Good Topics For A Mentoring Session

5 min read

Mentoring is widely acknowledged as a powerful tool for development. In organizations, in formal setting it is helps employees progress in their career, acquire or improve skill sets and learn how to deal with specific situations in the workplace. As mentoring is a long-term commitment, one of the challenges faced by mentors and mentees is structuring and planning their mentoring sessions.

Regular meetings, good communication where there is respect, trust and timely and appropriate feedback are all essential to making mentoring work for both mentees and mentors. But perhaps the most important component of planning is coming-up with good topics for a mentoring session. Too often commitment and dedication are there but the mentee-mentor relationship becomes stale for lack of good topics for a mentoring session.

If you are among those mentee-mentor pairings noticing that the topics during your mentoring sessions have become repetitive, this guide on choosing good topics for a mentoring session is for you!


Planning A Mentoring Session

There are many ways to structure a mentoring session. Some mentors and mentees prefer a free-flowing session while others are more comfortable with concrete and programmed mentoring sessions. Whatever is the preference, a good mentoring session will have the following pre-requisites:

  • Establishing mutual trust and respect. It may go without saying but this is a crucial first step before you go on your first mentoring session. Mentee and mentor should ask each other’s background information and know each other more before going on a mentoring session. It is also suggested to establish boundaries – on topics and areas of their lives that can be discussed. Although over time, some mentees and mentors develop friendships, in the beginning both might not be comfortable discussing topics that will cover their personal lives, work-life balance.
  • Deciding on schedule for meetings. It could also be that meetings are arranged on short notice. To maximize the mentoring sessions, it is best to plan out the meetings in advance by dedicating a regular schedule to mentoring sessions.
  • Establishing goals and creating an action plan. After learning about each other and deciding on the time and frequency of meetings, it is best to establish goals of the mentorship. Where do the mentee need help? Is it with developing or improving a specific skill set? Is it in planning for career advancement and progression? Is it with responding to certain situations at work? After goals are established, both can now craft an action plan to realize these goals.
  • Choose topics for mentoring session. The action plan can now be drilled down to specific topics for each mentoring session. Good topics for a mentoring session must support the goals outlined. They can be broad covering personal improvement, but they can also be specific like business mentorship topics, particularly if both mentee and mentor come from the same organization.


What Are Good Topics For A Mentoring Session?

Well-structured mentoring topics can spell the success of a mentee-mentor relationship. Business mentorship topics, for example can help mentees come up with creative solutions to workplace problems, identify areas for personal improvement and cultivate new business strategies to introduce changes in their industry.

Types Of Topics For Mentoring Sessions

In general, good topics for mentoring sessions can be broadly classified into four categories of questions:

  1. Stories. Topics that ask the mentee or mentor to relate story are good ice breakers to jump start a mentoring session. Examples include asking about how a mentor landed in his current role or asking a mentee to recall a story of a first job interview.
  2. Situations. Once you get the conversation going, each can then go to questions that relate to specific situations you want to ask each other. If you for example, your topic for the mentoring session is on handling a specific work situation, a mentee can ask the mentor on how he might handle the situation differently.
  3. Self-awareness. This is one type of topic or question that mentees can ask mentors and expect a tailored response. Questions under this category can be about asking the mentor on how the mentee is perceived by others. As the mentee and mentor most likely belong to the same network, the mentor is able to provide honest and constructive feedback.
  4. Skill-building. Mentees come to mentors to help them with career development. This often involves improving or acquiring a skill-set. For example, the mentor is a great public speaker. The mentee can ask about to get better at public speaking.

These four broad categories of topics can be further broken down into detailed topics from either the perspective of the mentee or the mentor.


Startup CEO Mentoring Guide

Mentees To Mentors

Topics Related To Skills

Talking about skills-related topics is a great way to make use of a mentoring session. If a mentee for example just got promoted to a position requiring project management skills; he can ask the mentor on ways to improve this particular skill-set. More concrete questions can include the following:

  • How can I improve my project management skills?
  • What do you think are my three best skills?
  • What skill areas do you think I could improve in?
  • What skills do you think are the most beneficial for me to have in my current position?

Topics On Career Stories

Another good topic for a mentoring session is to ask the mentor about his career path. If both mentee and mentor belong to the same industry, a mentee can ask how the industry developed over time. What significant milestones did the mentor witness ever since he started in the industry. Questions belonging to this type of topic includes:

  • What was your first job in the industry?
  • How did you reach the position you are currently in?
  • Do you have any regrets about your career choices?
  • Did you ever make a mistake in a job? How did you come back from it?

Topics On Feedback

Feedback is essential for improvement and can therefore be used as a good topic for a mentoring session. A mentee can ask the mentor’s feedback on a paper he is writing, a project he is managing or a presentation he is preparing. Questions like the ones below belong in this topic category:

  • How would you rate my presentation at last week’s meeting?
  • Do you think I am ready to apply for promotion?
  • How do you think other executives perceive me in my new role?
  • What changes would you make to my presentation?

