I learned this lesson the hard way: events where customers just sit and listen are wasted opportunities. The real magic happens when your customers are on stage, sharing their stories, leading discussions, and connecting with each other.

Three years ago, I organized what I thought would be a great user conference. We had polished presentations from our executive team, impressive product demos, and even hired a keynote speaker. Attendance was decent. Feedback was... fine. But six months later, I couldn't point to a single advocate we'd created or a customer relationship that had meaningfully deepened.

The next year, we flipped the script. Customer speakers led 35% of sessions. We ran roundtables where practitioners talked about real challenges (not our product features). We created space for organic networking instead of cramming every minute with presentations. The difference was dramatic—not just in satisfaction scores, but in renewal rates, expansion revenue, and the number of customers who proactively referred new business.

Here's what I've learned about turning customers from passive attendees into active participants.

Event Types and What They're Actually For

Customer Education Webinars

These are your bread and butter—monthly or quarterly sessions that teach customers how to get more value from your product. But here's what makes them work: they can't just be feature walkthroughs. The best education webinars answer specific questions your customers are already asking.

I run ours like this: 45 minutes of content, 15 minutes of Q&A. Sometimes it's us teaching. But increasingly, we invite customers who've mastered a particular workflow to co-present. When a customer shows other customers how they use the product, adoption rates for that feature typically jump 30-40% in the following month.

The format works because attendees see themselves in the presenter. When our customer success team shows how to build a dashboard, it's instructional. When Sarah from a mid-sized logistics company shows the exact dashboard she built and how she convinced her team to use it, that's transformational.

What customers do here:

  • Attend and ask questions in chat
  • Share their own approaches during Q&A
  • Occasionally co-present their workflow
  • Connect with other attendees who have similar challenges

Run these consistently. Monthly is ideal if you can sustain the content pipeline. Quarterly works if your product evolves more slowly.

Co-Hosted Webinars

This is where marketing meets relationship building. You're partnering with a customer to create something that generates leads for both of you while deepening your connection with them.

The economics work for everyone: they get visibility to your audience (which might include their ideal prospects), you get credibility through their endorsement, and attendees get real-world insights instead of a sales pitch.

I've learned these work best when you structure them as problem-solution stories. The customer owns the "problem and context" section—they talk about what they were facing, why it mattered, what they tried. Then you facilitate the "solution" section together, with them describing how they implemented it and what results they saw.

Give the customer 60-70% of airtime. They're the draw. You're the supporting actor.

Common mistakes I see:

  • Letting your team dominate the talking (it becomes a sales pitch)
  • Choosing customers with weak stories because they're easy to recruit
  • Not helping the customer promote it to their network (you're leaving attendance on the table)
  • Doing one-off webinars instead of building an ongoing series

Promotion reality check: If only you promote it, expect 50-150 registrants depending on your list size. If the customer actively promotes too (email to their network, LinkedIn posts, telling their industry peers), you can double or triple that. Make promotion easy for them—provide templates, graphics, even draft social posts.

User Conferences

Your annual gathering is either a massive opportunity or an expensive disappointment. The difference comes down to customer involvement.

When I talk to CSMs about which customers to invite to speak, I get the same response: "But our customers aren't good presenters" or "They're too busy." Sometimes that's true. But usually, we haven't asked the right customers or made it worth their time.

Here's what a good customer track looks like: 20-40% of your sessions are customer-led. Not just success stories (though those matter), but implementation lessons, best practices panels, peer roundtables where customers discuss challenges, and tips-and-tricks sessions where power users share their discoveries.

Planning timeline that actually works:

  • Six months out: Open call for customer speakers
  • Five months out: Select speakers and confirm participation
  • Four months out: Work with them on topics and content outlines
  • Three months out: Content development and slide creation
  • Two months out: Rehearsals (yes, really—it helps them and you)
  • One month out: Final tech checks and preparation
  • Event week: Support them through execution

The speaker recruitment reality: You'll need to invite 3-4 customers for every speaking slot you want to fill. Some will decline immediately. Others will commit and then drop out. Build in redundancy.

And honestly? Make speakers feel like VIPs. Separate speaker lounge, exclusive dinner, thank-you gifts in their hotel room, professional photos they can use for their own marketing. When speakers feel valued, they become advocates who'll speak again and refer others.

Industry Events and Trade Conferences

These third-party events are interesting opportunities if you approach them right. Instead of just sponsoring a booth, see if you can get speaking slots—and then invite customers to co-present.

I've done this with major industry conferences. We apply for speaking slots with a customer co-presenter already committed. The conference gets a practitioner voice (they love that), the customer gets industry visibility, and we get association with their credibility.

Joint booth staffing works too. When a customer hangs out at your booth for even an hour, prospects see it completely differently. It's not "vendor trying to sell me something" but "this company's customer is here voluntarily talking about their experience."

What I offer customers for this:

  • Free conference pass (we cover it)
  • Booth duty is optional and limited (one hour)
  • We handle all logistics and prep
  • They can network the rest of the time
  • We promote their company and role (good for their visibility)

Virtual Summits

These are bigger than webinars, smaller than in-person conferences. Usually 2-3 days, multi-track programming, global accessibility. I like them because they remove geography as a barrier—you can involve customers who'd never travel to a physical event.

