What’s the first thing you ask when the mic goes live?
That moment makes or breaks your show. Ask something bland and you’ll get a flat answer. Ask something sharp, personal, or unexpected and your guest lights up, the stories roll, and your listeners lean in.
I’ve been on both sides of the mic hundreds of times, and here’s what I know: the right podcast questions for business owners don’t just fill time. They drive the whole conversation.
This article gives you 80 examples from ice-breakers and probing questions to money talk, plus the best tips on avoiding dull or intrusive questions beforehand as a podcast host.
I’ll also show you how to use the Talks podcast question generator to make prep easier.
By the end, you’ll know exactly how to run business podcast interviews that grow your podcast and keep your audience hooked.
80 Best Podcast Questions for Business Owners
A great podcast episode starts with a great list of questions.
If you want an interesting conversation that’s real, practical, and gives your audience something they can use, you need to be deliberate about the questions you ask.
I’ve lined up 80 questions to ask guests that help you cut to the chase, get your guests talking, and uncover the real stories behind their business secrets for your next podcast episode.
10 Foundational questions to ask business owners
These questions help you get straight to the point and help your audience understand the business and mindset of your interviewee.
- What motivated you to start your business?
- How did you test your first idea in the real world?
- What was the hardest moment in your first year of your business journey?
- How do you measure success in your business?
- Who shaped your approach to running a business?
- What’s the toughest lesson you’ve learned so far?
- How do you handle risk when making big decisions?
- What keeps you moving when things get tough?
- How do you balance day-to-day operations with long-term growth?
- Looking back, what would you do differently?
What are good podcast questions to break the ice?
Kick things off naturally. These good podcast questions loosen up your guest and get them talking like a human, not a corporate bio.
- How did your day start today?
- What’s a hobby or interest most people wouldn’t guess about you?
- What’s a podcast, book, or show you’re into right now?
- If someone made a movie about your life, who would play you?
- How do you celebrate a big win?
- First thing you do when you wake up?
- Coffee, tea, or nothing?
- What’s the funniest thing that’s happened recently at work?
- How do you switch off after work?
- What’s one little-known fact about your business?
10 Fun and creative podcast questions to ask business owners
Move beyond the basics and get your guest sharing stories and perspectives that reveal personality by asking great podcast questions like these:
- If your business had a personality, what would it be?
- What’s the weirdest client request you’ve had?
- What advice would you give your younger self starting out?
- What unusual skill has helped you run your business?
- How would you describe your company if it were a person?
- What’s one industry myth you want to bust?
- What unexpected lessons have shaped you as a founder?
- If you weren’t running your business, what would you be doing?
- What’s the funniest mistake you’ve made on the job?
- How do you make work fun for your team?
10 Fun questions to ask an entrepreneur
These podcasting questions to ask a guest speaker highlight the human side and let listeners connect on a personal level.
- What’s the strangest place you’ve done business?
- Have you had a defining “aha” moment?
- What’s the riskiest move you’ve made?
- If your life were a book, what would the title be?
- What’s the most creative fix you’ve come up with for a problem?
- Which habit has most improved your work?
- What’s the funniest pitch you’ve heard or made?
- What misconception do people have about entrepreneurs?
- How do you celebrate small wins?
- Who in your network pushes you to do better?
10 Financial questions to ask an entrepreneur
Money drives decisions. These good interview questions to ask podcast guests dig into strategy, scaling, and the lessons learned from wins and mistakes.
- How did you fund your first venture?
- What’s your approach to pricing?
- Have you ever pivoted because of financial pressure?
- How do you balance cash flow with growth?
- Which metrics matter most to you?
- Have you worked with investors? Why or why not?
- What budgeting mistakes taught you the most?
- How do you prepare for unexpected costs?
- What financial lesson would you give your younger self before starting a business?
- How do you decide on ROI before big moves?
10 Good questions to ask small business owners
These focus on interview-style open-ended questions you should ask about operations, strategy, and scaling insights.
- How did you land your first client?
- Which tools or systems keep your business running?
- How do you keep your best employees?
- Biggest operational headache you’ve solved?
- How do you set goals for yourself and your team?
- How do you measure customer happiness?
- Which content marketing channels give the best return?
- How do you stay competitive in your niche?
- Unexpected lessons from running a small business?
- How do you plan for growth in the next year?
10 Bad questions to ask an entrepreneur
These are off-putting or shallow. Avoid them and keep your interviews smart, respectful, and useful.
- How much money do you make?
- Are you thinking of selling your business?
- Why isn’t your business bigger yet?
- Aren’t you worried about competitors?
- Did you ever consider giving up?
- Isn’t your product overpriced?
- Why don’t you copy your competition?
- Have you ever failed? (vague)
- Don’t you think your idea is too risky?
