40 Questions to ask a mentor

Mentorship isn’t just a one-way street of advice and guidance; it’s a dynamic partnership that can shape your career and life in profound ways. The importance of asking the right questions cannot be overstated. In this comprehensive guide, we’ll delve deeper into the mentoring relationship. We’ll explore why these questions are essential, strategies to make the most of your mentorship, and how to apply what your mentor teaches you.

The Power of Asking the Right Questions

Before we dive into the specific questions to ask a mentor, it’s crucial to understand why asking the right questions is so pivotal in the mentorship process. Here’s why:

Focus and Clarity: Effective questions help you pinpoint your needs and goals, ensuring that your mentor’s guidance is tailored to your unique circumstances. Without clarity, mentorship can become vague and less productive.

Engagement and Rapport: Thoughtful questions demonstrate your commitment to the mentorship, engaging your mentor on a deeper level. It also fosters rapport, encouraging the mentor to truly invest in your success.

Knowledge Transfer: No matter the structure of your mentoring relationship – traditional older mentor and younger mentee, reverse mentorship, one-to-many mentorship – questions unlock the treasure trove of your mentor’s knowledge and experience. They provide a structured way to extract valuable insights that may not be shared otherwise.

Effective mentoring

Questions to ask a mentor

As suggested by emily sobel, Executive Vice President of Savills – a commercial real estate titan in New York City – “True connection happens through transparency in two directions with open and honest dialogue. For a mentee to show a real commitment to being present, they should come with questions. Questions are the key to dialogue.” Taking Emily’s advice, let’s explore an extensive array of categories of questions to ask a mentor in detail, along with the rationale behind them:

Questions to ask a mentor at your first meeting

  1. How did you handle your first major professional setback, and what did you learn from it?
    1. Rationale: Asking about how your mentor tackled a significant setback reveals their resilience and problem-solving skills. Learning from their experience can prepare you for similar challenges.
  2. Can you share an example of a challenging professional decision you had to make and how you arrived at your choice?
    1. Rationale: Understanding your mentor’s decision-making process can help you navigate complex choices in your career effectively.
  3. In your experience, what are the key qualities that successful professionals share?
    1. Rationale: Identifying common traits of successful professionals can guide your personal development and career strategies.
  4. What strategies have you found effective for time management and productivity in your career?
    1. Rationale: Time management is critical for career success. Learning your mentor’s strategies can improve your efficiency.
  5. How do you approach building and nurturing professional relationships in a new workplace?
    1. Rationale: Building rapport and connections are essential for career growth. Your mentor’s insights can help you establish a strong professional network.

Questions to ask a mentor about work-life balance:

  1. How do you maintain work-life balance while advancing in your career?
    1. Rationale: Balancing work and personal life is crucial for long-term career satisfaction and overall well-being.
  2. What strategies do you employ to prioritise your mental wellness?
    1. Rationale: Prioritising mental health is essential for maintaining high performance and avoiding burnout.
  3. How do you stay inspired and motivated in both your personal and professional life?
    1. Rationale: Sustaining motivation is key to overcoming challenges and achieving your goals.
  4. What role has continuous learning played in your career advancement, and how do you stay updated in your field?
    1. Rationale: Lifelong learning is vital for staying competitive in your industry. Your mentor’s approach can guide your professional development.
  5. Can you recommend any specific personal development books, podcasts, or courses that have had a significant impact on your life?
    1. Rationale: Seeking recommendations for resources can accelerate your personal growth journey.
  6. How do you handle moments of self-doubt or imposter syndrome, and what advice do you have for overcoming these feelings?
    1. Rationale: Coping with self-doubt is common in any career. Learning from your mentor’s strategies can boost your confidence.
  7. What are your strategies for maintaining a healthy work-life balance, and how has this contributed to your overall well-being?
    1. Rationale: Understanding your mentor’s work-life balance practices can help you find your own equilibrium.
  8. How do you set and prioritise your personal goals, and what methods do you use to track your progress toward them?
    1. Rationale: Goal-setting is essential for personal growth. Your mentor’s approach can inspire effective goal-setting strategies.

Strategic questions to ask a mentor:

About Careers:

  1. Are you assertive or passive in the workplace, and what are the strengths and weaknesses of each approach?
    1. Rationale: Understanding different workplace approaches helps you adapt to various situations.
  2. What attributes do you believe are most critical for career advancement?
    1. Rationale: Identifying key traits for career success can guide your professional development.
  3. What guiding principles do you follow when making career decisions?
    1. Rationale: Discussing ethical considerations in career choices can help you make sound decisions.

