It’s the fifth meeting of the week, and your team is locked in a debate over a major strategic shift. Tensions are rising, opinions are clashing, and everyone seems convinced they’re right. As a leader, how do you cut through the noise, challenge assumptions, and steer the discussion toward a solution that makes sense? This scenario is all too common in the world of business. When you’re making tough calls, pitching to investors, or convincing your co-founder to take a calculated risk, your ability to think critically and argue effectively is a skill that can set you apart. Yet, these aren’t innate abilities. They’re learned, practiced, and refined over time. Two books that illuminate the path to mastering these skills are Think Again: The Power of Knowing What You Don’t Know by Adam Grant and Win Every Argument: The Art of Debating, Persuading, and Public Speaking by Mehdi Hasan. Grant champions the mindset of rethinking. Embracing intellectual humility, questioning assumptions, and remaining flexible in the face of new evidence. Hasan, on the other hand, offers practical strategies for making your case, influencing others, and thriving in high-pressure situations. This article, the second of a three-part series (Part One you can find here), unpacks their core insights. Showing how rethinking and skilful argumentation can transform your leadership, decision-making, and business outcomes.

Rethinking as a Competitive Edge

In Think Again, Adam Grant argues that the ability to rethink is not a weakness but a superpower. Most of us fall into familiar cognitive traps, which Grant categorizes into three mindsets:

1. The Preacher: Defends core beliefs without questioning them.
2. The Prosecutor: Seeks to prove others wrong rather than challenge their own assumptions.
3. The Politician: Seeks approval, aligning with popular opinions instead of deeper truths.

Grant advocates for adopting the scientist mindset. Constantly testing hypotheses, collecting evidence, and revising conclusions based on new data. This mindset is essential for leaders navigating uncertainty or facing rapidly changing markets.

Psychological Backing: The Ego and Cognitive Rigidity

From a psychological perspective, Grant’s emphasis on rethinking aligns beautifully with Carl Jung’s concept of the ego’s rigidity. Jung believed that when we tie our sense of self to being “right” or maintaining a fixed perspective, we not only limit our ability to grow but also create internal conflict. This rigidity often manifests as defensiveness or an unwillingness to question our decisions, as doing so feels like a threat to our identity. For leaders, this attachment to being right can be especially dangerous. It prevents them from adapting to changing circumstances or learning from their mistakes. Depth psychology provides a path forward: by loosening the ego’s grip and embracing flexibility, we open ourselves up to deeper layers of creativity and adaptability. Jung called this process individuation. The ongoing integration of different aspects of the self, including those we might initially resist or reject. For leaders, this could mean acknowledging not just external failures but also internal biases or fears that drive their decision-making. In business, this flexibility is not a sign of weakness but of strength. Leaders who are willing to question their assumptions and confront uncomfortable truths are better equipped to innovate and problem-solve effectively. They tap into a reservoir of ideas and perspectives that would otherwise remain hidden beneath the surface of rigid thinking. By letting go of the need to always “be right,” they create space for growth. Not only for themselves but for their teams and organizations. In practice, this might look like reevaluating a long-held strategic approach in light of new data. Or even stepping back to listen when a junior team member offers a fresh perspective. It’s not about abandoning conviction or decisiveness. It’s about being open to the possibility that the best solutions often emerge from unexpected places. In many ways, Grant’s call to rethink mirrors Jung’s idea of engaging with the unknown. Of finding growth not in what is comfortable or certain, but in the courage to explore uncharted territory, both externally and within ourselves.

Business Application: Rethinking in Action

A few years ago, I faced a decision that tested this mindset. One of the startups I co-founded was pursuing a promising market expansion strategy that, on paper, made sense. But sales data trickling in hinted at a mismatch between the product and the local market. My initial reaction was to defend the strategy. It had taken months to develop. We hired already additional sales people and expanded the partner management team. Yet, adopting a rethinking mindset helped me pause, reassess the data, and pivot early. Saving the company from a costly misstep. You can cultivate this mindset too:

• Hold “Rethink Sessions”: Make questioning assumptions a regular practice. For example, every quarter, review your strategies with fresh eyes. Ask: What’s working? What’s not? What blind spots are we missing?
• Welcome Constructive Conflict: Encourage team members to challenge each other respectfully. A healthy debate often unearths insights that consensus might overlook.
• Pivot Without Fear: Grant shares stories of companies like Blockbuster that failed to rethink their business models, leading to their downfall. Flexibility isn’t optional; it’s survival.

Winning Arguments: Hasan’s Tactical Playbook

In Win Every Argument, Mehdi Hasan reveals the art and science of persuasive communication. His approach isn’t about crushing opponents. It’s about structuring your arguments, reading the room, and finding common ground.

