How to plan an offsite without losing the plot.

A practical playbook for startups.

1. OVERVIEW.

What's in this playbook.

Hey, I'm Ryan, founder of huddle. We created this playbook to help busy startups plan a good offsite.

We know not every startup wants to invest in bringing in specialists to run their offsite. We wanted to create a simple guide aimed at those teams: to help them still get the basics right and ensure the offsite is still effective.

With that in mind, the playbook covers:

The key building blocks to get in place first
How to craft an agenda that lands well
Common mistakes to avoid

We hope you find it useful.

Teams we’ve worked with

& more

2. The Framework.

1. Start with Why.

It's useful to start by getting clear on the purpose of the event. That's probably already in your head, but being explicit will help you make the decisions to come. Are you trying to get everyone together to answer important strategic questions, or is it about helping the team come closer together?

Those different purposes inform the shape of the event: who should be there, where you go, how long it lasts, and so on.

Once you're clear on this, you can move into the fun stuff.

Why teams run an offsite.

01Integrate important new hires
02Strengthen ties in a distributed team
03Clarify and align on the product vision
04Celebrate a landmark success

2. The Foundations.

Now it's planning time. We suggest starting with these important building blocks.

Start with dates.

We suggest picking a target month first. Exact dates can come later, but getting a rough idea of when you can get everyone together informs your thinking on location and makes venue conversations easier, so it's worth starting here.

If you're travelling internationally, picking a target month will inform which destinations are appealing.

We suggest avoiding school holidays if you can. Venues will be less costly and more of your team will be able to attend.

Pick your location.

Once you have your date window, boil the location search down to three things: travel simplicity, estimated overall cost, and the likely team experience.

Travel simplicity. Where is the team based, and where is easy for most people to get to? If you're travelling internationally, focus on places with a high density of direct flights.
Overall cost. Aim for places that aren't more expensive than your home base. Staying domestic or picking somewhere you already have team members can keep costs down.
Team experience. You want a positive contrast with where most people are coming from. Sunny and near the beach usually lands well. For London HQ'd teams that are distributed internationally, European hubs like Lisbon and Barcelona often work well.

Narrow it down to two target locations before you start the venue search.

Find the venue.

There are a few basics to get right. A bad venue choice is hard to recover from.

Transfer. Don't be more than 90 minutes from the airport, or travel days get too long. For a domestic offsite, aim within a couple of hours by coach from your office.
Setting. Walkable surroundings are a big plus. They make it easier to get off-site and mix up the vibe. Avoid major cities, though. People are there to focus and connect, not get distracted.
Size. You don't need a full buyout, but you also don't want a huge hotel where you're lost in the crowd. Look for places with 2-3x your team's capacity. They're more likely to be available, and it still feels like the property is yours.
Meeting space. You need a main plenary space for your team, plus at least one good breakout space. A lot of hotels aren't set up for big groups to do quality work.
Rating. For most post-Series A startups, a character-filled four-star hotel hits the right balance between quality and price.

Avoid a bad choice by using a hotel that advertises corporate events on its website and has done this before. They'll handle a lot of the lift and you'll avoid nasty surprises.

💡 Top tip.

If you're travelling internationally, a beachside town within an hour of a major airport usually works well. You get the best of both worlds: it feels like a getaway, but there's still plenty to do. Good examples are Sitges near Barcelona, or Cascais near Lisbon.

3. Designing the Days.

We could write a PhD thesis on how to get the most from your time together, but here's a few key design principles to keep in mind.

Don't let every day feel the same.

Vary the shape of every section so it never feels like Groundhog Day. A heavy work day should be followed by an activity-rich one. Dinner at the hotel one night means dinner off-property the next. A morning of group sessions should give way to small-group work in the afternoon. Keep changing the rhythm and the energy stays high.

Start and end on a high.

The first night energy is high, so make the welcome party count. A short CEO welcome on day one reminds everyone why you're there, and should be followed by something special: a good dinner, drinks, or both. On the last night, go out with a bang: a recap, a few awards, and something special like a DJ. End on an emotional high.

Build in real downtime.

You'll have plenty of introverts in the team, and going away with colleagues can be intense. Give people meaningful free time or rest time every day so those who need quiet can recharge and show up fully for the big moments. The extraverts will fill it. You want everyone leaving energised, not like they need another holiday.

Prioritise at least one unforgettable shared experience.

We like to anchor every offsite around one signature activity. It's the moment people are still talking about a year later. See below for what a great one looks like in practice.

What makes a shared experience unforgettable.

A strong signature activity usually has four things:

Is tied to the place. It should be something you can only do in that location. That's what makes it memorable.
Gets people moving. This doesn't mean it has to be physically demanding. Cooking together is a good example. The point is to get people out of their heads and focused on the same task at the same time.
Is team-based. The activity should naturally split people into groups. Then mix the groups so people spend time with colleagues they don't normally work with.
Creates competition. It gives the activity structure, gets people engaged, and creates stories people tell for months.

Examples of signature activities we’ve run.

Canada

Team canoeing down a river

London

Sheep herding in the countryside

Spain

Paella-making masterclass

Branded event flag waving against a blue sky

Upload your logo

Try it: upload your company logo to preview your offsite merch.

4. Make it Yours.

Get the basics right and the offsite will feel like yours, not a generic hotel stay.

Brand the offsite so it doesn't feel generic. Flags, signage, or a few printed touches go a long way. Aim for something that shows it's yours in every major space you use. Ask the hotel if you can ship materials ahead so everything's ready when you arrive.See Hello Print note below
Hand out a welcome pack with a few quality branded items when people arrive. It sets a great tone from day one. Ask the hotel if they can leave them in rooms so everyone finds something waiting when they get in.See Merchery note below

Potential supplier: Merchery▼

For merch, we usually go with Merchery, because the quality holds up and people actually keep it. We have preferred rates with them, so get in touch if you'd like access.

Potential supplier: Hello Print▼

For event branding and print materials, we typically use Hello Print. They're versatile and cost-effective across the UK and Europe, and they handle everything from flags to signage to the small printed touches.

3. THE MISTAKES.

Six mistakes we see all the time.

The six we see most when teams plan solo:

Trap 01

Leaving it too late.

Good venues get booked up. Start planning at least 90 days out. Lock in dates and a venue early and everything else becomes easier.

Trap 02

Trying to do too much.

Cramming every day with work content drains people fast. Pick the one or two things the offsite really needs to achieve and build the agenda around those.

Trap 03

No hype.

How you frame the offsite sets the tone. Announce it on Slack, share rolling updates as the date gets closer, and put key info and FAQs in a simple micro-site. A tool like Lovable works well for that.

Trap 04

Over-complicating flights.

Give people a window and a budget, then let them book their own flights. Don't coordinate every booking yourself, but don't let people land hours apart. Perk and Navan make this easy.

Trap 05

Doing it all yourself.

Offsites have loads of moving parts: activities, catering, airport transfers, rooming lists, the closing party playlist. Share ownership so each piece gets proper attention.

Trap 06

Skipping the details.

Dietary needs and accessibility requirements aren't nice-to-haves, they're basics. Everyone needs food they can eat, so capture this stuff in advance and share it with caterers. Birthdays are worth noting too.

WRAP UP.

We hope you find these basics useful.

If you have any questions or want a bit of advice, you're welcome to get in touch with me directly at ryan@huddleoffsites.com.

And if you think you'd like to explore working with specialists to make the event something special, you can also pop a call in my calendar.

Book in a call Email Ryan