Planning an offsite for an all-remote team.

 I had an AMAZING time and really feel like I bonded with many of my colleagues over the last 3 days. It's significant to me because I have worked remotely for 12+ years (and I wouldn't trade it for anything), but I really, really miss the personal relationships that I form from in-office contact. This goes a long, long way to helping establish rapport with people whom I don't see everyday.

—New Engineering Hire

Company: Series A Startup

Context:

  • The company had a globally distributed team that relied on coming together bi-annually to develop healthy working relationships and a strong company culture.

  • Since the previous offsite, the company had almost doubled in size which led to a sense of diluted culture.

  • Over half of the company were self-identified introverts, posing a challenge for building a program that spanned several days that was both productive and enjoyable for those participating.

Painpoints

  • Company was globally distributed, posing a logistical and financial challenge around choosing a location. It was also necessary to consider these cultural differences to create inclusive programming. Simultaneously, this was a pivotal event for creating a strong sense of unity in the mission & future of the company.

  • While previous offsites were organized with loose budgeting, this event was the first during a season of cost-cutting. With a doubled team size, impact needed to be maximized while minimizing expenses where possible.

  • The diverse team also meant diverse needs. Over half of the participants self-identified as introverts, many would be jetlagged during the brief trip, and several had never met anyone on the team in person prior to the event.

Results

  • Successfully cut annual event spend by over 14%.

  • Post-event feedback highlighted increased satisfaction amongst employees, with particular appreciation for thoughtfully designed activities and inclusive scheduling.

  • The events significantly boosted morale and cohesion as a team, aligning the team more closely with strategic goals and contributing to zero employee turnover in the following quarter.

How I Helped

Event Design & Strategic Planning

  • The offsite was designed with an eye towards integrating our company’s culture & strategic objectives into the agenda. This involved:

  • Cross-functional activities — by utilizing activities designed to pair people with those they didn’t normally interact with, we were able to build trust across key teams which would impact future collaboration.

  • Team-specific connection points — while most teams had regular touch points, these were all virtual. We ensured that whether it was over a meal or a quick activity, people were able to connect with those with which they worked most closely.

  • Inclusive scheduling — I developed a flexible event schedule that accounted for a broad spectrum of preferences in activity type and energy level. In addition to the core sessions, these allowed participants to self-select an agenda that fit their needs.



Auditing & Negotiating

  • Undertook a detailed audit of our previous event expenditures to identify potential savings.

  • During the research phase, I created a formula that evaluated potential locations based on travel cost, accommodation fees, and activity spend. By evaluating several major cities using this formula, I was able to identify the most cost-effective locations.

  • Once a location was identified, I negotiated with vendors and leveraged competing bids to secure the best pricing possible without sacrificing quality.

Thoughtful Communication & Delightful Touches

  • Long before the team arrived at the offsite, I designed a communication schedule that anticipated questions and communicated details early and often via the company’s key channels.

  • I built an event guidebook on Notion for participants that shared key details about the flow of each day, menu selections, local spots of interest, and FAQs about venues.

  • We capped it off by adding delightful touches such as a surprise dessert delivery, a swag bag, and moments designed for fun, large group interaction as well as smaller 1-1 conversations.

Tools