Key Techniques for Effective Argumentation

1. Mastering Structure: Start strong, organize your points logically, and end with impact.
2. Equipping with Facts: Data matters. But how you frame and deliver those facts matters even more.
3. Using Metaphors and Analogies: Simplify complex ideas into relatable comparisons.
4. Appealing to Emotion: While logic persuades, emotion motivates. Use storytelling to connect deeply.
5. Reframing the Narrative: If an argument feels off-track, shift the perspective to regain control.

The Emotional Side of Persuasion

Hasan’s emphasis on emotion aligns with Daniel Kahneman’s research in Thinking, Fast and Slow, which you can read more about here. He shows that people often make decisions emotionally and justify them rationally. Understanding his dual thinking system can help leaders communicate more effectively.

Applying Hasan’s Insights to Business Challenges

1. Investor Pitches

Your pitch isn’t just about numbers; it’s about vision and belief. Hasan’s tactics, like using metaphors to simplify complex business models or telling a compelling story about your startup’s mission, can make your pitch unforgettable. Instead of describing your tech as “scalable and robust,” tell investors it’s “like planting a seed that grows into a forest of opportunities.”

2. Team Alignment

Winning an internal debate requires empathy. Acknowledge team members’ concerns while steering the discussion toward shared goals. During a heated debate about a risky product pivot, I once said, “I hear the concerns about timing, but imagine the opportunity if we’re the first to market.” This reframed the risk as a potential reward, shifting the room’s energy.

3. Negotiation and Conflict Resolution

Reframing is a game-changer in negotiations. If a deal feels stalled, shift focus to common ground. When a supplier hesitated over pricing, I reframed the discussion: “This isn’t just about cost. It’s about building a partnership that lasts beyond this one project.”

Combining the Mindset and the Skillset

What makes Grant’s and Hasan’s approaches so powerful is their synergy. Rethinking gives you clarity; argumentation gives you the tools to communicate that clarity effectively. Together, they’re a dynamic duo for any leader. Let’s say you’re rethinking your product strategy after a lukewarm market response. Grant’s principles encourage you to question whether your assumptions about the target audience were accurate. Hasan’s playbook equips you to present this pivot convincingly to your team, ensuring they’re not just onboard but energized by the change.

Thriving Through Intellectual Flexibility

From a depth psychology lens, Grant’s and Hasan’s teachings echoes the importance of individuation. The process of integrating new perspectives to grow as a person and leader. Carl Jung believed that true growth occurs when we challenge our preconceived notions, much like Grant’s scientist mindset. Similarly, Hasan’s focus on balancing logic and emotion echoes Jung’s idea of integrating both rational and intuitive aspects of the psyche. Effective argumentation, after all, is about addressing both the head and the heart.

A Personal Reflection: The Growth Mindset in Practice

Looking back on my nearly two-decade journey, I see how pivotal rethinking and argumentation have been. Early on, I often played the preacher. Clinging to my ideas, convinced they were right. With time and experience, I’ve learned that flexibility and humility are strengths, not weaknesses. Today, my teams and my co-founders and I engage in regular “rethinking sprints,” where we challenge our strategies, assumptions, and even our communication styles. These practices have profoundly impacted not just my business but my personal growth. I’ve also developed habits that align with this mindset. Like reading outside my comfort zone, practicing active listening, and seeking out diverse opinions. It’s a journey, and I’m still learning. The results are undeniable: clarity in decision-making, stronger relationships, and a more resilient business.

Conclusion: Building the Foundation for Strategic Thinking

Think Again and Win Every Argument aren’t just books. They’re blueprints for navigating the complexities of leadership, communication, and decision-making. They show that success isn’t about stubbornly sticking to your guns or overpowering others with your ideas. It’s about staying flexible, asking the hard questions, and communicating in a way that brings people along for the ride. As you apply these principles, remember: rethinking isn’t admitting defeat, and persuasion isn’t manipulation. They’re tools for growth. For you, your team, and your business. If you want to continue this deep dive you can continue with Part Three (here), where we’ll explore insights and perspectives from other thought leaders. Giving you even more tools to think critically, communicate effectively, and navigate complexity in an ever-changing world.

Takeaways

1. Adopt the Scientist Mindset: Question assumptions, seek diverse perspectives, and stay open to new evidence.
2. Create a Culture of Rethinking: Reward curiosity, constructive criticism, and intellectual humility.
3. Master the Art of Argumentation: Use structure, emotion, and storytelling to make your case compelling.
4. Reframe Challenges: Shift the perspective to find common ground or highlight strengths.
5. Balance Logic with Emotion: Persuasion requires addressing both the rational and emotional aspects of your audience.
6. Stay Flexible: Pivot when necessary, and don’t fear changing your mind. It’s a sign of growth.