Employee engagement, retention, and alignment at remote and hybrid companies is more challenging than ever before.
Layoffs, dwindling VC funding, and the constant demand for increased productivity make the workplace a stressful environment.
In the face of these challenges, it's essential to consider the value of team retreats and how they can boost your team's morale, productivity, and overall success.
Team retreats have evolved to become an indispensable part of maintaining a cohesive and motivated team, especially in remote and hybrid work settings.
In this guide, we'll explore the steps to plan a successful team retreat that not only re-energizes your team but also fosters alignment and peak performance.
As the founder/CEO of Offsite, a company that makes team retreat planning more affordable, faster, and stress-free for hundreds of VC-backed startups, Inc 5000s, publicly-traded companies, and others, I’m hoping these pro-tips can convince you that planning team retreats should become a high priority, especially if you manage a remote or hybrid team.
Before diving into the logistics of planning a team retreat, start by defining your objectives. It's crucial to understand what you aim to achieve through the retreat.
Ensure that only a select few, such as executives or team leaders, make these high-level decisions. Your objectives will shape the retreat's timing, location, agenda, and more.
Budgeting is a critical aspect of retreat planning.
You don’t want to be surprised by fees, last-minute additions, travel costs, etc. And so, budgeting at the beginning of your team retreat planning efforts will save some headaches later on.
Some of the top-line items to consider are:
One of the most expensive and consequential decisions will be your hotel, as you’ll likely spend most of your budget there between rooms, meals, meeting space, and more. Hotel contracts can get confusing, so at Offsite we’ve put together a guide to understanding terms on a hotel room block contract so you can ensure you’re educated and protected.
You can use Brex or Ramp to issue temporary credit cards with limits to your team so they can book their own airfare and cover incidentals while traveling, and work to negotiate with hotels and meeting space providers in order to save.
In all, you’ll likely spend $1,500 to $2,500 per person, per Offsite (unless you are really looking to ball out for a President’s Club event, executive team retreat, or Board Meeting, where it might get to $3,000+ per person).
While you don’t want to have “culture committees” of 10+ people chiming in with their ideas, slowing down the decision-making process at every turn, once you decide on high-level objectives for your offsite, you do want to send a pre-offsite feedback form to your team, asking them very specific questions to engage them months before your team retreat takes place.
This is a great opportunity to cover the basics of dietary preferences, any travel sensitivities your team may have, and expectations your team may have for the upcoming offsite.
You can also ask more specific questions about what type of activities your team might want to experience, what their hopes are in terms of career development, what ideas they have that can improve the agenda, and how you (as a manager or team leader) might be able to improve their work lives on a day-to-day basis even before the team retreat takes place.
Finally, you might want to poll the team for employee engagement metrics like an employer net promoter score before the offsite and after to see if regularly-occurring team retreats are making a measurable difference in employee engagement, satisfaction, and alignment.
Every team retreat will have a different agenda, but some of the building blocks are the same for all effective offsites.
For one, you have to factor in enough time for your team to travel in for the team retreat and travel back home.
That means the first day of your retreat should be lighter on programming, and it is recommended you provide your team ample time to recover from potentially stressful travel, acclimate to the new environment, and transition from their daily lives into the new experience of your retreat.
The first night, host a welcome dinner and activity and keep programming light and fun.
For the remainder of your time together, give your attendees a mix of team-building (through icebreakers, workshops with an outside facilitator, and activities that lead to deep, meaningful connections via unique shared experiences), skill-building (through keynote speakers or presentations from your team to one another to share what each other is working on), strategic planning, and fun.
Don’t forget to add lots of “flex time” to your agenda in case you run over, and to give your team time to call home, workout, take a nap, and stay energized through what might be an intense and emotionally draining time for those who aren’t used to being around lots of people.
Offsite has a free All Hands meeting agenda you may find interest in...
Hopefully, if you are intentional about how you’d like to use your team’s time at an offsite, you’ll walk away with breakthrough ideas, action items, and notes that you’d like to use post-retreat.
However, many teams forget to implement a system by which great ideas, notes, and conversations become action.
At Offsite, we recommend assigning someone company-wide to be the “scribe” during important sessions, or multiple scribes if there are breakout groups, to ensure notes are recorded during brainstorming and problem-solving exercises.
It is also recommended notes be recorded digitally for easy conversion to your project management system, be it Asana, Notion, or elsewhere.
Further, for action items, you may follow the practice of noting “who” (person on your team) needs to do “what” (action item) by “when” (due date).
The ROI from your team retreats truly happens in follow-up, so don’t forget this important step!
We recommend hiring a photographer and/or videographer for some or all of your team retreats in order to capture content. You can show the world how awesome your company is by sharing it on your website or social.
Additionally, these offsites should lead to peak experiences for your team. You can ask your employees in the weeks following to leave reviews on GlassDoor or other employment websites. This further helps to increase your ability to hire and retain more great people in the future.
If it’s also apparent you host regular team retreats for your employees, it will be all the more enticing for friends of your team to inquire about job openings at your company, and you’ll be able to find talent with ease.
While employer marketing shouldn’t be the main reason you host an offsite, it is added ROI that you shouldn’t forget about when planning an effective team retreat.
Team retreats are essential for building strong company cultures, particularly in remote and hybrid environments.
At Offsite, we specialize in helping teams plan memorable in-person experiences that combat isolation and enhance team cohesion.
To discover how we can save you time, money, and reduce the stress of planning retreats, visit www.offsite.com.