Topics On Situational Advice

Asking a mentor for advice on specific situations is a good way for mentees to make use of their mentor’s time. This particular mentoring topic can also be used repeatedly as there will always be situations that mentees where mentees can use a good advice from mentors. Mentees can ask mentors questions like these:

  • How do I implement new procedures and encourage adaption by my team?
  • How do I ask for a raise?
  • I am having issues with a team member’s untimely submission of deliverables, how I address this proactively
  • How do I decide on who to promote between two team members who have equal qualifications?


Mentors To Mentees

In the same way that mentees can lead on which topics to discuss for a mentoring session; mentors can also initiate and suggest the following topics:

Career Path Topics

A mentor’s first choice of topic is almost always around career paths. Mentors can ask mentees on their desired career path. They can also ask if the mentee thinks of his current career path as aligned to his goals or if he wants to change career paths. Leading questions like the following will help mentors see the mentee’s career path situation:

  • Are you happy in your current role?
  • What made you apply for this role? How does it relate to your long-term career goals?
  • Where do you see yourself in 5 years?
  • Do you feel you are already in your ideal job? If not, what is your ideal job?

Leadership Topics

Mentors are often in leadership positions. Therefore, they are a great resource if mentees want to improve their leadership skills or want insider information on what is like to be in a leadership position. Mentors can probe on leadership topics like this:

  • Are you interested in advancing to a leadership role?
  • What methods are you using to effectively communicate to your team?
  • Do you have any issues or reservations with your current responsibilities?
  • How are you adjusting to your new role as a team leader?

Topics On Long-term And Short-Term Goals

Short-term or long-term goals are among the very first topics that mentors should ask their mentees. Mentors can ask mentees about their career ambitions. They can help them prepare an individual development plan to achieve to progress from their current role to the role they are aspiring. Asking questions like this are examples of related to mentoring topic:

  • What do you want to achieve in the next six months?
  • What do you want to achieve in one year?
  • What higher positions in the company do you aspire for?
  • How do you measure your success?

Company-related Topics

If both mentee and mentor belong to the same company, talking about company culture, practices and directions can be a source of good topics for mentoring sessions. Mentors can ask mentees the following:

  • What do you think is our company culture? Does it resonate with you?
  • Do you see your role contributing significantly to the company?
  • What can you do in your role to improve the company?


A Sample Topic Planning For Mentoring Sessions

Meeting #1 – Introductions

• Career and educational backgrounds

• Goals and objectives for the year in the mentorship program

• Decide on the best form of communication for scheduling future meetings (i.e. virtual, in-person, telephone or email)

Meeting #2 – Career Planning

• Current role, aspirations, and potential higher roles

• Discuss 5-10 year planning on how to achieve career goals

• Discuss skills necessary to achieve these goals

Meeting #3 – Skill-set

• Discuss the skills necessary in achieving career goals

• Create a plan or tips to improve current skill-set or acquire new ones

Meeting#4 – Leadership and Teamwork

• The importance of leadership and teamwork to success

• Challenges in being part of a team

• What traits make a good leader

• How can you improve your leadership skills

Meeting#5 – Upcoming Professional Challenges

• Issues faced over the course of this year

• Lessons learned from handling these issues

Meeting #6 – End of Year Evaluation

• Evaluate the year in terms of goals achieved and quality of mentoring sessions

• Discuss what worked and didn’t work in your mentorship year

• Create a list of suggestions to help mentee and mentor progress in their mentorship


Startup CEO Mentoring Guide

Evaluating The Progress Of Mentoring Sessions

It is essential to evaluate the effectiveness of a mentoring session especially if it is part of a structured and organized company mentoring program. Both mentees and mentors will also be able to adjust and refine on how they conduct the mentorship if there as an evaluation in place. Here are four measures that can be used to evaluate mentoring sessions:

  1. Adherence to Process. If a mentoring program is in place then mentoring sessions must adhere to it – from the scheduling, frequency, deliverables, and other requirements of the program. The program director can intervene if basic program requirements like frequency of meeting are not being respected
  2. The Experience of Mentees and Mentors. The strongest indication of a successful mentoring session is that both mentee and mentors find in enjoyable and helpful. Mentees and mentors can also gauge how easy or difficult it is to navigate a mentoring program.
  3. Mentee’s Progress. Are the mentee’s goals set at the start of the mentoring sessions being met? If the mentee was aiming at getting a higher role in the company using the individual development plan (IDP) of the mentor; how is he progressing?
  4. Organizational Impact. Do you see an improvement on employee satisfaction? What about improvement in performance or employee retention levels?

Have we missed anything or have any questions? Get in touch

If you enjoyed reading this, don’t forget to share.

You might also enjoy these popular business mentoring related articles Questions For Mentors To Ask Mentees, What Is The Role Of A Mentor? and A Guide To Startup CEO Mentoring on the same topic.


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