Planning a Team Offsite
This brief post is to help any founders currently thinking through their first offsite with their team, or for those that are looking for inspiration on how to run a team offsite for more effective outcomes.
In order to capture all the key elements of an offsite, it is first worth exploring the ‘why’ of a team offsite and what you should expect to be able to achieve.
Studies show** that a when you achieve brain and/or heart synchronicity with others, decisions and conversations can flow more easily. Being that team work is basically about conversing and deciding, it would seem obvious that any investment you can make to improve on this, is an investment worth making. Team offsites offer a unique and focused way of achieving synchronicity with your colleagues.
In addition to synchronicity, team offsites provide you with an opportunity to deal with strategic matters without the typical day-to-day distractions. Which brings up various questions: how long should my offsite be, where should it be, and what components should it have?
Length: There is no ‘ideal length’ for an offsite, but generally speaking you need it to be long enough to cover the key components of an offsite, but not so long that it becomes tiresome and a bore for all attending. Pragmatically speaking, I just don’t see how an ‘offsite’ can be shorter than 3 hours, as it would strip a team from the necessary ‘time together’ to both synchronize and discuss enough topics to justify the effort.
Under ‘length’, it’s likely worth also talk about ‘regularity’. By definitions, team-offsites are ‘exceptional team gatherings’ vs. routine ones. Many companies therefore only have one a year and pragmatically speaking, I don’t see the need for more than two a year max, but if you differ, or have an alternative view on that, leave a comment below.
Location: A key part of an offsite is to create mental space for non-routine thoughts to surface. Thus, this might seem obvious, but it is important to find a location that doesn’t trigger ‘routine’ thinking. If you are using the same room for your offsite that you use for your normal team meetings, you might drag the whole team offsite into a feeling of it just being an average meeting.
Budget: Let’s talk about the elephant in the room. Money. Length and location both affect cash use, and in many cases, you or your team’s ideals don’t match the company’s budget. It’s even more annoying when you hear about such-and-such startup that held their team offsite in Ibiza and all the employees got company merch and free massages. Race your own race: None of that really matters. What matters is you cover the below components as a minimum in whatever context you can afford on the schedule you set.
The core components of a team offsite:
I call these ‘components’ because whilst I think an offsite benefits from having them all, you can choose to exclude some depending on the regularity you have an offsite in any given year. Additionally, there is no ‘time’ requirement for any of these components, as in, you can make them as long or short as you need them to be. The value really comes from how they amplify each other.
- A social activity — As per the synchronicity point above, if you don’t have a social activity planned (there is no rule here, just something that everyone can engage in, in some capacity), you will struggle to speed up the synchronicity between team members to achieve the goals of the offsite.
- A combined session on the vision and mission of the company — Not strictly necessary if you have more than one offsite per year, but you have to be mindful that whilst you may have clarity on the vision and mission of your company, many new joiners will not, and many colleagues who have been in your company for a long time will also be lost as day-to-day duties can sometimes create confusion on overall direction. If you want to think through this topic more, check out my post on the subject here.
- A combined session on the values of the company — this is a critical component, in my opinion, because it serves to remind everyone on the agreed way you interact with each other, how you deliver your product or services to your customers and partners, and how you overcome directional ambiguities. Make sure you make this an engaged conversation. Be open to hearing your colleague’s thoughts on each of the values (as you have them stated) and how they are clear, unclear, confusing, relevant or irrelevant and at the end of this session, get everyone to recommit to upholding these, as they are a huge part of your company culture.
- A combined session on the strategic goals of the company — This is more directly applied for colleagues than the session on vision and mission. You can have this be as short term or future looking as you need it to be for the scope of what you want to cover in your offsite. Topics include product roadmaps, fundraisings, hiring plans, go to market challenges, or any other topic that your team would benefit in discussing as a whole. Try and make sure people have a chance to comment or ask questions during this section vs. simply stating your views on the matter.
- Deep Dive Sessions (can be break out groups) on key topics that need discussing for the relevant time frame. Based on what surfaces on any of the above, sometimes you benefit from carving out time to address specific timely challenges (rolling out a key feature and how it applies to existing customers, for example, or the philosophical implications of a new pricing strategy on your customer base) with a subset of your team members. Feel free to use these deep dive session slots to also cover any iterations that are needed to the values session/strategic goals session.
In conclusion, the key things to remember in an offsite is that it’s an opportunity to synchronise with your colleagues, re-visit the key components that define your company culture, and make time to go more deeply into topics that the normal day-to-day hustle bustle of running a startup does not allow.
** Further reading on brain synchronicity and collaboration:
https://www.scientificamerican.com/article/brain-waves-synchronize-when-people-interact/
