Ep 187 - The Two Ladders of Leadership: Skills and Confidence with Cameron Herold

Paper Napkin Wisdom

In episode 187 of Paper Napkin Wisdom, we’re thrilled to welcome back Cameron Herold, a leader whose insights are reshaping the way we approach growth in business and life. Known for his impactful coaching and leadership strategies, Cameron brings us a fresh perspective on what it takes to climb the proverbial ladder of success.

This episode centers around an intriguing metaphor Cameron calls the “Two Ladders”—one representing skills, the other confidence. His vision is a balanced approach to leadership growth, showing us how essential it is to build both skill sets and self-assurance simultaneously. As Cameron says, “If my skills are shaky, then my confidence is going to be starting to shake. If my confidence is shaky, my skills start to shake.”

Let’s dive into some of the standout points Cameron made in this episode and explore how his “Two Ladders” concept can help leaders like you build a more resilient foundation.

Skills and Confidence: Two Ladders, One Goal

Cameron Herold believes that the journey to success isn’t linear; instead, it requires stability on two fronts—skills and confidence. He explains this idea using the metaphor of two ladders that you need to climb side by side. “If you’re climbing up one ladder, and your left hand and left foot are on one ladder and your right hand and right foot are on another,” he describes, “it starts to sway if either one is shaky.”

This imagery is a reminder that both skills and confidence must be developed in tandem. As leaders, we can sometimes focus too heavily on one while neglecting the other, but as Cameron points out, “It’s skills and confidence that will actually grow those people.” For entrepreneurs and leaders, building a solid foundation in these areas is essential for long-term success.

Creating a Supportive Environment for Growth

Cameron emphasizes the importance of creating an environment where team members feel safe to grow. Drawing a parallel with parenting, he explains, “We need to cheer them on… we need to coach them to success.” This idea underscores the need for leaders to foster a positive, encouraging environment that nurtures both skill development and confidence.

For Cameron, coaching isn’t just about holding people accountable; it’s about empowering them. He says, “I’m not going to hold you accountable… I hire accountable people.” This approach reflects his belief that leadership is about trust and autonomy. By hiring individuals who take ownership of their roles, leaders can focus on guiding them rather than micromanaging.

Coaching at Every Level of Leadership

One of Cameron’s most compelling points is that coaching should be a continuous part of a leader’s journey, no matter their experience level. Even at 59, Cameron invests in coaching to sharpen his skills and maintain his confidence. He encourages leaders to model this approach for their teams, saying, “If coaching is good for me, then it’s clearly going to be good for you, too.”

This willingness to learn and grow, regardless of one’s position, is a hallmark of effective leadership. By prioritizing their development, leaders can inspire their teams to do the same, fostering a culture of lifelong learning and improvement.

5 Key Takeaways

Here are five actionable takeaways from Cameron’s insights on leadership, each with a “Take Action” tip for entrepreneurs and leaders:

1. Embrace the “Two Ladders” Concept

Success is built on a foundation of both skills and confidence, and developing these simultaneously is crucial. Quote from Cameron: “If my skills are shaky, then my confidence is going to be starting to shake. If my confidence is shaky, my skills start to shake.”

Take Action: Reflect on areas where your skills or confidence may be lacking. Set aside dedicated time each week to work on specific skills and seek feedback to bolster your confidence.

2. Foster a Positive Growth Environment

A supportive environment encourages your team to take risks and grow. When people feel safe, they’re more likely to develop both skills and confidence. Quote from Cameron: “We need to cheer them on… we need to coach them to success.”

Take Action: Create a positive reinforcement plan for your team. Recognize and celebrate small wins regularly to build an atmosphere where growth feels rewarding and safe.

3. Hire for Accountability

Instead of enforcing accountability, hire self-managing people who take ownership of their roles. Leadership is about empowering others, not micromanaging. Quote from Cameron: “I’m not going to hold you accountable… I hire accountable people.”

Take Action: During your next hiring cycle, look for candidates who demonstrate initiative and responsibility. Develop interview questions that reveal how they’ve managed themselves in past roles.

4. Model Continuous Growth

Great leaders are lifelong learners. Cameron advocates for continuous coaching and personal development at every stage of one’s career. Quote from Cameron: “If coaching is good for me, then it’s clearly going to be good for you, too.”

Take Action: Enroll in a coaching program, or work with a mentor. Share your growth journey with your team to show that personal development is a priority.

5. Focus on the Setup for Success

Just as you need to set up a ladder securely, you must also establish a solid foundation for your team to grow. The right preparation helps them reach greater heights. Quote from Cameron: “How you set up the ladder is pretty important, too… you’ve got to set this up right.”

Take Action: Review your team’s current structure and support systems. Identify areas where they may need additional resources, training, or tools to be successful, and take steps to provide them.

Final Thoughts

In this episode, Cameron Herold challenges us to rethink leadership as a balanced journey of skills and confidence, supported by an environment that prioritizes growth and accountability.

Whether you're scaling a startup or leading a well-established organization, the insights shared today remind us that effective leadership is a constant climb.

Share your biggest takeaway with us by posting a photo of your notes on a napkin and using #PaperNapkinWisdom. How are you strengthening your own ladders of skills and confidence? Let’s keep climbing together!