Organize a Pep Rally for Offices Across the Globe? No Problem

“How will they click for the next slide?!”

This was keeping me up at 2:00 am on Thursday. I was still mentally reviewing the checklist I had filled with checkmarks over the previous week, but a Pep Rally has so many moving parts that I had forgotten to consider how the VIPs will move to the next slide.

This is what makes me bounce out of bed in the morning. Lying awake worrying about slides, and many more issues as I was about to find out, is what’s great about my job. Even though this was my third Datto Pep Rally preceding a DattoCon, it still felt like jazz: improvising on the fly based on what a collaborator jumbled, a technical glitch, or an oversight on basic presentation mechanics.

Months earlier, the UK team had approached me to spin whatever magic I did for our summer conference again for our fall conference in London. I was happy to oblige- bringing together a company across multiple time zones to share a common message? It was like catnip.

Unfortunately, compared to our summer conference, there was less clarity on exactly WHAT was going on at this fall conference. What was being released that the company should know about? Who should be celebrated for their hard work leading up to the conference? Even the simple question: When did we want to do this Pep Rally? The UK is five hours ahead of the US East Coast and eight from our West Coast team.

And Australia and Singapore? Sorry, mates, bet you didn’t want to get up at 2 AM.

At every DattoCon Pep Rally, there is some “fun event” that ties together the offices. For the summer we had a relay race between the offices that could participate. It was entertaining, but it could have been better, and it was a devil to coordinate. For the DattoCon London Pep Rally, I thought it would be more motivating to have the offices represent themselves doing the same task in each location. Originally I wanted a series of events like Pax East does the Omegathon, but I had somewhere around 15 minutes when they had multiple sessions over three days.

Fortunately, I remembered back when I was a Residence Director and had Resident Assistants do teambuilders at the start of the year during their orientation and training. One activity that was hilarious was watching them batter away at a frozen t-shirt until it was wearable. It was a hit for college students- why not a tech company?

When I floated this idea, my UK collaborator Emma instantly latched on and demoed the idea over the weekend. The weekend after she got married, mind you, she froze t-shirts in a variety of formats to figure out what the most effective freezing technique for the challenge should be.

Block of ice- no go, took too long. About five hours.

Wrung-out t-shirt folded tightly- much better. About 15 minutes.

On the day of the Pep Rally, the same day I laid awake wondering about slide transitions, t-shirts in Boston, Monroe, Norwalk, Portland, Rochester, and Reading UK were freezing according to Emma’s two pages of printed instructions. An additional challenge awaited the representatives of each office wherein contestants needed to arrange the planets of the solar system in the correct order to unlock the frozen t-shirt.

That Emma, bringing the fun event back on brand with the galactic theme for DattoCon London.

The Pep Rally got off to a great start, kicked off by the bow-tie-wearing emcee in the UK. We featured some product marketing managers to talk about the releases anticipated for DattoCon London (I figured it out: they shared their screen using a shared slide deck).

And then-

the challenge.

The contestants had not known what they were doing until I explained it live on the stream, during the introduction to the activity. Props to them, those brave souls signing up without knowing what they ultimately would be doing; they could have been doing anything, like math problems or pushups.

The frozen t-shirts were pulled from their freezers, the planets were handed to the contestants, and the race was on. Listening to the stream, there was furious “where does Neptune go” and “don’t forget the sun” and most of the teams finished that challenge at the same time. Frozen T-shirts were disbursed. Chaos ensued.

However, in the end, the Boston office had the most innovative and effective strategy. They sprinted to the kitchen and ran the hot water in the sink to quickly melt the shirt.

Four months of prep and a couple of sleepless nights, that was worth it.