About Leadership:

  1. How do you maintain focus and motivation outside of work to be a better leader within your team?
    1. Rationale: Balancing personal and professional leadership skills is vital for effective leadership.
  2. How do you handle negative feedback from those you manage?
    1. Rationale: Addressing challenges in leadership helps you become a more resilient leader.
  3. What is the most uncommon trait that the best leaders have?
    1. Rationale: Exploring unique leadership qualities can set you apart as a leader.

Questions for workplace mentors:

  1. How did you come to join this company, and how does it compare to your previous employers?
    1. Rationale: Understanding your mentor’s workplace journey provides insights into the company’s culture and values.
  2. What do you wish you had known when you first started here?
    1. Rationale: Learning from your mentor’s early experiences can help you navigate your workplace more effectively.
  3. Where do you envision the company in five years?
    1. Rationale: Gaining insights into the company’s future can inform your career decisions and goals.

Questions to ask a mentor for personal growth:

  1. What books, podcasts, or courses have had the most significant impact on your personal development?
    1. Rationale: Exploring resources for self-improvement can enhance your personal growth journey.
  2. How do you handle setbacks and maintain resilience in the face of adversity?
    1. Rationale: Developing resilience is essential for personal growth and overcoming challenges.
  3. What are your strategies for setting and achieving long-term goals?
    1. Rationale: Goal-setting is a fundamental aspect of personal development, and your mentor’s strategies can be invaluable.

Questions to ask a mentor about networking:

  1. How have you built and maintained your professional network over the years?
    1. Rationale: Networking is a valuable career asset. Learning your mentor’s networking strategies can help you expand your own network effectively.
  2. What are your top tips for effective networking at industry events?
    1. Rationale: Strategies for making meaningful connections at events can enhance your networking skills.
  3. How do you approach building relationships with colleagues and superiors within your organisation?
    1. Rationale: Building rapport within your workplace is crucial for career growth and success.
  4. Can you share a memorable networking experience that had a positive impact on your career?
    1. Rationale: Learning from your mentor’s experiences can provide valuable insights into the power of networking.
  5. How do you approach networking events or conferences with the goal of building meaningful connections?
    1. Rationale: Understanding effective strategies for networking at events can help you make the most of such opportunities.
  6. What are some effective ways to leverage social media for professional networking and personal branding?
    1. Rationale: In the digital age, online networking and personal branding are essential. Your mentor’s insights can guide your online presence.
  7. How do you manage and maintain relationships with your professional contacts over the long term?
    1. Rationale: Maintaining long-term relationships with contacts is crucial for ongoing career growth and support.
  8. Can you provide tips for effective online networking, especially in virtual or remote work settings?
    1. Rationale: In remote work environments, online networking skills are particularly valuable. Your mentor’s advice can help you excel in this context.

Questions for entrepreneurial mentors:

  1. What challenges did you face when starting your own business, and how did you overcome them?
    1. Rationale: Learning from entrepreneurial experiences can prepare you for the challenges of starting your own venture.
  2. What are the key factors you consider when evaluating new business opportunities?
    1. Rationale: Understanding how to assess business opportunities is essential for aspiring entrepreneurs.
  3. How do you manage risk and uncertainty in the business world?
    1. Rationale: Strategies for navigating risk and uncertainty are crucial for entrepreneurial success.
  4. What advice do you have for individuals considering entrepreneurship as a career path?
    1. Rationale: Your mentor’s advice can provide valuable insights for those interested in entrepreneurship.
  5. How do you identify market opportunities and trends in your industry?
    1. Rationale: Recognizing market opportunities is key to successful entrepreneurship.
  6. Can you share a specific example of a challenging moment in your entrepreneurial journey and how you navigated it?
    1. Rationale: Learning from your mentor’s real-world experiences can help you address similar challenges.
  7. What resources or support systems did you find most valuable when starting your own business?
    1. Rationale: Knowing which resources and support systems to leverage can facilitate your entrepreneurial journey.

Strategies for maximising your mentorship

Asking the right questions is just one facet of a successful mentorship. Here are additional strategies to make the most of your mentoring relationship:

Set Clear Goals: Work with your mentor to establish specific, measurable, attainable, relevant, and time-bound (SMART) goals. These goals provide a roadmap for your mentorship journey.

