No matter what stage your business is in, there are a few universal truths: people are one of your biggest expenses, company culture is critical, and your team needs clear goals.
A well-planned company offsite can help you excel in all three categories. It's a time to reset, make sure everyone is aligned, and gives the team an opportunity to connect outside of the office.
Even though my new venture firm was just established this year, I knew an offsite would provide time for us to come together as a growing team to collaborate on a shared vision for our future. That's why we recently took 24-hours away from the daily hustle for our first annual team offsite. I've found that offsites are helpful for businesses at all stages. As a young company that is in the weeds of building a business from the ground up, it felt particularly impactful to step back, spend time together and align on where we're headed.
Making everyone unplug for the day is quite literally a large business expense (this Harvard Business Review calculator estimates that 8 hours of time from 10 mid-level execs will run you over $11,000, for example). But it pays off. Investing in your employees and aligning on a clear roadmap and priorities will save you in the long term.
Here are my key takeaways to put together an offsite that's thoughtful and effective.
1. Invest in Planning
This is the most important tip I can give you: invest time upfront. Our offsite agenda was something we workshopped as a group. We talked about it in team meetings ("What are the items we must cover?"), we sent around a draft agenda and opened it up to comments, and we talked through the nitty-gritty of every plan (from dinner reservations to carpool arrangements).
Yes, it can feel excessive to spend so many hours planning for an event that's only a day long. But trust me--when you put the time in upfront, you'll maximize every minute you have together. You'll get everyone's best brain power and creativity, because you've done the work to clear obstacles in advance. When offsites don't have a clear purpose or set of goals, employees feel it. I've heard so many stories of offsites that felt like a waste of time, and it's usually because there wasn't clear direction. A productive offsite should be more than just a change of scenery. It doesn't need to be a huge production to be a success, but it does need to be purpose-driven from the start.
2. Time It Right
In order to be productive, we had a "no devices" rule during our group sessions. You have to be thoughtful about your business needs when you encourage everyone to fully unplug.
In the VC industry, summer can be a (slightly) slower season, so it made sense for us. Think through what works best for your industry. For example, no retail business should plan an offsite in the midst of peak holiday season!
Once you've zeroed in on a date, send a calendar invite to the team far in advance. If you're asking employees to stay overnight, they need to plan accordingly so they can come to the table fully present. Over time, find an offsite date that can be recurring (i.e. "we always have ours the second week in July") to make scheduling that much easier. Many companies choose to host their offsites yearly but the cadence can vary. In my experience, a yearly offsite allows teams to step back from the day-to-day and refocus their attention to bigger picture goals without being too disruptive to regular work.
3. Find a Great Location
The whole goal of an offsite is to step away from your usual surroundings. There are so many options now, from traditional retreat sites (like hotels and conference centers) to startups that will rent you a short-term space (like WeWork, Breather, and Convene).
Pick a spot that's easily accessible and make sure the space will be conducive to your work. At the Inspired Capital offsite, we reserved a room with ample whiteboards, tables, and even bean bags to allow for great brainstorms and active conversations. It didn't hurt that there was a restaurant right upstairs, which made breaks for breakfast and lunch incredibly easy.
I also love the idea of choosing a place you can return to again and again that becomes an ingrained company tradition.
4. Divvy Up the Work
Assign one point person to own the logistics and details of the day. For us, that was our Partner, Lucy Deland--co-founder and former COO of PaperlessPost--who is a master organizer.
But don't stop there. Give everyone attending ownership over a portion of the offsite. When people feel ownership, they'll be focused on producing a great session and they'll be more likely to participate respectfully in everyone else's sessions. Owners are responsible for building out the content, doing all the prep work, and making sure the session keeps moving.
Lastly, don't forget to pick a "master of ceremonies" who can keep an eye on the clock and adjust the schedule if needed (i.e. call for a 10-minute break if eyes are glazing over).
5. Make Time for Fun
Outside of walking away with a sharp strategic plan, offsites enable stronger team connections. You can max this out by bringing in professional coaches to lead you in group exercises -- or keep it simple. Whatever you decide, give everyone choices, from fun dinners to outdoor activities to board games. Ensure that there's an activity the whole group is excited to participate in.
6. Check Your Progress
You picked a great place, brought the whole team together, agreed on priorities -- now what? In order to make your offsite investment worthwhile, you have to carry through your takeaways throughout the rest of the year.
In the short-term, ask everyone to share their notes with the whole group. Then, add "offsite debrief" to your next team meeting agenda. Discuss big takeaways now that you've had some time to settle back in.
Over the long-term, codify the objectives you agreed on in a shared document. Each quarter, check back in on how the company is progressing. Are there initiatives you left the offsite incredibly excited about that have fallen off? Have priorities shifted? Keep it an open conversation throughout the year. Aligning your team is an ongoing process, and your offsite is just one milestone along the way.