Are Lavish Work Retreats Worth the Effort?

​The long-venerated corporate retreat has shaken off the cobwebs gathered during the pandemic lockdowns and is emerging as a useful management tool to strengthen employee engagement.

It's not a moment too soon.

Successful companies have long pampered their in-house talent with so-called work retreats that are often held at fancy resorts, all on the company dime.

"Being able to trust your colleagues is a cornerstone of great teams, and establishing human connection online is hard," said Raechel Timme, head of human resources at Coda, a cloud-based software company in Mountain View, Calif. "So, when teams do gather in person via company retreats, they get to focus on companywide relationship building, and not producing work."

Yet with pandemic-induced remote work and the now-skyrocketing remote and hybrid work opportunities, C-level executives are wringing their hands about what they perceive to be

an astounding lack of employee connection and engagement. A recent study by Thriver showed that 39 percent of U.S. executives indicate that employee engagement is "the most significant challenge" companies faced during the pandemic.

Corporate Getaways to the Rescue?

Generally speaking, retreats are not necessarily for setting strategy or drilling down on company goals for the year.

"While that can be a bonus, it's really about side conversations with people, building bonds and all the things that we as a primarily remote company don't get to do on a daily basis," Timme said.

One challenge with rolling out a corporate retreat is that employees are taken out of their comfort zone and dropped into a resort or vacation-like spot where they don't know what to expect.

"The idea of drinking on a beach with co-workers has some employees feeling uneasy, but the idea of not going [makes workers fear] of losing valuable networking opportunities," said Jennifer T. Long, chief executive officer of Management Possible, a management coaching firm in Denver.

In fact, she said, some workers may actually dread such gatherings and feel anxious about attending. She suggests articulating "a compelling and strong 'why' around your purpose to get together at a resort, and allow[ing] your participants to [suggest] some preferences. Then you'll have a better experience all the way around. Go in with a compelling purpose and outcome."

Long also advises company executives who run retreats to be careful about over-scheduling. "On a corporate outing, connecting your teams is critical, but 24/7 connectivity is invasive," she said. "You have to strike a good balance of togetherness and free time."

Best Practices on Corporate Retreats

Here are some suggestions for planning a successful corporate retreat:

Invest in planning. When you're getting everyone together in person, every message matters.

"Planning and prepping is just as important as the event itself to make sure that it's effective and the right messages are conveyed both formally and informally," Timme said. "Find the right amount of structure. Instead of focusing on planning or giving long presentations, be sure to make time for casual conversations."

Timme doesn't think corporate retreats need to be frequent. "You don't have to be constant. The infrequent but memorable cadence can be even more impactful," she said.

Keep it light. At Merchant Maverick, a small-business services company in Santa Monica, Calif., company executives host an annual retreat to create space for in-person interactions and to build and nurture existing relationships with team members.

"For us, setting expectations beforehand is really helpful," said Charlotte Kackley, human resources director at the company. "At our annual retreats, very little work is involved. The purpose is really to connect socially and get to know each other more."

Kackley and her team make sure there's time dedicated to group activities, and also designated flex time where team members can break off and do their own thing.

"Having optional downtime is especially nice for those who may be more introverted and would like to recharge independently," she said. "Unlike a lot of companies, the annual retreat at Merchant Maverick is not limited to certain departments [such as sales] or levels within the company [such as leadership]. The fact that everyone is included makes the event a lot more fun and enjoyable, and dispels the feeling that any one group within the company is more crucial to our overall success."

Know your goals. At Checkr, a human resource services company in Burlingame, Calif., management views regular retreats as an important investment in its team and in the company's culture.

"What's key for us is the business rationale for our retreats, which is twofold," said Linda Shaffer, chief people and operations officer at the company. "First, our retreats provide an opportunity for our team to bond and build relationships outside of work. Secondly, they allow us to invest in our team's professional development."

Checkr senior executives who plan and run these retreats expect multiple positive outcomes from the events.

"We expect to see improved communication and collaboration within the team, along with a deeper understanding of each team member's strengths and weaknesses," Shaffer said. "We also expect to set greater alignment between the team's goals and the company's strategy, and an opportunity to build trust and camaraderie within the team."

Make civility a priority. One of the main dangers of a corporate retreat is the potential for inappropriate employee conduct due to the more relaxed setting. Inappropriate conduct can range from overindulging in alcohol to sexual harassment.

"To avoid misunderstandings, management should remind employees that the retreat is an extension of the office and that office policies still apply," said Stefanie Camfield, assistant general counsel at Engage PEO, a human resource outsourcing firm in Orlando, Fla. "Leadership should be visible during the retreat, model appropriate behavior and look out for potential issues."

Know your audience. Any seasoned executive knows it's virtually impossible to please everyone all the time, so be sure to incorporate some variety when it comes to corporate retreat activities.

"That's why it's so important to know your audience," Kackley said. "If a large portion of your team doesn't drink alcohol, or prefers board games to sports games, keep that in mind."

Executives should also be clear about how much work time is expected (if any) so people come prepared.

"The retreat should be optional," Kackley noted. "If you end up finding that many people prefer not to attend, look into it, and find out why."

Also know that the maiden voyage won't be perfect the first time around.

"Group travel improves immensely after each experience," Kackley added. "Consequently, be sure to take note of things that don't go according to plan or things you didn't think of or forgot, and implement changes at your next retreat."

Brian O'Connell is a freelance writer based in Bucks County, Pa. A former Wall Street trader, he is the author of the books CNBC Creating Wealth (John Wiley & Sons, 2001) and The Career Survival Guide (McGraw-Hill, 2004).