Thoughtful Moderation


This week I found myself moderating an interview for an entrepreneurs lounge. A small group of women entrepreneurs came together for honest, open, and genuine conversation, I led the discussion.

While you might expect this account to be about the occasion or the entrepreneur being interviewed, it takes a different form.

This is my account of thoughtfully asking questions and moderating a conversation.

There is an art to public interviewing, and over the years I've found people get quite anxious about it in public settings. Yet it is something I enjoy, am good at, and realize it could be helpful for others to know about how I approach it. I don’t profess at all to be an expert in this space but I have found a methodology that works for me, and one where guests and audiences respond well. If you find yourself planning for a public interview or moderation it can be helpful to explore and hear about what others do, and how they plan.

Being thoughtful about interviewing is the place to start from. I learned this back in the 90s by observing Michael Parkinson interview guests on his U.K. Saturday night talk show, Parkinson. For me, “Parky”, as he was (and probably still is!) known, was the most gracious and inspirational interviewers I saw consistently in action. He was always a true gentleman in my mind, good natured, good humored, respectful of his guests and audience, made guests feel comfortable, and somehow he had the ability to make you feel as if it were just the three of you sat in the lounge having a chat, and without fail, you always learned something new. For whatever reason, he had a style that appealed to me and for a long time now since I’ve conducted public interviews or moderated panels, at some point in my planning his style comes to mind.

However, over time I also learned that the best interviews don’t just follow a prescribed or best practice model. The best interviews are where the interviewer brings their own personality to the conversation.

If the interviewer is at ease, the guest will be at ease, and when the guest is at ease the audience will be at ease.

By creating this ease in conversation you create an environment that is both comfortable and open. As the interviewer, in order to be comfortable you need to be prepared, and that requires planning. Learn about who you are interviewing, ask about their strength topics. Then plan for a series of themes or topics that are the building blocks for the flow of your conversation. Within those themes have a series of questions. Then memorize your themes so that when you’re talking you don’t have to look at a sheet of paper in front of you. In certain instances the paper reference is very necessary, but for many occasions the sheet of paper acts as a safety blanket, and gives a false sense of security. Even if you mess up a conversation it’s far better that it’s genuine and real, than scripted, robotic, or process led. I’ve seen many people flounder when their paper is missing, or their technology fails, and they literally go to pieces as they’ve become too reliant on their tools and not trusted their own capabilities enough. Learn how to trust yourself, it’s an empowering move.

Become so familiar with your themes and questions that you are easily able to ask them. Know them so well you can ask them in a different order based on how your conversation unfolds. Remember they don’t have to be word perfect based on how you wrote them out during your planning session.

Learn to be good at listening, really listen. The biggest mistake I see interviewers make is not listening to what is being said. Changing the question or asking different questions in response to what has been said is really important. You create more engagement between you, your guest, and your audience. When you do this your audience feels drawn in and connected to the discussion.

If you are fielding questions, join the dots for people, learn how and when to cut in respectfully and with empathy, and guide the conversation onward, or back to a topic if it’s gone down a rabbits warren and is in danger being stuck on one topic for too long.

Being thoughtful about your audience is critical to a successful interview. Know who is in the room, and assess their interests in the topics, plan accordingly, but also recognize everyone has different needs, so ensure you cover a good ground of topics that engages a cross section of your audience.

Examples of Founder Specific Questions:

Here are a set of building block themes and thoughtful questions to you help you plan for your next interview. Remember to customize though for your occasion and guest.

  1. Building Your Business - Understand the Landscape (Theme building block)

    • How did you start?

    • Why did you name your business X?

    • What’s your business model?

    • How many employees and / or contractors do you have?

    • Do you have office space or are you a remote team, or a hybrid?

  2. Investors

    • Contrary to popular belief, many startups don’t want VC funding, can you talk about why it was fitting for your company?

    • What’s your style and strategy of pitching to investors?

    • What’s your experience of west coast vs east coast investor and start-up discussions?

    • Investors are interested in growth, how do you prepare for conversations when revenues have not been good in the last quarter?

    • Knowing what you know now, would you still go for VC investment?

  3. Sales Model

    • How did you start to generate sales?

