70+ Questions To Ask a Startup Mentor

If you’re taking your first steps into the glorious world of entrepreneurship, it doesn’t hurt to have someone who has “been there, done that” by your side. Even though your endless Google searches may have helped you learn the “basics of building a startup” or “entrepreneurship for dummies”, in order to take the best foot forward, some practical examples are important.

Many entrepreneurs find that working with an experienced startup mentor goes a long way in helping them start their venture in the right manner.

Thanks to the years of experience and good credentials that the mentors have accumulated, the newbie founders not only get valuable advice, but also access to the right networks and resources.

Should you chance upon an opportunity with the right mentor, here are a list of questions you can skim through to be prepared for your first meet:

Motivation/ Tips for Productivity/ Working Right

1. How do you stay positive and keep moving when nothing seems to be working?
2. I want to quit my 9–5 job and start my venture, do you have any tips for success?
3. I have this business idea I just can’t get out of my mind but I’m scared of failing, how can I get past this mental block?
4. Failure is part of the process with entrepreneurship. How did you learn to overcome setbacks?
5. If you had the opportunity, what would you have done differently with your business/product/service/career?
6. When you first started working, did you foresee that this is where you would be?
7. What habits help you be effective with your productivity?
8. Do you have a morning (or evening) ritual that helps you be more efficient and productive?
9. How do you most effectively learn new things?
10. How do you balance being a parent with the stress of being a business owner? (maintaining work-life balance)
11. How do you suggest that I measure progress?
12. Where do you see my strengths and what should I focus on improving?
13. Do I have any blind spots in my business? Am I missing anything?
14. From email to meetings, how do you organise your day?
15. What three aspects of business building do you think are most important for early-stage founders?
16. Can you tell me about a setback you experienced, and how you recovered?
17. What are your tips for managing and overcoming burnout?
18. How can I communicate my ideas or business more clearly?
19. Risk is such a big part of business. How do you approach taking risks?

Decision Making

1. If you were in my position what would you recommend I do first (and why)?
2. How do you know if you are ready to launch a new product or service line?
3. Tell me about a time when you had a difficult time running your business. How did you manage it?
4. I feel overwhelmed. How do I prioritise what I need to do to move ahead?

Product/ Service

1. Is my product’s messaging clear and concise?
2. How do you decide to price your service/product?
3. How can you reposition a brand upstream after years of being a budget-friendly company?
4. What was your experience like trying to find product-market fit? Tell me the story of how you reached it!
5. My SaaS does a great job of converting visitors into sign up users, but hardly any of these users convert into a paying customer. How do you come up with ideas on how to improve free trial to paid user conversion rates?
6. I’m considering a pivot or new product for my business. What do you think are the pros and cons of doing this?
7. What makes my company attractive to outside stakeholders?
8. How do I convert users/clients to my business? Can you give me examples of how have you done this?

Marketing/ Branding

1. How do you prioritise your marketing to-dos and decide what to do first?
2. I just launched my new e-commerce website and am new to marketing, where should I start promoting my website to increase sales?
3. What are the most common pitfalls to avoid in growth marketing?
4. I’ve read books and taken courses and practiced what I could about marketing in the real world, but my results are just not really showing. Can you give me some tips?
5. I’m starting link building and need help understanding the process and what works/doesn’t. How do you systematise link building?
6. What’s the best way to increase followers on social media and then convert them into paying customers?
7. Based on your understanding of my business, what values should I be marketing?

Strategy/ Operations

1. How do you design a go-to-market strategy on a super tight budget?
2. How do you build partnerships with big-name companies in complimentary industries using cold email?
3. It’s easy to get users to sign up to my SaaS but they’re not reaching that “aha” moment, what would you recommend I do first?
4. I’m at a crossroads right now. I can position my startup as a premium service or a low-cost service. Can we talk through the pros and cons?
5. How do you decide what metrics to add to your KPI dashboard?
6. How can I get leads for calls/demos with C-level executives without being spammy and annoying?
7. What are the best ways to interact with sign up users from an MVP?
8. How do I communicate value to stakeholders, such as investors, clients, users. etc?
9. How did you stage growth for your business? Can you share stories of how you scaled your company?
10. What tools do you suggest (for HR, accounting, marketing automation, etc.)?
11. What are some other opportunities I’m missing to monetize or improve the financial returns of my business?
12. How do I measure differentiation among my competitors? What advice do you have for standing out in my market?
13. If you had the opportunity, what would you have done differently with your business/product/service/career?
14. How do you measure ROI in xyz area?
15. What do you see as my greatest challenge and how do you suggest that I overcome it?
16. What advice do you have to make my business more operationally efficient?

Team Building/ Leadership

1. How do you hire your first C-level employee? What are your thoughts on giving them equity or bonus incentives?
2. What is the most crucial leadership skill that you’ve learned and how do you suggest I apply it to my own business?
3. What advice do you have for delegating responsibilities to my team and/or hired help?
4. How do I develop trust within business relationships, including with employees, vendors, contractors, or others?
5. How can I improve at being a better manager?
6. What are your tips on founder’s equity? How should we be splitting the same?

Funding/ Pitching

1. I’m currently bootstrapping a startup but there’s a perceivable jump between solo pushing the company forward and getting traction with investors/angels and building a team. Can you give me advice on how to successfully raise funding as a solo founder?
2. What are the keys to a great business pitch?
3. How does equity work?
4. What do investors look for?

Networking

1. Who would you recommend I connect with?
2. What are your tips to effectively network?
3. How do you cultivate effective business relationships?
4. I will be attending a big startup conference soon and will even have a booth there. How can I maximize my investment and bring in new accounts for my business, meet people, make friends, and meet potential investors, advisors, and partners?
5. Is there anyone in your network who could help me with getting an enterprise level customer for my startup?

Sources (Some questions have been collated from different sources and divided in subject-wise headings):

• https://selfmadesisters.org/2018/11/30/mentor-questions-for-entrepreneurs/
• https://www.growthmentor.com/blog/questions-to-ask-a-mentor/