Leadership lessons from the trenches | Thoughts on leadership ep. 220

Welcome to the GliderCEO Podcast, where I, Mark Michael, dive into the raw and unfiltered thoughts on leadership, entrepreneurship, and the challenges of running a business. As I reflect on the journey so far, certain lessons about leadership have crystallized in my mind. These insights aren’t just theories—they’re hard-won truths that come from being in the thick of it, day in and day out. Today, I want to share three key lessons that have shaped my approach to leadership.

1. You're Always Being Watched

One of the first and most important lessons I’ve learned is that as a leader, you’re always being watched. This might seem obvious, but the depth of it only becomes clear when you experience it firsthand. Your mannerisms, how you dress, the way you speak—everything is under scrutiny. It’s not about being paranoid; it’s about understanding the weight of your influence.

People pick up on what you say and do, even when you think no one is paying attention. Months or even years later, someone might repeat something you said, something you didn’t even realize had made an impact. This realization can be both humbling and daunting. It’s a reminder that leadership is not just a role—it’s a responsibility that extends beyond the obvious moments of decision-making. Every interaction is an opportunity to lead by example.

2. You’re Always Leading—Even When It’s Hard

The second lesson is that leadership doesn’t take a break, especially in tough times. In the early days of my career, I would sometimes find myself overwhelmed, wondering why things weren’t going as planned. It’s easy to fall into the trap of frustration and despair. But as a leader, you don’t have the luxury to wallow. You have to keep moving forward, making the hard decisions, and guiding your team through uncertainty.

This aspect of leadership can feel almost psychotic at times—having to make tough calls, knowing the potential consequences, and yet still showing up with strength and conviction. It’s not about denying the difficulties; it’s about acknowledging them and leading through them. Your team looks to you for direction, and even in the most challenging moments, you’re setting the tone for how they should respond.

3. The Importance of Values

Finally, the importance of values cannot be overstated. Early in my entrepreneurial journey, I underestimated how crucial it is to establish and uphold core values within a company. When you’re starting out, especially if you’re coming from a place of financial struggle, values might seem like a luxury—something to worry about later when the basics are covered. But I’ve learned that values are the foundation upon which everything else is built.

Values guide your decisions, especially when times are tough. They shape the culture of your company and define the kind of people you want on your team. They help you navigate uncertainty and provide a sense of direction when the path forward isn’t clear. If I were to start another company today, I’d make defining our values a top priority right from the beginning.

Conclusion

These three lessons—being constantly watched, always leading, and the paramount importance of values—have been pivotal in my leadership journey. They remind me that leadership is as much about personal growth as it is about guiding others. It’s a continuous process of learning, adapting, and showing up, no matter the circumstances.

As I continue to share my experiences through this podcast, I’m grateful for those of you who tune in, who show up, and who find value in these reflections. Leadership isn’t just about the big wins or the grand gestures; it’s about the everyday moments that shape us and those around us. So, here’s to more episodes, more learning, and more leading.

Thank you for listening, and I look forward to sharing more insights with you in the future.

Mark Ashley