Questions For Mentors To Ask Mentees

5 min read

Mentoring is widely recognized as a tool to promote professional development both in formal and informal settings. Its follow-on effects are reflected in how people are more motivated in the workplace, resulting in increased productivity. In a  study conducted by, businesses that participated in mentoring programmes reported a revenue increase averaging US$47,000, or a 106 per cent increase. Those companies without mentoring programmes increased their revenue by an average of US$6,600, or only by 14 per cent. Another study found that 92 per cent of small business owners agreed that mentors had a direct impact on the growth and survival of their business. In the United States, companies whose founders have been mentored by top-performing entrepreneurs are three times more likely to become top performers themselves.

The Benefits Of A Mentoring Program

Companies and organizations put up a mentoring program for the following reasons:

  • It is an informal way for employees to get education and learning.
  • Proven to boost morale, motivate employees and reduce turnover.
  • Enables companies to transfer knowledge and management skills to junior employees.
  • Keeps employees focused on project-oriented tasks and developed better problem-solving skills.

From the standpoint of employees, they participate in a mentoring program for the following reasons:

  • Potential for higher financial compensation.
  • Opportunities for promotion.
  • More confidence for career advancement
  • Promotes job satisfaction
  • More significant commitment to a job within the organization

After a mentoring program is set up, the next most important thing is keeping it running and maintaining the mentors and mentees committed to the program. A crucial part of this happening is the quality of the mentoring sessions.

Planning The Mentoring Sessions

To achieve quality mentoring sessions, it is essential to plan. Here are the steps to planning a mentoring session:


Before actual mentoring sessions start, a pre-meeting would be ideal for defining the goals of the mentoring relationship and establishing a structure around the mentoring sessions. It is essential to consider the meeting schedules, considering the availability of both mentor and mentee. This is also the time to establish the expectations from the mentoring relationship of both mentor and mentee.

Identifying Effective Mentoring Discussion Topics

Based on the goals and expectations set out before mentoring sessions, both mentor and mentees can now decide and narrow down the topics that would best achieve said goals and expectations. The topics should be centred around the goals and expectations set. In the section below, we list some of these topics.

Building An Action Plan

Mentoring is often a long-term commitment. The goals and expectations are usually related to career or professional development that would require time and effort to achieve. Both mentor and mentee can create an action plan to achieve the long-term career objectives established at the beginning of the relationship. The mentor should help the mentee determine where to focus and how best to accomplish career or professional goals.

Maintaining The Relationship

To ensure that the mentoring relationship stays strong, mentors and mentees can do the following in addition to discussion topics already planned:

  • Knowledge sharing – examples include a mentor sharing the thought process of a difficult decision made or a mentee asking a mentor about a problem he/she is solving
  • Networking – attending industry events together or participating in panel discussions or focus groups
  • Skill Development – A mentee asking to observe mentor while he/she presents to a group and discussing insights and takeaways
  • Career Advice – Mentee asking to look at mentor’s résumé and have him/her walk the mentee through it.

Evaluating The Relationship

To ensure that both mentor and mentee benefit from the mentoring relationship, they must commit to evaluating the relationship every 3 to 6 months. Samples of questions that a mentor should ask the mentee when assessing the relationship are given below.

Types Of Discussion Topics For Mentoring Sessions

Mentors and mentees can suggest topics for the mentoring sessions, bearing in mind the goals and expectations set at the beginning of their relationship. Here are some sample of those topics:

Career Path Topics

Career paths are always the first choice topics for mentors. Mentors can ask mentees about their desired career path and if they think their current career path is aligned to his/her goals.  Mentees sometimes go into mentoring sessions to ascertain if they want to change career paths. Mentors can ask leading questions to mentees to see their career path situation.

Skills Related Topics

Skills-related topics include improving a current skill set or acquiring another one. The mentor may have both skill sets, and mentoring sessions are an excellent way for mentees to ask about these.

Situational Advice Topics

Asking a mentor for advice on specific situations is an excellent way for mentees to make use of their mentor’s time. This particular mentoring topic is recurring as there will always be situations where mentees may need advice from their mentors.

Feedback Related Topics

Feedback is needed for improvement and is a common topic for mentoring discussions. For example, a mentee can ask the mentor’s feedback on a presentation he is making or a project where he participates.

Leadership Topics

Mentors are almost always leaders themselves. Therefore, they are a great resource if mentees want to improve their leadership skills or want firsthand information on what it’s like to be in a leadership position.

Topics On Long-term And Short-Term Goals

Short-term or long-term goals are among the very first topics that mentors ask their mentees. Next, mentors can ask mentees about their career goals and ambitions within the organization. These goals will be the basis of the action plan prepared by both mentors and mentees.

Company-related Topics

If both mentee and mentor belong to the same company, talking about company culture, practices and directions is a good source for mentoring topics. It is also a way for the company to motivate mentees to buy into the company’s goals.

10 Questions To Ask A Mentee During Goal Setting

  1. What next steps would you like to make in your career? Are there any target positions you want to achieve?
  2. What do you hope to achieve from this relationship? What role do you expect your mentor to play?
  3. Are there any ground rules you would like to set (e.g., confidentiality, openness, candour)?
  4. What are your greatest strengths and weaknesses?
  5. How would you like to achieve your learning goals?
  6. What items would you like to discuss in these meetings?
  7. Are there any topics of urgent interest? Are any topics off-limits?
  8. What do you think will be challenging about this relationship?
  9. What would you like the regular meeting schedule to be (length, time, frequency)?
  10. What criteria would you like to use to evaluate the success of the relationship?

