User Guides

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 Help Your Mentee Set Goals

Realistic goals that can be measured and achieved will improve both party’s experience and satisfaction.
4 mins

Here are some requirements a goal should meet -

1. Inspiring

Your mentee should be excited and enthusiastic about working towards these goals. 

2. Challenging, Yet Achievable

 Your mentee will grow if there’s a bit of a stretch to the goal, provided it’s attainable. 

3. Measurable and Time-Based

Goals should be measurable so you both know when they are achieved. They also should have a time-frame.

5 Steps For Goal Setting

Ideally, your mentee should have at least three primary goals. Here are steps to help your mentee set goals. Use the MentorCloud worksheet to document and track progress.

STEP 1: Explore

You and your mentee should look at all the major friction areas of their work and personal life. Your mentee needs to identify at least three areas to focus on through their Mentoring Journey.

Here are some open-ended questions you can ask your mentee: 

  • What do you want to accomplish in the upcoming months?
  • What are some things you would really like to learn or do?
  • What comes to mind in terms of personal or professional friction areas impacting you?
  • What else have you always dreamed of doing?
  • What would you like to see in your life that currently is not there?

STEP 2: Identify

  • From these areas, you can help your mentee identify their goals. Eliminate goals that are not relevant to the mentoring journey
  • Encourage your mentee to record their goals using the MentorCloud worksheet. 

Here are some questions to ask your mentee:

  • Does the goal meet the requirements of being motivating, challenging, achievable, and time-bound?
  • How will you measure success and know when you have achieved the goal?

STEP 3: Needs Analysis

After the goals are recorded, help your mentee think about the steps to achieve them.

Questions to ask your mentee:

  • How do you see accomplishing this goal?
  • What will you need to achieve it?
  • What resources, knowledge, help, or collaboration will you need?

STEP 4: Obstacles

What could prevent your mentee from achieving their goals, and how could it be overcome?

Questions to ask your mentee:

  • What do you fear could prevent you from reaching these goals?
  • How can I help you?

STEP 5: Milestones And Action Plan 

Milestones will help your Mentee measure their progress. Start by identifying a milestone and timeline with each goal. Ensure your mentee has a reasonable action plan for each goal.

Questions to ask your mentee:

  • What milestones will help you track each goal?
  • What help, or collaboration will you need?

Once your mentee has identified some goals, discuss it with them, and ensure it’s entered in the Goals & Tasks sections under Mentorship so you can refer back to it. If a goal seems too broad or unrealistic, help your mentee break these down into doable tasks and review their progress.