Once the Director has secured the guest, preparing a great interview is the most important contribution usually made by the Director. An interview that is insightful and engaging, and which follows an intentional director and flow of conversation is not something you can improvise. While the speaker is expected to come relaxed and without heavy preparation, the Director is in charge of leading the conversation. Preparation is everything. Be sure to read any bios, articles, and watch videos of the speakers to be ready for the interview. Feel free to check out the Startup Grind video library for inspiration. Start this preparation at least 2 weeks in advance!

Interview Flow

The typical interview is built around the speaker’s personal story, experience in building his or her company, a few personal stories of the challenges that brought the company to success, and a closing with industry insights or opportunities. Another way of looking at it would be that the interview starts personally, then becomes professional, and ends with a high-level view. Here’s a loose flow that works well for first-time interviewers:

Background (10-15 minutes)

Give the audience a sense of the speaker’s background starting with family as well as early academic and entrepreneurial experiences. These might be as simple as parents who ran a hardware shop or your speaker’s first lemonade stand. Ask about their experiences with education: what did they study, where, and why? Speak about their work experience before starting their own company.

Experience & Challenges (30 minutes)

 Dig into the entrepreneurs’ companies in chronological order, focusing on the challenges and lessons during each startup. What was his or her vision in starting the company? How has the company or the vision evolved? What advice would the entrepreneur have given him or herself before he started to avoid the big mistakes? What drives the entrepreneur to continue in the struggle?

Industry Insights & Local Opportunities (15 minutes)

Catering to your local entrepreneurs or aspiring founders, ask for your speaker’s expert advice to help your audience grow their companies or get started. How should an entrepreneur maneuver in the space, whether its biotech or mobile development? How would they advise new entrepreneurs to begin their journey into their industry? To celebrate and understand your city, ask about the benefits the entrepreneur sees in doing business here. Ask about opportunities for improvement of your local scene.

Questions & Answers (5-10 minutes)

Accept questions from the audience, but warn the entrepreneurs in the room that this is not the time to pitch their company. The best way to filter out these questions is to ask your speaker to stay behind after the show for 15 minutes to answer 1 on 1 questions if it’s convenient.

Know Your Subject

Understand the speaker’s history, accomplishments, key turning points, and areas of their expertise when building the flow of your fireside chat. Having the chance to talk to the speaker ahead of the interview will give you feeling for the tone the interview will likely take and a better opportunity to build a stronger relationship. Going through your questions ahead of time will help you spend less time looking at your notepad and more time looking at the speaker and your audience.

Your Event is As Good as Your Preparation

Once you’ve researched your speaker’s past writing and interviews, and can truly say you’re familiar with his or her entrepreneurial journey, you can finally begin to compose your questions. Your familiarity with the speaker will come through in the quality of your questions and the flow you take with the entire interview. The most excellent interviews touch on personal stories and uncover gems that the speaker hasn’t talked about before, while leaving the audience with meaningful takeaways for their business.

Double-Check Your Speaker & Venue

The worst case-scenario for a Startup Grind event is getting the crowd but missing the speaker. Double-check he or she will be able to make it a week in advance, and then again the day before the event. Making plans a month in advance may have caused your speaker to forget the show or miss putting it into his calendar. Also email your venue to let them know you’ll be there a few hours in advance and to check everything is ready to go, especially the audio and visual systems.

Strategy: One VIP to Another

It is not a fixed rule that the Director must interview the guest, though the interviewer absolutely must be prepared. Some directors create exceptionally powerful events by inviting another successful entrepreneur to interview the guest, especially if the two parties are long-time friends. The friendly but insightful dynamic this creates is ideal for Startup Grind events, though this may be more challenging to arrange for the first event in the city.