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

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In an issue of Workforce Management, writer John Hollon identified key “Lessons from the Donald” as he put them, and we discussed these on our Coaching Lessons from The Apprentice show as well.
One lesson John summarized was “Leadership – even a little bit of it matters.” His point was the winners in the show were all people who showed basic leadership skills.
While our guests certainly concurred with this point, I loved that Ann Vanino added that as leaders, it’s also important to know when to lead, and when to follow.
I had a conversation with Carolyn Kepcher several years ago at an American Management Association event, and when I asked her to talk about the traits the winners from The Apprentice shared, she highlighted that adaptability was the biggest. She explained those who could quickly adjust to a constant changing environment and set of circumstances were the most successful.
This really rang true to me both on the show and in the workplace in general. While having the best intentions, leaders who consistently take the ball and run with it without letting others take the helm can often have a negative impact on motivation, teamwork, and the respect of their peers. While it may be difficult watching someone else in your company drive an important project in a way that you personally wouldn’t, it’s important to support them and become a part of the team if necessary.
It’s important for good leaders to keep on leadin’ – but also focus on championing and growing other leaders within the team.
For our coaches out there:
- How have you helped executives and managers lead – and be led – within their organizations?
- What would you recommend to leaders out there who struggle when managed by others? Any best practices or tips to keep in mind?
Your host,
Tom Floyd
CEO
IEC: Insight Educational Consulting
Specializing in Management Consulting, Change Management, Workforce Performance, and Employee Development
Coaching Lessons from The Apprentice

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Throughout our Insight on Coaching show dedicated to The Apprentice, we talked about the best practices and lessons learned that could be gleaned from the show from a leadership development, teamwork, and coaching perspective.
According to a February 2004 Business Week article, one of the lessons learned is “Always watch your back.” Troy McClain and Elizabeth Jarosz touched on this topic throughout our conversation.
When I asked Elizabeth how she collaborated and worked with team members who didn’t have her best interests at heart in many tasks, she shared it was important to not focus on the backstabbing and competitiveness, but to instead try to rally the team around a third point of reference that everyone could relate to.
In the case of The Apprentice, the third point of reference was winning the task. By keeping everyone’s attention on something mutually beneficial to the entire team, it helped reduce tension and bring the team together.
Share your strategies and thoughts with us:
- What strategies have you used to successfully “watch your back” in the workplace?
- How do you decide who to trust – and who not to?
- How have you handled backstabbers on your team who are focused on personal gain?
- Have you used a strategy like Elizabeth’s successfully in the workplace?
Looking forward to your thoughts!
Tom Floyd
CEO
IEC: Insight Educational Consulting
Specializing in Management Consulting, Change Management, Workforce Performance, and Employee Development
Coaching Lessons from The Apprentice

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The Apprentice is a television franchise that originated in 2004 in the United States on NBC. Billed as “The Ultimate Job Interview,” the show depicted a group of 15 to 18 businessmen and -women competing in an elimination-style competition for a one-year, $250,000 job of running one of host and executive producer Donald Trump’s companies.
Many magazines, newspapers, educational institutions, and organizations like the American Management Association have captured lessons learned from this hit reality show over the past several years.
For example according to The Boston Globe, institutions like Georgetown University and the University of Washington have weaved lessons learned from the show into classroom discussions on everything from what’s fair play in negotiations to how to win customers.
In fact, ABC’s news “Working Wounded Blog” cited that 4.8% of people listed The Apprentice as “their main source for information about how to survive the workplace.”
What are the best practices we can capture from the show? And how can we apply them both inside and outside of the boardroom?
Our panel of guests address these questions and more.
Highlights of the show include:
- An overview of seven leadership lessons that can be taken from the show.
- Anecdotes, best practices, and examples from former candidates on The Apprentice.
- The characteristics and personality traits successful candidates on the show possess.
- Why it was important to take risks on the show, and why it’s important in life in general.
- How to coach someone through a situation where their peers or team may be bent on sabotage.
Featured Guests:
- Duncan Brodie, Managing Director, Goals and Achievements Limited
- Lauryn Franzoni, VP and Executive Editor of ExecuNet’s Center for Executive Careers
- Elizabeth Jarosz, Candidate from The Apprentice, Season 2
- Troy McClain, Candidate from The Apprentice, Season 1
- Ann Vanino, Author, Leadership on Trial: Lessons Learned from The Apprentice
Tom Floyd
CEO
IEC: Insight Educational Consulting
Specializing in Management Consulting, Change Management, Workforce Performance, and Employee Development
Coaching Lessons from The Apprentice

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