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How to maximize your next meeting with your mentor

Aspiring and established small business owners should ask their mentor(s) these 10 questions to get the most out of their mentorship.

How to maximize your next meeting with your mentor
By Provide Advisory Network member Dr. Amrita Patel, DDS 

Mentorship is one of the most powerful tools available for entrepreneurs navigating business ownership, leadership, and professional growth. Having a mentor who has successfully walked the path before you can provide clarity, guidance, and invaluable insights as you strive to build and manage your own business or expand your existing one. Whether you’re just starting, preparing to transition into ownership, or scaling your business, having meaningful conversations with your mentor can set the stage for smarter decisions and faster progress.

To get the most out of your mentorship, ask purposeful questions to engage your mentor both thoughtfully and strategically. The following are 10 goal-oriented questions to ask your mentor to unlock their expertise and maximize your journey toward success.

1. How did you overcome the biggest challenges in your career?

Every successful business owner has faced obstacles. Understanding how your mentor navigates their challenges can provide a blueprint for dealing with your own hurdles. This question opens the door for your mentor to share personal experiences and strategies, allowing you to learn from their successes and setbacks.

You might gain insight into how they handle financial struggles, manage team conflicts, implement new technologies, or adjust to changes in market conditions. Their story could illuminate potential pitfalls and solutions, helping you approach your challenges with a proactive and informed mindset.

2. What do you wish you knew when you first started your business ownership journey?

This question taps into hindsight — one of the most powerful tools for growth. By learning what your mentor would have done differently or prioritized earlier in their career, you can save time and avoid similar mistakes. Their answer could include advice about leadership, time management, financial planning, customer communication, or strategic decision-making.

Hearing their reflections offers perspective and can help you align your business choices with lessons learned by others.

3. How have you defined and measured success throughout your career?

Success looks different to everyone, and defining it for yourself can be a challenging task. 

Asking your mentor how they define their success can give you clarity about your own goals and values. Their answer may also reveal how they balance professional achievements with personal well-being, growth, and lifestyle choices.

This question also allows you to explore the metrics they use — whether financial milestones, team satisfaction, or community impact — to gauge their progress and decisions.

4. What business systems or processes have been most valuable to your success?

Running a business isn’t just about industry-specific excellence; it’s also about implementing effective systems and strategies to support business growth. Your mentor can share which administrative, operational, or financial systems they find indispensable. This could include insights on customer  management, team leadership, efficient scheduling, bookkeeping, marketing, or technology integration.

Understanding these systems will help you identify areas of potential improvement in your own business. Their expertise could save you time, resources, and frustration by helping you adopt proven frameworks from the start.

5. How do you balance leadership and hands-on responsibilities?

One of the most common challenges for entrepreneurs is learning how to juggle leadership roles with hands-on duties. For example, ownership often involves a mix of team management, administrative obligations, and strategic planning.

Your mentor can provide tips on time management, delegating effectively, setting boundaries, and prioritizing responsibilities. Their guidance can empower you to lead confidently and find balance. 

6. How do you approach financial planning and investments in your business?

Financial literacy is essential for successful business owners, yet many owners find themselves unprepared for the complexities of financial planning. Asking your mentor about how they manage their finances — such as budgeting, debt repayment, capital investments, and planning for retirement — will help you learn from their experience.

Their advice could provide strategies for minimizing risk, maximizing cash flow, and making smart financial decisions during critical stages of growth. Financial planning can make the difference between sustainable businesses and ones that struggle under financial pressure.

7. What key leadership skills do you believe every business owner should master?

Leadership is at the heart of any thriving business. From managing teams to building trust with customers, leadership is about effective communication, adaptability, vision, and decision-making. This question allows your mentor to share their perspective on the most critical leadership lessons they’ve learned.

They may offer insights into how to inspire team members, resolve conflicts, implement change, or cultivate a positive workplace culture. Their feedback can help you identify the leadership gaps you want to address as you grow into or strengthen your role as a leader.

8. What’s the best way to stay ahead of industry changes and innovation?

The business world is constantly evolving, with advancements in technology, customer expectations, and market trends reshaping how businesses should operate. Your mentor likely has years of experience navigating these changes and can offer advice on how to adapt and stay competitive.

Ask them how they stay informed — whether through conferences, associations, peer networks, or continuing education — and how they evaluate which trends and innovations to integrate into their business. Their guidance could give you a competitive edge by encouraging proactive learning and innovation.

9. How do you foster a healthy work-life balance while managing a business?

Burnout is a serious risk for anyone, particularly those navigating business ownership. Your mentor can provide candid advice about how they maintain their mental wellness, manage stress, and create boundaries to ensure their well-being while achieving professional goals.

Their perspective on achieving balance while managing a business, administrative responsibilities, and a personal life can serve as a reminder that success is about long-term sustainability, not short-term hustle.

10. What books, tools, or resources have been most valuable to your career development?

Successful leaders and business owners are often avid readers and learners. Asking your mentor which books, tools, courses, or resources have impacted their development can give you a foundation for your learning journey. This could include leadership books, financial planning guides, business strategy frameworks, or even case studies.

Learning about these resources will allow you to broaden your knowledge base, explore different perspectives, and adopt proven methodologies in your journey toward building a successful business.

Ask, listen, and act.
These 10 questions are designed to spark meaningful dialogue with your mentor(s) while helping you define your path as a business owner. Actively listening, integrating insights, and applying lessons to your unique circumstances can help you make the most of your conversations. Each conversation provides an opportunity to gain wisdom, avoid pitfalls, and build confidence in your decision-making.

Remember: Mentorship is a two-way street. While you gain insights from your mentors, show gratitude by informing them of your progress and successes. Their advice has the potential to shape your journey, but it’s your commitment to growth, resilience, and action that will make the difference in achieving your goals.

Ask questions, listen with purpose, and let their experience guide your next steps on your path to business ownership and success.

This content is for informational purposes and does not constitute the rendering of legal, accounting, tax, or investment advice, or other professional services by neither Provide, its affiliates, nor Fifth Third Bank, and it is being provided without any warranty whatsoever. Please consult with appropriate professionals related to your individual circumstances.