Your obsession with flawless execution might be the very thing holding your company back.
Most founders rise to leadership because they're exceptional operators—they solve problems faster, think deeper, and deliver better than anyone else. But here's the uncomfortable truth: those same skills that made you invaluable as an individual contributor actively work against you as a leader. In this episode, Andrew Poles, three-time founder and executive coach, reveals why sixty-one percent of leaders struggle most with delegating, and it has nothing to do with trust issues. Discover how to build mental maps that allow your team to think independently, why transferring intention beats transferring instructions, and the neuroscience behind why people can't change behavior without changing perspective. This isn't about working less—it's about scaling your impact beyond what you can personally execute.
The fundamental problem is simple but painful: being great at doing the work makes you terrible at teaching others how to do it. When you're naturally skilled at execution, you've likely never needed management yourself. You just figured things out. This means you have no contrast, no framework for what good leadership actually looks like. Without that contrast, you're flying blind.
The solution isn't to stop being involved. The best leaders still dig into the biggest, hairiest problems. But they've offloaded the ones they've already mastered. They've learned to transfer not just tasks or goals, but intention itself. When your team understands not just what to do or even how to do it, but why it matters and how it connects to the larger mission, something powerful happens. They stop needing you for every decision.
Building this capability requires creating mental maps for your team. Not step-by-step instructions that break the moment something unexpected happens, but frameworks that allow people to think through problems themselves. This means answering the why behind every how, connecting KPIs to intentions, and making explicit the connections that feel obvious to you but invisible to others.
The hardest part? You have to actively develop skills you've never needed before. Leadership and management aren't traits you're born with—they're skills you build through deliberate practice. And unlike execution skills that reward individual capability, leadership skills require something entirely different: the ability to see the world through someone else's eyes and communicate in ways that shift their perspective.
People only act in ways consistent with how they see the world. If someone isn't performing the way you need, telling them what to do differently rarely works. You need to change how they see the situation. This is where emotional intelligence becomes critical. Research shows EQ accounts for roughly fifty percent of success in early management roles, but jumps to ninety percent at the CEO level.
The angry response to a quote-unquote stupid question reveals the real problem: you haven't built the map well enough. When someone asks something that feels like step one when you think you're at step ten, that's feedback. It means the connections between steps, the logical framework, the mental territory—something is missing. Creating psychological safety for those questions is how you build autonomous, high-performing teams.
This transition from operator to leader isn't comfortable. It requires betting on yourself while simultaneously questioning whether you're the right person for the role. You have to hold that tension. The skills that made you a great founder won't automatically make you a great CEO. But the good news? Both are learnable. You just have to apply the same self-directed push you used to master execution toward mastering influence.
Watch the Full Episode on Why Your Execution Skills Are Sabotaging Your Leadership with expert Andrew Poles below:
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