How to Manage Difficult Personalities with Hywel Berry

What if the very people you think are holding your team back—the cynics, challengers, and so-called problem children—are actually the key to unlocking your team’s potential? In this episode of World’s Greatest Boss, host Jackie Koch sits down with dynamic keynote speaker and corporate trainer Hywel Berry to explore how to harness dissent and resistance for team growth and innovation.

Hywel shares insights from his 15+ years of experience working with global brands like Nike, Deloitte, and Coca-Cola. Together, Jackie and Hywel unpack the myths about leadership styles, the value of diverse perspectives, and how to manage resistance effectively during times of change. You’ll learn practical strategies to identify productive pushback, foster psychological safety, and turn conflict into collaboration.

What You’ll Hear in This Episode:

[00:00:00] Intro: Why dissent is key to team success

[00:02:15] Common myths about leadership and management

[00:10:30] Recognizing the difference between negativity and valuable feedback

[00:20:45] How to manage resistance during change

[00:32:10] Creating a safe space for disagreement and innovation

[00:42:50] Tools for leaders to navigate emotional change curves

[00:54:00] Final thoughts: How leaders can support personal and team growth

Key Takeaways:

  • Valuable dissent: Embrace the cynics on your team—they might see risks and opportunities others overlook.

  • Psychological safety: Leaders should thank team members for dissenting and create an environment where all perspectives are valued.

  • Handling change: Minimize resistance by understanding its root causes, fostering open communication, and managing emotional transitions effectively.

  • Diverse hiring: Avoid the “like-me bias” by hiring people with different skills, backgrounds, and perspectives to drive innovation.

Resources and Links:

  • Learn more about Hywel Berry and his training programs at Alicorn Learning.

  • Connect with Hywel on LinkedIn: Hywel Berry.

  • Recommended reading: Lateral Thinking by Edward de Bono.

Connect with Jackie:

Read Instead:

As a business leader, you’ve likely encountered resistance within your team. Whether it’s skepticism, pushback, or outright cynicism, it can feel like these behaviors derail progress. But what if, instead of viewing resistance as a roadblock, you saw it as a valuable tool to foster innovation and strengthen your team?
Here’s how to identify the difference between destructive negativity and productive dissent, and how to leverage pushback for growth.

Recognize the Value of Pushback

Team members who voice disagreements often hold valuable insights. They challenge assumptions, spot overlooked flaws, and can serve as a safeguard against avoidable mistakes. Instead of silencing dissent, embrace it as an opportunity to:

  • Uncover blind spots: Constructive criticism can highlight issues others may be hesitant to mention.

  • Enhance decision-making: Diverse opinions force teams to evaluate ideas more thoroughly.

  • Foster creativity: Resistance often sparks conversations that lead to innovative solutions.


Tip:When someone challenges your idea, respond with gratitude: “Thank you for pointing that out.” This opens the door to collaboration and ensures the team member feels heard.

Differentiate Between Productive and Unproductive Resistance

  • Not all pushback is created equal. Effective leaders learn to distinguish between:

  • Productive dissent:These team members want to improve outcomes. Their challenges are solution-focused and come from a place of care for the team or project.

  • Unproductive negativity: Persistent complainers or resistant employees who derail progress without offering solutions can harm morale.

How to Respond:

  • For productive dissent, give the individual space to voice their concerns and discuss actionable changes.

  • For negativity without substance, address underlying issues like burnout, fear of change, or poor communication.

Create an Environment for Healthy Debate

To encourage constructive criticism and diverse perspectives:

  • Build trust: Teams need to feel psychologically safe to share differing opinions. Make it clear that dissent is not only allowed but valued.

  • Set the tone early: At the beginning of meetings, invite challenges by saying, “What about this doesn’t sit right with you?”

  • Rotate roles: Assign a “devil’s advocate” in meetings to critique plans. Rotating this role ensures it’s seen as a positive contribution rather than criticism.


Address Resistance Rooted in Change

Change is a common trigger for resistance. Employees may fear the unknown, mourn the loss of past routines, or struggle to see the benefits of a new direction.

Steps to Manage Change-Related Resistance:

  • Acknowledge fears: Empathize with employees’ concerns and validate their feelings.

  • Communicate early and often: Share why the change is happening, how it impacts the team, and what the benefits will be.

  • Provide support: Offer training, resources, and one-on-one check-ins to help team members adapt.


Remember, even your top performers can resist change if they feel it threatens their success. Approach resistance with empathy to guide them through the transition.

Diversify Your Team’s Perspectives

Teams of people who are alike often miss opportunities for innovation. When hiring or restructuring teams, prioritize diversity in backgrounds, experiences, and perspectives. A well-rounded team fosters robust discussions and solutions that cater to a broader range of challenges.

Actionable Tips:

Combat “like-me” bias: During hiring, focus on candidates who bring skills or experiences your team lacks.

Leverage varied work styles:Recognize that not all employees contribute in the same way. Some thrive in brainstorming sessions, while others prefer to reflect before sharing ideas.

Turn Conflict Into Collaboration

Dissent doesn’t have to lead to discord. With intentional leadership, resistance can become a catalyst for deeper connections and better results.

  • Listen actively: Don’t just hear objections—seek to understand them fully.

  • Facilitate dialogue: Encourage open conversations where team members can respectfully challenge one another.

  • Act transparently: When dissent leads to a decision, explain how feedback was considered. This builds trust and reinforces a culture of inclusion.

Build a Culture That Values Growth

Resistance, when harnessed correctly, can fuel innovation and drive business growth. By fostering an environment that encourages diverse perspectives and constructive pushback, you’ll unlock your team’s full potential and ensure your business stays agile in a competitive landscape.


Take the next step: Reflect on your current team dynamics. Are you creating space for meaningful dissent? If not, start small by inviting feedback and actively listening. Over time, you’ll see how turning resistance into collaboration can transform your business.

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How to Get More Honest Feedback From Your Team