When we did our first retreat in January 2016, we knew we'd hit a point where bringing the whole company together in one place made good business sense. We'd been growing fast, essentially tripling headcount in the previous 12 months and staffing up three offices in three different countries.
Different challenges arise when a company reaches about 150 employees. To keep moving fast, everyone should be aligned and collaborating effectively, even as new faces get plunged into the whirlwind of work. We also want new hires to understand and become immersed in our culture and know they're part of something bigger than a job. And we want to recognize and celebrate the contributions of valued employees and everything we've accomplished as a team.
Moreover, at Udemy, we move crazy-fast. We work in sprints and don't often get to stop, take a breath, and think ahead 12 months or more. In the early days, scrappy startups can operate in short cycles--who knows if they'll still be around in a year--but we know we're here to stay and our vision extends decades into the future. The retreat gives us a chance to see the big picture and make big bets on what we can achieve over the longer haul.
Most important, it becomes harder to get to know coworkers on a personal level when you're growing fast and moving fast. We know teams work better together when they forge relationships and have a shared mindset. That's how empathy develops, and it's what keeps us going when stuff inevitably hits the fan.
It's no small undertaking to convene 270-ish people at a retreat and take them away from "real work" for three days, but the payoff is huge and lasts all year. Our retreats blend fun bonding activities with substantive business content in order to build the trust and connections from which great teamwork happens. Here are a few things we've learned that can help others considering this type of event.
1. Start planning early.
When balancing customer-facing activities against an employee-only event, it can be tempting to give short shrift to the latter. I'd strongly caution you to treat this as seriously as any major initiative your company undertakes and give it the due time and attention it requires. If you try to wing it, your audience will feel it and come away with very different responses than what you intended.
2. Assemble the right team.
Not only do you need to allot plenty of time for planning, you need to assign proper resources to the effort. First, your entire executive team needs to define the vision and objectives of the event. You'll probably need to take people off other work too. Event planning is intense, and you shouldn't expect this project team to juggle too many unrelated tasks close to the event date.
3. Outsource the tactical.
Let your employees focus on aspects of the event that are core to your mission and culture--setting the agenda, developing presentations, prepping speakers, etc.--and let an outsider handle operational responsibilities that are time-consuming but don't require an understanding of your business.
4. Be extra-thoughtful about messaging.
Of course, you should always think before you speak on behalf of the company, but everything carries even more weight at a retreat, where daily demands and distractions are absent and full focus is on presentation content. If you can't back up the words with action once you get back to the office, you might need to revise.
5. Make it personal.
It may be a crowd of 200 or more people, but you can still communicate "what's in it for me" and help employees understand how the content applies to their department and role. Follow up with breakout sessions and continuing conversations that connect the dots from individual contributors to broad, company-wide goals and priorities.
6. Balance content, interactivity, and fun.
Part of the intent is to reward people for their hard work with a getaway and enjoyable activities, however, if you offer nothing but fluff, they'll consider it lost productivity. We spent more time on business content this year, based on 2016 post-event survey results, but we found engaging ways to deliver it.
Hosting a retreat doesn't mean you're putting important work on pause. On the contrary, it's an investment in the future that becomes a special part of your company lore and culture that people will remember and talk about.