- Why didn’t you start sooner?
10 More podcast questions to avoid
These are overused and predictable. Skip them if you want your episodes to feel fresh, direct, and worth listening to.
- Can you tell me about your business?
- What’s a typical day like?
- How did you get started?
- What’s your favorite book?
- Who inspires you?
- What’s your biggest challenge?
- Where do you see yourself in five years?
- What advice do you have for new entrepreneurs?
- What’s your favorite quote?
- How do you handle stress?
What Podcasts Do CEOs Listen To?
CEOs aren’t just listening for entertainment. They’re hunting for ideas, strategies, and perspectives that give them an edge.
Podcasts with high-profile guests are an easy way to pick up insights while commuting, exercising, or even making lunch.
If you want to understand what’s shaping their thinking, these shows are a solid start to know the answers:
- WorkLife with Adam Grant: Learn how leaders improve teams, tackle challenges, and create better work environments.
- The Knowledge Project: Shane Parrish breaks down decision-making, mental models, and strategies that top performers use.
- HBR IdeaCast: Short, sharp conversations on leadership, management, and emerging business trends.
- Masters of Scale: Reid Hoffman explores how companies grow from zero to massive, with stories from real founders.
- The Indicator from Planet Money: Quick takes on market trends, business shifts, and economic insights.
- How I Built This: Founders share their journey from startup to global brand, including the struggles and wins along the way.
- The Twenty Minute VC: Bite-sized insights into venture capital, fundraising, and startup growth.
These shows aren’t just “listen and forget.” They make you think, offer new ways to ask your favorite questions, and even influence how you approach your own business or podcast interviews.
Business Talks Podcast
The Business Talks Podcast is where CEOs go for practical lessons and real stories. Some standout episodes:
- CBD and Business: Rick Leslie, Chris Wood, and Danny Gemma talk the business, benefits, and future of CBD.
- HR+AI: Todd Raphael explains how AI is shaking up HR in a positive way.
- Solving the People Problem: Brett Cooper and Evans Kerrigan on the skills you need to lead and succeed.
These episodes highlight both wins and challenges, giving you insight into specific questions that get great answers.
Podcasts about business startups
CEOs tune into startup shows to see how others handle the early grind: scaling, funding, and the tough calls that decide whether a business sinks or soars.
I’ve been lucky to share my own stories on a few of these, and here’s a taste:
- How To Start A Successful Virtual Events Business (Svencast): I break down how to design a virtual event, sell high-ticket offers, and automate your business so you can focus on growth and lifestyle flexibility.
- How To Be A Podcast Guest & Get Booked With Liam Austin (Lyndsay Phillips): I share how to get booked on the right podcasts, create a strong speaker profile, and turn guest appearances into authority and visibility.
- How to Book More Podcast Appearances and Build Authority (Louise McDonnell): I walk through pitching the right way, using AI to find shows, and turning guest spots into real business opportunities.
These episodes are packed with real-world lessons and the kind of conversations that make you rethink what’s possible in your business.
Perfect for pulling ideas for your own podcast questions or just getting fired up to grow.
Famous business podcasts
CEOs want answers and they want them fast. They tune in to podcasts that hit real problems, tackle decisions head-on, and give actionable strategies you can actually use as soon as the show is done:
- The Tim Ferriss Show: Deep dives with top performers reveal routines, tactics, and decisions that drive real results.
- The Ed Mylett Show: Focused lessons on leadership and performance you can actually apply, not vague theory.
- Smart Passive Income: Pat Flynn shares tested strategies for scaling businesses online and generating consistent revenue.
- The GaryVee Audio Experience: Straightforward marketing, growth, and branding advice from someone who’s been in the trenches.
- Diary of a CEO: Steven Bartlett gets founders to open up about the wins, mistakes, and hard truths behind running a business by asking the right questions.
How to Ask Good Questions for a Podcast
Great questions are a great way to get your guests talking, sharing stories, and giving your audience something valuable. Nail these, and your episode won’t just fill airtime. It’ll stick.
- Know your guest: Research their background, career, achievements, and recent projects. Tailored questions get better answers.
- Define your goal: Decide what you want your target audience to take away like advice, insights, or inspiration.
- Plan but stay flexible: Have your unique questions ready but chase interesting tangents. The best answers often come from podcasting detours.
- Start strong: Open with interesting podcast questions or podcast questions about life that prompt a story, personal or professional.
- Mix question types: Combine professional, personal, and thought-provoking questions and podcast topics to build rapport and engage your target audience through a great interview.
- Listen actively: Pay attention to your guest, react to what they say, and dig deeper to learn more about your guest. Ask follow-up questions to deliver the most quotable moments.
- Challenge politely: Ask clarifying questions that push them to explain decisions, personal experiences, mistakes, or unconventional approaches.