Maintain Regular Communication: Establish a consistent meeting schedule and mode of communication with your mentor. This ensures ongoing support and guidance.

Seek Feedback Actively: Don’t wait for feedback to come to you; actively seek it from your mentor. embrace constructive criticism as an opportunity for growth.

Practice What You Learn: Apply the insights and advice provided by your mentor in your day-to-day activities. Experimentation and learning by doing are powerful tools for growth.

Celebrate Achievements: Acknowledge and celebrate milestones with your mentor. This fosters a positive and motivating mentorship environment.

Final thoughts

Mentorship is a transformative journey, and the questions you ask are your compass. By understanding the significance of asking the right questions, delving into key categories, and implementing strategies for success, you can unlock the full potential of your mentoring relationship.

Remember, mentorship is not just about gaining knowledge; it’s about applying that knowledge and growing both personally and professionally. So, ask, engage, learn, and thrive with your mentor by your side.

Coaching vs mentoring – a stellarup guide

Coaching vs mentoring

Coaching vs mentoring is a comparison commonly made by individuals seeking guidance on their journey of personal or professional growth. In this guide, we’ll delve into the critical distinctions between the two programmes. Coaching and mentoring programmes are frequently used by organisations to foster growth, enhance employee performance, and facilitate career development.

While they share common objectives, the journey, structure, and goals of coaching and mentoring are distinct. By the end, you’ll have a clear understanding of which path suits your needs best and how to structure a coaching or mentoring programme that closely aligns with your desired outcomes.

Also have a look at 40 Questions to ask a mentor.

Coaching vs mentoring: definitions

Let’s start by defining coaching and mentoring:

Coaching: Coaching is a structured process in which a coach, often a certified professional, partners with a client to help them achieve specific goals. The coach facilitates growth and development by asking powerful questions, providing feedback, and supporting the client’s self-discovery.

Mentoring: Mentoring, on the other hand, is a nurturing relationship where a more experienced individual, known as the mentor, provides guidance, advice, and support to a less experienced individual, known as the mentee. Mentoring is typically a long-term, relationship-based approach focused on the overall career and personal growth of the mentee. An effective mentoring relationship provides learning opportunities for both participants, encouraging joint sharing and growth.

Key differences between coaching and mentoring

Directive vs. Non-directive

One of the most fundamental distinctions between coaching and mentoring is their approach to guidance.

  • Mentoring: In mentoring, a mentor typically takes a lead role, offering guidance based on their expertise. It is often a directive process where the mentor shares knowledge and experience.
  • Coaching: In coaching, the approach is non-directive. Coaches guide clients primarily through questions, encouraging self-reflection and empowering clients to find their own solutions.


The duration of coaching and mentoring relationships can significantly differ.

  • Mentoring: Mentoring relationships are often long-term, lasting for months or even years. In some cases, mentorship can evolve into lifelong connections.
  • Coaching: Coaching relationships tend to be shorter-term, typically lasting for weeks or months, depending on specific goals and objectives.


The qualifications of those involved in coaching and mentoring also vary.

  • Coaching: Coaching often involves certified professionals who have received formal training in coaching techniques.
  • Mentoring: In contrast, mentoring typically does not require formal qualifications, making it easier for organisations to implement mentoring programmes quickly.


The structure of coaching and mentoring processes differs in terms of formality and goal-setting.

  • Coaching: Coaching usually follows a structured agenda with clear goals and action plans. Coaches use various tools and frameworks to help clients achieve specific outcomes.
  • Mentoring: Mentoring is generally less formal, allowing mentees to set their own goals. This fosters a more organic and adaptable process.


The purpose and focus of coaching and mentoring also vary significantly.

  • Mentoring: Mentoring is primarily development-driven, allowing the mentee to determine their goals and objectives. It focuses on holistic growth, personal and professional development, and knowledge transfer.
  • Coaching: Coaching is performance-driven, targeting specific skill improvement, behavior change, and goal attainment. It aims to enhance individual and team performance in a focused manner.