The production burden is real though. You need solid platform technology, session hosts who can keep energy up virtually, and more aggressive session variety (because Zoom fatigue is real).

Customer involvement looks like:

  • Speaking across different tracks and topics
  • Panel participation (easier commitment than solo presenting)
  • Moderating discussions (great for customers who are nervous about presenting)
  • Live Q&A hosting

The beauty of virtual summits is the content library you build. We've gotten 18 months of marketing content from our annual summit. Every session becomes a standalone asset, blog post fodder, social media clips, and sales enablement material.

Roundtables and Peer Forums

These intimate discussions are my favorite format for building deep relationships. Eight to twelve customers in a room (virtual or physical) discussing a specific challenge they all face. No presentations. No sales pitch. Just facilitated peer conversation.

I run these quarterly for different customer segments: VPs of Customer Success in mid-market companies, implementation leaders in enterprise accounts, CFOs evaluating ROI. The homogeneity is intentional—when everyone's dealing with similar contexts and challenges, the conversation gets real fast.

Ground rules matter: We use Chatham House Rules (you can share what was discussed but not who said it or who attended). This creates space for honesty. People will admit struggles, share salary benchmarks, discuss vendor frustrations, and ask questions they'd never ask in a public setting.

What makes these work:

  • Small enough that everyone speaks
  • Homogeneous enough that conversation stays relevant
  • Facilitated lightly—ask questions, don't lecture
  • No recording (people are more honest)
  • Follow-up with summary themes and connection facilitation

I've seen customer relationships transform through these forums. When you create space for vulnerable, practical peer discussion, people remember. They're more likely to renew, expand, and refer because of the community value, not just the product value.

How Customers Can Participate (Beyond Sitting in Seats)

Attendees

Look, most customers will be attendees. That's fine. But even as attendees, there are participation levels. Some people register and ghost. Others show up, lurk silently, and leave. The best attendees engage in chat, ask questions during Q&A, network with peers, and actually implement what they learn.

Make attending valuable: relevant content, good production quality, networking opportunities, and follow-up resources. If someone takes an hour for your webinar, respect that time.

Panelists

This is the easiest ask for first-time customer speakers. Being one voice among three or four is less intimidating than solo presenting. Prep is lighter—usually a 30-minute prep call to discuss themes and potential questions, then the 45-minute panel itself.

When to use panels:

  • You want diverse perspectives on one topic
  • You have multiple customers with related experiences
  • You're recruiting customers who are nervous about solo speaking
  • You want to cover more ground than one story provides

Panel composition: Three or four customers is ideal. Two feels thin. Five gets chaotic and some people won't get enough airtime. Mix industries, company sizes, or use cases for more interesting discussion.

Speakers

Solo or duo presentations require more commitment—probably 10-20 hours of prep when you include content development, slide creation, and rehearsals. But the payoff for them is bigger: maximum visibility, clear expertise demonstration, career development (especially if they're junior to mid-level), and marketing assets they can use.

I wrote a whole guide on this—Customer Speaking Opportunities—because there's a lot to getting this right. Speaker recruitment, content development, prep, and appreciation all matter.

Selection criteria for speakers: They need a strong story (real results, interesting challenges, compelling arc). They need to be decent communicators (doesn't have to be polished, but clear and engaging). And honestly, they need to be willing to put in the work. Some customers say yes and then ghost during prep. Don't let that happen—establish clear expectations upfront.

Co-Hosts

This is a partnership-level relationship. Your customer is an equal presenter, not a guest. You're developing content together, promoting together, presenting together. Usually this happens with strategic customers where there's already a strong relationship and aligned incentives.

What co-hosting looks like:

  • Joint webinar development over 3-4 weeks
  • Equal or near-equal presentation time
  • Both companies promote to their audiences
  • Co-branded materials and landing pages
  • Shared lead flow (sometimes)

I've done this with customers who are also industry influencers or who have complementary offerings. One customer ran a consulting firm and co-hosted a webinar with us on change management for software implementations. She got leads for consulting services. We got credibility through her expertise. Attendees got genuinely useful content instead of a product pitch.

Moderators

Some customers are great facilitators but nervous about presenting content. Make them moderators. They guide panel discussions, ask questions, manage time, and ensure everyone contributes. It's a leadership role with less content pressure.

Good moderator candidates:

  • Customers who are naturally curious and ask good questions
  • Those who know the topic area but don't have a specific case study to present
  • Executives who want visibility without the time investment of content development
  • Natural facilitators who like helping others shine

Advisors and Planners

Your most strategic customers can shape the event itself. Form an event advisory board that meets quarterly to discuss themes, topics, formats, and speaker recommendations. Give them early access to agendas and ask for feedback.

This serves multiple purposes: better event design (they know what resonates with customers), deeper relationship (they feel heard and valued), and advocate development (when customers help create something, they're invested in its success).

What advisors help with:

  • Topic selection and session themes
  • Speaker and panelist recommendations
  • Format and schedule feedback
  • Pre-event content review
  • Post-event improvement discussion

Honestly, I wish I'd started an advisory board earlier. The insights have been invaluable.

Recruiting Customers (The Actual Hard Part)

Getting the right customers to participate is harder than it should be. Here's what I've learned.

