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2. Initiate Relationship

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22 mins

How to Prepare for Your First Mentoring Meeting with Your Mentee

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Your first meeting is about getting to know each other and determining if it’s a good fit. Will you be able to guide your mentee and help them achieve their goals?

It’s worthwhile to spend some time preparing for your first meeting. Here are some useful tips to make it more productive -

1. Contact

The mentee needs to reach out to you to set up the first meeting. Making your dates visible on MentorCloud will make scheduling easier. If you have synchronized your calendar, it’ll be easier to set up a date and time for your session without any scheduling conflicts. Ensure you have selected the correct time zones to avoid any confusion later.

Your meeting place, whether in-person or virtual, should be a quiet, safe space where you can both share openly. You could also select your preferred video conferencing tool.

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2. Background

Read up on your mentee on MentorCloud. Your mentee might also have added a link to his/her LinkedIn profile for you to learn about their background and professional experience.

What is their background and experience, achievements and interests?

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3. Agenda

Your mentee should send you an agenda a few days before your meeting. When you create a Session, there is space for you to note down an agenda for your meeting.

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PREPARATION

1. Who are you?

What do you want to share about yourself?
What are your strengths, values and achievements?
Have you mentored before?
What lessons did you learn from that experience?

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2. Why are you a mentor?

What do you hope to get out of the relationship?
What do you hope to learn?

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3. What are your expectations?

Reflect on what you expect from your mentee and how you see your role in the mentoring relationship.

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4. Parameters?

How often do you expect to meet, how you want to communicate, and any needed boundaries you want to establish?

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How to Ask Challenging Questions

Asking challenging questions can be helpful to encourage deeper thinking about a situation.

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1 min

Asking challenging questions can be helpful to encourage deeper thinking about a situation. However, these questions need to be asked with care and sensitivity.

Sometimes “Why” questions can be seen as judgmental or speculative, for example, “Why did your team react that way?”; however, when used sparingly, they can be effective. Sometimes a “Why” question can be rephrased using a “What” or “How” question.

Asking questions that are challenging can lead to critical and reflective thinking and may help your mentee generate insights.

Challenging questions are usually:

difficult to answer
slightly out of the respondent’s comfort zone
non-judgmental
personal to the respondent and specific to the topic
push the respondent to think more deeply

Examples include: “What’s unique about your situation?”, “What critical feedback do you most often receive, and do you deserve it?”, “What dream have you given up on?”, and “What are you risking by not stepping out of your comfort zone?”.

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