Skills required for coaching and mentoring

Both coaching and mentoring demand unique sets of skills:

Mentoring Skills:

  • A strong desire to help others: Effective mentors are genuinely interested in the growth and development of their mentees. They offer support and guidance willingly.
  • Profound expertise and insights: Mentors should possess substantial knowledge and experience in the mentee’s field or industry. This expertise serves as the foundation for valuable advice and guidance.
  • Exceptional relationship-building: Building trust and rapport with the mentee is crucial. Strong interpersonal skills help mentors establish meaningful connections.
  • Long-term commitment: While not a traditional skill, long-term commitment to the mentoring relationship is vital. Mentoring requires patience and dedication to see the journey through.
  • Motivational and inspirational qualities: Effective mentors motivate and inspire their mentees to strive for excellence and overcome challenges.
  • Goal identification: Mentors help mentees identify and set clear, achievable goals for their career and personal development.

Coaching Skills:

  • Establishing a trusting, equal relationship: Coaches must create a trusting and collaborative environment where clients feel safe to explore their challenges and opportunities.
  • Maximising resources and inspiring growth: Coaches help clients unlock their full potential by providing tools, resources, and inspiration for growth.
  • Recognizing strengths and challenging improvement: Coaches identify clients’ strengths and weaknesses, helping them leverage strengths and address areas needing improvement.
  • Problem-solving: Coaches assist clients in overcoming obstacles, finding solutions, and developing strategies for success.
  • Goal-setting: Coaching involves setting clear, measurable goals aligned with the client’s desired outcomes.
  • Time management: Coaches help clients manage their time effectively to achieve their goals.
  • Adaptability: A key skill for coaches is the ability to adapt their approach to meet the unique needs and preferences of each client.
  • Patience: Coaches provide clients with the space and support they need to explore their thoughts and ideas.
  • Practical feedback: Constructive feedback is essential in coaching, helping clients understand their progress and areas for improvement.

Benefits of coaching and mentoring

Both coaching and mentoring offer numerous advantages, making them valuable tools for personal and professional development:

Effective Learning Techniques: Both coaching and mentoring provide effective learning experiences, allowing individuals to acquire new knowledge and skills.

Formal and Informal Application: organisations can implement both coaching and mentoring programmes in formal or informal settings, adapting them to their specific needs.

Increased Employee Engagement and Retention: Engaging in coaching or mentoring can enhance employee job satisfaction and commitment, leading to increased retention rates.

Enhanced Confidence and Interpersonal Skills: Individuals receiving coaching or mentoring often develop greater self-confidence and improved interpersonal skills.

Improved Individual and organisational Performance: Both approaches contribute to enhanced performance at the individual and organisational levels, leading to greater success and achievement of goals.

Transition from coach to mentor

A coach can transition into a mentor when specific coaching goals are achieved, and a deep connection is formed between the coach and client. This evolution often occurs when the coach has successfully guided the client in achieving their predetermined coaching objectives. The relationship becomes more mutually beneficial and may resemble a mentorship, with the focus shifting towards holistic development and personal growth.

Choosing the right path

The decision between coaching and mentoring hinges on your needs and objectives:

Choose mentoring when seeking holistic development, expanding your network, and gaining diverse insights from a more experienced individual.

Opt for coaching when targeting specific skill improvements, behaviour change, and performance enhancement in a structured and time-bound manner.

Organisation’s choice

For organisations, the choice between coaching and mentoring depends on their specific goals and objectives:

Mentorship is suitable for organisations looking to support career development, facilitate knowledge transfer, nurture their organisational culture, or promote diversity and inclusion.

Coaching is ideal for addressing specific skill gaps, improving employee performance in targeted areas, implementing standardised training, or achieving well-defined organisational objectives.

Final thoughts

In conclusion, coaching and mentoring are powerful tools for personal and professional growth. While they share some similarities, they each offer unique approaches to development. Understanding the distinctions between the two will empower you to make informed choices tailored to your needs or your organisation’s objectives. Whether you embark on a coaching journey or seek mentorship, remember that both paths can lead to unlocking your full potential.

As you navigate your career or organisational development, use this knowledge to harness the power of coaching and mentoring effectively, ensuring your success and growth in the dynamic landscape of the business world.

Fostering a culture of continuous learning

Fostering a culture of continuous learning

Hiring the perfect candidate is just the beginning of a successful journey with your employees, but for them to truly evolve and excel, continuous learning is key. Emphasising this aspect not only benefits new staff members but also provides a competitive advantage to organisations, as their employees grow and maintain a fresh and relevant skill set.

