Questioning is a key skill in mentoring. By understanding how to ask the right questions, you can unlock your mentee’s thinking and generate valuable insights. 

Closed and open-ended questions
Use both closed and open-ended questions in your mentoring conversations.

1. Closed-ended questions: 

Can be answered by a few words and provide information about facts. Use them when you need clarification or a specific answer. They usually begin with “Who,” “Where,” and “When,” and “How much?”.  

Examples: 

• “Who was part of the conversation?”
• “Where did you work previously?”
• “When did you join the company?”
• “How much was your quota?”
  
  

2. Open-ended  questions: 

Open-ended questions cannot be answered with one word, or a simple “Yes” or “No”. Typically, they require more thought and can lead to deeper thinking and insights. Open-ended questions often begin with “What”, “What if”,“How?” and “Why”. 

Examples:

•   “What motivates you?”
• “What accomplishments are you proud of?”
• “What if you had an unlimited budget for this project, how would you spend it?”
•   “How will you go about motivating your team?”.
  

Tip: Asking questions can be stressful for some new mentors. Remember, it’s more important to actively listen than to think about what question to ask next. After fully listening, reflecting back and summarizing, the right question will come to you.

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?”.

Time you spend building rapport and trust with your mentee will improve the success of the journey. 
Here are key components you need to build that relationship -

1. Confidentiality in both directions is key. Do not discuss anything your mentee shares with you unless you have their permission. Remind your mentee of confidentiality at the beginning and end of every session. 

2. Building rapport and trust are essential. Here are some ways you can build trust.

• Don’t rush. Spend enough time in the beginning getting to know each other, rather than rushing into goal setting and solutions. 
• Do your research about your mentee so you’re not starting cold. Acknowledge their strengths.
• Believe your mentee has the best answers within themselves. Your job is to ask the right questions.
• Follow through – do what you say you are going to do.
• Be prepared to be vulnerable – don’t just share your hero stories. Also share the times you failed.
• Ask for and be open to feedback from your mentee.
• Be non-judgmental.
• Listen a lot! Talk a little.‍
• Ask open-ended questions‍

3. Ask open-ended questions to get to know your mentee.

• What ^are your values? 
• What do you believe are strengths? 
• What are you passionate about? 
• What motivates you? 
• What are you most proud of? 
• What successes have you had? 
• What have you taken away  from your failures? 

Having a structure can help you and your mentee make your time more productive. The format can be adapted to suit your requirements so there’s a natural flow. 
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1. Feedback And Update 

Remind your mentee about confidentiality as well as any ground rules. 

Talk to your mentee about:

• Feedback on their progress on the action plan. 
• An update on what has happened in their work or personal life since you last met. 

• Progress on what you committed to do since the last meeting.

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2. Discussion

This is where you will spend the bulk of your time. Ask your mentee to go through the discussion points on their agenda, and identify the issues they want to discuss.
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Example of prompting questions:

“What would be most useful for you to discuss today?”

“What would you like this session to focus on?” 

Ask questions to clarify the issues your mentee has presented; be sure you fully understand before moving on.

Guide your mentee to think about their issue more thoroughly. Ask open-ended questions to encourage them to think more deeply.
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Example of prompting questions:

“What options have you considered?”

“What do you see as the pros and cons of each?”

You can then share some of your experiences and advice, if it's requested.

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3. Close

Action Plan - Ask your mentee to put together an action plan of what they would like to work on before the next meeting. If needed, help them to think through options. Make a note of anything you could provide, such as an article or video, to help them.  Make sure you send them to your mentee.

Discuss and schedule your next meeting. Set up a recurring meeting if you mutually agree on a time that works for both of you. Finally, sincerely thank your mentee for their hard work.

Your mentee is responsible for most of the preparation for their mentoring meeting; however, here are some things you can do to make it more productive -
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1. Be in the right frame-of-mind:

• Take time before your meeting to reflect on your mentee’s progress-to-date. Is the relationship working as expected?
• Be fully present. Eliminate distractions (especially your phone!).  

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2. Review the agenda and action plan:

• Your mentee should have sent you an agenda before your meeting. It should include a timeline, an update from your last meeting, and input needed from you. Be prepared to suggest any needed changes to the agenda.
• Review the action plan and tasks set from your last meeting and ask for an update at the beginning of your session.

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3. Goals: 

• Review the stated goals and milestones from your initial meeting and reflect on your mentee’s progress-to-date. 

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4. Your Action Items: 

• Have you done your action items from the last meeting? Be prepared to provide an update. 

Your mentee should be setting the agenda and sending an invite before each meeting. Be prepared to help them at first if necessary. Ensure you have synchronized your calendar so you can set up a date, time, topic and set an agenda for your session. You can also choose your preferred video conferencing platform so that you don’t have to set up new meetings every time you schedule a mentoring session.