Who to Ask

For speakers and panelists: You need customers with strong results and compelling stories. But also: decent communicators (they don't have to be professionals, just clear and engaging), enthusiasm about your product (lukewarm customers make awkward speakers), and diverse representation across industries, company sizes, use cases, and demographics.

That last point trips people up. It's easy to default to the same customer types—usually whoever's loudest or most accessible. Push yourself to recruit broadly. When all your speakers are from enterprise tech companies, you're excluding SMB customers and other industries who won't see themselves represented.

For roundtables: Homogeneity is your friend here. All VPs, or all practitioners. All mid-market, or all enterprise. All logistics companies, or all financial services. The tighter the peer group, the more honest and useful the conversation.

For advisors: Strategic accounts, product power users, customers with relationship depth, and thought leaders in their industries. You want people who'll actually show up and contribute, not just want the title.

The Invitation That Actually Works

Generic email blasts don't work for recruiting speakers or panelists. You need personal outreach that shows you've thought about why this specific person for this specific opportunity.

Here's an invitation structure that works:

Subject: Quick question about [Event Name]

Hey Marcus,

I've been thinking about our [Event Name] coming up in June and immediately thought of you for our customer panel on scaling implementation teams.

Given how you grew your implementation team from 3 to 15 people in 18 months (without the wheels falling off), I think your perspective would be really valuable for other attendees trying to scale.

Here's what's involved:

  • 45-minute virtual panel with 2-3 other customer success leaders
  • Join from wherever you are—no travel
  • One 30-minute prep call two weeks before to discuss themes
  • Main topics: hiring fast without compromising quality, structuring teams as you scale, and maintaining consistency
  • Audience: 150-200 CS leaders facing similar growth challenges

What you get:

  • Visibility to peers in your space (good for hiring, networking, your personal brand)
  • Connection with other panelists who've scaled teams
  • Full-access pass to the whole event (great speaker lineup this year)
  • Plus it's honestly just fun—I think you'd enjoy the conversation

Want to chat this week about it? No pressure if the timing doesn't work, but thought it was worth asking.

Tara

Why this works: It's personal and specific (not a template). It acknowledges their actual experience and expertise. It's clear about time commitment upfront (no surprises). It articulates what they get out of it (not just asking a favor). And it makes the ask easy—just a conversation, not a hard commitment immediately.

What Different Customers Value

Career-focused professionals care about thought leadership positioning, resume building, visibility in their industry, and speaking experience. Junior to mid-level employees especially value this—it's career development their company isn't funding.

Marketing-oriented customers want co-marketing opportunities, lead generation, brand exposure, and content they can use for their own promotion. If your customer is a consultant, agency, or business that relies on visibility, this is a compelling offer.

Product-engaged users care about insider access, roadmap influence, beta features, and building relationships with your product team. Power users often fall into this category—they want to help shape what you build.

Community-oriented people want peer connections, networking with others like them, community status, and ongoing relationships. They're not trying to get anything transactional—they just like being part of something.

Tailor your pitch to what they actually care about. If you lead with "great networking opportunity" to someone who's heads-down in product work, you'll lose them.

Actually Achieving Diversity

This requires intentional effort. Left to default, you'll end up with speakers who look and sound similar (probably because they're easiest to recruit or most similar to your team).

Be intentional about:

  • Industry and vertical representation (don't let it be all tech companies)
  • Company sizes (show that your solution works across SMB to enterprise)
  • Geographic diversity (especially for global products)
  • Roles and levels (mix executives with practitioners)
  • Gender, race, and demographic diversity (it matters)
  • Use cases and applications (different ways people use your product)
  • Customer maturity (new implementations vs. longtime users)

When planning speaker recruitment, literally make a spreadsheet with these dimensions and track whether you're hitting diversity goals. It won't happen by accident.

Locking in Commitments

Early interest doesn't mean someone will actually show up. I've learned this the hard way.

Confirmation process:

  1. Initial interest conversation
  2. Send specific date, time, format, and topic in writing
  3. Get calendar acceptance
  4. Written confirmation (email saying "yes, I'm in")
  5. Two weeks out: reminder and prep scheduling
  6. One week out: confirmation they're still good
  7. Day before: tech check and final confirmation

This feels like overkill but it prevents no-shows. People's calendars fill up, priorities shift, and something that felt doable six weeks ago might feel impossible now. The reminder sequence gives them graceful exit points rather than ghosting at the last minute.

Co-Hosting Webinars With Customers

Co-hosted webinars are high-leverage if you do them right. Here's what I've learned from running dozens of these.

Picking Topics Customers Can Own

The topic has to be something your customer has genuine expertise on. Generic topics ("How to Drive ROI") don't work because they're too broad. Specific topics ("How We Reduced Onboarding Time by 60% While Doubling New Hires") work because they're concrete and credible.

Strong topic pattern: "How [Customer Name] Achieved [Specific Result] in [Context]"

Examples that have worked:

  • "How Morrison Logistics Cut Route Planning Time by 40% in Six Months"
  • "From Manual to Automated: Regional Bank's Digital Transformation Journey"
  • "Scaling Support from 5 to 50 Agents Without Losing Quality: Zephyr's Story"

Topic selection criteria: The customer has authentic expertise (they lived it). The story is compelling (real challenges, interesting solutions, measurable results). It's relevant to your target audience (they have similar challenges). Value is clear (attendees will learn something useful). And there's a natural role division—they tell their story, you facilitate and provide product context where relevant.

