5 Critical Lessons Learned Organizing WordCamp Ann Arbor for the Third Time

In early 2014 I had just gotten married and recently moved into a new home. With two major life events out of the way, I decided I was ready to lead a WordCamp.

I originally planned to organize WordCamp Detroit. I was an organizer twice before and the event had missed a year and I didn’t want a continued loss in momentum.

WordCamp central had another idea. I live and participate in the Ann Arbor WordPress community, I should host “WordCamp Ann Arbor.”

I led WordCamp Ann Arbor for two years. Both were successful and we were gaining momentum.

In 2016 I suggested to my good friend Kyle Maurer that he take over as lead. After some thought he agreed. Kyle elevated WordCamp Ann Arbor from a solid medium-sized camp to a memorable and talked about experience. I’ve detailed his contributions here.

After his two years of organizing ended, we set out to find a new lead organizer. With no one volunteering, I decided to step up one last time.

Despite being lead organizer twice before and being an organizing an additional four times, I still came away with five important lessons about putting on a WordCamp.

1. Starting early doesn’t matter if you don’t finish early

We started WordCamp Ann Arbor extremely early. I was approved to organize the event and had a venue secured about 11 months out from the conference. We already had an organizing team of seven or eight people and kicked off the planning with plenty of time…

…yet, we were still scrambling during the last three to four weeks. This included tasks with less than five hours of total effort. Eleven months to get five hours of work done. Eek.

This was my fault.

I know how busy life is. Organizing a WordCamp is a voluntary, under appreciated job. Organizers need someone to lead, keep an eye on the schedule and assist in keeping eyes on the ball. I didn’t do a good job of doing so.

I mistakenly thought “Oh we can just chat on Slack from time to time,” but I was essentially offloading my management responsibilities onto my team members.

So despite starting early, we didn’t reap many of the benefits of starting early outside of venue selection (which we ended up having to move anyway after WordCamp US announced the same dates.)

Lesson learned

Starting early is incredibly valuable. It gives you the pick of venues, sponsors, and speakers. However, if you don’t move quickly it doesn’t matter. Someone needs to take the lead and help guide the team towards the end goal with a regular, predictable cadence.

I recommend having monthly or twice monthly check-in calls– even if they are short– so you can help answer questions and do your job in enabling your team to complete their responsibilities.

2. Don’t make any assumptions

If you’ve hosted a WordCamp (or any event) before you’ll likely have assumptions about how easy or hard particular aspects of the event will be. This year we made assumptions about sponsors.

Every year prior we’ve had overwhelming sponsorship support. In fact, the past three camps were well over funded. This past year we had little worries about raising enough funds… but we should have worried.

In the past we had three sizable hosting companies, all local to Michigan, contribute approximately $10,000 in sponsorship dollars between them.

This year, one became a national sponsor and bought out the other, eliminating half of our expected sponsorship contributions. We also found significantly lower sponsorship interest than years past.

Two weeks out we were scrambling to raise the last few thousand dollars required to host the event.

Luckily we had two amazing local companies, LearnDash and A2 Hosting, who purchased additional sponsorships on top of what they’d already contributed.

Lesson learned

Approach each camp as if it were your first time. What went well in the past might not this time around. We waited longer than we should to try and address our budget deficit because we assumed a regular sponsor was going to contribute… only to find out they were acquired.

Similarly, we used the same venue as the two prior years. In the past we had almost no issues, but this year the A/C broke in one room. The “event manager” on staff was a student and didn’t know how to get it fixed.

Plan for everything, even if it was fine before.

3. Document, document, document

Big picture organizing a WordCamp isn’t that complex. There are a host of relatively straight forward tasks to complete:

• Recruit people to help
• Secure a venue
• Accept speaker applications
• Attract sponsors
• Select speakers
• Plan a schedule
• Design and order swag
• Design and order marketing assets
• Host a two hour speaker / sponsor dinner
• Host a two hour after party
• Plan breakfast / lunch / coffee

Many of these tasks are probably less than eight hours start to finish… but the devil is in the details.

• When will the event start? End?
• How many speakers can we accept?
• What topics do we want to have discussed?
• Should we have free drinks or paid?
• Full dinner or just appetizers?
• What’s more important in an after party venue, location, price of quality of food?
• What size shirts should we order?
• What signs do we need?

There are lots of details to decide and discuss. If you don’t document what’s required, what’s discussed, and what’s decided it disappears into the ether.

I did a very poor job documenting our conversations. We used Trello to manage the planning and it worked out just OK. I’m sure in part because I could have done a better job transferring information and keeping it current.

As a result we had some hiccups that could have been easily avoided. Not getting the right sizes for T-Shirts was one of the biggest mistakes made, which is so easily preventable.

Lesson learned

After every meeting notes should be saved and transferred into the appropriate places. This way your team has an easy reference when they are ready to work on again. Remember, these are volunteers and it could be weeks between working on the project again.

In the future I’d keep things simple and use a combination of Google Docs and Google Sheets. I don’t think you need a full fledged PM system, just a place to record status and notes.

4. Volunteers are the life blood of any WordCamp

You can’t run a WordCamp without volunteers.

We’ve always struggled attracting volunteers. I get it, I almost never volunteer unless I’m also an organizer. You give up a portion of the camp (if not the whole camp) to help run the event without the benefits of being a full organizer.

We were extremely fortunate to get a dozen helpful volunteers who did an amazing job, but we still were short and had to pull in key organizers instead.

I’d like to thank the volunteers for 2019:

• Cheryl Gong
• Dave Rottervision
• Tana Dean
• Suzanne Seible
• Evan Farmer
• Declan O’Neill
• John Castallesse
• John Wright
• Evan Farmer
• Moe Ahmed
• Jess Bowyer
• Kyle Maurer
• Lyndsay Johnson
• Amanda McDonald

Lesson Learned

Do a better job making volunteering desirable.

• Invite the volunteers to the speaker / sponsor dinner
• Give them a free ticket
• Give them a unique volunteer gift
• Give them a link on the camp website

Maybe even more?

5. Timing is everything

The past four WordCamp Ann Arbor’s took place in early to mid fall, largely because of venue availability and nearby camps. In Ann Arbor, the only venues for a multi-hundred, multi-track event are University of Michigan buildings.

We’re also restricted based on home-game weekends. This cuts out about half the available weekends during the late summer and fall seasons.

We initially scheduled the conference for early spring. As mentioned earlier, WordCamp US announced the same date and we had to reschedule. The only weekend available was in late August and required that we shift from a Friday and Saturday event to Saturday, Sunday.

This significantly impacted attendance. In 2017 we had over 350 attendees, with even attendance across both days. In 2019 we had around 100 fewer. Saturday was extremely well attended, Sunday only had about half as many people attend.

More people are on vacation in late August, school is about to start, the weather is nice, maybe you’re less focused on work and less motivated to attend a professional conference.

Giving up an entire weekend is hard as well. Personally, I’d rather use one work day and one weekend day over giving up an entire weekend.

Lesson learned

The days selected and time of year dramatically impact attendance. In hindsight, I should have pushed the event into late fall or even early winter.

In summary

No matter how many events or WordCamps you host, something unexpected will happen. You’ll learn something new. What to do and what not to do.

When this happens document it like I have. Even if you don’t plan on organizing again (I don’t) you can help the next person avoid the same mistakes.