From Startup to Scale Up: Learn from Entrepreneurs with the Right Questions

Interviewing entrepreneurs provides an incredible opportunity to get the inside scoop on starting and running a business.

Whether you want to become an entrepreneur or are just curious about the business world, asking the right questions can help you gain valuable insights.

In this article, we will cover key questions to ask entrepreneurs about their motivations, challenges, lessons learned, and tips for aspiring founders.

From idea generation to scaling a business, this list of questions will inspire you to dream big and avoid common mistakes on your own entrepreneurial journey.

Let’s dive in!

Key Takeaways

Interviewing successful entrepreneurs can provide invaluable lessons, including:

• Their origin stories reveal motivations and mindsets that drove early progress
• Lessons from failures expose pitfalls to avoid on your journey
• Leadership anecdotes uncover effective strategies for hiring, motivating teams, and scaling
• Questioning techniques like using open-ended wording and actively listening help extract maximum insights
• Asking about routines, books, and productivity hacks surfaces practical tips you can implement
• Financial questions provide guidance on bootstrapping, tracking metrics, and growth decisions
• Fun questions break the ice, build rapport, and reveal their personality
• Follow-up reflections allow you to distill key takeaways to apply to your own venture

Approaching interviews with focus and the right blend of questions unlocks access to a wealth of entrepreneurial knowledge and networks gained from years of experience.

Allow their journey to accelerate your own.

1. Reasons to Interview an Entrepreneur

Interviewing an entrepreneur can provide invaluable learning and inspiration for your own entrepreneurial journey. Here are some of the top reasons why you should make time to pick an experienced founder’s brain:

Gain Insights from Their Successes and Failures

Every business leader has stories of both victories and defeats.

By asking about an entrepreneur’s proudest accomplishments as well as most difficult challenges, you can learn vicariously from their real-world experience.

Understanding how they achieved key milestones or overcame major obstacles can help you chart your own path to success.

Learn Their Thought Process and Decision Making

Understanding how experienced entrepreneurs evaluate ideas, assess risks, and make major business decisions can provide priceless perspective. You can gain insight into how top founders synthesize information, trust their instincts, and balance logic with creativity. Learning from their analytical approach can improve your own judgment and ability to make sound choices.

Discover Their Sources of Motivation and Inspiration

Many entrepreneurs are fueled by powerful internal drivers and influences. Asking about their motivations and inspirations can uncover relatable lessons about perseverance, passion, and leadership. Gain perspective on how they maintain energy and stay focused during difficult times. Learn what gets them excited and keeps them engaged each day.

Get Advice and Tips Directly Relevant to Entrepreneurs

Experienced entrepreneurs have navigated the challenges of starting and scaling a business first-hand. They have accumulated wisdom that only comes from experience.

Take the opportunity to get tailored advice and tips for core startup activities like raising funds, building a team, handling regulations, business planning, marketing, managing finances, and more.

Glean Perspectives on Industry Trends and Innovations

Seasoned entrepreneurs have their finger on the pulse of emerging technologies, changing consumer behaviors, and evolving marketplace dynamics. They can provide unique insights into innovations and trends within their industry. Staying up-to-date can generate new business ideas and help you adapt appropriately.

Find a Mentor Who Has “Been There, Done That”

One of the best ways to shortcut your own path to success is to learn from someone who has already been there. Interviewing entrepreneurs can help you identify a potential mentor who can provide ongoing guidance, feedback, and support. Having a seasoned advisor in your corner through the ups and downs is invaluable.

Get Inspired and Boost Motivation for Your Own Goals

Speaking with passionate founders about their purpose, vision, and definition of success can be tremendously inspiring. Their energy and stories can help reignite your motivation during periods of frustration or fatigue. Connecting with those who have achieved ambitious goals can expand your sense of what is possible.

Interviewing entrepreneurs provides a chance to connect with those who have real-world experience in starting and running a business.

Take advantage of the opportunity to build your knowledge, gain actionable tips, find inspiration, and identify potential mentors who can support your own entrepreneurial aspirations and journey.

2. Qualities Every Entrepreneur Should Possess

Successfully starting and running a business requires a diverse set of skills and qualities. Here are some of the top traits and abilities shared by many successful entrepreneurs:

Passion and Strong Motivation

Launching a new venture takes an incredible amount of drive and determination. Entrepreneurs must have a deep passion for their idea to push through all the hurdles and challenges.

A strong internal motivation energizes them to put in long hours and make sacrifices for potential future rewards.

