatility is crucial - rather than simply responding to change, leaders should anticipate it and drive business outcomes[5]
- In high-pressure situations, leaders can learn to evaluate risk more effectively, viewing it as a part of progress instead of something to avoid, following Annie Duke's suggestion that smart decision-makers separate the quality of a decision from its result.
- Effective leaders use questions to uncover insights and reduce defensiveness when making decisions. They employ tactical empathy and finely calibrated questions, similar to the methods used by former FBI hostage negotiator Chris Voss, to foster open dialogue and trust.
- Being unable to concentrate is a significant barrier to powerful decision-making. Leaders can regain control of their attention by focusing on reducing distractions and using techniques outlined by author Nir Eyal in his book "Indistractable."
- A foundation of psychological safety is essential for good leadership. Leaders who cultivate a culture where learning is valued over perfection, like former CEO of WD-40 Company Garry Ridge, empower their teams to make stronger and more resilient decisions through open dialogue, challenge, and collaboration.