Where to Start in Designing Your Offsite

Offsites – or "onsites" for some leaders with remote teams – are expensive and high-stakes. The team is often asked to travel away from family and the normal rhythms of life. Flights, hotel rooms, meals, meeting rooms, snacks, coffee, supplies – it is a lot of time, money, and energy for all involved.

There are good reasons for a leader to make such an investment, and once you’ve made such a decision, well, you need to get it right.

But where to start in planning the time together?

Think of it this way. The offsite needs to successfully move the team along a journey together, from the appropriate Point A on the first morning to the right Point B at the end of the last day. To be successful, Point B must be defined wisely, and Point A accurately determined.  

Start by answering these three simple questions:

1) Where is the team now?

If you as the leader have identified an inflection point, what is it? What brought you to this point? What's going on that warrants this team  investment? You must find a diplomatic, positive, honest way to communicate this context to the team. Otherwise, they will be wondering and will make up their own stories. As the leader, it's important to be out in front of any misunderstandings.

2) If the offsite is successful, what will be different afterwards?

Keep your expectations simple here. What are the outcomes you hope to leave with? In addition to clear decisions and other work products, it's likely to include subtle shifts in the team's energy, and perhaps more profound shifts in their alignment. These will change the trajectory of their work and success over the coming months, maybe years. Envisioning what you want to be different afterwards will directly inform the meeting results – your ‘Point B.’ Aim for simple and high-leverage outcomes. 

3) What is the 'Point A' that allows us to begin together the first morning?

Ask yourself: what is the key work that needs to happen live, together, at this time?

Working backwards from the outcomes you listed in #2 above, and factoring in how much time you have, you'll determine what needs to happen during the meeting. The biggest mistake leaders make is trying to fit too much into the time frame. Plan in time for true alignment-building, which can't be fast-tracked. Factor in complexity due to the topic and the number of people. Work backwards and see where your starting point needs to be on the first morning. Know that you cannot start at a Point A that is further along in progress than some team members actually are. Point A needs to include everyone.

Based on this, there may be some prework. Team members may need to review previously built documents like mission statements, strategic plans, protocol amendments, previous team offsite documents, an inspiring article, any number of artifacts. Then, all team members arrive with the same information at hand.

The 'Point A' depends heavily on your answers to the first two questions. If a team is butting heads, for example, your time may be spent on healing relationships and reconnecting. That needs to come before business outcomes. It's something that can't get handled in pre-work. If, on the other hand, relations are good and this is a roll-up-our-sleeves and get-important-decisions-made type meeting, you may be able to dive right in, assuming team members have briefed themselves on any background information (again, something that doesn't need to happen during precious live meeting time).

Once you have defined the appropriate Point A, go back and check that your Point B represents the right amount of ambition, given the time you have. There may be some iterating here. Remember, the offsite is a synchronous journey the team will take together. In order to stay together, those beginning and end points need to be chosen and designed for wisely.

If this topic fascinates you, you might be interested in our recent post on taking a design approach to your meetings.

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