Building Content Together (Not For Them)

Don't make the mistake of drafting all the content yourself and asking the customer to approve it. They become a cardboard cutout reading your script. Instead, build it collaboratively.

Four-week development process:

Week 1: Alignment Jump on a call and talk through the story. What was the challenge? Why did it matter? What did they try? What worked and didn't work? What results did they see? What lessons did they learn?

Record this call (with permission). Their words from this conversation often become the actual content—it's more authentic than anything you'll write for them.

Agree on the arc: problem → solution → results → lessons. Define who covers what (usually they own problem and results, you provide solution context together).

Week 2: Draft Development They draft their sections based on your conversation. You draft framing, transitions, and product context. Create slides collaboratively (Google Slides works well for this).

Send them a slide template and clear guidance on what slides they own. Don't make them start from scratch—provide structure but let them fill in their content.

Week 3: Refinement First full rehearsal. Actually present to each other as if it's the real thing. This reveals timing issues, awkward transitions, and content gaps.

Adjust based on what you learn. Usually this means cutting content (we always try to cram too much), smoothing transitions, and clarifying their key messages.

Week 4: Final Prep Last rehearsal focused on timing and tech. Practice the hand-offs between speakers. Test screen sharing and slide control. Run through Q&A preparation (what questions might come up, who answers what).

Tech check the day before the actual webinar. Do not skip this.

Setting Customers Up for Success

Most customers haven't presented webinars before (or haven't in a while). Your job is to make them feel confident and prepared.

Prep call two weeks out: Walk through the full flow. Show them the platform. Practice transitions. Discuss timing (and what happens if you're running long). Prepare for Q&A (what questions might come up, how you'll filter and pass questions to them). Tech walkthrough (screen sharing, slide control, audio settings).

Record this rehearsal. Sometimes customers want to review it to see how they sound.

24-hour reminder: Confirm they're still good to go. Send final slides. Review tech requirements one more time. Share high-level attendee profile (who's registered, what companies, what roles—this helps them tailor their delivery). Answer any last-minute questions.

Day of, 15 minutes before: Log on early for tech check. Test audio and video. Make sure screen sharing works. Confirm slide control plan (are they advancing their own slides or are you?). Do a quick emotional check-in—are they nervous? Reassure them it'll be great.

Your Role During the Webinar

You're the co-host, which means you facilitate and support but don't dominate.

What you do:

  • Open the webinar and set context (5 minutes)
  • Introduce the customer and their story (2 minutes)
  • Provide transitions between sections (1 minute each)
  • Manage time (gently cue if running long)
  • Filter and pass Q&A questions
  • Handle any technical issues
  • Fill gaps if needed (but this should be rare)
  • Close with clear calls-to-action (5 minutes)

Let them shine: They should be talking 60-70% of the time. If you find yourself talking more than them, you're doing it wrong. Your job is to enable their story, not tell it for them.

Q&A handling: Monitor the questions coming in. Group similar ones. Pass relevant questions to the customer ("Maria, this question is perfect for you..."). You can answer product-specific technical questions, but most should go to them—that's why attendees are there.

Promotion That Actually Works

Both parties should promote, but make it easy for your customer to do their part.

Your promotion: Email your full database (customers and prospects). Post on LinkedIn and Twitter with tagging. Feature on your website and blog. Consider paid promotion if budget allows. Have your sales team personally invite relevant prospects.

Customer promotion: Provide an email template they can customize and send to their network. Create co-branded social graphics they can post. Draft a LinkedIn post for them (they can edit, but starting from blank is hard). Make it one-click easy—most customers want to help promote but don't want to spend an hour writing copy.

Co-branded materials: Landing page with both logos. Social graphics featuring both brands. Email signatures promoting the webinar. If it's a big customer or timely topic, consider a joint press release.

When both parties promote actively, you typically get 2-3x the registration you'd get alone. Plus, their audience sees your brand associated with a company they trust.

Running User Conferences (The Big One)

Annual user conferences are significant investments. Here's how to make them work.

Customer Track Planning

Your agenda should be 20-40% customer-led sessions. Mix formats: solo customer presentations, panels with multiple customers, peer roundtables, tips-and-tricks sessions, and maybe one customer keynote if you have the right person.

Session type breakdown:

  • Customer success stories: 20% of schedule
  • Implementation lessons and best practices: 15%
  • Panel discussions: 10%
  • Peer roundtables: 10%
  • Tips and tricks from power users: 10%
  • Customer keynote: 1-2 sessions

The rest can be your team, product updates, training, and vendor sessions if you have sponsors.

Planning timeline:

  • 6 months out: Open call for customer speakers
  • 5 months out: Select speakers and confirm
  • 4 months out: Topic refinement and content development start
  • 3 months out: Content development and rehearsals
  • 2 months out: Final rehearsals and tech checks
  • 1 month out: Final prep and logistics
  • Event week: Showtime

Six months feels early but it's not. Customers need time to get internal approval, block calendars, arrange travel (if in-person), and develop content.

Speaker Recruitment at Scale

Recruiting 20-40 customer speakers is different from recruiting 2-3 for a webinar. You need a system.

