My First Team Retreat - Here’s What I Did (All the Details)

My First Team Retreat - Here’s What I Did (All the Details)

28 minute read

I’m just back from my first team retreat ever, so as I’m putting together a summary for us to keep as a record internally, I thought it might be helpful to share some specific details for anyone else considering hosting their own team retreat.

This is a long one so if you need a summary then:

  • I spent $17k on my first team retreat to Split, Croatia
  • It was epic
  • Catering was expensive
  • The villa didn't need a pool
  • A few of the team got Covid
  • Ten beers can be used to show the team how our goals are easily achievable
  • I feel hugely proud of the awesome people that work for me
  • I'm so excited for what's to come.

first team retreat in Split

First off, what is a team retreat?

Typically, it’s where you bring your team together in one place for anything from a few days to a week for a mixture of work and fun activities. 

Large corporate businesses sometimes refer to these as off-sites and where people work together in an office these are more commonly just a night or two.

Why did I want to hold a team retreat?

It’s been nearly four years since I bought JobRack. While in the early years it was just me and one team member, in the last 18 months we’ve hired a lot, and while not all have worked out we’re now at 15 team members with a few more on the way before the end of the year.


For a business of our size, adding 13 team members in a little over a year is quite an achievement and not without challenges. One thing that has been really important for me is how I want it to feel being part of JobRack so we’ve focused a lot on ‘team'.


There’s a range of things we do to help drive the culture I want, everything from afternoon tea and chat to team meetings where I get every team member to contribute something, through to gratitude shares in Slack. 


From talking to other people that have held team retreats, I was confident that this culture and feeling of being a proper team would be helped a lot by getting together in person and really getting to know each other. 


We’re also at a key point in our growth and getting people to step up in terms of their thinking and actions is something that’s going to be crucial. I felt that getting together would make it a lot easier for me to talk to them about where we’re going, how we’re going to get there and the opportunity for them to grow and develop as we do.

What was the theme?

I hadn’t thought about having a theme until a few days before when I read this article.

Oomph’s theme was ‘Celebrate and Elevate’ which instantly grabbed me.

That’s exactly what I wanted to do with the team:

  1. Celebrate everything we’ve achieved so far
  2. Elevate the team both collectively and individually

A quick trip to Fiverr and 24 hours later I had a ‘retreat logo’, imitation being the sincerest form of flattery and all that! (Matt from Oomph was highly supportive of this!)


Having this theme did prove really useful as it gave us a bit of structure to connect everything we were talking about as a team.

It also perfectly tied into my vision of the team stepping up in various ways which will free me up to focus on the things I really should, and want to, be doing.

How long did we go for?

I split the retreat into two portions:

First was management team time, so from Sunday to Wednesday it was just me, and my two managers.

This gave Monday, Tuesday and Wednesday morning for the three of us to spend time together, work through a range of things big and small and really get to know each other so much better than we have on Zoom!


Then the rest of the team arrived on Wednesday, staying through to Sunday when we all left.

This gave Thursday, Friday and Saturday with the full team.

One week in total away for me and the managers.

Five days away for the rest of the team including travel days. 

Where did we go?

We went to Split, Croatia, all staying in a big villa together. 

Choosing where to go was tricky. 

We started by surveying the team and asking them where they’d like to go.

Then we looked at accessibility. Where was easy to reach for as many of the team as possible?

Whilst not massively distributed (all our team are in Europe and the majority are in Serbia or Bosnia and Herzegovina) considering travel time was important to me especially as we were only planning a few days together.

We decided on Split as a good location for all to get to, close to the beach and with enough, but not too much, going on and accessible locally.

We really struggled to find a villa big enough in Split, this was difficult even if you cranked the budget way higher than I was happy with but eventually we got lucky.

We considered switching to Istanbul and doing a hotel-based retreat then realised that it was the relaxed ‘villa vibe’ we really wanted so continued the hunt in Split for the right place.

Whilst geographically Split was a good choice for us, due to the days we were travelling over half of our team ended up having to take indirect flights which wasn’t ideal. It all worked out ok but it added some cost and a lot of time to their travels. 


When did we go?

We chose the second week of September. This is outside of the height of the summer in Croatia so avoiding very high temperatures whilst still giving a high chance of good weather. 


What accommodation did we choose?


We went here:


An 8-bedroom villa around 25 minutes outside Split and a 15-minute walk from nearby restaurants and the beach.

