Building a Killer Event Machine - 5 Lessons Learned From Hosting 500+ Events


Here at Work-Bench, we’re a small but mighty team of seven. As a venture fund, we have two missions: (i) to invest in the best startups building the next generation of enterprise technology and (ii) to grow and support the enterprise technology ecosystem in New York City. Central to the latter, we love using our 32,000 square foot workspace as a home and dynamic events space for enterprise startups and Fortune 500s, hosting over 200+ community events and meetups a year.

We’ve come a long way since we first started two years ago, and we’re always looking to improve the multiple events we host each week, from intimate, industry leader dinners to monthly sales meetups and sold-out annual data science conferences. To make it all work seamlessly, we’ve prioritized operationalizing, learning, and fine-tuning our events machine. Here’s a look at some of the most actionable lessons we’ve learned along the way:

1. Overorganize, Always

Prep work is even more important than you think. When things get hectic the day of, you want to have everything you can control under control.

Checklists reduce oversights - We love checklists. Modeled on The Checklist Manifesto, we’ve developed checklists for each step of event planning, along with day-of paper checklists for each member of our event team. Like doctors using checklists before surgery to reduce mortality rates, we use them to create common team expectations, reduce avoidable oversights, and make sure all goes smoothly. We use checklists for everything from mic tests and speaker asks, to making sure the lights and air conditioner stay on.

Logistics phone calls - Unlike panel prep, we schedule logistics phone calls for every event we host here at Work-Bench, no matter how small the event. We have found that these calls help us collaborate more easily, and understand their event more holistically than emails can. It also lets our hosts know that we are here to help them make their event successful, and paves the way for future partnerships and collaboration opportunities. Interestingly, one question we always ask organizers is about nametags - they often forget.

Postmortem documentation - After the event, a little bit of time spent discussing and documenting will save you a lot of work in the future - if you don’t document it, then it didn’t happen. We have event recaps and quick postmortems after every event to discuss in detail what went well (and what didn’t), so that we can always be iterating and learning from our past events. Celebrating event successes and recognizing achievements builds team morale and gives us momentum to plan for upcoming meetups and conferences.

2. Prepare for What You Can't Predict

As any event organizer knows, there is only so much you can do beforehand to prepare for the event. Even when you think you have everything covered: unimagined scenarios arise, speakers show up late (or not at all), and computers crash. That’s why dry runs are so important, but beyond that you have to get creative.

Know your attendee drop off rate - While it’s more art than science predicting exactly how many people will show, there are a few rules of thumb we’ve discovered. We see much lower drop-off rates for paid events, so we’ve started charging (and encouraging meetups) to charge a nominal amount for their event ($5 to $15) to ensure their guests show up. The more an event costs, the less drop-off you can expect, but for most types of free events, expect an average of a 50% drop-off.

Give back - If you order catering for a large event, odds are you may end up with way too much food. However, several NYC charities are willing to pick up donations of this type, as long as they’re arranged a few days beforehand - include scheduling a leftover pickup as part of your catering plan. Covenant House is a great organization we’ve worked with in the past, and NYC institutions Bowery Mission and NYC Rescue Mission will pick up as well (email us if you want contact info for any of three - we know some amazing people there).

Keep backups and doubles at the ready - Have backups and doubles at the ready (a computer, a charger, a converter, etc). One of our favorites for AV setup is this handy converter!

3. Build Relationships with Trustworthy Vendors

Anyone who’s ever waited for a mover long past an acceptable time can understand why it’s critical to have a team you can rely on. Events have a lot of moving parts. In order to ensure the event runs smoothly, you need to make sure all your vendors understand your vision for the event, what is expected of them, and when they need to execute. Quality, dedicated vendors can make or break your event.

Vendors can be your best friend in emergencies - We learned this during our first ever, sold out R Conference. Halfway through the afternoon coffee break, our coffee canisters had completely run dry. Because of the relationship we had built with our catering company, Cater2Me, we were able to call and request coffee on a Saturday. It was delivered within 30 minutes, and our attendees were able to make it through their afternoon slump.

Use trial and error, and don’t be afraid to switch - We’ve hired our fair share of sloppy vendors. After recommendations, there’s only trial and error. For example, we often hire TaskRabbits for general help, and invite back those who do an exemplary job. Over the past two years, a couple TaskRabbits have really stood out as exceptional event coordinators, and we have brought them on as part-time production coordinators. They’re always our first call when we’re hosting an event.

Remember your A-B-P’s (Anything but pizza!) - Helpful staff go a long way towards people’s impressions of an event, and so does high quality food. Unless you're Jared Lander's R Stats NYC Meetup, and you're known for your high-quality pizza selection, a nicer spread can help signal a quality event. Rather than fall back on something “easy” like pizza, spend a little bit of time figuring out an order from anywhere else. In the past, we’ve had empanadas from CaterCow, dumplings from Vanessa’s, and more. We add a variety of craft beers and some wine to the events when possible, and we’re always complimented on our food and drink selection.

4. Rely on Your Community

Your community is a killer marketing tool - If you let people who are already excited about an event know you need help spreading the word, they can blast that out to like-minded networks. When one of our events was lagging in sign-ups, we armed the parties involved with discount codes and offers to help put us at full capacity. It helps to partner with someone who knows the space well, who can help try engagement and interest around a certain topic.

Ask for help - Don’t be afraid to ask for help from friends or attendees. Members of your community might have the projector part you need or be able to hold their own on a panel of data scientists if someone doesn’t show.

5. Wins Are Wins - Broaden Your Definition of Success

It’s easy to get caught up thinking that event success is directly correlated with the number of attendees and revenue, but there are actually (and arguably much more important) underlying metrics to consider, such as these ones illustrated by Kaitlin Pike of StackOverflow. In the service of Work-Bench’s goal of building a strong, engaged enterprise tech community, we like to think about these questions instead:

  • Was the content original, tactical, and implementable (e.g. did the audience walk away with something they can use in their business or current role)?
  • Was the audience engaged, did they stay for the full event, and did they ask smart, related questions?
  • Were the attendees and speakers inspired and enabled to have in-depth conversations afterwards?
  • Did attendees make connections which are important to their business goals?
  • Do attendees come away with an understanding of what Work-Bench does and our mission?

Did we miss anything you think is critical to a great event? As we continue to improve our events strategy, we’d love to hear any battle-tested ideas from event organizers out there! Shoot us a note if you have any tips, and make sure to check out our upcoming events.

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