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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How to Set Your Goals

The purpose of setting specific and measurable goals in the Mentoring Journey is to identify concrete and meaningful areas to work towards.
4 mins

The purpose of setting specific and measurable goals in the Mentoring Journey is to identify concrete and meaningful areas to work towards. This will help ensure that the time during your Mentoring Journey is well spent.

Requirement for Goals

Inspiring - You should be excited and energized about working towards these goals.

Challenging But Achievable - Your goals should challenge you, yet be realistically achievable.

 Measurable and Time-Based - Your goals should be measurable, so both you and your mentor will know when they have been accomplished. They should be clear and well-understood, and need to be completed within a certain timeframe. 

Steps to Identify and Set Your Goals

Ideally, you should have up to three primary goals for your Mentoring Journey. Here are five steps to help you think of some goals -

STEP 1: Explore/Reflect

Take some time to prepare for your meeting with your mentor to discuss your goals. Reflect on your values, purpose and vision. What’s important to you? What do you stand for? What are areas in which you want to improve?

Reflect on the major focus areas of your work and personal life. You want to identify at least three areas relevant to your Mentoring Journey.

Questions to think about:

  • What do you want to accomplish in the upcoming months?
  • What are some things that you would really like to learn or do?
  • What comes to mind in terms of work or life you are dealing with right now? 
  • What have you always dreamed of doing?
  • What would you like to see in your life that’s currently missing?

STEP 2: Identify

From the areas described in Step 1, identify and record 2-3 goals related to your Mentoring Journey. Use the MentorCloud worksheet to document your goals and track progress.

For each goal, ask yourself: 

Are these goals positive, challenging and motivating to you?

  • Do they inspire or excite you?
  • Are they challenging? Do they need a bit more stretch?
  • Is each goal achievable?
  • How will you measure success for each goal?  How will you determine when you have achieved it?
  • Are they time-based?

STEP 3: Needs Analysis

Reflect on what needs to be done in order to achieve each goal and invite your mentor to brainstorm with you. Identify where you are now with each goal. 

  • What is your vision for each goal? 
  • What skills do you need so you can achieve this goal?
  • What resources, information, knowledge, help, or collaboration do you need?

STEP 4: Obstacles

  • What could get in the way of you achieving these goals?
  • Who could hold you accountable to help you achieve these goals?

STEP 5: Milestones and Action Plan

For each goal, define milestones and set a timeline. Ensure that you have an action plan for achieving each goal.

  • What milestones would help you track your progress for each goal?
  • What resources, information, knowledge, help, or collaboration do you need?
  • What is a reasonable timeline for you to achieve each goal? 

Once you have identified some goals and discussed them with your mentor, use the Goals & Tasks sections under Mentorship to set and document a goal to accomplish during the relationship. Break these down into tasks that need to be done to achieve the goal, and review your progress.