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Common Mentoring Dilemmas

written by: Mike Sweeney•edited by: Linda Richter•updated: 4/9/2011

A successful mentor understands the many common mentoring dilemmas that can surface during a mentoring relationship. With a plan in place, and a strategy to manage the unforeseen challenges, the mentor can realistically expect to achieve his goals and those of the mentee and the organization.

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    Create a Mentor-Mentee Agreement

    Mentor greeting mentee 

    One of the first things a mentor should do is arrange a meeting with the mentee for the specific purpose of creating a meaningful mentor-mentee agreement. The mutual creation of the agreement will help identify some of the challenges that the mentor and mentee may both face. Time constraints, differences in expectations, learning and teaching styles, and organizational and management pressures are a few examples.

    The openness of the meeting and the honest exchange of information and viewpoints are critical in drafting an agreement that both sides can agree to and easily work from.

    Some typical questions that work well in this environment center around expectations, personal needs, organizational and management requirements, and measurable results.

    Examples of Questions for the Mentor-Mentee Meeting

    Here are a few questions to help you get the meeting off in the right direction. These questions are designed for the mentor to ask the mentee to help draft the agreement.

    ♦ What would you like to gain from this relationship? How do you plan on measuring the success of this relationship?

    ♦ What are your expectations going into this agreement?

    What skills are you looking to improve upon during our partnership?

    ♦ How do you prefer to learn new information or skills?

    ♦ What can I do to increase the level of comfort between us?

    ♦ What is the most effective way for us to communicate beyond our one-on-one meetings?

    ♦ How often should we meet? What time constraints do you have imposed on you from your job?

    ♦ How long should we schedule to meet? Is there a location you prefer that is different from this one?

    Once you establish rapport with the mentee, crafting the mentoring agreement becomes a great deal easier. You are much more likely to get better information, and the agreement will then have much more validity. This type of initial meeting also indicates your willingness to listen to the mentee and suggests you are open to the mentee's feedback and suggestions.

    It’s important for both parties to recognize the differing levels of talent, time and responsibilities. With that appreciation understood, the achievement of the agreement’s goals becomes the overriding factor in making decisions on actions and challenges that may surface unexpectedly.

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    Identify Common Challenges

    Mentor meeting with mentee 

    With a mentor-mentee agreement in place, handling common challenges will become easier and your responses to any mentoring dilemmas will be more effective. Whether it’s a time issue, trying to figure a way to handle a situation, or deciding on what actions to take, the focal point becomes the mutual agreement and not the mentee or mentor. However, without an agreement, decisions may be perceived as arbitrary and appear somewhat subjective and could jeopardize the mentoring relationship.

    Suppose, for example, that a mentee needs to cancel a meeting at the last minute. Instead of just leaving a message for the mentor, the mentee could look at the agreed-upon cancellation or re-scheduling process and refer to it for guidance: This solution is simple, easy to implement, and shows a sense of responsibility and respect for the mentor.

    A few other common behavioral issues or mentoring dilemmas that may arise for a mentor include giving advice instead of providing insights and guidance, showing some level of favoritism, or being too judgmental and discounting the mentee’s abilities. Mentors also need to be careful in giving feedback and be conscious of any criticisms that are offered. Criticisms generally shut-down mentees, whereas coaching and positive reinforcement encourage better listening and communication and invite repetitive positive behaviors.

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    Women in Technology Mentor-Protégé Program: Anitha Raj; Retrieved at

    Tests and Challenges in Mentoring Relationships: Ellen Ensher & Susan E. Murphy; September 2006; Retrieved at

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