Mastering Mentoring 2 Getting to Know You

At the start of every mentoring relationship, I take the time to do a deep dive into the other person’s background, preferences, hobbies, personal family life, and any other thing I can think of as a baseline for the other person.

Many leadership mentors feel it is inappropriate to probe into matters outside the professional life of a protégé. I believe that mindset is flawed, because in order to be of maximum assistance to this person, you need to really know what makes him or her tick.

Note: for the remainder of this article, I will use the male pronoun in order to avoid the cumbersome “he or she” structure as much as possible. The concepts should apply to each gender equally.

You are not embarking on a casual relationship here. You are entering into a relationship that will impact every aspect of the other person’s life. I am not advocating that you pry into areas where he wants privacy.


The caveat here is to gently test the comfort level for any topic before getting involved in a discussion in that area. For some topics, it may take a long time to build up enough trust to share details about the individual’s past. Other times a person may be perfectly comfortable sharing any detail from the past right from the start.

 I believe it is important for you to know as much as you can in the following areas:

What does he find motivating?

We each have a key to what gets us excited.  We may not even be able to articulate it accurately, but it is there. If a person draws a blank on this issue, try using a “Strength Finder” instrument that may help uncover some hidden keys to the person’s motivation.

When is he most happy?  When does he feel most fulfilled? What does he dislike? What are his opinions on different management styles?

Identify his background

In as much detail as he will offer, find out about his upbringing and what events shaped his life up to this point. Pay particular attention to how he describes his feelings as he talks about his background.

Find out his current family situation, if he will share that

What forces are acting on him at the moment, and what is he proud of? What does he worry about? Who were some of his heroes when he was growing up?  How did he get along with the other kids in the neighborhood?


What does he like to do with his free time?  What things does he avoid at all cost? Who does he like to hang out with and to what groups does he belong? What was it about these groups that was of interest to him?


What types of situations get him angry, and why does this occur? How does he act when angry? How does he go about resolving his anger?


Where does he want to be in 5 or 10 years?  What steps is he taking to get there? What does he think are the biggest obstacles?

How can you be most helpful to him?

The person may not have a good grasp of this variable at the start, but there may be some directional ideas he can share that will be useful.


Learning these things about the other person will enhance the relationship in many ways. First, you will not be making false assumptions about the individual. Second, you can relate to his personal traits as you brainstorm what actions might be helpful next. Third, it will be easier to show empathy for the person when times or topics get tough.

You can often find out about these and many other personal traits in just a couple hours of chatting. You may also want to let him know these things about you, since a good mentoring relationship is bilateral.


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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