10 Questions To Ask A Mentee During Mentoring Discussions

On Career Development

  1. What recent successes do you feel you’ve had in your career? Why do you consider them as successes?
  2. What important issues have you been handling?
  3. How are you motivating others on your team? Do you have an approach for influencing others?
  4. Have you had a recent situation at work that required you to manage conflict? How did you handle it?
  5. Which work relationships are complicated for you?
  6. Where and how could you enhance the effectiveness of your team?
  7. What difficult decisions have you had to take on in your job recently?
  8. What recent changes have taken place in your department? What opportunities or challenges do you feel these created for you?
  9. Which decisions are easiest for you to make, and which ones do you struggle with the most? Why?
  10. How are you asking for feedback about your performance?

On Career Guidance And Personal Development

  1. What made you take your current role?
  2. What parts of your career would you like to develop further?
  3. What do you see as the following goals for your career?
  4. What reservations do you have that you may be able to reach the next steps?
  5. What is your long term vision, career-wise?
  6. Do you have educational goals? What are they?
  7. What are your current strengths? What are areas still needs to be developed?
  8. What steps would you like to take towards improving these areas?
  9. What individuals/books/events left the most impact on you?
  10. Do you feel that your work-life balance is effective?

10 Questions To Ask A Mentee During Evaluating The Mentoring Relationship

  1. Are we meeting with the correct frequency and for the proper amount of time?
  2. Are you following up on the action items from every meeting?
  3. Am I doing a good job following up on my action items?
  4. What do you like most about our mentor-mentee relationship?
  5. What do you like the least about our mentoring relationship?
  6. Are you learning from this mentor-mentee relationship?
  7. What skills have you acquired or acquiring as a result of this relationship?
  8. What should I do differently to help you achieve more out of this relationship?
  9. Are we reaching the goals and objectives we set at the beginning?
  10. Is there anything we should change in the action plan?

Beyond Asking Questions – Core Mentoring Skills

Active Listening

Beyond asking powerful questions that will lead to insightful answers, mentors must possess core mentoring skills for effective mentoring sessions. The first of these skills is engaging in active listening. There is a difference between listening and hearing. Hearing is a physical process, while listening is an “interpretative process” taking place with what we hear.  For example, we may listen to a loud, sudden, or unfamiliar sound, but listening will tell us about the meaning behind the sound. Listening involves attention, interpretation and understanding. Listening to another person takes time and effort. We listen to understand instructions at work, receive new information, understand changes in procedures, and interact with other people.

Building Rapport

Building rapport in any relationship is essential. It is about mentors developing a relationship with mentees based on mutual respect, influence, and trust. Rapport is an honest attempt to understand other people on their terms. It is to see the world from their perspective and feel what it would be like to walk in their shoes. Mentors that have a rapport with their mentees will encourage them to open up and share their thoughts and feelings. They will feel comfortable discussing issues they encounter. Mentees need to know that mentors support them. In turn, mentees will grow in confidence, develop their skills, and look upon mentors as trusted friends.

Effective In Conversations

Mentoring sessions are done within a set period of times, typically no more than one hour at a time. This is why mentors must be influential in conversations that can drive the session towards its goals. Several models can help mentors achieve this. One such model is called the GROW or the Goal, Reality, Options and Wrap-Up. The GROW Model provides the key elements to create an effective conversation in a mentoring session. This simple model supports a non-direct approach, using effective questions to identify progress and action. There may be several topics, issues, or ideas that the mentee will want to discuss, resolve, or clarify during a mentoring session. The four steps of the GROW Model are used for each new mentoring conversation within the session. It is important for mentors to first ask for consent from mentees before applying the GROW Model within a conversation. Doing this will create trust, and the mentee will open up his/her thinking to the exploration of possible solutions.

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 startup growth-related articles Good Topics For A Mentoring SessionA Guide To Startup CEO Mentoring and Steps To Successfully Expand And Scale Your Business on the same topic.

Scaling Partners – Who We Are

At Scaling Partners, we are experienced at scaling startups. 

Scaling Partners helps you bridge the knowledge, process and gaps in your business. Connected services. Hands-on solutions. Real experience. 

We know business growth isn’t easy. But we make it easier. Faster. More sustainable. How do we do that? By partnering you with the processes and insight you’re missing and the people who’ve been through it all before. And because we do it as a service, it’s brilliantly affordable.

Learn more about how we support startups with their growth and Business Mentors needs.

Photo by NeONBRAND on Unsplash

Don’t forget to share this post!

Don’t forget to share this post!

Related Articles

What Is An International Strategy, And Why Is It Important?

What Is An International Strategy And Why Is It Important?

Are you looking forward to expanding your business in the international market? Domestically or internationally, growing your business horizons involves a lot of planning, organizing, and research. This is when international strategy comes into action. So, what is an international strategy and why is it important?

What It Takes To Expand A Business

What It Takes To Expand A Business?

Just like Rome wasn’t built in a day, you cannot expand a business in a single day. It involves years of hard work to expand boundaries and reach a larger stage eventually. 

What Is An International Strategy, And Why Is It Important?

What Is An International Strategy And Why Is It Important?

Are you looking forward to expanding your business in the international market? Domestically or internationally, growing your business horizons involves a lot of planning, organizing, and research. This is when international strategy comes into action. So, what is an international strategy and why is it important?

What It Takes To Expand A Business

What It Takes To Expand A Business?

Just like Rome wasn’t built in a day, you cannot expand a business in a single day. It involves years of hard work to expand boundaries and reach a larger stage eventually.