People, plans and the big picture

Thoughts on running an effective offsite for your startup


I’m always surprised when I speak to startups who shy away from taking time out for offsites. It seems that there can be a stigma around any sort of lengthy planning meeting, let alone one that might last two days. If you previously worked at a large organisation you may well have had to endure long, drawn-out sessions and bad corporate team building exercises. Or it might be that you’re currently in an early-stage startup, where the thought of taking two days away from building your product, finding customers or fundraising just seems impossible.

To be honest, whilst at SoundCloud, I don’t remember having these types of sessions until a few years in. But later on our yearly and quarterly management offsites became a routine. And as the organization grew, we started to run sub-team offsites too (eg. product, content, marketing teams etc). I always looked forward to them and found the time spent to be highly rewarding.

That’s why I was so keen to continue the habit after joining the team at Seedcamp. We’re fewer people and have so many different constraints on our time. Seedcamp Week London is coming up quickly and in the past few months, the whole team has travelled a lot. Luckily, we managed to block out two days earlier this week. A rare opportunity for us to get together as a group, take some time to reflect on the bigger vision of what we do at Seedcamp and think about what’s in store for 2015.

I took some time beforehand to jot down some thoughts on what I think makes a good offsite. I’d love to hear how others do it.

So what works?

For me, the mix should be roughly as follows:

30% big picture — It’s easy to get lost in the daily grind, reacting to immediate problems and short term needs. An offsite is a perfect setting to zoom out from the day-to-day. It’s a rare chance to focus on all things vision, mission and strategy. To do this you’ll definitely need to actually go ‘off site’. This doesn’t need to be a Bulgarian ski resort or an Airbnb in San Francisco (although I can recommend both), but make sure you get away from your usual environment. This means you won’t be disturbed and can more easily switch into a different mode of thinking. You don’t need to spend too much money either. For Seedcamp, we asked a few friends and partners if we could use their space for a day.

30% planning — An offsite is a good anchor for your yearly or quarterly discussion of key initiatives, goals, milestones, prioritisation etc. How detailed your planning process is really depends on what stage your startup is at. Early on, you’re likely to have a limited ability to project and stick to a detailed year-long plan. But don’t let that be an excuse. Even if your plans are likely to change, it’s great to get into good habits early on, and some form of setting and co-ordination of key initiatives, goals and milestones is essential.

30% people — Some people view offsites purely as planning forums. But for me, a key purpose is to help build and develop the team. Offsites are a great time to focus on the softer side of the organization. Developing personal relationships, team dynamics and fostering a high level of trust is essential. It’s also a perfect time to reflect on your startup’s culture, its values and other people-related topics that usually don’t make it into the day-to-day, as you scramble to build your business.

10% fun — if you’re doing a 2-day session then it’s nice to schedule in at least one team dinner on the first night. Or do something fun. It’s a great opportunity to reflect on the day’s proceedings in a more informal setting, and over a few beers or bottles of wine. Once a year, maybe even bake a bit more fun in, and take the team away somewhere. But not until you’re making good revenues of course ;)

When it comes to team exercises, there are both good and bad ways to do them. You’ll also find that people’s receptiveness can change based not just on their personalities and backgrounds, but on the level of trust that you’ve already built-up in the team.

I’m certainly not an advocate for the fall back into your teammate’s arms stuff. However, it is nice to have something slightly out of the norm to break up the day. Something that always works is a good envisioning exercise, to get everyone warmed up and thinking big. Who would your dream user be? What integrations or partnerships would be game changers? What new technologies will be disrupting your business 10 years from now?

Some other tips

There’s a surprising amount that goes into a good offsite. Don’t expect to get it right the first time, but here’s some tips…

Have a clear goal — make sure you know what you want to achieve at the offsite. Discuss it before you kick-off.

Plan in advance — the more time you have to prepare, the better the session is likely to be. In some cases this will just mean having a clear agenda. In others it might mean giving all leaders time to gather inputs and plan with their own teams.

Follow-up — make sure that someone is taking note of all necessary follow-up actions that arise. Loop back around at a pre-determined time to make sure it actually happened. It’s all too easy to get sucked back into the day-to-day.

Effective moderation— at SoundCloud we had a habit of talking around certain subjects a little too much. Figure out who the culprits are likely to be and make sure there’s someone who takes responsibility for calling time on conversations that either take too long or deviate.

Encourage conflict — I usually go out of my way to avoid conflict. But in order to move things forward and make the hard decisions about a business you’re going to need a certain level of conflict. Go hard on the hard subjects and don’t shy way from the things that might be being left unsaid. But make sure you’ve got the right level of trust in the room in order to make this constructive.

‘I will’ — I’m often guilty of putting out lots of ideas in settings like this. But without taking responsibility the words can often be meaningless, just loosely help opinions. Strive to turn any ‘we should’ statements into ‘I will’. Action speak louder…

Practise makes perfect — if you’re not used to doing these sessions as a group then don’t worry, you will get better. It takes a while to learn the dynamics of how you work as a team, what goes well, how much time needs to get allocated for different sessions, what makes a good environment and what planning will need to go in.


I’d love to hear how other teams have run offsites. Good ones? Bad ones? Ugly ones? Tweet me @haynes_dave . Thanks to @lenberg for reading a draft of this post.