With the average employee now staying in a job for approximately four-and-a-half years, and skills becoming outdated within five years, fostering a culture of ongoing learning and personal growth has become imperative. As the retirement age continues to rise, professionals must embrace continuous learning to stay ahead in their expertise.

Implementing intuitive and comprehensive software lowers the barrier to entry and empowers individuals to learn new skills and develop professionally. It is the responsibility of companies to cultivate a mindset that encourages employees to pursue continuous development. According to Gallup, a renowned global performance-management consulting company, staff members are most engaged during the first six months of employment. Capitalising on this period while setting them on a path of lifelong learning is crucial for their success and the organisation’s growth.

Promoting continuous learning

Creating an environment where employees are naturally inclined to learn is vital. Starting a new role can be overwhelming for individuals, but it is also when they are most eager to succeed and prove themselves.

At StellarUp, we believe in integrating learning seamlessly into the work process, making it an essential part of the employees’ personal ecosystem. The ability to host both structured and unstructured learning opportunities allows for a diversification of delivery that meets the needs of learners of all kinds.

To foster a culture of continuous learning, it is critical to align the educational aspects with day-to-day work tasks. Every organisation has its unique values regarding training, and it is essential to tailor the learning tactics to meet both the organisational and individual needs.

Managers play a critical role in establishing a learner-centric atmosphere by providing the right tools and resources that enable employees to learn while they work. By doing so, companies can significantly increase staff engagement and productivity.

Investing in mentoring

Mentoring is a powerful tool for employee development. It plays a pivotal role in creating a skilled and motivated workforce. According to the International Coaching Federation, a remarkable 86 percent of businesses experience a return on investment from coaching and mentoring programs– outstanding statistics and outstanding impact on participants.

Further, around 35 percent of staff who don’t receive mentoring within the first 12 months look for another job.

But what other aspects make mentoring so essential? For one, it provides much-needed guidance. In busy organisations, managers may not always have the time to closely monitor their staff’s progress. However, by implementing a dedicated mentorship program, some of this responsibility can be delegated to mentors.

Mentoring offers a personalised support system that pairs mentees with experienced individuals who have been in similar positions before. These mentors provide invaluable insights, help mentees overcome obstacles, and develop both professional and personal skills.

Whether through one-on-one sessions or group interactions, mentoring helps employees get up to speed and boosts their confidence to excel in their roles. As a result, they acquire specific skill sets that fast-track their career growth, leading them towards managerial positions and beyond.

Providing access to digital resources

While mentoring is a reliable method for on-the-job learning, it is equally important to offer access to digital resources. The workforce is increasingly composed of millennials who value flexibility and convenience. They seek to supplement their learning using smart devices and in their own time.

The need to provide high-quality digital resources that facilitate instant access to learning materials is legitimate and urgent. Focusing on creating short, engaging, and easily digestible content that caters to the learners’ needs at the moment of necessity makes an organisation not only appealing but also more successful.

Unlike traditional corporate learning platforms with overwhelming documentation, this approach ensures that employees have the right information at their fingertips.

Making an enduring shift towards continuous learning

Creating an environment that seamlessly blends learning and work lays the foundation for better employees and a stronger organisation. The positive impact of this approach on the bottom line is undeniable. As the nature of work continues to evolve, it becomes paramount for organisations to ensure that their staff remains up-to-date and adaptable.

At StellarUp, we take a holistic approach to mentoring and learning, offering specific tracks that champion employee development and continuous education. Our platform allows you to utilise our track templates or design your personalised track, tailored to meet your organisation’s unique needs.

By implementing StellarUp’s mentoring and learning solutions, you can empower your employees to become higher-skilled, engaged, and motivated individuals, driving your organisation towards sustainable success.

Final thoughts

Nurturing a culture of continuous improvement through avenues like mentoring and virtual learning is a powerful strategy to enhance employee engagement, skill development, and organisational success. StellarUp understands the significance of continuous learning and personalised guidance in today’s rapidly evolving professional landscape.

By promoting lifelong learning within the work environment, integrating educational aspects seamlessly, investing in mentoring, and providing easy access to digital resources, StellarUp helps organisations create a workforce that remains relevant and proficient. As the corporate world continues to change, StellarUp equips your employees with the tools they need to adapt, grow, and succeed. 

Book a demo of our product today to find out more about how our fully customisable platform can change the landscape of your organisation.