Call for speakers (6 months out): Email all customers with a clear invitation to submit speaking proposals. Create an online form (Typeform or Google Forms work) where they submit topic ideas, their story, and relevant results.

Make the criteria clear: What makes a good story? What topics are you looking for? What's the time commitment? What do speakers get?

Set a deadline (usually 4-5 months before the event) and stick to it. You need time to review submissions and select speakers.

Selection criteria: Story strength and measurable results. Presentation ability (ask for video samples if possible, or at least a phone screen). Diverse representation across industries, company sizes, roles, and demographics. Company and role fit with your target audience. Availability and willingness to commit.

You'll get more submissions than you can accept. That's good—it lets you be selective and build a waiting list for cancellations.

Acceptance process (4 months out): Notify accepted speakers promptly. Get written confirmation of their participation. Kick off content development with a welcome packet explaining next steps. Assign each speaker a liaison from your team (usually a CSM) who'll support them through prep.

For speakers you really want who didn't submit: Reach out personally with a specific invitation. Sometimes your best speakers won't respond to a general call—they need a personal ask that shows why you want them specifically.

Session Formats That Keep Energy Up

Don't make every session a 45-minute solo presentation. Mix it up.

Format variety:

  • Solo presentations (25 minutes): Deep dive into one customer's story
  • Panels (45 minutes): 3-4 customers discussing a theme
  • Roundtables (60 minutes): Small group discussions on specific topics
  • Workshops (90 minutes): Hands-on learning sessions
  • Lightning talks (10 minutes): Quick hits, 4-5 in one time slot
  • Fireside chats (30 minutes): Intimate interview format

Different formats appeal to different learning styles and different time commitments from speakers. Some customers are happy to do a 10-minute lightning talk but wouldn't commit to a 45-minute session.

Energy management: Start mornings with high-energy formats (panels, fireside chats). Mid-morning is good for solo presentations. After lunch, do interactive formats (roundtables, workshops) because attention dips. Late afternoon, go back to high-energy or offer shorter sessions.

Creating Real Networking Opportunities

People remember the connections they make more than the sessions they attend. Design for this.

Structured networking: Customer-only reception (no vendor staff except hosts). Industry-specific meetups for people in similar sectors. Role-based roundtables (all VPs in one, all practitioners in another). Speed networking if your audience is open to it. Speaker dinners (make speakers feel special and facilitate connections among them).

Technology-enabled networking: Event app with attendee profiles and messaging. Matchmaking based on interests, industry, or challenges. Conversation starter prompts in the app. Birds-of-a-feather tables at lunch with topic signs.

Organic networking space: Don't schedule every minute. Build in 30-45 minute breaks where people can just talk. Create comfortable spaces with seating, coffee, and no agenda. Have expo hall time that's actually long enough to have conversations, not just quick booth drive-bys.

I've learned that attendees rate networking value almost as highly as content quality. Don't pack the schedule so tight that networking becomes an afterthought.

VIP Treatment for Speakers

When customers take time to speak at your event, make them feel valued. This investment pays off in ongoing advocacy.

VIP elements: Exclusive speaker lounge with comfortable seating, good coffee, and quiet space to prep. Welcome gifts in their hotel room (if in-person) or shipped before the event (if virtual). Speaker-only dinner or reception with your executive team. Premium seating at keynotes and main sessions. Professional photography (they can use these photos for their own marketing). Dedicated staff support (someone they can text with questions or issues). Thank-you gifts after the event.

Recognition: Special speaker badges (different color or design). On-stage recognition during keynotes ("Let's give a round of applause to our customer speakers"). Speaker showcase display in a high-traffic area. Social media spotlight during the event. Post-event thank you video from your CEO.

This stuff matters more than you think. I've had speakers mention these touches months later as reasons they feel connected to our company.

Keeping the Community Alive Post-Event

The event is the beginning of community, not the end.

Post-event community building: Create a speaker alumni community (Slack or Teams channel). Run quarterly virtual meetups. Facilitate peer connections between speakers who hit it off. Share content and collaborate on ideas. Get their input on next year's event planning.

Some of our strongest advocates came from speaker communities. When you facilitate ongoing connections, customers stay engaged with each other and with you.

Roundtables and Peer Forums (My Favorite Format)

I love roundtables because they create space for honest, practical conversation that doesn't happen anywhere else.

Structure That Works

90-minute roundtable flow:

Introduction (10 minutes): Moderator welcome and ground rules. Quick participant intros (name, company, role, one sentence on their interest in the topic). Topic framing and agenda. Chatham House Rules explanation ("You can share what was discussed but not who said it or who attended").

Discussion (60 minutes): Open conversation on the topic. Moderator facilitates but doesn't dominate. Everyone should contribute. Questions and challenges are welcome. Real talk encouraged—this is the point.

Wrap-up (20 minutes): Summary of key themes. Action items or takeaways. Connection facilitation (who should talk to whom after). Feedback on the session. Next steps or future roundtable ideas.

Group size: Eight to twelve participants is ideal. Smaller than eight feels too intimate (people are less willing to open up). Larger than twelve means not everyone gets adequate airtime and side conversations fragment the group.

Picking the Right Participants

Homogeneity enables honesty. When everyone's dealing with similar challenges and contexts, conversation gets real.

