Finding the right business mentor is a game-changer for any entrepreneur.
But, to truly benefit from their experience, you need to ask the right questions. The best business questions to ask a mentor go beyond surface-level advice—they unlock deep insights, help you avoid costly mistakes, and accelerate your success.
Whether you’re just starting or scaling your business, here are 9 powerful questions to ask a business mentor to gain the most value from your mentorship.
Plus, don’t miss our five expert tips on how to craft your own questions and make the most of your mentor’s guidance.
10 Best Business Questions to Ask a Mentor
1. What’s the biggest lesson you’ve learned in business?
Why ask this?
Every successful entrepreneur has faced challenges, made mistakes, and learned valuable lessons along the way. This question helps you fast-track your learning by understanding what really matters in business.
Instead of figuring things out the hard way, you can gain insights that might take years to discover on your own. This also gives you a peek into the mindset of your mentor and how they approach problem-solving.
Follow-up: Can you share a specific moment when this lesson really hit home for you?
2. If you were starting your business today, what would you do differently?
Why ask this?
This question provides a shortcut to success by revealing what they would change if they had to start from scratch. The business landscape constantly evolves, and what worked years ago might not be effective today.
Learning about their biggest regrets or inefficiencies can help you avoid the same pitfalls and focus on strategies that yield results in today’s market.
Follow-up: What’s one outdated strategy that used to work but no longer does?
3. What are the top skills I should develop to succeed as an entrepreneur?
Why ask this?
Entrepreneurship requires a diverse skill set, from leadership and sales to management and resilience. Instead of trying to master everything, this question helps you prioritize the most impactful skills.
Your mentor has already been through the journey and knows which abilities make the biggest difference in long-term success.
Follow-up: How did you personally develop those skills?
4. How do you make tough decisions when the right choice isn’t clear?
Why ask this?
Entrepreneurs constantly face difficult decisions—hiring, funding, scaling, or pivoting. Knowing how an experienced business leader approaches high-stakes choices can give you a framework for making your own decisions.
This question also reveals whether they rely more on data, intuition, or mentorship when faced with uncertainty.
Follow-up: Can you give an example of a tough decision you made and the outcome?
5. How do you stay motivated when facing setbacks?
Why ask this?
Running a business is filled with ups and downs. Many entrepreneurs give up too soon because they aren’t prepared for failure. This question helps you learn how to build resilience and keep pushing forward even when things don’t go as planned.
Your mentor’s personal strategies can inspire you to develop a mindset that embraces challenges as part of the journey.
Follow-up: What’s the biggest setback you’ve faced, and how did you push through it?
6. What are the key habits of highly successful entrepreneurs?
Why ask this?
Success often comes from small, consistent steps rather than one big move. Your mentor likely has daily, weekly, or monthly habits that contribute to their achievements.
Learning about these routines can help you build discipline and create your own success habits.
Follow-up: Which of these habits took you the longest to develop, and why?
7. How do you determine which opportunities to pursue and which to ignore?
Why ask this?
Not every business opportunity is worth your time. Many entrepreneurs waste resources chasing too many ideas. This question helps you understand how successful people evaluate opportunities and focus on the ones with the highest potential.
It also teaches you the importance of saying no to distractions.
Follow-up: Have you ever passed on an opportunity you later regretted?
8. What’s the best networking strategy you’ve used to grow your business?
Why ask this?
Business success is often tied to relationships. A strong network can lead to investors, customers, partnerships, and mentors.
Your mentor has already built valuable connections—learning how they did it can help you speed up your own networking efforts and avoid ineffective approaches.
Follow-up: How do you maintain and strengthen those connections over time?
9. If you were mentoring your younger self, what advice would you give?
Why ask this?
This question gives you a direct window into what your mentor wishes they had known earlier in their career. It can reveal common mistakes, overlooked strategies, and mindset shifts that could have changed their journey.
Their answer might save you years of trial and error.
Follow-up: What’s one mistake you wish you had avoided early on?
5 Tips to Ask Your Mentor the Right Questions
While these 10 questions are a great starting point, the best mentorship comes from thoughtful, personalized conversations. Here’s how to ask the right questions and make the most of your time with your mentor:
1. Be Specific, Not Generic
Avoid vague questions like “How do I succeed in business?” Instead, ask targeted questions based on your current challenges, like “What are the top three things I should focus on in my first year?”
2. Do Your Research First
Before asking your mentor for advice, research their past work. This helps you ask insightful questions and avoid wasting time on things you could find out on your own.
3. Ask Open-Ended Questions
Avoid yes/no questions. Instead of “Should I launch this product?”, ask “What factors should I consider before launching this product?” Open-ended questions lead to richer discussions.
4. Relate Their Experience to Your Own
When they share advice, connect it to your situation. If they talk about scaling a company, ask, “How would you apply that strategy to a business in my industry?”
5. Listen More Than You Talk
Your goal is to learn, not to impress. Let your mentor speak freely and resist the urge to jump in with your own ideas too soon. Take notes and reflect on their advice.
Final Thoughts
A great mentor can accelerate your success, but only if you ask the right questions. Use these questions to ask a business mentor to gain valuable insights and avoid common mistakes. More importantly, develop your own unique questions tailored to your journey—because the best lessons come from real conversations, not just pre-written scripts.
Matt Logan is the Founder and Managing Partner of Rise North Capital, where he works closely with entrepreneurs, startups, and business leaders to unlock real growth.
Leave a Reply