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22 mins

How to Ask Challenging Questions

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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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How to Prepare for Your First Mentoring Meeting with Your Mentor

Your first mentoring meeting can be stressful.

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xyz_mentee

3 mins

Your first mentoring meeting can be stressful. The first meeting is all about getting to know each other and gauging whether it's a good match. The better prepared you are, the more you will get out of it.

Here are some useful tips to make it more productive.

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Meeting Practicalities

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1. Make Contact and Set the Date

The mentee sets up the first meeting, so you have the option to either Request a Session to meet a prospective Mentor or to straightaway Request Mentoring.
Reach out to your mentor and set a date and time. If your mentor gives you permission, you can schedule your meeting right on MentorCloud. Ask your mentor if they would prefer to connect virtually or in-person.
To Schedule a Session, go to the Mentorship Tab and select View Relationship. You will see a button to propose a session. Fill out the information for the session. If both parties have synchronized their calendars, you can set up a date and time for your session.
Ensure you have selected the correct time zones to avoid any confusion later.
Select a private place to meet where you can both share openly. Simply select Schedule and go to Session Location and select your preferred video conferencing tool or location. You can type in the address for a physical location within the Location details text box.

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2. Background

Learn about your mentor’s background on MentorCloud. Your mentor might also have added a link to his/her LinkedIn profile for you to learn about their background and professional experience.
What is their experience, achievements and interests?

Have they mentored before?
Read any announcement, insights or posts they have contributed on the Community tab.

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3. Agenda

Send an agenda to your mentor a few days before your first meeting. This will help your mentor be better prepared.

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Meeting Preparation

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1. Who are you?

What do you want to share about yourself?
What are your strengths, values and achievements?
What brings you joy and energizes you?

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2. Why do you want to be mentored?

Have a strong understanding of what you want from your Mentoring Journey.
Do you have goals you want to achieve or anything specific you want to learn?

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3. What do you want to learn from your mentor?

Send an agenda to your mentor a few days before your first meeting. This will help your mentor be better prepared.

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4. Parameters?

Think about how often you want to meet, how you want to communicate, and any needed boundaries.
You have the option to set up recurring meetings under Sessions. Simply tick the box “Make this a recurring session” when you create a Session.

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