Taking Risks – Coaching Lessons from The Apprentice
Taking Risks
It was a pleasure having Ann Vanino back on our show to discus her book, Leadership on Trial: Lessons from The Apprentice. We’ve highlighted the lessons from her book on Insight on Coaching in the past, but went deeper on this show with several of them, including Lesson One: Take Risks.
The majority of contestants on The Apprentice certainly took risks. On our show, Troy McClain stressed if he hadn’t taken a big risk at the encouragement of his wife, he never even would’ve applied for the show in the first place.

Ann emphasized risk is a part of our lives every day, and that there will always be unknowns. It’s because of this she stressed, that if we strive for absolute certainty, we may not get very far in life.
To quote her in her words, “If you stay in the box, you’ll have a fairly safe life. However you may not have a very interesting life or even perhaps a fulfilling life.”
I found myself nodding all the way through this discussion.
I wouldn’t be where I am today professionally or personally if I hadn’t taken risks in my life, and I’ve been fortunate that many of those risks have worked out favorably. Personally it’s strange to find myself in a place in life where I have become extremely comfortable taking risks – yet I still totally understand why taking risks continues to be so uncomfortable or downright frightening for many people as well.
- For our listeners and readers out there, what’s helped you get more comfortable taking risks?
- For our coaches out there – when should we take risks in the workplace – and when should we not?
- How have any of you as coaches guided clients in determining if taking a risk is worth it?
Best,
Tom Floyd
CEO
IEC: Insight Educational Consulting
Specializing in Management Consulting, Change Management, Workforce Performance, and Employee Development
Coaching Lessons from The Apprentice
risk management Troy McClain leadership development change management Ann Vanino Insight on Coaching risk adversity The Apprentice life coaching coaching podcast Turbo Tagger
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