40+ questions to ask your mentee

Why is asking questions important within mentorship?

An important aspect of mentoring is to be a good listener. A mentee will want to talk through their career pathway, including concerns and doubts. As a mentor, you’ll need to be able to fully listen and consider the best questions to ask your mentee, to help guide them to success.

Every mentorship relationship will be different. In general, we expect you as a mentor to be listening 70% of the time, with the additional time spent on coaching, giving advice and asking questions.

Using this list of questions to ask your mentee will be essential in understanding your mentee better (personally and professionally), understanding their career ambitions and what their goals look like. Questions also give you further insight into the mentee, beyond the answer they may offer up to. For example:

• what do they perceive their strengths and weaknesses to be?
• does their body language change when discussing a certain area of their development?
• are there certain areas the mentee is reluctant to discuss?

As a mentor, asking questions allows you to open the dialogue and gain trust within the mentorship partnership. You can also encourage them to find their own answers to a challenge if you know the right questions to ask.

What is the role of a mentor?

The practical application of a mentor’s knowledge, skills and experience can add substantial value to those starting out in their industry or looking to develop their career further.

A mentor is often a senior member of a specific industry that helps a mentee by:

• sharing industry knowledge and experiences
• sharing details of their own career path, and any learnings
• providing guidance, motivation, and sometimes emotional support to tackle obstacles
• being a role model within the industry
• helping with explore and develop a career, by setting goals, sharing contacts and resources
• providing coaching towards goals, rather than direct line management
• providing constructive feedback to help develop the mentee further

A mentor should meet with their mentee each month. There are a few different ways to conduct mentorship meetings, depending on the goal at hand. We have compiled a list of the different meeting approaches and have listed questions to help guide you in your mentor role.

Types of mentorship meetings:

• Introductory: getting to know each other and building trust.
• Goal setting: exploring their industry, role and career path
• Teaching: providing tools, resources, knowledge, domain expertise and contacts to help achieve goals
• Coaching: listening to challenges and asking questions to guide the meeting, coaching them to define their own goals and solutions
• Feedback: listening to progress on action items and goals set, presenting constructive feedback and insights to help your mentee get to the next level.

A complete guide of questions to ask your mentee

Get to know your mentee

• Tell me a bit about yourself – where do you live, your family, your job history, your current role?
• How long have you been working within product management?
• What do you enjoy about working in this sector and your current role?
• What’s the main challenge you’re facing in your career?
• Who do you look up as a role model, and why?
• What inspires you to develop?
• What kind of company culture do you thrive in?
• What is the last professional book or blog you read? Why did you pick that one?
• What is your favourite podcast? Why?

Understand ways of working well together

• As your mentor, what do you hope I can bring to these sessions?
• How do you like to learn?
• What projects and tasks energise you?
• What communication methods work best for you?
• How would you like me to deliver constructive feedback?
• Are there any sensitive areas / issues that you would not like to discuss in these sessions?
• What support do you need from me to meet your goals?
• How do you respond to change?

Identify areas to work on

• What do you consider to be your strengths?
• In what areas do you think you need to improve?
• Do you think your opportunity areas have held you back in your career? How so?
• What things have you tried to overcome your perceived weaknesses? How successful has this work been? What other ideas do you have?
• How much time do you have available to work on an action plan?
• When things are going well in your career, describe what is happening?
• When things are not going well in your career, describe what is happening?

Understand career goals

• What interested you about having a mentor?
• Why did you decide to join the mentoring programme?
• Do you have a clear idea of the goals you would like to set for the mentorship? Or do you need help to define these?
• What are your short, medium and long-term goals?
• What are your personal development goals? (e.g., influencing people, assertiveness, presentation skills)
• What skills do you want to develop?
• Is building your industry network important to you?
• Where do you see yourself in 1-, 3-, and 5-years’ time?

Career development

• What obstacles do you think you may need to overcome to meet your goals?
• Are you taking on enough challenges?
• What soft skills do you need to develop further?
• What training, skills or resources do you need access to, to help you reach your goal?
• What have you done previously that made you step outside your comfort zone?
• What do you want to learn next?
• What projects or tasks would you like to be more involved in at work?
• What conferences and/or events are happening in your space that you’d like to attend?
• Do you need to form any new habits? What are these?

If you would like more information about how to conduct mentorship meetings, view our 10-step checklist here.