Impactful Offsite Series 
Darcy Marie Boles, Shift
The award-winning remote org. consultant and former head of remote at Stripe and TaxJar shares her thoughts...
Quick biography:

Darcy Boles is a Future of Work Thought Leader and Remote Experience Designer. Her deepest why is that "work doesn’t have to suck", and she has dedicated her career to ensuring that it doesn’t.

Darcy was leading remote teams before it was “a thing.” She pulls her design architecture from global experiences and cultures from around the world, using positive psychology research to align company ecosystems with shared intrinsic values and experiences.

She believes that we all have the power to create a better world and live the lives of our wildest dreams when building flexible workplaces on a stakeholder mindset model. After spending 8 years in high-value tech companies, she now operates as a remote-first work consultant at Shift with Darcy Marie

The Basics

Where were you born and what were the experiences that shape who you are?
Eugene, Oregon. I wore nothing but fairy wings until I was 5 and spent my childhood travelling on trains, busses and planes around the world. I learned that share culture and values are super important from an early age! I spent years in the hospitality world and live to create work experiences that don't suck - knowing that it's truly possible when you choose to be a host.

What do you like to do outside of work to keep energised?
surf when I'm not injured :)

The Big Picture

How many offsites do you have a year, on average? How do these differ, in terms of goals and attendees?
For any remote team, I've found that no more than 4 and no less than 2 in-person offsites per calendar year is the magic number for building in-person trust and connection.

How do you help prepare the team for your offsite? (Do you issue invites, swag, get them to pledge into the offsite experience, send a baseline survey, or anything else?)
Pump em' up! there's nothing worse than being a remote employee - accustomed to your daily routine, and then being asked to get on a plane and have no idea what you are stepping into.

Months of hype and preparation are needed leading up to any in-person event for a remote team. Invites, drip campaigns, travel tips, expectations, pre-swag and more can truly help to shape the feeling of the upcoming event, calm any nerves for those who don't travel often, and set your team up for success!

What is your approach to programme building?
I use a 3 full day formula with 2 additional travel days.

What are the biggest myths or foes around offsites? How is that changing?
That offsites should be full of content, content, content. People will begin to realize how intentional we should now be spending any synchronous time together to support autonomy outsides of onsites and connection within them.

At the Offsite

How have you tackled the approach to attendees at the offsite or not attending? Do you cater for those attending or do that another time?
Belonging, thinking differently, getting creative, planning 2 experiences with an overlay. Example: I had an astronomer coming to our offsite location to do a telescope tour of the stars - 30% of the company chose not to attend this particular onsite (covid) so I used to per person budget to send the ones at home telescopes and a how-to of how to map their stars seeing how we're all connected...

How do you cater for diverse team needs and varying levels of adventurousness? Do you have multiple activities on offer?
Yep - belonging and accessibility are key to a successful offsite.

What’s your approach to large teams, do you go “all-hands” or break down into smaller teams?
Both are integrated into my 3-day formula :)

After the Offsite

What have been your favourite breakthrough offsite moments?
Someone flying all the way from Spain and looking into me and my CEO's eyes and saying "thank you for making magic". A salty, always grumpy VP line dancing with 45 other employees from all over the world smiling bigger than I've ever seen anyone smile. Watching a room of 75 people tear up as we talked about what #remotelife means to us as individuals, and as a winning team.

What have been any learnings you have made from previous offsites?
Moments matter.
You'll never please everyone - be OK with getting a C.
People are picky about food
PEOPLE LOVE SWAG. I don't get it, but it's a thing.

Are there any favourite venues, coaches, facilitators, speakers, or experiences you want to give a shout-out to?
Kimpton hotels!!

How do you measure the impact of offsites?
Post mortem, survey and after-action reports

Are there any people, projects, podcasts, books or resources you’d like to give a shout out to who have helped shaped your thinking in this space?
The Art of Gathering by Priya Parker :)

Thank you Darcy

Go and check out Darcy's work at

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