Crucially it had outdoor space, a pool and enough separate beds for us, something a lot of villas don’t have (they say they sleep 16 but it’s in double beds, for instance).

When we surveyed the team, we asked if they were happy to share a room. Only one person (plus me) didn’t want to share so this made it a lot easier. 

We ended up with 14 of us on the retreat and had enough beds/bedrooms for everyone including three of us not sharing with anyone else.

One benefit of this villa is that it was actually three apartments which meant more social space to be able to hang out in smaller groups.

Lovely little pool but it didn’t get used!

How did we handle meals?

When it’s just a few people it’s pretty easy, although not always ideal, to manage things yourself. 

A collaborative shopping list and a trip to the supermarket and the job is done. 

With 14 people…. Not so easy, so I knew I wanted the meals with the full team to be catered for us. 


This was surprisingly difficult to arrange in Split (or at least where we were 25 minutes outside of Split).

A few other business owners had warned me that Croatian catering isn’t always great so I was already facing a challenge however from around 15 companies contacted none of them would / could cater for us. 

The villa owner did offer catering but it felt expensive ($19 for breakfast, $39 for lunch and $59 for dinner per person) so I was keen to at least have some other options. 

We didn’t manage to get any other options so we went with the villa option which worked out fine. 

We only did one dinner at the villa as it’s nice to go out, nice for people to have a choice of their meal and at $59/person we could get much better food elsewhere for a lower cost and have these other benefits too.

Even for a smaller group, I’d highly recommend having caterers.

Just knowing that breakfast and lunch were taken care of, knowing that we could be working or hanging out right up to the meal time and then we simply went downstairs and it was all ready for us just made everything simple. 

It also meant that all the clearing up was done for us too!

We did a supermarket shop for drinks and snacks. We bought too much but I’m not sure there was any way to know how much people will eat/drink so I’d always rather have more than less. 


One thing I hadn’t thought about was water. In a place where some people don’t want to drink tap water, 14 people can drink a lot of water in five days!

On the upside, carrying 14 six packs of water to and from the car gave me a quick strength workout!

In total we spent $2,905 on the catering for 1 x dinner, 4 x breakfasts 2 x lunches for 14 people which to me felt like a LOT of money. 

That said, it was worth it and I wouldn’t have changed anything as the convenience of having it there when we needed it far outweighed the cost.


What did we do?

I intentionally planned the time to not have too much work/business-focused time. 

I had a hunch that there would be a lot of value and fun in people just hanging out together which was part of the desire for a villa rather than a hotel. 

The random moments like late at night ‘one last drink’ around the pool, or early morning coffee chats were some of the best of the week and I felt that they simply wouldn’t happen if we were in a hotel and everyone was heading off to their own rooms away from each other.

Here’s what we did:


Travelling day for me and my two managers. I arrived around midday, collected a hire car (super useful imo for the random trips like pharmacies and supermarkets), and took a trip to a stationary store and a supermarket where I met Slobi, my recruitment manager, for the first time ever!

Where’s the best place to meet one of your managers that you’ve never met before?

The supermarket of course!!

Suitably stocked up on snacks, drinks and food for the few days it was just the management team, we headed to the villa, then out for dinner and we collected Noemi, my operations manager, from the airport ourselves.

Slobi and I meeting Noemi at the airport



9 AM start for the three of us out on one of the terraces armed with a big list of things to discuss that we’d worked on together over the previous few weeks. 

The key thing we worked through was my vision for JobRack and the various aspects of the business. 


I really want to enable and support my managers to step up to more of a ‘head of’ level so we had a lot of discussion around what that means and what they’ll need to successfully make that step. 

A pad of A3 paper (children’s drawing paper I think it was), some marker pens and masking tape proved to be hugely useful as we could stick them to walls and windows creating our own ‘whiteboards’ wherever we needed them!

Midday - Stopped for lunch and general chat then we each worked separately on our normal work for the afternoon. 

A couple of hours’ break and then out for dinner locally. 



We followed the same format as Monday and added in spending time thinking about the agenda for when the full team arrived.

We all agreed that keeping to just the most important topics was the most important thing.

One big topic we nailed was what we’re going to offer our team in terms of ‘benefits’. 

This was huge for me as it’s been really difficult to figure out what’s most important for people and will be meaningful vs offering benefits that get ignored or don’t make a real difference.

