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Driving meaningful change doesn’t start with a new strategy—it starts with deeper self-awareness. Because the very thing that makes you great as a leader can also hold you back if you’re not paying attention.

When leaders face downturns, global instability, or any kind of brutal reality, the instinct is often to either sugarcoat the truth or brace everyone for the worst. But the most effective leaders do neither—they tell the truth and inspire belief in what’s possible.

In this episode of The Better Leadership Team Show, Mike sits down with Jeff Massone to explore what it really takes to prepare the next generation of leaders—and why coaching plays a central role in that process. They dig into the challenges today’s workforce faces, from managing expectations to developing the mindset and skills required to lead in a fast-moving world.

A lot of people assume great speakers are just born that way. And yes, some are. But the truth is—even the naturals have to work at it. Because whether you’re gifted with the mic or just getting started, the leaders who consistently move people to action all have one thing in common: they study, practice, and sharpen their skills over time. Speaking isn’t a talent—it’s a tool. And it only works if you know how to use it.

In this week’s episode of The Better Leadership Team Show, I had a fun and insightful conversation with Fred Joyal—author, entrepreneur, and boldness expert. One of the most practical takeaways from our chat was this: if you want to build boldness, you don’t need to make some massive leap. You can start by simply talking to strangers…and giving what he calls “drive-by compliments.”

In my conversation with leadership expert John Gallagher, we explored something every leader needs to hear: the most effective leaders don’t wait for perfection—they build discipline. Discipline to show up. Discipline to act. Discipline to take the first step even when the path isn’t fully clear. Perfection is a myth that stalls progress. Discipline is the practice that builds momentum.

We often talk about fear in the context of failure—but what about the fear of success? What happens when you finally reach your biggest goals… and you still feel unfulfilled? That kind of fear doesn’t get discussed enough, yet it’s a powerful indicator that your career might need more alignment with your values and purpose.

Most leaders think they’re doing a good job when it comes to giving feedback—but their teams often feel very differently. In a recent poll, the gap between how leaders rated their feedback effectiveness and how their people perceived it was shockingly wide. Why the disconnect? Many leaders hold back for fear of conflict, discomfort, or damaging relationships, but that silence creates bigger problems in the long run.

Too many leaders spend their time trying to fix what’s broken in their team members—focusing on weaknesses, correcting flaws, and micromanaging shortcomings. But here’s the truth: when we coach people to lean into their strengths instead, we elevate their confidence, productivity, and impact. When every member of the team is playing to their strengths, the whole organization wins.

Attracting the right people to your company—whether they’re clients, team members, or partners—is only half the battle. The real magic is in keeping them. Retention requires intentionality, and that’s exactly what this week’s guest emphasizes through his signature WOOO framework: Win Others Over and Over.

Too often, leadership teams get caught up in setting goals, chasing opportunities, and pushing forward without ever asking the uncomfortable—but essential—question: What would failure look like? By identifying what could go wrong, you create a proactive plan to avoid the pitfalls that derail progress.

Most leadership teams believe that being adaptable means staying loose, keeping things flexible, and reacting to what comes. But without a clear plan—both short-term and long-term—what ends up happening is you don’t adapt… you drift. The team constantly plays defense. Ironically, the best way to remain agile is to first get clear on where you're going.

We often hear about the importance of fixing our weaknesses, but what if that mindset is holding us back? When leaders spend too much time trying to "fix" what's wrong, they end up diminishing their greatest strengths—and ultimately becoming mediocre across the board. Focusing energy on what you do best isn't just a feel-good strategy; it’s the smartest way to maximize your impact.

Middle-level leaders often get overlooked, but they’re the glue holding your company together. They translate strategy into action, support frontline teams, and keep communication flowing in both directions. When they’re weak, the whole system wobbles. When they’re strong, the entire organization becomes more resilient, aligned, and high-performing.

Your inner dialogue can make or break you—whether you're competing on the water or leading a team in business. The way you process setbacks, missed opportunities, or tough decisions determines how quickly you can recover and move forward. Just like in elite sports, business leaders need to master their self-talk to stay resilient, learn from mistakes, and make the next best move with confidence.

Strong leadership teams don’t avoid tough conversations—they lean into them with intention and respect, where accountability and direct communication are paired with genuine care. Unlike confrontation, which can feel aggressive or adversarial, carefrontation fosters trust, strengthens relationships, and drives meaningful progress by ensuring difficult topics are addressed constructively.

Leadership models and styles provide valuable frameworks, helping leaders navigate challenges and make better decisions. But in a complex and ever-changing world, relying too rigidly on one model can be a limitation. True leadership isn’t about following a blueprint—it’s about adapting, evolving, and meeting the moment with the right approach.

Growth only comes from taking risks, learning from missteps, and continuously pushing forward. The most successful people aren’t the ones who never fail—they’re the ones who refuse to let failure stop them.

When leaders dismiss or undermine their colleagues' perspectives, it erodes trust, weakens collaboration, and ultimately impacts the entire organization. The strongest leadership teams are built on mutual respect, even when viewpoints differ.

Trust is the foundation of any high-performing leadership team, yet it’s often one of the biggest challenges. When team members don’t fully trust each other, they hold back. They avoid speaking up, hesitate to challenge ideas, and sidestep tough conversations—fearing judgment, backlash, or that their input won’t matter. And the organization suffers, as a result.