Selection criteria:

  • Similar roles (all VPs, or all managers, or all practitioners—don't mix levels)
  • Similar industries or challenges (industry-specific works well)
  • Comparable company sizes (a solo founder and an enterprise exec have different problems)
  • No direct competitors (people won't open up if their competitor is there)
  • Compatible personalities if you know them (one dominator can kill a roundtable)

I run separate roundtables for different segments: VPs of Customer Success at mid-market SaaS companies. Implementation managers in healthcare. CFOs at professional services firms.

Why homogeneity matters: Shared context and language. Comparable challenges. Safe environment to admit struggles. Relevant insights from every participant. True peer feeling.

Mix too much and conversation stays superficial because people are hedging for the least-informed person in the room.

Topics That Generate Real Discussion

Choose topics people actually care about and struggle with.

Strong roundtable topics:

  • "Building CS Teams from 0 to 20: What to Hire When"
  • "Navigating Budget Cuts When Revenue Goals Stay the Same"
  • "Scaling Support Without Losing Quality or Burning Out Your Team"
  • "Measuring Marketing ROI When Attribution Is a Mess"
  • "Managing Remote Teams When Culture Feels Like It's Dying"
  • "Pricing Discussions: What to Negotiate and What to Hold Firm On"

Topic criteria: Relevant to all participants. No easy answers (requires real discussion, not just sharing best practices). Everyone has perspective to share from their experience. Practical and actionable (not theoretical). Not about your product (let them talk about their work, not your features).

The best topics are ones where everyone says "Oh thank god, I thought I was the only one struggling with this."

Moderating Well (Harder Than It Looks)

Facilitation makes or breaks a roundtable. You're not there to present or teach—you're there to enable peer learning.

Effective moderator behaviors: Set the stage with clear ground rules and topic framing, then step back. Ask open-ended questions, don't lecture. Ensure equal participation (gently pull back dominators, actively invite quiet folks to contribute). Build on what people say ("That's interesting—Maria, have you seen something similar?"). Surface tensions productively ("It sounds like there are different philosophies here—let's dig into that"). Manage time so key themes get adequate airspace. Synthesize themes at the end.

Questions that drive discussion:

  • "What's working for you in this area?"
  • "What's not working and why?"
  • "How have others tackled [specific challenge someone just mentioned]?"
  • "What would you do differently if you could start over?"
  • "What assumptions did you have that turned out to be wrong?"

What to avoid: Pitching your product (seriously, don't). Dominating the conversation (you should talk less than 20% of the time). Letting one person monopolize (politely redirect: "That's great, Chris. I want to make sure we hear from others too. Alicia, what's your experience with this?"). Letting it devolve into a complaint session (acknowledge frustrations but redirect toward solutions and learning). Selling to them (this is community building, not lead gen).

Creating Safety for Honesty

People will only be honest if they feel safe.

Chatham House Rules: "You can share what was discussed, but not who said it or who attended."

Explain this at the start and why it matters. It means someone can say "In a recent roundtable, a VP mentioned they're struggling with X" but can't say "Jane from Acme Corp told me X."

Why safety matters: Enables people to admit struggles without fearing it'll get back to their boss or board. Allows vulnerability about challenges they're facing. Lets them share real challenges, not sanitized versions. Prevents competitive intelligence concerns (if competitors were allowed, which they shouldn't be). Builds trust within the group.

Reinforce safety: State Chatham House Rules at the start. Model appropriate sharing yourself. Don't record (notes are fine, but no recording). Respect confidentiality after—don't gossip about what was shared. If someone shares something particularly sensitive, acknowledge their trust.

I've had customers share things in roundtables they'd never share in a public setting: budget constraints, team conflicts, executive disagreements, fears about job security. That vulnerability builds community.

Following Up

The roundtable isn't the end—it's the beginning of ongoing connections.

Post-roundtable follow-up: Send a summary email with key themes discussed (no attribution to who said what). Share resources that came up during discussion (articles, tools, templates). Facilitate connections between participants who want to continue discussing specific topics. Invite them to the next roundtable. Consider creating a private Slack or Teams channel for ongoing conversation.

Quarterly cadence: If the group works well, invite them back quarterly. Same group, rotating topics. Relationships deepen over time. Community forms. They start reaching out to each other between roundtables.

Some of our strongest customer communities started as roundtable groups.

Getting People to Actually Show Up

You can plan a great event, but if nobody comes, it doesn't matter.

Email Sequences That Work

Multi-touch campaign for a major event:

Announcement (6-8 weeks out): "We're excited to announce [Event Name] on [Date]." Share what makes it valuable (agenda highlights, customer speakers, networking opportunities). Include clear CTA to register. Early bird pricing if you're charging.

Speaker spotlight (4-6 weeks out): Feature customer speakers and their stories. "Meet Sarah Chen, VP of Customer Success at TechCorp, who'll be sharing how she scaled her team from 5 to 30." This builds excitement and provides social proof. It also motivates speakers to promote (they want their spotlight seen).

Agenda deep-dive (3-4 weeks out): Share the full agenda with session descriptions. "Here's what you'll learn at [Event Name]." Help people see the value and plan their attendance.

Reminder (2 weeks out): "Registration closes in two weeks." Create urgency. Share logistics info (virtual platform, time zones, what to prepare).

