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Conversation Questions for Growth Stage Entrepreneurs

Last week, I had the opportunity to moderate a MAC panel of growth-stage entrepreneurs as part of Venture Atlanta. Whenever I moderate a panel, I like to approach it as a conversation. It usually take

David Cummings
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October 18, 2025

Last week, I had the opportunity to moderate a MAC panel of growth-stage entrepreneurs as part of Venture Atlanta. Whenever I moderate a panel, I like to approach it as a conversation. It usually takes a few minutes to find the flow and develop some rapport with the room, but once that connection is made, the discussion tends to unfold naturally—and this event was no different.

For growth-stage entrepreneurs, typically defined as those with at least $5–10 million in revenue, the conversation and topics are quite different from those of seed-stage founders who are still searching for or refining product–market fit. At the growth stage, there are more employees involved, more capital at play, and generally much greater complexity in the business.

To get a panel conversation going, I like to start with the basics: Who are you, and what’s your elevator pitch? Now, we’re talking about a short elevator ride. Entrepreneurs can easily go long when describing their company, so I like to frame the desired brevity by asking for a pitch that can be delivered in a single breath—if you have to stop to breathe, you’ve gone too long.

After that, I like to dive into deeper, more nuanced topics that reflect the experience level of the panelists. Here are a few of my favorite questions:

  • What’s your corporate culture like? What do you do well, and where would you like to improve?
  • What’s your personal leadership style? How would your team describe you?
  • How has that leadership style evolved as your company has grown and scaled?
  • Looking back, what would you have done differently—or what advice would you give your younger self, knowing what you know now?
  • What are the top one or two projects you’re currently working on?
  • How do you choose which projects to focus on?
  • What’s been your biggest learning over the past 12 months?

Once we’ve covered those, I like to move into current and trending topics. Naturally, right now, that means AI. Some of the questions include:

  • What role does AI play in your business today?
  • What AI capabilities are customers asking for?
  • What would you like AI to do that it can’t do yet?
  • Can you share an example of how AI is already improving your operations?

To wrap things up, I finish with some “pay-it-forward” questions:

  • How do you like to help other entrepreneurs?
  • What do you do to continue learning and growing as an entrepreneur yourself?
  • What can we do as a community to better support our startup ecosystem?

This format always gets the conversation flowing, and once we hit our stride, time just flies by. I really enjoy talking with entrepreneurs and learning from their perspectives and insights. This particular panel was excellent—special thanks to everyone involved.

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