How to Spark Better Conversations and Keep Audiences Watching

Guest speakers are one of the fastest ways to elevate a webinar. They add credibility, perspective, and variety. They also give audiences a reason to show up and stay engaged.

Nearly half of webinar attendees say a high-profile or expert speaker is the main reason they register. But a great guest alone is not enough. The quality of the conversation matters just as much as the name on the slide.

The right questions turn a webinar from a presentation into a dialogue. This guide gives you 60 proven questions you can use to warm up your speakers, unlock real insight, and keep your audience leaning in.

How to Choose the Right Questions for Webinar Guest Speakers

The best webinar questions do three things:

• Reveal insight the audience cannot get from a blog post

• Help the speaker tell a story, not recite credentials

• Invite participation from the audience

Before the webinar, research your guest. Look beyond their job title. Understand what they have built, changed, failed at, or challenged in their career. During the session, listen actively. Strong follow-ups often matter more than the original question.

Attention spans in virtual environments are short. Plan moments of interaction every 8 to 10 minutes. Use polls, chat prompts, or audience-submitted questions to keep energy high.

Icebreaker Questions for Webinar Guest Speakers

Use these at the beginning to humanize your speaker and set a relaxed tone.

• Who has influenced your career the most?

• What is something most people do not know about you?

• What surprised you most this year?

• If you could host a dinner with anyone, who would be there?

• What professional do you admire and why?

• If you could experience another era firsthand, which would it be?

Career and Industry Questions for Guest Speakers

These questions anchor the conversation in real-world experience.

• What decision had the biggest impact on your work this year?

• How has your role changed in the past 12 months?

• What do people misunderstand about your profession?

• What excites you most about where the industry is headed?

• What opportunity are most teams overlooking right now?

• What was the first moment you knew you were on the right path?

• What did you work on yesterday?

• What differentiates great teams from average ones today?

Leadership Questions for Webinar Guest Speakers

Ideal for executive audiences and internal webinars.

• Is leadership a skill or a mindset?

• What trait matters most in effective leaders today?

• What makes collaboration hard at scale?

• How do you handle conflict on a team?

• How do you encourage innovation without chaos?

• What leadership mistake taught you the most?

• How do you create trust across distributed teams?

• What does strong culture look like in practice?

Advice-Driven Questions Audiences Love

These tend to drive the most chat activity and follow-up engagement.

• What advice would you give your younger self?

• What helped you stand out early in your career?

• What do you look for when hiring?

• How do you define success for your team?

• What obstacles still challenge you today?

• What skill matters more now than five years ago?

Follow-Up Questions That Unlock Better Stories

Use these to go deeper when a response resonates.

• What made that decision difficult?

• What would you do differently now?

• What factors shaped that outcome?

• How much did timing matter?

• What lesson took the longest to learn?

• What changed your perspective afterward?

Light and Human Questions to Reset Energy

These are ideal mid-session or near the end.

• What app would you miss most on a desert island?

• What question do you wish people asked you more often?

• What does a perfect evening after a long week look like?

• What is the strangest interview question you have received?

• What keeps you curious about your work?

Questions You Should Avoid Asking Guest Speakers

Avoid topics that put speakers on the defensive or off-topic:

• Politics or religion

• Personal or sensitive issues

• Anything the speaker has flagged as off-limits

Always ask your guest in advance if there are topics they prefer to avoid. Psychological safety leads to better answers.

How Many Questions Should You Ask in a Webinar?

Quality matters more than quantity.

Plan a short list of core questions. Leave room for follow-ups and audience participation. A mix of prepared questions and live audience prompts creates the most natural flow.

Why Platform Choice Matters for Guest Speaker Engagement

Great questions fall flat if the experience is passive.

Look for webinar tools that support:

• Live Q&A

• Polls and reactions

• Chat moderation

• On-screen prompts for audience participation

Engagement tools turn good questions into shared moments instead of one-way answers.

Questions Shape the Experience

Guest speakers bring credibility. Questions create connection.

The right questions help speakers open up, help audiences participate, and help your webinar feel intentional instead of scripted. With thoughtful preparation and a flexible format, guest segments become the most memorable part of the event.