Overcoming Leadership Challenges is one of the most critical priorities for any growing organization—and in this episode, Stephen Smith, President & CEO of Strike Group, shares a wealth of hard-earned wisdom on how to do it right. Drawing on years of leading a large, complex organization, Stephen unpacks the leadership lessons that have shaped his approach and the practical steps leaders can take to build stronger, more resilient teams.

From the start, Stephen emphasizes that leadership isn’t about title or power—it’s about accessibility, clarity, and authenticity. He explains why leading from the front builds trust and inspires teams, and how leaders can make themselves truly approachable without losing authority. His “Reach” philosophy breaks down specific ways leaders can connect with their teams on a personal and professional level.

The episode dives deep into a major pitfall for growing companies: over-promoting employees before they’re ready. Stephen shares how “red boxing”—clearly defining leadership boundaries—prevents setting people up for failure, and instead allows them to grow into roles at a sustainable pace. This ties into one of the episode’s central themes: scaling leadership is not about rushing promotions, but about building the skills, confidence, and decision-making ability leaders need to succeed long-term.

One of Stephen’s most actionable tips is the use of a one-page plan to keep teams aligned. By simplifying strategic vision into a clear, concise format, leaders can ensure everyone—from executives to frontline staff—knows where the organization is headed and how they contribute to its success.

He also talks about the importance of vulnerability in leadership, explaining why showing your human side fosters trust and strengthens relationships. Being open about challenges, and even mistakes, creates a culture where team members feel safe to share their own concerns and ideas—driving innovation and engagement.

The conversation covers how to balance ambition with ability when mentoring employees, including the tough conversations leaders sometimes have when aspirations outpace readiness. Stephen provides strategies for managing these situations in a way that preserves morale while still protecting organizational performance.

Authenticity runs as a thread throughout the discussion. For Stephen, leadership isn’t about adopting a persona—it’s about “being who you are” and staying consistent, even under pressure. That authenticity not only builds credibility, it also makes leadership more sustainable and less exhausting over the long haul.

Listeners will walk away with a toolkit for overcoming leadership challenges that includes:

• Setting clear leadership pathways to avoid over-promotion
• Making leadership accessible without undermining authority
• Using strategic planning tools like a one-page plan for clarity and alignment
• Building trust through vulnerability and authenticity
• Coaching employees through ambition-versus-readiness gaps
• Identifying and developing the traits of great managers

Whether you’re a CEO scaling a large company, an HR leader building a leadership pipeline, or a manager wanting to grow into a more effective role, this episode offers practical, experience-backed advice you can implement immediately.

0:00 Introduction to this episode

2:00 Who is Stephen Smith and what is Strike Group?

7:15 Leadership styles from an expert

Strike website

Strike Group News

Stephen’s Bio

Stephen’s LinkedIn profile