Self-Confidence and Resilience

Entrepreneurs inevitably face setbacks and critics. Powerful self-belief and resilience enable founders to trust their vision and bounce back from mistakes or failures. Healthy confidence empowers them to make bold decisions and guide their team through adversity.

Organization and Planning Abilities

Juggling many responsibilities and tasks requires excellent organizational skills. Successful entrepreneurs plan thoroughly, set strategic priorities, and manage their time efficiently. Their ability to develop detailed business plans establishes a roadmap to reach goals.

Problem-Solving and Analytical Skills

Innovative thinkers with strong analytical abilities can find creative solutions to complex problems. Top entrepreneurs synthesize information from many sources to make informed, strategic decisions that advance their ventures.

Risk Tolerance and Decisiveness

Launching a new business requires taking calculated risks. Successful founders have the courage to place big bets but also the judgment to mitigate risks. Their boldness and decisiveness enable them to commit to a vision and take action without hesitation.

Financial Literacy and Bootstrapping Abilities

Entrepreneurs must have a strong grasp of financing, cash flow, profit margins, and other key financial concepts. Many bootstrap in the early stages so the ability to judiciously manage capital is critical. Financially savvy leaders make their limited resources go further.

Persuasive Communication and Influencing Skills

Strong communication and influencing skills help entrepreneurs connect with investors, partners, and customers. They are master storytellers who persuasively pitch their vision. Their engaging style inspires teams, secures funding, and attracts early adopters.

Adaptability and Learning Agility

In dynamic, fast-paced markets, the ability to rapidly learn and adapt is vital. Top entrepreneurs are flexible, agile learners who quickly pick up new skills. They listen, absorb new information, and constantly refine their strategies.

The most successful founders share key traits like resilience, risk tolerance, financial acumen, and excellent communication abilities. Developing these core competencies can help position aspiring entrepreneurs for their own success stories.

3. Interview Questions

When interviewing an entrepreneur, ask a mix of open-ended questions to uncover their story. Here are some great options to get the conversation started:

Why did you decide to start your own business?

This intro question reveals their origin story and early motivations. Listen for factors like a desire to fill an important unmet need, recognition of a market opportunity, ambition to build financial independence, or aspiration to create a positive impact. Their founding story can provide your first glimpse into their mindset.

What advice would you give to someone just starting their own business?

Seasoned founders have a wealth of hard-won lessons to share with aspiring entrepreneurs. Listen closely for tips related to core startup elements like crafting an MVP, validating demand, raising funds, hiring team members, handling legalities, and developing lasting habits to pace yourself. Ask follow-ups to get details.

How do you deal with fear and doubt?

Every entrepreneur confronts fear and doubt at some point in their journey. Gain insight into how they work through inevitable anxieties, build their confidence, and silence their inner critic. Look for relatable tips you can apply when imposter syndrome strikes.

What routines do you follow each day?

Understanding how experienced entrepreneurs structure their day provides a template you can model. Ask about their schedules, productivity hacks, and daily habits. What reservoirs do they tap for energy and focus? How do they balance strategizing with doing? When do they carve out time for creativity?

Where do you see your business in five years?

This reveals their long-term vision and goals. Does their “5-year plan” focus on building a fast-growth, venture-backed company or on sustaining steady profitability? Get a window into how their definition of success and preferred pace of scaling has evolved over time.

How does your business look different now vs. when you first started?

Entrepreneurs experience incredible changes as their companies grow. This question surfaces lessons from their pivots, restructuring, and adaptations over time. How has their role or focus shifted? What key skills did they need to develop? What core beliefs have endured?

How do you set your business apart from others in your industry?

Every competitive market has rivals. Smart entrepreneurs identify and develop key differentiators to stand out from the crowd. Listen for unique elements like superior product quality, hyper-targeted services, or value-added offerings that earn loyalty and command higher prices.

Interview questions centered on their founding story, evolution, and lessons learned can uncover priceless insights from experienced entrepreneurs applicable to your own venture. Keep an open and curious mindset – you never know what gems you may uncover.

4. Fun Questions to Ask an Entrepreneur

Beyond nuts and bolts business questions, consider asking some entertaining questions to get to know your entrepreneur on a more personal level:

What has been your most surprising experience in business?

Running a company guarantees unexpected twists and turns. This light question lets entrepreneurs share a story that made them go, “Whoa, I didn’t see that coming!” Listen for amusing anecdotes that provide a glimpse into their charm and humor.

What business or personal goals do you still want to pursue?

There’s always more ground to cover! Learn what lofty targets still remain on their bucket list. Upcoming climbs, races, investments or passion projects they aim to tackle? Vivid dreams of future growth or legacy impact? This reveals enduring life ambitions.

