Mastering Mentoring 1 A New Series

I have been writing a series called “Leadership Barometer” for the past couple years. Thus far there are 100 articles in the series.  At this point I am not tapped out, so  that series will continue, but there is a subset topic that deserves a new series of its own. The topic is mentoring: specifically mentoring for leaders.

My observation has been that there are many candidates to become great leaders, but the world still suffers from a shortage of great leaders. The problem is not having enough candidates but having adequate teachers. When teaching skills such as leadership, we usually refer to the activity as “mentoring.”

The reason so few high caliber leaders take the time to mentor other leaders is that they are so consumed with being successful themselves; there is very little time to mentor others.  I consider that mindset as a big mistake. Unfortunately, the problem is very common.

For this series, I will use my experience to recall many techniques that I have found helpful when mentoring would-be leaders.  I will also share some caveats or things that do not seem to work very well.  Each article will focus on just one facet of mentoring.

One negative practice has sunk many a well-intended mentoring effort. If we start to think of a mentoring effort as a “program,” we start off on the wrong foot.  Often groups will do a kind of “matching” effort in order to pair people who should work well together.

The more senior person (called the mentor) is introduced to a protege, with whom he or she will work in the future. This mechanical pairing of people has a low batting average in terms of a solid long term mentoring relationship. The reason is simple; to achieve a sustainable effort both parties must benefit by the relationship.

The way to avoid this common trap is to not think of mentoring as a program. Instead, encourage individuals to seek out a person who would resonate with them personally and who is willing to provide access. Don’t over administer the relationship with fixed meeting schedules or forms to fill out.  Let the relationship progress at a rate and with such tools as the two people invent themselves.

This “ownership” by both parties is a critical first step.  Each party will be interested in making the relationship work and be willing to invest time and effort into a process that they mutually own.

In my own case, I was blessed with a very strong mentoring relationship with a senior leader.  We did not call it “mentoring,” we just had a very close relationship where we both got large advantages out of spending time together. There was no paperwork or fixed schedules to adhere to, rather the interfaces occurred naturally as the opportunities for coaching became evident.

Communication was almost daily, and it was mostly done through the mode that was most comfortable for the mentor. In this case voice mail was used extensively to coach each other. I, the protege, gained insights and techniques in the form of ideas or suggestions. My mentor gained by my sharing my observations of how my mentor was engaging the entire population. So, we were kind of coaching each other along on a daily basis for more than 25 years.

The first piece of advice in this series is to encourage the organic formation of mentoring relationships and do not over-administer the effort as a “program.”  You will be much more successful in the end.


Bob Whipple, MBA, CPTD, is a consultant, trainer, speaker, and author in the areas of leadership and trust.  He is the author of: The Trust Factor: Advanced Leadership for Professionals, Understanding E-Body Language: Building Trust Online, Leading with Trust is Like Sailing Downwind, and Trust in Transition: Navigating Organizational Change.  Bob has many years as a senior executive with a Fortune 500 Company and with non-profit organizations. 

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