21 Next-Level Questions to Build Relationships with Entrepreneurs


I think we'd all agree that listening is at the heart of what we do as fundraisers. What powers that process, though, is asking questions. In this post, you'll find (1) links to help you build a repository of high-impact questions; (2) a total of 21 questions just for entrepreneurs; and (3) a way to see some specific ideas applied in a real-life situation. Enrich your relationships with alumni founders. Read on!


I recently came across Sean MacCready’s The Philanthropy Podcast after we connected on Twitter, and I'm really enjoying it.

Sean is VP of Development at Horizons for Youth in Chicago, and has been a fundraiser for over a decade. In his podcast he earnestly explores both the tactics of fundraising and the deeper purpose that drives our work as development professionals. 

Sean’s episode on high-impact questions inspired me to compile a few of the next level questions I ask specifically of entrepreneurs and others in the innovation sector. 

I use them to learn about alumni, of course, but they can do so much more. Questions are powerful, versatile tools! Use questions with alumni entrepreneurs to signal interest in their work, enthusiasm for their ideas, and how well you understand their needs. Asking questions can power your referral engine and add to your story bank. A journalistic approach can offer a framework for deeper conversations, and take your alumni relationships in new directions. 

ask about their approach to entrepreneurship

An innovator’s perspective on the work of building projects, teams, and companies is honed over time—often though intense effort. This hard-won experience becomes part of the individual's personal brand, and it often reflects their approach in other areas of life. Sharing lessons learned is a big part of startup culture, so chances are good they'll be comfortable doing this. 

  1. When did you know you wanted to take an entrepreneurial path?

  2. What do you enjoy most about being an entrepreneur? What's hardest about it?

  3. What have you taken from your [insert college] experience to your startup career?

  4. What characteristics or skills are most important for startup leaders?

  5. Do you have any systems or axioms for decision-making, learning, and execution? This question can also help you provide the right information in the preferred format for your alum through all stages of their involvement.

  6. Entrepreneurship can be a tough road. In the difficult moments, how do you stay focused on moving forward and making progress?

  7. Who do you look to for advice or mentorship?

  8. Has anyone in the [insert college] network been important to your journey?

  9. What advice do you have for students about using their time, relationships, and opportunities at [insert college] to prepare for this kind of career?

ask about their business

Understanding an entrepreneur’s work— challenges,  competitors, products, etc. — helps you better curate engagement opportunities. You’ll bring more value to the relationship and deepen your personal connection. Don’t worry, you don’t need to learn to code or splice DNA — just understand on a basic level what your entrepreneurs do each day in the office. I guarantee your interactions will become more authentic and enjoyable.

  1. What problem are you trying to solve?

  2. How did you decide to tackle this particular issue?

  3. What are you most excited about at work right now? What keeps you up at night?

  4. In a general sense, who can I connect you to that might be helpful? This is a great way to bring value to multiple alumni. Use this question to find alignments between what your alumni need and what they offer. The benefits are often mutual.

  5. What's the road ahead look like for your company?

  6. What can I do to support your work? How can I help? Always ask this question. Prepare for it by understanding your school's entrepreneurial ecosystem, and knowing where to go for help.

--> For more on this, read this essential post: The 4 Things Entrepreneurs Want from their Alma Maters.

ask about philanthropy and inclination

More and more founders consider giving back a core value. But it's difficult to act on this with a young startup and scarce resources. It doesn't get much easier as the company grows. Though a founder's equity may increase in value, it remains illiquid, and her time and mental energy still focus on guiding the company. It's a recipe for feeling overwhelmed (and exhausted!) when that liquidity finally does come. Using a few questions at various points in your relationship might help alums feel more prepared without adding much to their to-do list. 

  1. How do you think about philanthropy now?

  2. Do you ever dream about what might be possible for you as a philanthropist if [startup] achieves its vision?

  3. If you could support [insert college] at a significant scale now, what would you do? What would inspire that kind of passion? I love creating a 'future self' with a donor and testing out some ideas together.

  4. How have you learned about philanthropy up to this point? What would you like to know more about?

  5. What's the best way to format information for you? Invite them to be candid about how they absorb info. If they never read your carefully drafted narrative summary of the fellowship selection process, you're no better off than before.

  6. Do you feel you have the support you need in planning for a liquidity event? Best for mid/late-stage entrepreneurs. Offering to put them and their advisors in touch with your gift planning team 6-12 months before a liquidity event can help with critical tax planning and gift structure issues. 

Use questions to accomplish multiple goals

Questions work in multiple settings, of course — not just meetings. A couple of quick ideas: 

1. Try flipping the script and using them upfront to get the meeting. I once landed a rare hourlong session with a successful serial entrepreneur simply by asking him a few of next level questions directly in an email. This alum — who’d never once returned a general outreach email or call — responded within five minutes.

2. Develop a standard set of questions that you can use to interview alumni and profile them on a website or blog. The answers to these questions are probably interesting to other entrepreneurs in your community. This is an easy, scalable way to share lessons learned, gain new insights, and help entrepreneurs build visibility. In fact, one of my next few posts will feature an interview with an entrepreneur, so that you can see this specific idea in action. Subscribe below and be notified when it drops.

There are dozens (hundreds?) more questions that you can use to propel your relationships forward. Which of Sean MacCready's high-impact questions do you use most with your startup folks? What are your own next level questions for entrepreneurs and innovators?