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? 

Why become a mentor? Many people assume mentoring only benefits the mentee. In fact, mentoring can be mutually beneficial, with the mentor gaining as much as their mentee. 

Here are some reasons why you should become a mentor -

1. Personal Reflection: Mentoring gives you the rare chance to reflect on your own career, values and purpose, and sometimes to course correct. 

2. Learn New Things: Mentoring forces you out of your comfort zone. Your mentee can share insights on new technology and trends, and you can learn new things and stay fresh. Make sure your mentee knows you are learning from them too. 

3. Improve Your Interpersonal Skills: Mentoring requires developing your social skills, such as listening, feedback and questioning. Through mentoring, you will have a lot of opportunities to practice with them. 

4. Give Back: Experience the satisfaction of making a difference in another person’s life and seeing them grow and learn. It’s the right thing to do and will make you feel good. 

5. Strengthen  Your Leadership Bona Fides: Mentor experience is required for many executive positions and will boost your career development. 

You and your mentor will have acknowledged that your next meeting will be your last. Here’s how to prepare for your last meeting. 
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1. Prepare for your final meeting

• Set aside some time to reflect on what you have achieved so far. What have you learned? Did the journey meet your expectations? What would you do differently? 
• Go through the goals you set. Were they achieved? 
• Make notes on what you would like to discuss during your final meeting. Is there advice you would like?
• What would you like to thank your mentor for? 
• Would you like to be a mentor in the future?

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2. Your final meeting

• Now is the time to celebrate your journey together. If possible, make it special by choosing a different place to meet, such as for lunch in a nice restaurant. You can choose a location to meet and enter it under Sessions. Simply select Schedule and go to Session Location and select Physical Location. You can type in the address within the Location details text box. 
• Reflect on what you have achieved so far and celebrate your successes. Share what you learned and how you have grown.
• If you did not achieve all your goals, discuss your plans going forward. 
• Share with your mentor what you felt was effective and where their mentoring could be improved.

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3. What’s next?

• Your formal mentoring journey is over, but you both may decide to remain in contact. If so, how will you stay in touch? 
• Appreciate your mentor. Thank them for what they have done for you.

Don’t let your mentoring journey fizzle out without formally concluding it. When a mentoring journey ends well it adds to the overall positive experience.