Week of: Access instructions and technical requirements. "Here's how to join tomorrow." Schedule reminders. Last-minute details and excitement building.

Day of: "Starting in 2 hours!" Link and access info. Brief agenda. Encouragement to show up.

For customers specifically: Don't rely just on marketing emails. Have CSMs personally invite customers during regular check-in calls. That personal touch dramatically increases attendance.

Social Media That Actually Drives Registration

LinkedIn (primary for B2B): Event announcement posts. Speaker spotlights with tags (speakers often share). Countdown posts in final week. Behind-the-scenes content (speaker rehearsals, team prep). Live coverage during the event. Post-event highlights and recordings.

Use video when possible—it performs better than static images. Tag speakers and partners to extend reach.

Twitter: Quick updates and reminders. Live-tweeting during events (people love following along even if they're not attending). Hashtag campaigns (#UserConf2025). Engaging with attendee posts and questions.

Company blog: Speaker interview series (publish one every week leading up to the event). Topic deep dives that preview session content. Testimonials from past attendees. Detailed recap posts after.

Making Customers Your Promoters

When customers help promote, you reach new audiences and build credibility.

Make it easy: Provide email templates they can customize and send to their networks. Create co-branded graphics sized for LinkedIn, Twitter, and email. Draft social media posts they can edit and use. Provide talking points if they're promoting verbally or at industry events.

Incentives that work: For speakers: Promotion of their session increases their audience (and thus their ROI on speaking). For customers generally: Referral incentives (bring a peer, get a gift card), +1 passes (they can bring someone from their team), exclusive access (customer-only sessions or networking).

CSM role: Customer Success Managers should personally invite customers during regular check-ins. "I saw you mentioned challenges with X. We have a great session on that at our upcoming event. Can I send you the details?" Personal invitations convert 5-10x better than email blasts.

Tracking What Actually Works

Monitor sources and optimize.

Track in your registration system: Registration source (which email, which social post, which referral). Customer vs. prospect segmentation. Drop-off points in registration flow (are people starting but not completing?). Demographic data (roles, industries, company sizes). Email engagement rates (open, click, register).

Optimize based on data: A/B test email subject lines. Adjust promotion schedule (if a certain email time works better, use that). Increase emphasis on high-performing channels (if LinkedIn drives 2x more registrations than Twitter, weight your effort accordingly). Retarget people who opened emails but didn't register. Personalize outreach to different segments (VPs get different messaging than practitioners).

We've improved our webinar attendance rate from 45% to 68% over two years just by paying attention to this data and optimizing continuously.

Running the Event Well

All the planning comes down to execution.

Technical Setup (Prevent Disasters)

Pre-event: Test the platform with every speaker. Set up backup communication channels (Slack, phone). Train moderators on platform features. Have a technical support team on standby. Set up recording and test it works. Create a runbook for common technical issues.

During: Monitor audio and video quality constantly. Have a dedicated tech support channel for speakers and attendees. Respond to issues quickly. Execute backup plans smoothly if needed (if a speaker has audio issues, switch to phone dial-in). Manage screen sharing and slide transitions. Watch for platform issues (bandwidth, platform outages, browser compatibility problems).

Day of, for webinars: Log on 15 minutes early with all speakers. Test audio, video, screen sharing, chat, and polls. Confirm everyone knows the flow and their cues. Have a quick "how is everyone feeling?" check-in.

I've learned to always have a backup plan. If your main speaker has connectivity issues, can you present their slides? Do you have pre-recorded content you can fall back on? Can someone call in via phone?

Coordination and Timing

For single-track webinars: One person manages the run-of-show. They handle speaker intros, time cues, transitions, Q&A filtering, and technical direction. Create a detailed runbook with timing for each segment, speaker cues, and slides that go with each section.

For multi-track events: Each session needs a dedicated runner. Central coordinator oversees all rooms and handles escalations. Real-time communication between coordinators (Slack works well). Established protocol for handling issues.

Timing discipline: Start on time (even if not everyone's there yet). Give speakers time cues (10 minutes left, 5 minutes left, wrap up). Be ruthless about ending on time—going long trains attendees to show up late next time.

Engagement During the Event

Keep people actively involved.

Tactics: Live polls and Q&A (people love seeing poll results in real-time). Active chat moderation—respond to comments, ask follow-up questions, surface good comments to speakers. Gamification if your platform supports it (points for participating, prizes for most active attendees). Networking features (introduce people in chat, facilitate connections, set up breakout rooms). Interactive elements (ask questions, request people to share in chat, acknowledgements).

Chat management: Someone needs to own chat. They respond to participant comments, filter and elevate questions for speakers, facilitate side discussions, surface insights, and keep energy up. Chat can be chaotic—active moderation makes it valuable rather than distracting.

Q&A handling: Collect questions throughout (don't wait until the end). Filter for quality and relevance. Group similar questions together. Pass to speakers with context ("We have several questions about implementation timelines. Maria, this one from James at Acme Corp might be good for you..."). Follow up on unanswered questions after the event.

Capturing Content

Every event is a content library.

What to capture: High-quality video recording. Audio-only versions (some people prefer podcasts). Full transcripts. Session slides. Screenshots of key moments. Quote graphics from compelling speaker statements. Poll results and chat highlights.

