116. How to Lead Without Losing Your Team - Andrew Oxley

In this episode, I’m joined by Andrew Oxley — a seasoned executive coach, author of The Four Faces of Frustration, and founder of The Oxley Group. With a career spanning decades and companies like Coca-Cola, CNN and Progressive Insurance, Andrew has spent over 30 years helping leaders cut through complexity and lead with impact.

We dig into the hidden trap many sales leaders fall into — showing up as the hero or the villain — and why the real shift is to become the guide in your team’s story. Andrew shares how a “morning smile” clipping in a newspaper changed his life, how your limiting beliefs are likely driving your performance issues, and why asking the right questions is more powerful than having the answers. He’s got hard-earned wisdom on leading with accountability, performance and clarity, and it’s all delivered with clarity, humour and precision.

How to lead as a guide, not a hero or villain:

• Start by being radically honest about the role you play in your team’s results — change starts with you.
• Remember: your team’s performance story includes you as either a villain, hero or guide — choose wisely.
• Use questions you don’t know the answers to as a compass — keep asking, keep searching.
• Identify the real problem before trying to solve it — most leaders waste time fixing the wrong thing.
• Trade in limiting beliefs like “I don’t have time” for empowering questions like “Who can help me grow?”
• Connect leadership development to business outcomes, not just “HR initiatives”.
• Hold people to high expectations and support them in the growth to get there — that’s how guides lead.

Timeline summary

[03:00] – Leading a top sales team at 27: the ‘player coach’ phase and what it taught him [04:40] – The quote that changed everything: “Even if you win the rat race, you’re still a rat” [05:15] – The power of keeping a question front of mind: “How do I change my life?” [06:58] – “The problem wasn’t the job. The problem was me.” [12:00] – The three roles leaders play in their employees’ stories: villain, hero or guide [15:05] – Why the hero boss actually disempowers your team [16:30] – What it really means to lead as a guide: tough, supportive, accountable [17:25] – “You’ll never solve a problem you’re not trying to solve.” [18:44] – Busting the “I don’t have time” myth and how to reframe it [20:55] – If you want to double your income, go buy someone lunch and ask better questions [23:03] – Why most leadership training fails: it doesn’t move the business needle [25:52] – Start with business results, then work backwards to behaviour and leadership [27:26] – How to use AI (like ChatGPT) to help your reps diagnose their own problems [32:02] – Understanding how frustration shows up in different people and what it’s telling you [34:15] – “Thank you. Please tell me more.” The only right answer to feedback [35:00] – The billboard test: how much honesty are you willing to accept about yourself?

Links & resources

• Free leadership training: transformingresults.com
• Andrew’s book The Four Faces of Frustration: Available on Amazon