How to start a mentoring relationship


Amicitia Maloon-Gibson, an executive coach and co-author of the best-selling book “Stepping Stones to Success,” recommends you begin a mentoring relationship with two documents: a worksheet/questionnaire for your mentee and a set of binding agreements between you and your mentee.

The worksheet/questionnaire is intended to help your mentee conduct a rigorous self-assessment of his strengths, weaknesses, short-term goals and long-term goals. The resulting information should help you both identify the focuses of your future coaching sessions, which skills you should help the mentee develop and which obstacles you should help him conquer.

For example, suppose the mentee’s worksheet reveals that he is doggedly aiming for a leadership position but has a fear of public speaking — a skill that is obviously required of effective leaders. Your mentee’s worksheet responses would suggest that you should encourage your mentee to improve his public speaking skills, no matter how intense his fear may be. So after explaining to your mentee the importance of developing his public speaking skills, you might, for example, suggest that he join Toastmasters International, take a class or receive individual coaching on public speaking. After the training, you might want to help identify or arrange opportunities for your mentee to use his improved public speaking skills.

In addition, the worksheet responses may reveal the types of expertise you should offer and the types of support the mentee needs. For example, suppose you are a woman and your mentee is a young woman who is striving to break certain types of glass ceilings. These results suggest that you should share any relevant experiences or observations you may have about breaking similar glass ceilings, and that you should regularly initiate discussions about your mentee’s progress in this area.

The worksheet should also ask mentees to describe their expectations for the mentoring relationship so that you can gauge whether their expectations should be negotiated further.

The binding agreements — or contract — between you and your mentee will help protect your investment of time and energy in your mentee. This document should establish what types of communication you both will use and how often you will communicate. Will you, for example, plan regularly scheduled face-to-face meetings or e-mail conversations, or will the mentee contact you as needed? Whatever mode of communication you choose, both of you should double-check that neither of you is pledging more time than you can realistically spare.

Also, the contract should establish rules of accountability for your mentee. For example, this document should commit the mentee to being coached and showing up on time to your planned meetings or phone calls; cite how much notice the mentee should give if he must cancel a meeting or phone call; and warn the mentee of consequences he can expect for failing to give notice (unless he is involved in an emergency). For example, the contract may state, “If the mentee fails to show up at more than X number of meetings without giving notice, the mentor-mentee relationship will be dissolved.”

In addition, the contract should prepare the mentee for the full range of feedback you will provide. Maloon-Gibson explains, “I use the contract to ensure that each mentee will be open to feedback — good or bad, positive or negative. Some people just want to be pumped up. But my contracts tell mentees that they can expect to hear the truth from me (in a tactful way).’’

She continues: “If I see a problem, I will discuss alternative courses of action with them but I won’t tell them what course of action to take. This is all part of teaching mentees to take ownership of their goals, and empowering mentees to make decisions for themselves.”


About Author

Lily Whiteman is a federal communications expert and author of “How to Land a Top-paying Federal Job,” and a trainer of career advancement skills and communication skills. Her website is Ask your career questions by email to or by Twitter to @Lilymwhiteman.

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