Posts by Kyle Courtaway
Leadership, AI, and the Danger of Outsourcing our Humanity
We’ve been canoeing and traveling the Boundary Waters Canoe Area for years, long before GPS became a standard tool. In wilderness travel, one of the most critical skills you develop is reading a map. But here’s the thing: map reading is a misnomer. You’re not just reading paper or tracing a route — you’re using…
Read MoreThe Other Shadow: When Keeping the Peace Costs Us the Truth
One of the programs I teach on having difficult conversations asks individuals to think about how they got their way as a child. The responses are telling. You can imagine the range—from throwing a tantrum to wearing parents down with persistence, or even invoking fairness by saying, “X got to do this, why didn’t I?”…
Read MoreSometimes we want the win more than we want the relationship.
I had a colleague ask me a question last week: “What’s the one thing you’d teach someone about being a better leader if you could only teach one thing?” Here’s what came to mind. I don’t know if it’s the ultimate answer, but it rose straight to the surface in that moment. Let’s be real—sometimes we…
Read MoreIt’s the conversations you’re not having that are shaping your leadership the most.
We’ve explored how defensiveness hijacks our internal dialogue and how control can quietly close off connection. But there’s a third force—quieter still, yet just as disruptive: avoidance. Avoidance doesn’t raise its voice. It doesn’t make a scene. In fact, it often disguises itself as patience, professionalism, or keeping the peace. Especially in organizations that prize…
Read MoreWhen Control Closes the Conversation
I’ve been playing guitar for over 30 years, but recently I went back to taking lessons—to challenge myself and to reconnect with the basics through a fresh lens. Not long ago, my teacher stopped me mid-song and said, “You’re gripping the neck way too tightly.” I hadn’t even realized it. What I thought was focus…
Read MoreWhen Defensiveness Hijacks Your Internal Dialogue
Some topics can be discussed once and easily understood. Others require regular reminders, surfacing again and again as we navigate real-world interactions. Defensiveness is one of those. Even when we recognize its impact, it has a way of creeping back into our conversations, shaping how we respond, and influencing what we take away from an…
Read MoreLeadership Development Is Relational Development—And That’s the Hard Part
Are You Consuming Knowledge or Are You ACTUALLY Learning? I’m lucky enough to work with some of the smartest, most dedicated leaders in the world. My role is to challenge and support them with the conversations that matter most. Lately, we’ve been trying to get to the bottom of this question: Are we actually learning anything with all…
Read MoreLeading from the Middle: The Director’s Crucial Advantage
Most leadership conversations focus on frameworks and strategies at the front-line leadership or executive leadership level, but what’s often overlooked is the missed opportunity organizations face when they fail to recognize the pivotal role of Directors and Senior Directors. If organizations aren’t careful, they risk underutilizing the very leaders who bridge vision and execution, shaping both strategy and…
Read MoreThe Balancing Act of Effective Leadership
Leadership is a constant balancing act. We want results, we need accountability, but we also know that people don’t operate in a vacuum. We recently introduced a framework for understanding behavioral influences to a group of plant supervisors, the reaction was immediate: “If we start looking at all these factors, aren’t we just making excuses…
Read MoreThe Impact of Training Directors in Fostering a Culture of Continuous Learning
In today’s rapidly changing business landscape, organizations are realizing the importance of fostering a culture of continuous learning to stay ahead of the competition. And it all starts with effective training directors. These unsung heroes play a critical role in transforming good employees into great ones by providing them with the tools and resources they…
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