- Time your tough ones: Don’t be afraid to ask certain questions but make sure you drop sensitive or complex questions mid-interview once trust is established like asking personal types of questions.
- Tie back to the audience: Ask questions that connect the guest’s insights to your listeners’ struggles or goals.
- Close with reflection: End your interview-style podcasts with a question that leaves them thinking and your audience inspired.
How to come up with better podcast interview questions
Think outside the standard ice-breaker or “tell me about your journey” podcast interview questions.
Here are some unconventional approaches that help your guest feel more comfortable and create conversations your listeners actually care about:
- Reverse engineer: Note which great podcast interview questions triggered great stories on other episodes and adapt them.
- Use guest content: Pull ideas and podcast interview questions to ask your guests from blogs, LinkedIn posts, or social media. Every business owner will notice you did your homework.
- Scenario-based prompts: Ask “what if” or hypothetical questions without bias to get unexpected answers.
- Audience-driven questions: Collect interview questions to ask your guests from podcast listeners or followers for direct relevance like podcast questions for friends or podcast questions about relationships.
- Tools and generators: Use platforms like Talks to generate prompts based on topics your guest actually cares about.
- Current events hooks: Tie questions to trends, news, or industry shifts to get timely insights.
- Peer comparisons: Ask how they’d handle situations differently than competitors or peers to help your listeners gain more perspective.
- Challenge assumptions: Pose questions that explore common myths in their field.
- Story triggers: Ask about moments of failure, risk, or unexpected wins.
- Wildcard questions: Throw in something fun or unconventional to break monotony and reveal personality.
Talks podcast question generator
If you want to take the heavy lifting out of prep, the Talks podcast question generator is a lifesaver. Here’s how to use it:
- Go to the generator and enter the topics of your podcast episode.
- Click GENERATE and watch it produce a list of tailored questions.
Example prompt you can use in the generator:
- Podcast episode topics: business growth, startup challenges, leadership lessons, scaling teams, innovative marketing strategies
Here’s what the generator might give you:
- How did you navigate challenges to achieve significant business growth?
- What were the biggest challenges you faced when starting your own business, and how did you overcome them?
- Can you share a valuable leadership lesson you’ve learned while building your company?
- What strategies have you implemented to successfully scale your team as your business grows?
- How have you leveraged innovative marketing strategies to stand out in a competitive market?
These types of podcast questions are ready-to-use, specific, actionable, and designed to get your guest to answer these questions. All you have to do now is ask.
Why You Should Interview an Entrepreneur
If you want your new podcast content to provide real value and stay memorable, entrepreneurs are ideal guests.
Here are five reasons why asking great questions to successful business owners can help you create a successful podcast and a deeper interview experience:
- Unfiltered reality checks: They’ll tell you what really works and what fails spectacularly without sugarcoating it.
- Unexpected stories: Their journey often includes weird detours, offbeat strategies, and surprises your audience won’t see coming.
- Frameworks in disguise: Every success or mistake can be broken down into a repeatable process your listeners can adapt.
- Contrarian thinking: Entrepreneurs challenge standard wisdom, giving fresh angles on problems your audience thought they already knew.
- High-stakes energy: The pressure, risks, and hustle behind building something from scratch make for magnetic conversations listeners can’t ignore.
How to find an entrepreneur to interview
Finding the right entrepreneur doesn’t have to be a random hunt. Focus on quality, relevance, and alignment, and the conversations practically write themselves. Here’s how:
- Tap into curated networks: Platforms like Talks connect hosts like you with entrepreneurs actively looking for podcast appearances. No more email tennis.
- Look for recent movers: Entrepreneurs who’ve launched something new or pivoted recently have fresh insights and stories your audience hasn’t heard.
- Follow the industry buzz: Trade shows, online forums, and LinkedIn conversations spotlight entrepreneurs making waves. Perfect leads for dynamic interviews.
- Check out their content: Blogs, videos, or social posts can reveal unique angles and unconventional ideas that spark engaging questions.
- Ask for intros: Leverage mutual connections to get warm introductions. Entrepreneurs are more likely to say yes if someone they trust vouches for you.
These methods ensure your podcast isn’t just another list of guests. You get entrepreneurs with real stories, bold moves, and lessons your listeners can apply right away.
Keep the Mic Hot
If you want your interview podcasts to actually deliver, podcast questions for business owners are your starting point. The right questions get into the decisions, lessons, and stories that matter, not generic soundbites.
And here’s the kicker: you don’t have to hunt for guests alone.
With a free Talks creator profile, you can connect with business owners and experts who match your show and book episodes that actually matter.
No constant back and forths, no endless chasing. Just guests who bring authority, personality, and insight.
Set up your free Talks profile now and fill your calendar with episodes that people can’t stop talking about.
