A Guide to Hosting Your Next Work Retreat

There’s something magical about the third location. It’s why writers head off to that cabin in the woods. Heck, maybe it’s why you find unlikely productivity on that 4-hour flight with spotty WiFi, sandwiched between two people. There’s something about being outside of your usual element (like your home office or that same conference room) and in a new place that doesn’t have the same distractions that hinder your creativity.

When you can bring your colleagues to that third location for a work retreat, you’re unlocking all kinds of potential.

Casey, Amanda, and Rand at our “third location” for a recent team offsite.

I think there are typically two types of work retreats:

  1. Time-focused. Maybe your company hosts an annual retreat at the end of Q3 in order to plan for the following year. Or maybe you’re able to do twice-annual or quarterly retreats to levelset on the time frame ahead. The advantage is that you get a fresh space (and hopefully, mindset) to tackle the potential foreseeable problems before they happen, and that you get to proactively plan for the next few months or year. A disadvantage is that depending on the full scope of work that’s discussed, it could be tough to make sure you both spend enough context on all the business problems and enough time ideating the solutions in a short time frame of a day or two.
  2. Project-focused. Or maybe there’s a key initiative — like a major product launch or cornerstone event — and your retreat is focused on alignment and execution in service of that launch. The advantage of this is that you and your team get to laser-focus on one, neatly defined goal.

Whichever one you decide to do, make sure you set up the day(s) for success.

What makes up a strong backbone for a retreat?

Ultimately, it’s the facetime and shared experiences that make for a successful retreat. But as you’re in the early stage planning process, you may want to consider your company’s role in your team’s overall wellbeing. We spend about a quarter of our day at work, and work makes the biggest direct impact on our financial wellbeing. Consider your company’s mission & brand, and how they correlate with the seven dimensions of wellbeing:

  • Emotional – How can you ensure your retreat — and of course, your office as a whole — fosters emotional safety wherein people can comfortably express themselves?
  • Physical – How can you incorporate movement into the day? Instead of being huddled up in a hotel conference room, consider breaking up the day across a couple of walkable locations. If you’re a fitness-focused brand, it might make sense to consider a bold physical activity like a boxing class.
  • Social – Will you be sure to include social activities in the agenda? It’s worth considering what you can do beyond a standard happy hour. Maybe the team can do an improv class, take a glassblowing class, or engage in a cooking competition.
  • Intellectual – How can you elevate intellectual discussions? It might make sense to facilitate a group brainstorm to tackle a well-defined problem. Or maybe you can ask various colleagues to present on their team’s opportunities. For instance, a junior marketer on the brand marketing side might be a great person to present a “state of PR” session.
  • Environmental – What opportunities are there to involve your team with the company’s environmental policies? If you’re a mission-driven company who’s working toward B corp certification, you may want to update the team on this status.
  • Financial – How can you coach your team on advocating for a raise? It’s often uncomfortable to talk about raises and promotions, so you might want to get ahead of that and dedicate a session to giving your team guidance on how they can advocate for themselves in the future. Perhaps you can share what the funding pool looks like for the next raise cycle, how the most successful employees got to the next level (with examples of recent promotions), and your advice for how to actually make that ask for more money.
  • Spiritual – This one’s tricky as not everyone is comfortable discussing spirituality or religion with their colleagues. But it could be worth having a broader discussion on tolerance and inclusion.
Amanda making a glass bowl at a work retreat in 2016.

There are many ways to consider how you would foster wellbeing at your team retreat, and these ideas aren’t mutually exclusive. You could even argue that the very notion of a team retreat is already the social wellbeing element.

Here are recommendations for a schedule — and how you can plan a team retreat in Seattle this fall.

We have our first in-person SparkTogether summit on October 8 in Seattle, WA. This day-long conference at 415 Westlake will feature nine of the finest speakers in the marketing world sharing valuable, vulnerable stories they’re not telling anywhere else. Think: Your marketing heroes doing a Moth StorySLAM.