If you could have dinner with any historical business leader, who would you choose and why?

This thoughtful question reveals their role models and the historical icons who inspire them. Listen for what leadership qualities or business strategies they hope to glean over a dream dinner with a titan like Henry Ford, Steve Jobs, or Oprah Winfrey.

What is the best business or entrepreneurship book you’ve read?

Bibliophiles will enjoy this exchange about impactful books. Asking a fellow reader for recommendations is a fantastic way to uncover new titles and potential must-reads. Keep a list of any intriguing books they mention to add to your own reading list.

What is your favorite productivity hack?

Entrepreneurs are always fine-tuning ways to maximize their time and output. This question surfaces actionable tactics you can test out, from useful apps to ingenious organizational systems. Listen for simple but impactful habits you can incorporate into your own routine.

What is the most worthwhile investment you’ve made in your business?

Savvy entrepreneurs know where to allocate resources for maximum effect. Learn what equipment, software, training, or consultant spend has provided the greatest ROI in their view. Listen for nuggets of wisdom on cost-cutting and value creation.

What is the silliest business idea you’ve ever had?

This light question gives entrepreneurs a chance to poke fun at their own expense and share a laugh. An amusing interlude in the conversation can surface their playful side and their ability not to take themselves too seriously.

Injecting fun personal questions into your entrepreneur interview adds color and personality to the conversation. Tapping into amusing anecdotes, favorite books, and productivity tips provides enjoyable moments of connection.

5. Financial Questions to Ask an Entrepreneur

The numbers matter when running a business. Ask targeted financial questions to gain insights into an entrepreneur’s approach:

How did you fund your business in the early stages?

Raising startup capital is tricky but vital. This question reveals how they scraped together those critical early funds through savings, loans, crowd sourcing, or outside investors. Listen for creative tips on bootstrapping and fundraising you may be able to leverage.

What financial metrics do you track regularly?

Leading entrepreneurs stay laser focused on key performance indicators that matter most. Ask which metrics they measure and monitor to take the pulse of business health. Listen for examples like cash flow, customer acquisition cost, lifetime value, churn rate, and more.

What is the most important financial advice you received?

Experience brings wisdom. Ask entrepreneurs to share the best money-related counsel they got from a mentor or advisor. Tips for managing payroll, projecting cash flow needs, establishing financial controls, or contingency planning are gold.

How do you value a new business opportunity?

Understanding an entrepreneur’s process for assessing potential new initiatives provides a blueprint you can model. Listen for factors they weigh like total addressable market, risks, initial investments required, projected ROI timeline, and opportunity cost trade-offs.

How do you know when it’s time to scale up investments?

Ramping up spending carries risk. Veteran entrepreneurs develop a sixth sense for when the timing is right. Ask how they determine when the business fundamentals justify expanding into new facilities, territories, staff or other scale plays.

How do you know when to pull back on spending?

Savvy entrepreneurs also spot signals indicating when belts should be tightened. Ask how they recognize and respond to changing market conditions or metrics that suggest a period of judicious cost management could be wise.

What is the biggest money-related mistake you made?

Everyone stumbles. Ask entrepreneurs to share an example of when they regretted a major spending or investment decision. What would they do differently if they could have a “do-over”? Their reflections can help you avoid similar pitfalls.

Thoughtful money-related questions can provide guidance on vital topics like fundraising, budgeting, scaling investments, and avoiding costly errors. Take advantage of the hard-won financial experience sitting across the table.

6. How to Find an Entrepreneur to Interview

Pinpointing the ideal entrepreneur to interview takes a bit of preparation and outreach:

Identify Specific Goals for the Interview

Get clear on what you hope to gain from the experience. Are you seeking specific advice about your industry or business model? Hoping to learn about building a culture or scaling challenges? Establish focus areas so you can identify well-suited candidates.

Look Within Your Existing Network

Scan your personal and professional contacts for entrepreneurs to approach. Startups founders you already know make ideal interviewees. Warm outreach to existing connections improves response rates.

Attend Local Startup Events

Startup mixers, pitch events, and incubator open houses provide venues to connect face-to-face with founders. Briefly share your interview project and contact info. Following up quickly after meeting substantially boosts positive responses.

Ask Colleagues for Introductions

Tell friends, professors, or coworkers about your interview quest. Ask if they can facilitate a warm introduction to any entrepreneurs in their network who might be willing to participate. That extra credibility can pique interest.

Join Founder-Centric Online Groups

Facebook groups, Slack channels, LinkedIn groups, and Subreddits targeting entrepreneurs provide additional connection points. Pay attention to group rules before posting any interview requests.

