The Art of Project Management: Expert advice from experienced project managers in Silicon Valley, and around the world

Mentoring Circles – Better Leveraging a Mentor’s Time

Table of contents for Getting and Making Good Use of a Mentor

  1. Still Don’t Have a Mentor?
  2. From Mentor to Colleague
  3. Mentoring Circles – Better Leveraging a Mentor’s Time
  4. It’s Just Lunch – Asking an Executive to Mentor You

Having a mentor all to yourself might seem like the ideal, but it can get a little awkward sitting across the table from a person whose experience greatly surpasses your own. Sometimes having one mentor meet with several people at the same time can be very effective way to leverage the precious time of a highly experienced person. While you might like to keep them all to yourself, having a bigger audience could increase your chances of landing a highly skillful mentor, make the experience less awkward, and you might also learn a lot from the other people in your mentoring circle. Try group mentoring!

When I was starting my project management consulting business I was fortunate enough to be mentored by an extremely talented and experienced consultant. The professional association I attended was launching a mentoring program, and it turns out that only two people signed up for it. We both wanted to be mentored by this extraordinary gentleman, so he offered to mentor us together. What a great idea! I wish I’d have thought of it.

Every month for the next year we met for coffee at a quiet little cafe convenient to his home. I learned a tremendous amount from him . . . AND . . . I learned a lot from the other person who was getting mentored. Honestly, she could have mentored me as well, so I really got two mentors for the price of one – and the price was free!

One big bonus was that the casual discussions in a relaxed atmosphere among the three of us transformed the relationship from  mentoring to friendship. Having three of us there instead of only two somehow made the whole process much more “social”. There was less pressure to keep the conversation flowing, and we were never at a loss for discussion topics. In the end it was much more relaxed and fun than other mentor meetings I’ve had! Eventually life took us our separate ways, but I still feel the impact of the deep connections we all made as we got to know each other deeply over the course of our discussions.

If you’d like to benefit from mentoring from an expert who’s truly extraordinary, but you feel a bit daunted by their presence, consider gathering two or three people who’d like to share the journey with you. Here are some ideas that will can make your mentor circle a positive experience for everyone involved:

  • Gather a couple of people who are sincerely committed to learning and growing.
  • Suggest the prospect of group mentoring to your potential mentor.
  • Schedule a regular meeting time, such as the second Wednesday morning of each month. Monthly is a good frequency.

Make it easy for your mentor for them to increase the chances they will continue the mentoring relationship. For example:

  • Choose a location that’s convenient to your mentor – something close to their home or business, and certainly not like the place in this picture!
  • Find a place that’s pleasant and relaxing. (Conversations held outside in a beautiful setting tend to be more open than those in a meeting room.)
  • Make the experience enjoyable!

Practice the “Attitude of Gratitude”:

  • Show Appreciation. Send a hand written note to your mentor from time to time to let them know you appreciate their time.
  • Let Them Know the Impact They Have. When you implement their advice give them feedback on how it helped you.
  • Pay the tab! Don’t ever make your mentor pull their wallet out at your meetings.

Business is about relationships, and mentoring in groups is another way to build high quality relationships while building your skill set. And remember to  pass on your wisdom to others when someone approaches you for this kind of help!



About the Author

Kimberly Wiefling is the author of one of the top project management books in the US, "Scrappy Project Management - The 12 Predictable and Avoidable Pitfalls Every Project Faces", and the founder of Wiefling Consulting, LLC, a scrappy global consulting enterprise committed to enabling her clients to achieve highly unlikely or darn near impossible results, predictably and repeatedly. Her work focuses on keynote speaking and workshops on practical and sensible business leadership and project/program management scaled for the size of the company and the project. She has worked with companies of all sizes, including one-person ventures and those in the Fortune 500, and she has helped to launch and grow more than half a dozen startups, a few of which are reaping excellent profits at this very moment. She spends about half of her time working with Japan-based companies that are committed to developing truly global leaders. Kimberly holds a B.S. in Chemistry and Physics from Wright State University and a M.S. in Physics from Case Institute. She spent 10 years at HP working in product development project management and engineering leadership. She worked with several startups, including a Xerox Parc spinoff where she was the VP of Program Management. In 2001 she launched her consulting practice and never looked back. She holds a certificate in project management through UC Santa Cruz Extension, where she is an instructor in the Project and Program Management Certificate Program. Kimberly spends about half of her time facilitating leadership, communication and execution excellence workshops for leaders of Japanese companies committed to becoming truly global. Thousands of people have viewed the hysterical video documenting the final phase of completing her book at You can reach her via email at
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