Doing Your Own Events Well
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Even though peak-pandemic days are behind us, there’s still a deeply pent up desire for human connection, where you spend time with like-minded people, if only to see if God is singling you out or everyone might be in the same boat.
I’m penning these thoughts from two vantage points: someone who does 15-20 keynotes every year, and someone who puts on a half dozen events every year as well.
I’m still learning what works and what doesn’t, but I’m going to suggest what an ideal event might look like. My hope is to influence things a bit and help them be better for the participants and the speakers. And I’m going to tell you about a very special event coming up in Tuscany this September, too.
Keys for Attendees
Here’s a quick list of how we try to make the event great for attendees. All of these are not possible in any given event, of course:
- The quality of attendees is just as important as the programming. You’ll get better attendees if you charge enough to make sure this event means something to people. This is supplemented by the spirit you bring to the place (transparency) and how you talk about it, overtly, from the stage (“this is our hope for you at this event”).
- Leave 30 minute breaks instead of 15 minute breaks between sessions. Give people time to connect and breathe. Again, it’s not just what they hear from the front but what they learn from each other.
- Engage attendees, wherever possible, by having them lead informal roundtables or discussions. They’ll be prepared, they’ll tell people about their participation, and they’ll jumpstart the connections that make events so valuable. Have people apply and screen them to keep the topics balanced.
- Run the thing like a train schedule in Switzerland. Start on time, end on time, and above all, honor the attendance of the participants by sticking to the schedule. Implore your speakers to be prompt, and pull them off stage when they aren’t.
- Don’t record it. People come in person or they don’t. And recording it complicates things with rights…and speakers won’t be as likely to speak freely. Underneath this is an assumption: the event should be all in-person or all remote. Nothing mixed. It’s messy and doesn’t feel right.
- Slide some unpopular topics in—the things that attendees need to hear even if they wouldn’t choose to. You’ve earned that right, and one or two of these is an example of you, leading. Make them eat vegetables with the steak.
- Employ one or two gracious, empathetic, extraverts to just “notice” things among the attendees. These are Happiness Aides, and they have money and the freedom to spend it to elevate the experience for individual members. Maybe it’s a pharmacy run, finding an extra charger, or rescuing someone who’s obnoxious.
- Be careful with Q&A after a keynote. If you’re going to do Q&A, encourage people to submit questions to a moderator, who can decide if we should use the entire group’s time on a single person’s question. Q&A sessions are especially vibe killing if you’ve had a rousing keynote where a dismissal is perfect, followed by people streaming to the speaker for more.
- Speaking of speakers after they finish, have the MC gently guide the speaker to the back or a side room so that the next speaker can get in place and prepare for their start. Attendees want to connect with a speaker, but it shouldn’t impede the next one. This is crowd control, essentially.
- Consider adding some drama from the stage. You could do some role-playing, an unrehearsed “audit” of an attendee firm, a panel of opposing viewpoints, etc.
- Facilitate connections for 1 month ahead of the event and 3 months after. Since we attract an international audience, we prefer WhatsApp for this.
Keys for Speakers
And here’s how I think about speakers, as a speaker myself and as someone who hires lots of them:
- I’ve hired professional speakers and professionals who speak, and I’ll never hire a professional speaker again, even though we’ve had some of the best. But even the best come across as highly rehearsed, barely personalized, too expensive, and not all that memorable. Done with that. Even if I’d paid $4,000 instead of $40,000, I’d still not do it.
- Be aware of diversity, but use it mainly as a tiebreaker. The hardest diversity to achieve is diversity of thought, because you won’t necessarily be connected with those people.
- Reserve one slot for someone who shows early promise as a speaker but hasn’t yet had many opportunities.
- Trust your speakers or don’t hire them. Trusting them means chatting about an appropriate topic, but letting the speaker gravitate toward something they are passionate about. And no approval of content. Ever. Trust them or don’t.
- Having said to trust your speakers, make it very clear that there is no selling from the stage. Charge enough so that you can pay speakers enough money (or give them enough exposure, instead) so that they don’t feel the need to sell. Selling from the stage is a major error and attendees gag a little when it happens.
- Give each speaker a free pass to the entire conference, but staying should be their choice. The best speakers probably have a busy life.
- Let speakers attend any future occurrence of the same event free of charge. If you run a great event, they’ll love that, and any time they come back, attendees get more exposure to great thinkers.
- Pay them a flat fee. Let them make their own travel arrangements, always. Book them a hotel if they want it, but never book their flight. Let them choose coach or first class, and their choice comes out of the flat fee.
- Don’t fear your competitors. In fact, put your competitors on stage. You get the spotlight for conceiving of an event and putting it on. Be the adult.
- Never require speakers to promote your event. When you do that, you’re essentially borrowing their fame. Don’t do it. If the event is amazing, a speaker will naturally want to promote their participation. This is one of the silliest elements of the modern event world: a nobody puts on an event that features well-known names, and those speakers are contractually required to promote it to their followers. Silly.
- Find speakers and don’t ask for them. You’ll want to turn down most people who ask to speak at your event. Most of your awesome speakers are the ones you discover on your own or you hear about from people you trust. And issuing a “Call for Speakers” is like smothering your body with BBQ sauce and jumping into a pond of crocodiles.
How to Not Lose Money
If you’ve done events (you should), you’ve already discovered the easiest way to lose money, and that’s to book a room block that you’re responsible for if it doesn’t sell out. You’re not going to have fun if you’re lying awake at night calculating how much money you’ll lose and then burning your brand begging people to come. No, make it a wonderful experience for you, for the speakers, and for the audience. If you’re terrified about filling a room block, nobody is going to have fun.

