Mentoring Engagements – The First Steps

Earl R Smith II, PhD

(Read More From My Blog)

Initial meetings in any mentoring engagement set the tone and tenor for the rest of the engagement. Getting it right has a great impact on how the work is going to go and how successful the engagement will be.


During my years working as a mentor I have developed a number of useful tools that help me survive and thrive in the world of one-on-one, high impact mentoring. One that is particularly useful is a checklist that guides a new client and me through the process of designing a customized approach.

The checklist has become part of my ‘survival kit’ – a collection of tools and ideas that help me consistently produce results with clients that are highly educated, mentally agile, and very literate – who are accustomed to directing the action rather than participating in it or being directed by it. Here I want to discuss some of the purely prophylactic items on the list and one proactive item – all of which have proven their value over and over again.

What I Avoid:

Early on I learned an important lesson – others may be; but I am not fit for marketing a ‘one size fits all’ approach to mentoring. I shy away from mentoring systems which are designed to benefit ‘everybody’. Mentors and coaches who follow this or that ‘system’ always remind me of a favorite saying of Lotfi Zadeh (the father of fuzzy logic) – “When all you have is a hammer, everything tends to look like a nail.” I regularly encounter people who have been obsessively ‘hammered on’ in one way or another.

My own approach to mentoring begins with the assumption that general prescriptions (homilies) are ineffective when it comes to highly educated, literate people – most of whom are very skilled at gaming life and, by derivation, have raised the necessary process of self-delusion to a high art. ‘Packaged goods’ are insulting to these types. People who have thrived by recognizing how wonderfully complex and diverse life is – and by developing an understanding of how to relish and effectively deal with these complexities – are not likely to be long entranced with generalist proscriptions. So here is one item on my list: Don’t insult your client’s intelligence by attempting to sell them COTS solutions to their individual problems. It is the client’s needs rather than the mantra that should be center stage.

The search for an engagement focus cannot come out of a book written by someone else about nobody in particular. Begin the engagement by helping a client search out their challenges and then to confront those challenges directly and forcefully. People – particularly well educated, successful and highly literate people – tend to see themselves in a ‘mostly proactively positive’ light. Mentoring begins with a challenge to some part of this self-image – either by the mentor or (preferably) by the client. For the most part their self-image is probably an accurate reflection but, as they say, the devil is in the details. And good mentoring begins with the details – or, more properly, a carefully selected detail. In highly effective mentoring, substance always trumps form.

When it comes to a mentoring/client relationship, trust either is or isn’t. If it isn’t you don’t have a client you have an adversary. Each new relationship (including a mentoring engagement) is seen as a challenge to their ability to figure out the new game and how to win. But in mentoring it is very important that the relationship not be reduced to a zero sum game. As a result of the mentoring engagement, there is a new sheriff in town – and everybody needs to check their zero-sum revolvers at the town limits. The client needs to trust the mentor enough to follow his guidance and mostly abide by his rules. He has to be willing to join in a common journey as a student of his new mentor. The engagement needs to be a common journey in service of the best interests of the client – and on that journey the mentor is the guide.

I figure that most of my clients at one time or another played a lot of monopoly – and won most of the time. One reason is that they seem to have a real appreciation for the ‘get out of jail free’ card – and like to have a fair stock of them on hand just in case. To say it another way, highly educated and successful people tend to be very good at rationalizing (and forgiving) their shortcomings.[1] The old saying that “I have never met anyone capable of telling it straight; including me” might bring the idea into focus for you. By a simple sleight of hand they are free, and self-justified in being free, of any responsibility for their actions. A mentor needs to aggressively enforce the idea of personal accountability – on your terms not theirs – otherwise you are lost and the engagement is as well.

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