Production quality: For major events, consider professional editing. Remove dead air, technical glitches, and awkward transitions. Add intro/outro graphics and lower-thirds with speaker names and titles. Create chapter markers for easy navigation.

Usage: On-demand library for people who couldn't attend live. Marketing content (promote clips on social). Sales enablement (prospects want to see customer stories). Blog posts and articles. Lead generation (gate access for new prospects). Customer success resources (customers reference event content months later).

We get 12-18 months of content from our annual user conference. Every session becomes multiple assets.

Post-Event Follow-Through

The event ends but your work doesn't.

Getting Recordings Out

Timeline: Raw recording to registrants: 24-48 hours (people want it fast). Edited professional version: 1-2 weeks. Full transcript: 1-2 weeks. Highlight clips: Ongoing (create these as you identify compelling moments).

Distribution: Email to registrants and attendees. Feature in your website resource center. Upload to YouTube or Vimeo. Post native video on LinkedIn. Add to sales enablement portal. Share in customer success platforms (Gainsight, ChurnZero, etc.).

Access control decisions: Gate recordings for lead generation (require registration to view). Provide free access for customers. Make some content public, gate others. Time-limited availability or evergreen access. Our approach: customers get immediate free access, prospects can register to view, general public can access after 30 days.

Turning One Event Into Many Assets

Repurpose content aggressively.

Content opportunities: Blog post for each session or speaker (that's 20-40 blog posts from a major event). Social media quote graphics (pull compelling statements from sessions). Email nurture sequences (use session content as educational emails). Podcast episodes (audio from sessions or speaker interviews). Slide decks uploaded to SlideShare. Infographics created from data and stats shared. Case study material (customer stories become formal case studies).

Get customer approval for public use beyond the event recording. A quick email: "We'd love to feature your story in a blog post and social media. Can we send you a draft for approval?" Most customers say yes, especially if you make them look good.

Following Up With Attendees

Close the loop with everyone who participated.

Day 1 post-event: Thank you email with recording link, survey link, and next steps.

Week 1: Send satisfaction survey. "How did we do? What should we improve?" Keep it short (5-7 questions max). Offer an incentive for completion (entry into gift card drawing).

Week 2: Share resources mentioned during sessions (templates, articles, tools). "Here are the resources our speakers recommended."

Week 3: Related content or next event invitation. "If you enjoyed [topic], check out this related resource" or "Save the date for our next event on [date]."

Segmented follow-up: Customers: CSM personal outreach ("How was the event? Did you get what you needed?"). Hot prospects: Sales follow-up ("I saw you attended our session on X. Want to discuss how that might apply to your situation?"). General attendees: Marketing nurture sequence. No-shows: "Sorry you couldn't make it. Here's the recording."

Thanking Speakers

Customer speakers made your event work. Show appreciation.

Within 24 hours: Personal thank you email or call from the event organizer. Share their recording and any materials. Let them know initial feedback if you have it.

Within one week: Send metrics and impact: "Your session had 180 attendees, 4.8/5 satisfaction rating, and generated 12 follow-up questions. Here's what people said..." Professional photos from the event (speakers love these). Social media recognition and highlights. Physical thank you gift (we send a nice bottle of wine, gift basket, or company swag box).

Ongoing: Create speaker spotlight content (blog post, social media feature, video interview). Invite them to future events as alumni speakers. Facilitate connections with other speakers. Include them in speaker advisory conversations for future events.

I wrote a detailed guide on this: Customer Speaking Opportunities.

Building Ongoing Community

The event was a moment, but community is ongoing.

Post-event community options: Slack or Teams channel for attendees (opt-in during registration). Monthly virtual meetups on specific topics. Quarterly roundtables for different segments. Email newsletter with event content, industry insights, and community updates. User group chapters by geography or industry. Annual reunion at next year's event.

Content sharing: Ongoing educational content. Peer introductions and networking facilitation. Success stories from community members. Product updates and early access for community. Industry trends and insights.

Community management: This requires ongoing effort. Someone needs to own community engagement: share content regularly, facilitate connections, respond to questions, moderate discussions, organize activities.

Our most engaged customers are those in our community. They renew at higher rates, expand more, and refer more new business. The community value compounds over time.

Measuring Success (Beyond Attendance)

Track what matters.

Event metrics: Registration rate (how many people registered vs. how many you invited). Attendance rate (registered → actually attended). We aim for 70%+ attendance rate. Session engagement (attendance across different sessions, time spent). Satisfaction scores (we aim for 4.5/5 or higher). Net Promoter Score for the event (we aim for 50+ NPS). Would-attend-again percentage (target 90%+).

Business impact metrics: Pipeline influenced (how much deal value among attendees). Customer health score changes (do attendees have higher health scores after?). Retention and expansion rates (do event attendees renew and expand at higher rates?). Referral activity (do attendees refer new business?). Community engagement (do they stay engaged after the event?).

Content metrics: Recording views and engagement. Asset downloads (templates, guides shared during event). Social media reach and engagement. Blog traffic from event-related content. Lead generation from gated event content.

Learning and improvement: What worked well (preserve for next time). What didn't work (fix for next time). Speaker feedback (what was their experience?). Attendee suggestions (what do they want next time?). Operational issues (where did things break down?).

We do a thorough post-event debrief within two weeks while everything's fresh. We document lessons learned and create action items for the next event.