How To Plan Engaging Team Retreats Without Blowing Your Budget

Team retreats.
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Planning engaging, high-ROI team retreats without breaking the bank is critical for remote and hybrid companies striving to maintain high employee engagement, retention, and alignment.

Given the complexities of modern work environments—characterized by layoffs, reduced VC funding, and relentless demands for productivity—team retreats stand out as valuable tools for enhancing morale, productivity, and success.

Plus, it’s cool to get some face time with co-workers and get to travel, am I right!?

This guide outlines effective strategies for organizing team retreats that energize and align teams, especially valuable in remote and hybrid settings. 

As the founder/CEO of Offsite, we’ve used the following strategies to make team retreat planning affordable, fast, and stress-free for hundreds of VC-backed startups, Inc 5000s, and publicly-traded companies.

I hope you find them helpful, too! 

Step 1: Define Clear Objectives For Your Team Retreat

Identifying clear objectives is your first step when planning a team retreat for your remote team.

Understanding your goals—whether engaging top talent, incorporating strategic planning, or focusing on relaxation and motivation—is crucial. 

Many offsites will have a mix of objectives, such as strategic planning and increasing cross-department collaboration.

Other offsites might be incentive trips for sales teams, board meetings, customer conferences, or other types of events where the objective is employee retention, marketing, or some other singular focus. 

Whatever your objectives, keep them at the center of your decisions surrounding the budget, location, timing, agenda, and other decisions for your team retreat. 

Step 2: Create A Budget For Your Team Retreat That Considers All Possible Expenses

Effective budgeting is essential. Anticipate potential costs early to avoid surprises, considering expenses such as airfare, hotel accommodations, meeting spaces, meals, transportation, and activities.

Leveraging tools like Brex or Ramp for managing expenses and negotiating with service providers can help control costs, generally ranging from $1,500 to $2,500 per participant.

Some of the budget line items to consider are:

  • Airfare
  • Hotel room blocks (including room nights, tax, resort fees, and parking)
  • Meeting space (including A/V, food and beverage minimums, and tax)
  • Meals at your venue, as well as out-on-the-town and consumed during travel
  • Uber, Lyft, or shuttle service to and from your venue(s) from the airport
  • Uber, Lyft, or shuttle service to and from your venue(s) to team activities
  • Any activities you plan for your team
  • Keynote speakers and/or outside facilitators
  • Photographers and/or videographers
  • Swag

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. 

With Offsite, you can save 20-40% on room blocks, meeting space, and more at hundreds of premier offsite venues globally. Click here to make a free account and check out our Airbnb-style marketplace.

Step 3: Gather Input Before and After Your Team Retreat

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.

It can be simply 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.

Step 4: Plan Thoughtful Team Retreat Agendas

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.

Step 5: Implement an Action Plan For What Happens *After* Your Team Retreat

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!

Step 6: Leverage Team Retreats for Employer Marketing

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 media accounts.

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 can be added ROI that you shouldn’t forget about when planning an effective team retreat.

Myriad360 offsite in Orlando, FL organized by
Myriad360 offsite in Orlando, FL organized by

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

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About Jared Kleinert

Jared Kleinert is the Founder/CEO of Offsite. If you're planning a team retreat, Offsite can save you time, money, and stress. Visit to learn more! Jared is also a TED speaker, 3-time award-winning author, and USA Today's "Most Connected Millennial".

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