User Guides

How to Ask Productive Questions

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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?”.  


  • “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”. 


  •   “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?”.

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.

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What is Expected of Mentees?

Mentoring partners have expectations for each other.
2 mins

Mentoring partners have expectations for each other. The better they are understood, the more likely the journey will be successful. 

  1. Confidentiality: Confidentiality is the cornerstone of a mentoring relationship and is expected of both partners. Nothing can be shared outside of the meeting unless it is mutually agreed to ahead of time. You can write private messages by going into a current Mentorship and clicking on the Messages tab – other mentors and mentees can’t see these interactions.
  2. Be Prepared: Both Mentees and Mentors are expected to come to meetings prepared, on time, and committed to the process. Unless it’s an emergency, don’t change or cancel meetings. When you set up a Session with your mentor, you can select up a date, time, topic and set an agenda for your session.
  3. Show Initiative: Mentees are responsible for reaching out to their mentor, arranging the meetings and sending the agenda. They are responsible for their own learning with the mentor acting as a guide. The Goals & Tasks sections under Mentorship will help you set and document a goal to accomplish during the relationship, create tasks that need to be done to achieve the goal, and review your progress. Mentees must follow through on action plans and do what they have committed to. They also understand things can change and stay flexible. 
  4. Remain open to being challenged: Mentees ask for feedback and are open to receiving it. They understand feedback is an essential part of the mentoring process and provides an opportunity to learn and grow.