    • How do you generate sales now and how has it changed?

    • What approach do you take to marketing?

    • What have you learned about your business as a result of your sales?

  4. Growth

    • As entrepreneurs we are frequently in the space of not knowing how to do something, how do you overcome that and work out what you need to do?

    • How do you sustain sales growth?

    • How do you balance your original intention for your business, the investors needs, and managing sales and growing the business?

    • Where do you see your growth evolving?

  5. Managing the Business

    • How do you find good people to bring into your business? In essence, your hiring strategy?

    • When and how do you recognize that you need to let go of the people or services that aren’t working for your business?

    • How do you manage the roles you each have in the business?

    • Where do you go from here?

    • Do you have an exit plan?

  6. Emotional Wisdom

    • Entrepreneurship is often glamorized, what are some of the home truths you’ve learned?

    • What’s your experience of being a female entrepreneur and founder?

    • How did you manage your emotions around bringing investors onboard?

    • How do you learn to let go?

    • How do your instincts play a role in building, running, and growing your business?

    • What is your antidote to imposter syndrome?

    • What have your learned about yourself as a result of creating your business?

10 Steps to Interview a Guest

How to plan and conduct your interview of a guest in front of an audience:

  1. Understand your subject. Read about it, and read about your guest, learn about what they have done.

  2. Ask your guest (or their team) for their topic strengths and what they enjoy speaking about (I enjoy interviews that reveal more about the person in question in a positive way, find their strengths, get them talking, open up and share. Even if you have to dig into trickier topics, you can do this by being human and empathetic. Create a connection first.)

  3. Remember it is a conversation. Create flow and paint a picture. Resist the urge to jump around, but guide your audience along a path as if you’re giving them a guided tour of a garden and pointing out sights along the way, responding to their questions about what they’ve seen as you go. You might stop in one spot for a little, but don’t linger too longer, keep walking along.

  4. Have 3-6 major themes or subjects that you plan to navigate the conversation through. Don’t be rigid with your set of themes or questions. The duration of the interview determines how many themes you can explore in your conversation. You also have to assess and take account of the rhythm and speed of your guests answers. Sometimes guests can be very talkative in preparation mode, but on the day they are less chatty, that’s ok. As the interviewer you have more questions in your back pocket to ask and follow up with should your guest not be talking as much. Equally if your guest is talking with a lot of content, assess where they are heading, and then either let them continue, or guide them onward to a deeper or next question.

  5. Be curious, learn to really listen, and respond to what they are saying. (I have listened to too many interviews where the interviewer is intent on asking their list of questions, or advertising themselves, and hasn’t really listened to what was said by their guest.) If audience questions or discussion is involved the same applies. Sometimes conversations go down a new route and your skill as the interviewer is to assess if it’s fitting or not. To do so you take account of 4 areas: 1) understand the background of the guest, 2) what the needs of the audience are, 3) observe body language and words chosen, and 4) the overall atmosphere. Your instincts play a major role here, so work on sharpening your intuition if this is an area that you are less confident in.

  6. Be flexible and act that way too. When you hear something of interest, ask another question to dig a little deeper. You can respond with questions that uncover more about what the guest just said, or you can parlay into a new or aligned topic.

  7. Vary the length of your questions and ask questions that invite the guest to share more, let go of yes / no answer questions as they don’t reveal anything. When you’re in a great conversation with someone you vary your questions. This ensures you not only uncover more about your guest, but you stay engaged with the conversation. By giving your guest your full attention, they are more likely to give you theirs, and so will your audience.

  8. Above all, be yourself. At times, share snippets of your own thoughts, or experiences in response to the discussion, yet release the idea of talking for too long. You are not the subject of the interview, your guest is. Allow your personality to shine through. You’re not trying to be the world’s greatest interviewer, you’re having a conversation and creating a connection that everyone else in the room will feel when you are yourself.

  9. Have fun! It’s a conversation with another human - you are human too, enjoy it.

  10. After your interview, write down everything you remember about it, the questions you asked, the flow, the answers that stood out to you. Why? Because you can learn from the experience. It will give you time to reflect on it, and it will help you prepare and plan for your next interview occasion, when that time comes.