What Are the Best Questions to Ask an Entrepreneur for Your Startup Plan?

Speaking with an established entrepreneur is one of the most effective ways to de-risk your own startup journey. Based on our assessment experience, a prepared list of strategic questions can unlock invaluable insights, helping you avoid common pitfalls and accelerate your planning process. This guide provides a focused set of questions designed to extract the maximum value from your conversation.

Why Prepare Specific Questions for an Entrepreneur?

An informational interview is a strategic meeting where you seek advice and insights from an experienced professional, rather than interviewing for a job. For aspiring business owners, these conversations are crucial for grounding ambitious ideas in practical reality. Entrepreneurs who have successfully navigated the path from concept to profitable business possess a wealth of tacit knowledge that isn't found in textbooks. Preparing thoughtful questions ensures you respect their time and guides the conversation toward actionable takeaways for your own business development strategy.

What Are the Key Questions to Unlock Actionable Entrepreneurial Advice?

The goal is to move beyond superficial answers and understand the how and why behind their success. Here are essential questions categorized by theme to structure your informational interview effectively.

Understanding Motivation and Concept Validation

• What was the core problem you identified that inspired your business, and how did you validate there was a market for the solution? This question moves beyond simple inspiration to uncover the initial market research process. The answer can help you assess if your own idea addresses a genuine, paying need.
• What was the biggest misconception you had about starting a business, and what was the reality? This directly taps into lessons learned, providing a shortcut for your own expectations and planning.

Navigating Startup Challenges and Funding

• What was the most significant early-stage challenge you hadn't anticipated, and what specific steps did you take to overcome it? Learning about unforeseen obstacles prepares you for the inevitable hurdles of entrepreneurship.
• Beyond personal savings, what funding avenue was most critical for your initial launch (e.g., angel investors, small business loans, crowdfunding)? Understanding their capital acquisition strategy can reveal alternative funding sources you may not have considered. The following table compares common early-stage funding options based on typical entrepreneur experiences:

Building Operations and a Team

• What single marketing tactic delivered the highest return on investment for your first customers? This cuts through the noise of modern marketing to identify the most efficient starting point for customer acquisition.
• What are the top three qualities you looked for when hiring your first employees? Early hires are critical as they shape company culture. This answer helps you define the non-negotiable traits for your founding team.

How Can You Structure the Conversation for Maximum Benefit?

An effective informational interview is a two-way street. Begin by briefly stating your own goals to provide context. Actively listen to their answers and ask follow-up "why" questions to dig deeper. Most importantly, always respect the time limit you initially requested. Conclude the meeting by asking, "Is there anyone else in your network you think I should speak with?" This can open doors to further valuable connections. Finally, send a personalized thank-you email within 24 hours, reiterating one key piece of advice they shared.

To maximize your next entrepreneurial conversation, focus on questions that reveal the decision-making process behind the success. Key takeaways include: validating your core business idea by understanding their inspiration, preparing for challenges by learning from their unanticipated hurdles, and identifying efficient funding and marketing strategies they used. This approach transforms a simple chat into a strategic planning session for your own venture.