Mahdi Shariff has just got back from a week in Spain — a trip he took with his team from Humble, the work assistant AI company he founded.
As a team that mostly works remotely, Mahdi says it can be easy to overlook the importance of face-to-face interactions, but he’s found “in-person moments are more than just nice-to-haves; they are essential for building strong relationships, fostering collaboration, and reinforcing company culture”.
Here are his top tips for taking your team away.
Understand your ‘why’
Hybrid and remote work offer great flexibility but is there something missing in your company culture that could be filled with in-person gatherings? For us, we want to transform work into a collaboration with friends and people we respect so it feels more meaningful and energising. That drives us to create:
- Moments that aren’t just meetings.
- Safe spaces so people can connect as individuals, not just as colleagues.
- Opportunities for clients and partners to join us to transform work relationships into personal ones.
Plan way ahead
We hold two ‘Humble Gatherings’ each year. It has to go into the calendar early as we are flying the team in from around the world. We also need to ensure places don’t get booked up as there are a lot of us.
Get someone who is hot at logistics
The trip needs to be light on admin for the team. Consider hiring in someone or assigning a team member — like a chief of staff or someone in HR — to take care of the planning.
Things to take into consideration include:
- Comfort. You don’t want your team on ridiculously early or late flights or having to do a tonne of transfers to save £100.
- International travel rules. Consider visas (and the time they can take to get) and other travel complexities, like vaccines.
- Jet lag. If you’re going somewhere in Europe, for example, you might want to fly in your colleague that are in vastly different time zones a day earlier than your European team so they can acclimatise.
Ask the team what they want
What did they like about the last event? What could have been better? What locations do they suggest for the next one? Gather feedback, iterate on your events and make each one better than the last.
Don’t be stingy with your budget — if you can afford it
Depending on the stage of your company, the budget will vary. I recommend allocating the equivalent of 3-5% of a team’s annual salary budget to fund these gatherings. It’s a material investment but it does pay off.
Choose your location carefully
It needs to be easy to reach. There needs to be enough space for everyone to be comfortable and not live on top of each other. Consider things like sleeping arrangements — do you want everyone to have their room or are there certain people who would be willing to share?
We favour locations with access to nature — it’s grounding and provides a much-needed break from screens and desks.
Balance work and fun
It’s tempting to pack the schedule with activities, but we’ve found a mix of fun and informal discussions works best. The first few days should focus on relaxation and connection — think shared meals, downtime to explore the local area, etc. There will be colleagues who haven’t met before who will need to build rapport, people who want to catch up with their work BFF from across the world, etc. The slow approach also helps introverts find their comfort zone — it’s not too much all at once.
Put thought into activities
Cooking together, for example, can be a more bonding experience than simply dining out. When it comes to work, we favour collaborative discussions over traditional sessions. We also bring in outsiders who can teach us something new.
Also, don’t plan everything early or lots of things late at night. There will be early birds versus night owls. You don’t want either of those parties getting frustrated with the other so make sure they have options that take them away from the main sleeping area (that way everyone can get enough sleep and thrive).
Think about inclusivity
This is key to the success of a group getaway.
- When considering activities, remember not everyone will want to do that high-adrenaline activity you’re dying to do. Give people options. They’re adults.
- Create space for both quiet reflection and social interaction.
- Ensure men and women feel comfortable in the same space.
- Keep religious needs and considerations in mind.
- Accommodate food preferences.
- Create unity. Company swag can do this — it’s a small detail but creates a sense of community.
Think about the micro barriers that stop people from engaging. For example, if some of the team are into board games, get them to bring beginner-level ones so everyone can get involved. If people don’t drink, how do you make sure that the space doesn’t feel uncomfortable?
Track your return on investment
There are downsides, the costs and the carbon footprint being at the top of the list. You need to have proof, year on year, that these gatherings are still beneficial. For us, we look at team alignment, the effectiveness of sharing ideas in person and the camaraderie built.
From this perspective, the costs feel almost immaterial in the bigger picture — they are intangible returns. We can convey the passion behind the company’s vision and mission in a way that no Zoom call can match, for example. It also builds memories and positive associations with the company as well as massively re-energising people.
On the subject of... working holidays
1. How to run an offsite for your team.
2. Remote but not too remote. The story of the remote work startup targeting ‘not-quite nomads’.
3. Your workation packing list.
4. The problem with hotels. There are some good recommendations in the comments.
