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Running Dynamic Offsite Meetings Can Bolster Your Startup - Here’s How

By Christopher Steiner  •  Apr 27, 2017

Christopher Steiner co-founded Aisle50, YC S2011, which was acquired by Groupon in early 2015.

Offsite meetings have become standard fare in workplace culture. Big companies, medium-sized companies, and startup-sized companies rely on offsites for all kinds of critical or additive missions.

In most cases, companies use offsites to deliver on a number of fronts, including:

  • Generating camaraderie
  • Producing new ideas/innovations for the company
  • Rewarding periods of hard work
  • Teaching and learning new things as a team
  • Reemphasizing or adjusting the main mission of the company

No perfect formula for offsites exists, as every company, team and market is different. But offsites that are well executed can be powerful levers for startups. And when called for, offsites can even be transformational for a company that's seeking a new tack or looking for ways to change its business.

We've gathered findings from our own experiences, plus the input of other founders and team leaders in our network, and put together a set of best practices for holding offsites. Adhering to these suggestions provides founders and companies a steady base onto which they can build a culture and tradition of effective and impactful offsite meetings.

In brief, these best practices include:

  • Take planning and preparation for the offsite seriously   
  • Fit offsite activities, even the fun ones, to the meeting's goals and desired outcomes
  • Have goals for the offsite, make them known
  • Mix formats of presentations and events at the offsite
  • Engage the whole team in planning and putting together the focus of event
  • Get feedback about the offsite during the event
  • Revisit the learnings and outcomes of the offsite three months afterwards
  • Leave room for downtime at the event
  • Engage the whole team in planning and putting together the focus of event

Mix formats of presentations and events at the offsite

Watching people parade up to the front of the room and launch into different presentations all leveraging the vagaries of PowerPoint slides and a well-rehearsed set of verbal cues can make for a long day. Team members will inevitably find their minds wandering. Only some of the material and presentations will be absorbed.

Organizers of an offsite are well-served to get participants moving, physically and mentally, engaging them in different spaces through different mediums, says Scott Heimes, CMO at Sendgrid, which holds two large-scale retreats every year for its employees, one of them in Mexico.

Heimes recommends that presentation formats switch between keynotes, panels and fireside chats, among other things, so that the material isn't coming strictly via one-way communications, where things are simply being told to employees. Heimes likes to use video content to add energy to the room when needed, sometimes in kicking off an event or a single session.

Sendgrid will also break up its sessions by inserting fun trivia-type games where employees are called up to the stage or the front of the room to participate in an activity or game.

Have goals for the offsite, make them known

Most offsites have themes, but many don't have goals. They should. Giving the event a purpose, an end focus, will help crystallize the mission behind every session, and help team members stay engaged and follow a thread through the event from beginning to end.

Thoughtful offsites with specific goals can be quite powerful.

Tien Tzuo, the CEO and founder of Zuora, which helps companies manage subscription-based products, turned to an offsite after the company's growth stalled following its first 12 quarters of steady expansion.

Churn had grown faster than new bookings for Zuora at this point, and Tzuo sensed the company was at an inflection point that could lead to its ruin.

“We were starting to lose touch with our customers," Tzuo says. "We had become more focused on the metrics that mattered to our departments than the ones that mattered to our customers. And because our product is complex, it was hard for any single employee to understand everything we do for any customer.”

At this time, all of Zuora's teams were focused on their specific tasks, which they tended to do well. The sales team could sell. The implementation team could implement and the support team could support. But the company as a whole had lost touch with what its customers wanted and needed.

"The departments weren’t communicating, and customers were frustrated every time they had to explain their needs all over again," Tzuo says.

So Tzuo and his team planned out an event where the entire company—from receptionists to engineers, about 200 people—went offsite to develop what they called a 'customer service formula.'

It was this specific goal that led to an invigorating event that would change the direction of the company.

At the offsite, Tzuo and the rest of Zuora developed a formula built around what it calls "Nine Keys." The entire company has since been organized around the Nine Keys, which run through Zuora's entire customer engagement cycle. The process was transformational, and the team emerged unified with a focus on the new stated tenets of the business.

Zuora made its customers happier, turned around its churn problem and has now raised more than $250 million, with more than 600 people working at the startup that was founded in 2008.

“The keys are in the DNA of all 200 employees," Tzuo says.

Get feedback about the offsite during the offsite

Just as with anything, ideas and feedback around an offsite are more valuable when they're fresher. There's a reason airlines and hotels send you email surveys asking about your experience within 24 hours. This is the period where you remember everything clearly, where you remember the good aspects of the experience as well as the bad ones–and this is a time were you still may care enough to comment.

The same idea is why founders and companies should get feedback on their off-site meetings at the end of the event.

