33 Essential Questions to Ask an Entrepreneur Mentor

As a new entrepreneur, surrounding yourself with experienced mentors is one of the most valuable things you can do to stack the odds of success in your favor. Studies show that founders who receive mentoring increase their company‘s revenue by an average of 83% and are more likely to secure funding.

But to fully tap into your mentor‘s hard-won wisdom, you need to be intentional with your time together and arrive prepared with thought-provoking questions. Having been both a mentor and a mentee many times over, I‘ve experienced firsthand the kinds of queries that lead to true lightbulb moments and those that fall flat.

To help you make the most of your mentoring sessions, I‘ve compiled a list of 33 essential questions across four crucial categories—business strategy, leadership, fundraising, and personal development. Use these as a starting point to spark insightful conversations and take your business to the next level.

Business Strategy Questions

Defining a winning strategy is key to outmaneuvering the competition and achieving profitability. Tap into your mentor‘s expertise with these questions:

1. What customer problem is your product or service solving and how did you validate the need? Understanding your "why" and building something people truly want is a crucial first step.
2. How do you differentiate yourself from competitors? Successful businesses have a clear unique selling proposition. Brainstorm ways to make your offering stand out.
3. What metrics do you track to measure success and make decisions? Learn how your mentor defines and monitors KPIs related to growth, engagement, and profitability.
4. How did you price your product/service in the early days vs now? Pricing is equal parts art and science. Discover different strategies for aligning price with your overall business model.
5. Can you share an example of a strategic pivot you made and why? Adapting to market feedback and competitive threats is essential. Hear how your mentor has successfully navigated changes in direction.

For instance, when investor and advisor Scott Belsky interviewed Uber co-founder Garrett Camp, he uncovered fascinating insights into Uber‘s early strategic decisions around supply constraints, surge pricing, and political battles. Hearing these kinds of in-the-trenches anecdotes can completely reframe the way you approach business challenges.

Leadership & Management Questions

Building and leading a high-performing team is one of the most difficult parts of being a founder. Turn to your mentor for guidance with questions like:

6. How has your leadership style evolved as your company grew? As organizations scale, founders must transition from doers to coaches. Learn how your mentor adjusted their approach over time.
7. What do you look for when hiring early employees? A-players can make or break a startup. Understand the skills, traits, and values your mentor prioritizes in the recruiting process.
8. How do you build a strong company culture? A positive culture is key to retention, productivity and customer satisfaction. Discover the rituals and behaviors your mentor instills to shape their environment.
9. What‘s your process for delivering constructive feedback? Giving criticism is one of the toughest parts of leadership. Ask your mentor how they share feedback to maintain standards and relationships.
10. How do you keep your team motivated through ups and downs? Every company goes through rough patches. Extract tips for aligning your team and maintaining morale when times get tough.

A great example of a leader who built an incredible culture through authenticity and transparency is Hubspot co-founder Dharmesh Shah. Dharmesh is renowned for his commitment to radical candor and empowering his team to take risks and own their results. Emulating that kind of servant leadership is key as your company matures.

Fundraising & Finance Questions

Whether you bootstrap or raise VC funding, getting a grip on your financials is non-negotiable. Have your mentor share their money management wisdom through questions like:

11. How did you fund your company initially and at later stages? Every founder takes a different path when it comes to capital. Understand the trade-offs your mentor weighed between bootstrapping, loans, grants, angels and VCs.
12. What metrics do investors care most about? While every firm is different, most evaluate startups on a core set of numbers. Learn the benchmarks your mentor used to prove traction and secure checks.
13. How do you decide on a target valuation for a funding round? Company valuations are based on both quantitative and qualitative factors. Pick your mentor‘s brain on striking the right balance.
14. What are common pitfalls to avoid when pitching investors? Fundraising is filled with minefields, from dodgy deal terms to unscrupulous backers. Benefit from your mentor‘s battle scars to avoid rookie mistakes.
15. What tools do you use to keep your financial house in order? From accounting software to cash flow forecasts, staying on top of your money takes dedicated processes. Note your mentor‘s go-to resources to implement in your business.

