The success of an event starts with strong foundations — and one of the earliest (and most delicate) decisions is the format. Should Checkout Summit be a single intense day or a multi-day experience? Should it have concurrent talks in multiple rooms or a single, shared track for all? These aren’t just logistical choices — they define how attendees will engage, network, and retain what they learn.
As usual, I didn’t take this decision lightly. I brainstormed internally, asked around in masterminds and Slack groups, and finally turned to my favorite validation tool: a Twitter poll. In this post, I’ll walk through the reasoning behind each option, what the community voted for, and how I reached the final format decision. Spoiler: the people spoke loud and clear — and I’m happy they aligned with my gut feeling.
Let’s take a look behind the scenes at how Checkout Summit’s format came to life.
The Starting Point: Format Questions
The logistics of an event are more than schedules and spreadsheets — they shape the entire experience. When I first started thinking about Checkout Summit, I knew I had two big format questions to answer:
- Should the event run over multiple days or be condensed into one?
- Should we pick weekdays or weekend days?
These questions impact everything — how much it costs, how attendees plan their trip, how much content they can consume, and how much hallway conversation can actually happen.
So I started with a bit of solo brainstorming, then moved to group feedback via mastermind calls, Slack chats, and finally… Twitter.
Poll #1: One Day vs Multi-Day
Here, I asked: “How long should a WooCommerce conference like Checkout Summit be?”. The choices were:
- One day
- Multi-days
The results were clear: 27% voted for a 1-day event, with Multi-days totaling 73%. That gave me a strong signal — people prefer a longer commitment if they need to arrange travel and accommodation.
This matched what I was seeing elsewhere too. A single day simplifies logistics, costs, and speaker availability, but I liked the idea of allowing people to enjoy a longer event.
Poll #2: Weekdays or Weekend?
This was a trickier one. My initial gut feeling leaned toward weekdays — especially Thursday and Friday — because I wanted Checkout Summit to feel like work, not a side activity squeezed in between errands or family time.
But of course, assumptions need testing. So I asked the community again: Should Checkout Summit happen on weekdays or over the weekend?
The result? Weekdays won with 66.7% of the vote, versus 33.3% for weekends.
This was important validation. It confirmed the audience sees this as a professional conference, not just a casual meet-up. People are willing to carve out a Thursday or Friday, treat it as a legitimate business trip, and even get their employers or clients to cover the expense.
A weekday format also helps attract speakers and sponsors — who tend to have more flexibility during the workweek, and might be hesitant to give up weekend time.
And from a venue standpoint, weekday availability is better, prices are more reasonable, and there’s less competition with weddings or other private events.
Multi-Day, Weekday: Why It Works
With the community feedback in hand, the format became clear:
- Two full conference days
- Midweek (Thursday and Friday)
- Arrival on Wednesday, departure on Saturday (unless they want to extend their stay!)
This format gives space for more talks, longer breaks, deeper conversations, and a more relaxed pace. Rather than cramming everything into one day, we can create a flow — opening keynotes, sessions that build on each other, and time in between to actually connect and reflect.
It also makes the trip more worthwhile for those flying in. If someone’s coming from far away, giving them two solid days of content (plus optional extras on the surrounding days) feels like better value — and more respectful of their time and investment.
There’s also room now for creativity: maybe a morning walk, a beachside coffee session, or a sponsor-led dinner. And still, it doesn’t feel overwhelming — because everyone is already planning to stay for a few days.
Why I’m Happy With These Decisions
Deciding on a multi-day format has actually simplified things in a surprising way. With two days to work with, I don’t have to stress about squeezing every idea into a tight schedule. I can space out talks, include more networking, and even accommodate more speakers without sacrificing quality or attention.
The weekday slot — Thursday and Friday — is perfect. It keeps the event within the work calendar, encourages business expense coverage, and leaves the weekend open for rest, travel, or optional side trips.
From a community-building perspective, more time together means stronger relationships. A longer event fosters better conversations, repeated encounters, and a sense of shared rhythm.
And as the organizer, it gives me more time to adapt, to observe, and to enjoy the event alongside everyone else — not just run around for 12 hours straight.
Conclusion
Thanks to two clear Twitter polls, Checkout Summit now has a solid foundation: two days, midweek, professional but relaxed.
It’s a format that gives space for learning and human connection. Now that the structure is set, I can move forward — with clarity — into speaker outreach, program design, and all the pieces that will bring Checkout Summit to life.