Search Founder Databases

Online databases like Gust, AngelList, and Crunchbase let you search for founders by location, industry, or characteristics. Cold outreach to intriguing prospects through these platforms can yield interviews.

Look for Founders Speaking at Events

Entrepreneurs are often invited to speak at conferences, podcasts, or virtual events. Their participation signals openness to sharing their expertise. Contact speakers aligned with your interests through event websites, social media, or hosts.

Identify Interview Targets Strategically

Focus on founders with qualities most relevant to your goals, whether years of experience, sharing your tech niche, raising VC funding, or scaling rapidly. Think through optimal learning scenarios.

Be Clear About Your Interview Purpose

When reaching out, explain you are a student or aspiring entrepreneur interested in learning from their experiences. Share your end goal to publish the interviews or use insights to build your business. Transparency builds trust.

Persist Diplomatically

Not everyone will reply. Politely follow up if you don’t receive a response within 2 weeks. If they decline, ask for introductions to other founders who might be open to participating.

With a bit of creativity and persistence, you can connect with seasoned entrepreneurs willing to share their journey. Define your priorities, leverage your network, and tell founders how they can help aspiring entrepreneurs by participating.

7. Tips for Asking Questions

The way you ask questions impacts the insights you’ll gain. Use these techniques:

Know Why You Are Asking the Questions

Having a clear purpose focuses your curiosity and helps formulate relevant questions. Are you seeking advice? Hoping to learn their story? Before your interview, note topics where you need guidance so you can steer conversations productively.

Be a Good Listener

Actively listening builds rapport and surfaces golden follow-up questions. Avoid multi-tasking. Make regular eye contact. Reflect their emotions and rephrase key points. Vocalize affirmations like “I see” and “That’s interesting”.

Use the Right Wording

Strive for open-ended wording like “What motivated you to…?” instead of closed yes/no phrasing like “Were you motivated by…?”. Leading with “how” and “why” generates descriptive responses packed with insights.

Build a Hierarchy of Questions

Organize your questions thoughtfully starting with rapport builders, moving to core topics, and leaving lighter fare for last. Hierarchy prevents jarring topic shifts and ensures you cover priorities first.

Ask the Right Types of Questions

Include a variety at different levels like knowledge, experience, opinion, feeling, analysis, evaluation and vision questions. This elicits comprehensive perspectives from multiple angles.

Avoid Yes/No Questions

Yes or no questions are conversation dead ends. Promise yourself you’ll rephrase any yes/no questions that slip out into open-ended wording during the interview.

Be Clear and Specific

Vague questions generate vague answers. Ask pointed questions and insist on specifics like names, numbers, and concrete examples that provide clarity.

Following solid questioning techniques, actively listening, and structuring your inquiry systematically helps extract the maximum value from your entrepreneur interviews.

8. Types of Questions to Ask

When interviewing entrepreneurs, pull from different categories of questions:

Icebreaker Questions

• How did you get your start in this industry?
• What surprised you most when you became a founder?
• What’s your favorite part about being an entrepreneur?

Icebreakers establish rapport. Start with 1-2 friendly questions before diving into business topics.

Personal Background Questions

• Who has been your most important mentor?
• What motivates you each day?
• What is your biggest personal accomplishment?

Ask 2-3 personal questions to uncover their story and values.

Business-Focused Questions

• Walk me through your typical work day.
• What has been your most effective marketing strategy?
• How do you promote company culture?

Core business questions let them share hands-on advice and lessons learned.

Storytelling Questions

• Can you tell me about a challenging situation you faced?
• What is one company milestone you celebrate?
• What has been your most memorable entrepreneurship experience?

Anecdotes and stories add color and personality. Dig for tales.

Leadership Questions

• How do you motivate your team?
• What is your hiring process?
• How do you handle difficult employees?

Ask 2-3 leadership questions to glean management insights.

Vision Questions

• What is your long-term vision for the company?
• How do you plan to grow/expand?
• If you could change one thing about your industry, what would it be?

Conclude with future-focused vision questions.

Using a mix of question types creates a rich, engaging discussion while targeting multiple areas of expertise.

Conclusion – Questions to Ask an Entrepreneur

Interviewing entrepreneurs provides invaluable real-world insights you can leverage for your own venture.

• Ask thoughtful questions that reveal motivations, lessons learned, and strategies. Listen closely for practical tips and words of wisdom to apply to your journey.
• After, reflect on key takeaways and how you can use their experience to accelerate your success.
• Approaching interviews with focus unlocks access to entrepreneurial knowledge gained from years of experience in the trenches.

Allow their journey to inform your own.