For example, one of my colleagues was torn on whether to raise a seed round or continue bootstrapping his SaaS startup. After consulting with his mentor, a seasoned software founder, he got clarity on his burn rate, revenue growth, and funding needs to make an informed decision to raise capital at a $5M valuation. That round allowed him to scale his team, invest in marketing, and accelerate product development to gain a competitive edge.

Personal Development Questions

Building a successful business while maintaining your health and relationships is a herculean challenge for even the most grounded entrepreneurs. Turn to your mentor for honest advice on striking a sustainable balance with questions like:

16. How do you structure your days/weeks to maximize productivity? We all get the same 24 hours, but top founders squeeze more juice out of each one. Discover your mentor‘s productivity hacks to get more done in less time.
17. What habits or routines help you manage stress? Entrepreneurship is a pressure cooker. Learn how your mentor stays cool under fire through exercise, meditation, hobbies or other outlets.
18. What skills have you found most vital to develop as a founder? From selling to hiring to financial acumen, being a founder requires you to constantly evolve. Zero in on your biggest areas for growth with your mentor‘s help.
19. How do you make time for family and friends with such a demanding schedule? It‘s all too easy for founders to neglect their personal lives in service of their companies. Hear how your mentor balances it all and what boundaries they maintain.
20. If you could go back in time to your first year of business, what advice would you give yourself? This is one of my favorite questions to ask mentors, as it often elicits profound insights with the benefit of hindsight. Soak in those kernels of wisdom!

One cautionary tale that comes to mind is Elon Musk admitting that his 100-hour work weeks and sleeping at the Tesla factory took a serious toll on his health and relationships. While that kind of singular focus can yield world-changing innovations, it‘s important to be clear-eyed about the potential downsides. Your mentor can help you walk that tightrope.

Key Takeaways

Finding a mentor is one of the highest-ROI things you can do as an entrepreneur to shorten your learning curve and avoid costly mistakes. But like any important relationship, mentorship requires cultivation and give and take.

To maximize your meetings, prepare specific questions across core areas like business strategy, leadership, finances, and personal growth. Focus on topics where you feel stuck or see the biggest opportunities to level up.

Remember, your mentor has a wealth of knowledge but it‘s up to you to put their advice into action. After each conversation, distill your learnings into clear next steps. Update your mentor on your progress to demonstrate your commitment.

Most importantly, recognize that mentorship is a two-way street. Look for ways to provide value back to your mentor, whether it‘s making an introduction, sharing a resource, or simply expressing heartfelt gratitude.

Entrepreneurship is a challenging journey, but with the support of a wise mentor, you‘ll be well-equipped to navigate the ups and downs. All you have to do is start the conversation.

Questions to Ask an Entrepreneur Mentor

Category	Questions
Business Strategy	1. What customer problem are you solving and how did you validate the need? 2. How do you differentiate from competitors? 3. What metrics do you track to measure success? 4. How did you determine pricing for your product/service? 5. Can you share an example of a strategic pivot you made and why?
Leadership & Management	6. How has your leadership style evolved as your company grew? 7. What do you look for when hiring early employees? 8. How do you build a strong company culture? 9. What‘s your process for giving constructive feedback? 10. How do you keep your team motivated through ups and downs?
Fundraising & Finance	11. How did you fund your company initially and at later stages? 12. What metrics do investors care most about? 13. How do you decide on a target valuation for a funding round? 14. What are common pitfalls to avoid when pitching investors? 15. What tools do you use to manage your financials?
Personal Development	16. How do you structure your days to maximize productivity? 17. What habits help you manage stress? 18. What skills are most vital for founders to develop? 19. How do you make time for family and friends? 20. What advice would you give yourself in your first year of business?