5 Lessons From Our First Startup Offsite
5 Lessons From Our First Startup Offsite

5 Lessons From Our First Startup Offsite

Kosta Kolev
Kosta Kolev

February 23, 2024

Offsites are having a welcomed return to startup culture after the pandemic, but they can be expensive and take valuable time away from building products. Ideally, the outcomes, like alignment and collaboration, outweigh those costs.

In December, Calliper had our first offsite. Our team, which is normally distributed across Europe, spent a week together in Edinburgh. The time we spent in-person was invaluable. We left with new energy for our work fuelled by getting to know the individuals that make up our team–understanding their drivers, communication preferences, and working style. Here are the top 5 takeaways from our offsite and how we plan on maximising the impact of our next one:

1. Have a clear purpose for the offsite.

As an early-stage startup, there’s a lot of work to be done. The workload is why many of us join a startup to begin with. That’s why when we decided to step away from our normal pace, we learned it was important for us to be clear on the purpose of the offsite.

Setting goals for an offsite helps the team align on why we’re shifting our focus for the week. You should ask yourself questions like “What do we hope to accomplish?”, “Do we want to build team cohesion, come up with new ideas, or something else entirely?” Once you know what you want to achieve, you can start planning a schedule and activities that will help you reach your goal.

By Wednesday morning in Edinburgh, it was clear to us that our offsite purpose and goals were somewhat too broad to accomplish in a meaningful way. After checking in with the team, we pivoted to focus on making progress on a few key work projects and decided to push out some strategy and culture sessions to a later date.

To solidify this going forward, Calliper will have two flavours of offsites:

  1. Deep Work: Where we step away from normal day-to-day work and spend the week as a team focused on a specific sprint or hackathon for an important objective.
  2. Strategy + Culture: In-person time to host sessions and brainstorms focused on strategy and to spend time as a team to build and reflect on our culture. While you should plan logistics for any offsite as early as possible, we’d suggest holding off on at least a part of the session planning for a time closer to the offsite date. Startups change quickly so waiting helps you pick the most relevant sessions.

2. Set expectations.

Before the offsite, it’s important to make sure that everyone is on the same page. Send out an agenda and any relevant materials in advance so that everyone knows what to expect. Create a schedule to achieve the goal of the offsite and ask for feedback from the team. This will help ensure that everyone is able to participate fully and that you can hit the ground running on the first day.

A few days into our sprint in Edinburgh, we had made a lot of progress and were moving faster than ever before but we realised that our high-level goals didn’t totally capture all the work we were doing. Knowing this, we plan to break down our high-level offsite goals into small, achievable pieces, similar to ticketing a normal sprint. That way we can set expectations across the team for who’s accountable and what’s achievable in the offsite timeline and celebrate all the progress made.

3. Create an environment to accomplish your offsite’s purpose.

Offsites are a great opportunity to get out of the (home) office and into a new environment. Your venue decision should depend on your offsite’s purpose:

If you’re focused on work, make sure you have:

  • Collaboration Equipment: whiteboards, displays for screen sharing
  • Wifi: if you’re renting a large home, double-check the wifi strength
  • Seating: look for both a proper table and chair set-up and comfortable lounge options

If you’re focused on collaboration:

  • Look for a venue that has plenty of space for breakout sessions and group activities.
  • Proximity to nature can cultivate creativity among team members.
We prioritised a morning hike to break up our work week and enjoy some time outdoors together.

4. Prioritise impactful in-person activities.

When you’re planning your schedule, stay focused on the benefits of being in-person. Something that helped us prioritise was to ask if this *session, activity, project* would be better because we’re in-person or not.

We learned that things like brainstorming content strategy and playing games were impactful in-person because of the ease of natural discussion. While sessions that required thoughtful and structured reflection, like the offsite retro and reviewing our company values, were better remote where we could utilise tools like Miro to prompt and guide discussion.

Curling as a team! Because it was a completely new activity for everyone, we enjoyed learning the basics and coaching each other on the skills we picked up from our instructor.

5. Always ask for feedback.

We had two important feedback cycles. First, in the planning stage, we asked the team for inputs for logistics and schedule. While you should have a single decision-maker, this practice helps everyone feel heard and considered.

Don’t forget to follow up after the offsite. Send out a survey to get feedback from attendees. Besides an overall rating, we asked for feedback from 3 categories:

  1. Rating 1-5 and explanation for each of the categories: logistics, activities, hackathon.
  2. Rating 1-5 on how well we accomplished our offsite goals.
  3. Open-ended questions: favourite and least favourite parts, what can we do differently next time, and what was missing.

Overall, it was great to see our team live and work together outside our boxes on Google Meet. Our team’s average offsite rating was a 4.3/5, and we’re going for 5 stars next time by actioning the lessons we shared here. If you’d like to hear more about building a remote startup team or how our next offsite fares, subscribe to our email list below.

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