Many Halftime Alumni have had rich and rewarding experiences mentoring younger leaders in their business careers. 

When we ask them what they enjoyed most about their day-to-day work, they often say it was seeing those behind them find success and grow as individuals and leaders.

So, it’s natural that mentoring is a portion of what many Halftimers want to do in their next season. But without the corporate structure, it’s hard to know exactly where to start:

– Where would you find these emerging leaders, what material would be most helpful?

– Doesn’t it seem prideful to ask someone if they want you to mentor them… as if we have all the answers?

– Are there existing platforms that would help me match up with the right kind of mentees?

– Are there new skills I need for mentoring in a whole life context vs. just career?

Rick Woolworth is a Halftime Alum, longtime mentee of Bob Buford, and 35-year veteran of Wall Street. Lloyd and Rick have been friends for 20+ years and together have been deeply engaged in this kind of work.

In 2010 Rick formed something called Telemachus Network — building a community of emerging and experienced leaders engaged in mentoring relationships and inter-generational friendships.

In this brief webinar, you will discover why mentoring is a highly leveraged use of time, plus glean simple ideas to begin and best practices + resources to help. 

CLICK HERE to watch or listen to the recording of our conversation.

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1. Ask Questions:

This is key. Be quick with questions and slow with answers. For example, “What is success?” is a great area to begin exploring together. Taking notes is a helpful practice throughout this process.

2. Share Stories:

Be authentic about your own life and experiences. Share the articles, books, resources, and videos that have been helpful to you.

3. Connect + Encourage:

Introduce your mentee to your own network (this is one of your greatest assets). Use voicemails or texts to share encouraging messages with your mentee as you journey together. 

“I believe that mentoring has the highest ROI per unit of time of anything we do. If you spend just 2-3 hours a month for a few months, you can change the entire trajectory of a young person’s life. It is a win-win.

Ready to put these principles into practice? Check out Rick’s Great Mentoring Questions for a resource on where to start and don’t miss his Harvard Business Review article for a holistic mentoring strategy. 

Rick also recommends this article and this book for those looking to dig in deeper. Halftimers with adult children may find this article published by Fast Company to be a helpful resource to pass along. 

At Halftime, our programs bring greater impact, purpose, and joy for the whole family. 

Getting connected with a group of like-minded peers and a Halftime Certified™ Coach to create a custom, holistic plan for your family’s next season of life could be a great next step.

It is our privilege to walk with leaders like Rick as they navigate all the ups and downs that come with pursuing leveraged impact and thriving relationships. How could our support system best come alongside you?


Rick Woolworth is married to Jill and the father of three adult daughters. He resides in Greenwich, CT and is a 35-year veteran of Wall Street, having spent the majority of his career at Morgan Stanley. Rick pursues his passion for mentoring and coming alongside emerging leaders as President of Telemachus which he co-founded in 2010.

For 18 months ending in June 2018, Rick and Jill were Fellows in Stanford’s Distinguished Career Institute where they were full-time students taking classes in their respective fields of interest alongside of graduate and undergraduate students.

Rick is a graduate of Dartmouth and Stanford Business School and led the leadership group that founded Trinity Church in Greenwich. He loves staying connected with friends, is a passionate golfer and an undistinguished guitar player.

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The Halftime Institute is the leading authority on creating a next season defined by joy, impact, and balance. For more than 20 years, we’ve served thousands of men and women from varied backgrounds. The concept of ‘halftime’ was born out of the best-selling book, Halftime: Moving from Success to Significance, written by Bob Buford. Following the popularity and resonance of his book, Bob founded the Halftime Institute in order to provide a hands-on process and community for growth, support, and learning for people walking through their own season of ‘halftime’. Since then, the Institute has expanded to include world-class Coaches, Staff, and Resources – equipping leaders all over the globe. Interested in gaining clarity for your next season? Fill out the contact form below!