"Your first offsite won't be your last offsite, and in the rush to get to the agenda, to get to the activities and execute the logistics of the offsite, people often forget to close the loop and collect feedback," says Ada Chen Rekhi, former SVP of marketing at SurveyMonkey and now the founder of NoteJoy, a social document editor built for teams to capture, share and discuss their work.

Rekhi recommends using a simple lightweight survey at the end of the offsite, issued to all attendees with the promise of anonymity to ensure honesty and constructive comments, with questions such as:

  • What worked and what didn't work during the offsite?
  • What content was especially good, and what missed the mark?
  • What is the likelihood you'd recommend this offsite to a peer?

The aggregated and usable feedback becomes an opportunity for improvement as well as coaching for later on.

Revisit the learnings and outcomes of the offsite three months later

Offsite meetings shouldn't just be special snippets in time in which the whole team gets along, has fun, and comes together to form well thought-out hypotheses about the company and its mission. The learnings from offsites should live on indefinitely with the company, with its employees.

"Offsites typically fail because they are viewed as events," says Nancy Halpern, a Fortune 500 executive coach who has facilitated dozens of offsites.

Halpern suggests having a team meeting three months after the offsite to follow up and ensure that its outcomes have made it into company processes and remain top-of-mind.

If the goal was to build camaraderie between departments, the offsite will end up being ineffective if the friendships and discoveries made at the event aren't carried through to the office, if changes aren’t made according to the findings of the off-site.

That's why it's important to circle back and examine if the company has in fact absorbed the learnings of an offsite and made progress with them as a company.

Fit offsite activities, even the fun ones, to the meeting's goals and desired outcomes

For offsites with specific goals, such as the one run by Zuora, it's important to ensure that activities scheduled around the event dovetail with desired outcomes.

For instance, for teams who are seeking more togetherness and a unifying experience overall, it may be wise to avoid scheduling a hyper-competitive ping-pong tournament during the offsite. A scavenger hunt where 4-6 employees—perhaps each from different parts of the company—work together on teams is a better choice.

For a company-wide effort focused on improving customer service and empathy, activities focused on teamwork and understanding others might do the trick. Here's where games like charades and 20-questions make sense.

Take planning and preparation for the offsite seriously

Preparation is critical to holding a successful offsite meeting. For employees at the event, it should feel well-orchestrated, thought out, and knit together. This isn't a larger version of stand-up meeting, where everybody shoots from the hip and walks through their tasks at hand.

This is about achieving something specific, about imbuing participants with a set of values or knowledge they didn't possess before. Hastily set up meetings won't achieve those goals.

"If the event looks effortless, it probably means that a tremendous amount of planning went into it," says Jen Coyne, the co-founder and CEO of The Peak Fleet, which works on event curation and helping company management better engage their teams.

Coyne recommends that the facilitators keep the agenda flowing and portion out the right amount of time for each event. Putting the events together with a theme and a story is important, as well, as it will raise the perception of cohesiveness with the attendees and help achieve the goals of the event.

The preparation behind an offsite meeting comprises a good deal of the challenge of holding a good one.

Engage the whole team in planning and putting together the focus of event

People are used to hearing the leaders of the company, the co-founders or CEO, talk all of the time. A good offsite will put other people in front of the group at different times. This shouldn't be an exercise of having the co-founders prattle on for an entire day.

Giving team members assignments and presentations that will be part of the offsite shows that founders trust their team, and it will also further engage the rest of the team, including those who are presenting.

Long before the offsite is to take place, suggestions can be taken from all employees on the topics it should focus on. Founders may eventually steer the meeting's focus and theme to where they think the time will be best spent, but going through this exercise will sometimes raise issues and topics of note.

Some startups may choose to let team members propose segments. A front-end designer may want to put together something on user experience, or the CFO might want to build a presentation on how capital runs through the company and how it can be most efficiently used.

Just as with anything else, involving people in the conception and planning of an event will increase the level of buy-in from all participants.

Leave downtime during the event

An off-site event shouldn't be an all-day firehose of information. Not only can that format be exhausting, but it's also likely that it won't be as effective as a more balanced day that leaves time for team members to do other things—or even to just take a nap.

Darren Eich, who has a Ph.D. in in Educational Leadership & Policy Analysis, and who has developed innovation and idea programs for clients such as the United Nations and Procter & Gamble, says that the times when people are allowed to be "off" rather than "on" can be some of the most productive of an offsite.

"The best learning, connecting, and action happens during downtime, like on a bus to an offsite location, at dinner, or during a break where people go hiking, sit around a fire, or even play a game," Eich explains. "Make sure to see these opportunities as part of your offsite event."