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What questions should I ask Advisors, Mentors and/or Experts?

Original post: What questions should I ask Advisors, Mentors, and/or Experts?

This blog was originally posted by New Mexico State University’s Arrowhead Innovation Center. Thanks for the partnership with Kristin Morehead. Do you have ideas for good questions to ask? Send them to us at and we’ll give you attribution in the update.

Some entrepreneurs aren’t sure how to engage in dialogue with an Advisor, Mentor, Industry Expert, or potential Professional Trade Vendor (lawyer, accountant, etc.). If you haven’t done it much before, it can be intimidating, for sure. But, it doesn’t have to be. As you acquire more experience or expertise in this arena, it will get easier. Most people want to be helpful. Enable them to do so for you by being prepared.

Here are some questions to get you started – to think about. These are just some starting points. Some of these you would consider for yourself – you wouldn’t ask them directly. And, not all questions will be applicable for you or your company’s situation. Feel free to adapt and build from here what will be most useful.

And, if you aren’t sure, it is okay to admit that. You aren’t expected to know everything. But, you are expected to be able to know who to go to for what you need and how to ask for what you are looking for.

We’ll work to build out more tips and tricks for building your start-up through a blog. If you have topics you’d like to see, let us know.

Here are some questions and topics to connect with an Advisor, Mentor, and/or Industry Expert.

Regarding the Legal Entity of Your Enterprise

  • What type of legal business entity registration should I consider?
  • What are the major pros/cons of those most applicable (i.e. LLC v. C Corp)?
  • What are the reasons you believe this is the best choice?
  • What state should I register my business in? If outside of New Mexico, what are benefits to nationally known locations like DE and NV?

Personnel & Hiring

  • What roles do you think are most important for early hires / my company at its current state?
  • How do I attract talent given the capital I have?
  • How do you feel about advisors and advisory circles?
  • What talent and type of advisors would I most benefit from at this stage?
  • What type of people do I need to attract into the company to complement my skill set?
  • What does the business most need in talent now?
  • How do you feel about interns? And, where can I get that type of talent?
  • Who should be on your team, and what are key strategy for team building?

Investors& Investment

  • What are investors looking for in a business of this type and this sector when considering investment?
  • What are investor return expectations these days given the economy?
  • How should equity work for your company and what does it mean for this business structure?
  • What are some strategies for preparing a strong pitch deck and being ready to approach investors (aka the pitch)?
  • How do you sequence your steps: should you seek investment first or build a prototype? Why?
  • What should I know about my market before talking to investors? What homework do I still need to do?
  • What information on business financial projections are investors looking for in a pitch deck?
  • How confident am I in my financial projections and what do I still need to determine?
  • Who is customer #1? Who will be customer #10?

For Lawyers:

  • See questions above on legal registration
  • What legal documents do you suggest I focus on for my business at this stage of development?
  • For intellectual property (IP) specialists: Should I register IP? How do I do that? What are the pros/cons? What stage should I be at to do so?
  • How do I best work with you (or any lawyer)?
  • What are best examples of clients that haven’t gone well? What are good examples of client behavior you recommend?
  • What mistakes do you see entrepreneurs keep making?

For CPAs and Accountants:

  • Tell me about your style of work?
  • How do you find it works best for me to get you information and data?
  • How frequently should I look to be generating financial statements?
  • How do I best work with you (or any CPA/Accountant)?
  • What are best examples of clients that haven’t gone well? What are good examples of client behavior you recommend?
  • What mistakes do you see entrepreneurs keep making?
  • Would you recommend a cash basis or accrual?

About the Authors & their organizations:

Kristin Morehead, Kristin Morehead manages the Arrowhead Innovation Network and the Arrowhead Ventures program at New Mexico State University’s Arrowhead Center, The programs she manages support projects, partnerships and initiatives that support entrepreneurship and business growth.  She also oversees NMSU’s role in the New Mexico Small Business (NSMBA) Program, in partnership with Los Alamos and Sandia National Laboratories.  She supports entrepreneurial education and technical assistance initiatives for businesses across New Mexico and the Borderplex region. Contact Kristin at

Drew Tulchin is Managing Partner of UpSpring Associates, UpSpring is a network of consultants using the power of the marketplace for good. Based in New Mexico, Tulchin brings nearly three decades of experience moving start-up companies from idea to reality, putting together the right materials to define them, and securing the capital they need to advance. His efforts have led to companies raising more than $300 million in new capital in equity, debt, government programs, and other sources. Reach them at