We’re offering bulk deals where you’ll save at least 20% if you buy at least 2 tickets together.

You could consider making SparkTogether a team-building activity, and staying the extra day to huddle on strategy and overall wellbeing.

A banner promoting the SparkTogether event in Seattle on October 8, 2024.

Other ideas for team activities:

You could also consider any number of walkable or short-driveable activities near 415 Westlake like the Chihuly Garden and Glass exhibit by the Seattle Space Needle. And funny enough, Seattle Glassblowing Studio is nearby as well if you want to do a group glassblowing class after all. (And for what it’s worth, Unexpected Productions Improv is about a mile away if the team is willing to take an improv class together.)

Retreat venue and co-working space recommendations:

There are some great co-working space in the Seattle area, like Thinkspace and Labour Temple.

But if you want to get out of Seattle, consider Workhorse Coworking in Edmonds, WA. SparkTogether attendee and Head of Content at ZenMaid Erika Musser says it’s her favorite co-working space! For out-of-towners, the ferry from Edmonds to Kingston could be a nice evening adventure.

Food recommendations:


Right by the SparkTogether venue, 415 Westlake, are the Fresh Flours Bakery and 203 Degrees Fahrenheit. Start the morning with single origin drip coffee, cappuccinos, cortados, London Fogs, lavender lattes, or nitro cold brews from either shop. Grab some croissants, danishes, or galettes from Fresh Flours.


You’re likely best off finding a restaurant within a three-block radius of your co-working space. But near 415 Westlake are Thai Thani Kitchen, Hurry Curry of Tokyo, La Palmera Mexican Restaurant, and Bar Harbor (which might be great for happy hour if you want to have drinks on the patio).

Sample schedule:

October 7: The team arrives in Seattle by 4pm to check into their hotels then meet at the SparkTogether pre-conference mixer. If you’re local, consider having the team get together here as well.

October 8: The team spends the day (9:30am – 5:30pm) at 415 Westlake for the SparkTogether summit. Hopefully you’ll all stay for the post-event afterparty as well!

October 9: The team has their official retreat day.

9:30AM – 10:00AMBreakfast & reflection on the previous day
10:00AM – 11:30AMSet context: Discuss the challenges & opportunities ahead, problems at large, and/or the campaign/project that you’re all planning for.
11:30AM – 12:00PMStart to bridge the gap: Shed light on some potential solutions or early stage planning the leadership team is considering for the time frame ahead.
12:00pm – 1:30pmLunch: Hopefully, you can walk to a nearby restaurant for fresh air and a break. This might also be a good time for team recognition, calling out each team member’s recent achievements.
1:30PM – 2:45PMFinancial wellbeing: Nothing like talk of the raise and promotion cycle to get people back into their professional mindsets after lunch. This could also be a good opportunity to discuss environmental and spiritual updates, if appropriate.
2:45PM – 3:15PMBreak: Half an hour to stretch, check email, or a quick coffee run may be exactly what people will want at this time.
3:15PM – 4:45PMDiscuss solutions: Now that the team has had several hours to marinate on the challenges & opportunities discussed in the morning, this might be a good time to brainstorm solutions, discuss creative ideas, and stress-test concepts.
4:45PM – 5:30PM Actionable next steps: Assuming the previous session is productive, this would be a great time to write down specific, actionable to-dos so that everyone knows what they need to do next.

Happy hour and dinner: Take this opportunity to express gratitude for your team, thanking each person for their presence and participation.
Above: sample company retreat schedule, drafted by Amanda, edited by Rand!

Post-retreat followup

After your team retreat, it’s crucial to follow up on the action items discussed and decided upon during the sessions. Make sure everyone is clear on their responsibilities and timelines for implementation. Consider setting up regular check-ins to track progress and provide support where needed.

And maybe you can plan ahead for next year’s retreat and SparkTogether attendance. 🙂