I’ll post more on this separately but once we’ve reached a key goal for three consecutive months then the team will all get:

  • $100/mth contribution to medical insurance (that’s enough to get private medical in the countries our team are in)
  • $50/mth laptop allowance
  • 5% of salary pension contributions (on top of their salary)

These three are the ones that ‘remote workers’ most commonly miss out on by not working for an ‘in-country’ company that properly employs them so I’m pleased to have got to a good place with it. (It was subsequently well received despite an underwhelming initial reaction caused by some fear about the goal - more on that below).


Management time in the morning cementing the agenda for the days with the team, then an afternoon hanging out in the villa with the team as they all arrived.

Dinner was catered allowing people to settle in and us to relax and chat.

I did do a very brief welcome ‘speech’, just two minutes thanking them for coming, reiterating the theme and purpose of the retreat and encouraging openness and good conversation. 

As a big fan of going beyond small talk, I posted up a ‘conversation menu’ on the wall with a few questions to give a bit of inspiration if it was required. 

After a day of travelling with a few of the team having to take indirect flights this was the perfect first night as we could relax and focus on gentle chat rather than getting ready, going out etc. 



My original intention was that Thursday would be a normal working day just with us all co-working together across the various spaces of the villa. 


We made some changes to this as the weather for the following days (when we were due to be out and about) wasn’t looking so good so while it was sunny on Thursday, we changed things around so we could make the most of the sun.


We did our first session for an hour in the morning where I focused on Vision, Goals and Benefits.


This was the point where I told them about the benefits they’d be getting once we reached our next significant goal.

This didn’t land as well as I expected (more on that in the ‘what I nearly messed up section)!


We then worked for a few hours before a quick 15-minute review of the morning and I had the chance to rectify the near miss of earlier before breaking for lunch. 


In the afternoon we walked down to the beach, some of us swam in the sea, others chilled on the beach and some just chilled in the beach bar with a few cocktails and good chat.


That night we went out for dinner in a local restaurant, had a stunning meal and plenty of wine that got the team singing along with the guitarist and singer doing rounds of the tables!




Team session in the morning from 9.30am to midday (with a coffee break midway) on values followed by time on What Will It Take (WWIT) for us to achieve our next goals. 


This was a great session talking about the different friction points we face with clients that slow things down and make things harder as well as some ideas on what we can do about them. 


I’d planned for us to break into smaller groups for discussion and ideas but it was flowing really well just as a group discussion so I kept us all as one group. 


With the weather forecast not looking great our afternoon boat trip had been cancelled so we had lunch and then went into Split.  The team had a few hours free time before we had dinner and drinks out in Split.


Once back at the villa around 11pm some of the team headed for bed whilst others had a few drinks around the villa and in some cases ‘in’ the very cold pool!




Our final day and very similar to Friday. 


The morning was another team session, this time out in the sunshine by the pool, talking about problem solving and feedback techniques that randomly resulted in some really really good conversations about discrimination and ‘preferences’ when hiring and both how to handle them and when and where we should take a stand as a business either publicly or with our clients (eternally tricky!)


Lunch we left to the team to split up and get whatever they wanted in Split. 


I’ve never seen someone so excited by Mcdonald's but they don’t have them in Macedonia so Slobi gets her fix whenever she visits another country!

The afternoon was back in Split, we had a walking tour arranged, then a bar, and a stunning dinner (Portofino is the most incredible restaurant in Split, if you go then ask for Nina the waitress, the epitome of 12-star service in every way!), one final bar and it was time to head back to the villa. 

Partway through our walking tour in Diocletian’s Palace in Split we took this epic photo on a raised balcony



Travelling day - we all left the villa at 10am to make our way home on various flights and transfers. 


How did we get around?


With a group of this size and our location, figuring out how to get people to the right place at the time was key. 


14 people requires either 4 normal taxis or 2-3 large vehicles. 

Being 25 minutes outside of Split meant that Bolt / Uber wasn’t a reliable option (tbh it’s not always great in central London either!)


I wanted to make sure that the team were really taken care of when they travelled to and from Split so we arranged private cars to meet them in arrivals and to bring them the short distance to the villa. 


The same company handled our local trips and were super helpful when we made changes and wanted a few extra trips out that weren’t planned.


One night it was forecast to have heavy rain and storms so while the restaurant was only a 15-minute walk away I didn’t want to be risking it so had them come and take us and collect us later. 


This particular evening and transport felt a little ‘expensive’ - $50 for an 8-minute taxi ride. However, it just being handled made things so much simpler and relaxed all round. In the scheme of things, it’s not a lot of money but it’s interesting how it triggered me thinking ‘ouch that’s a lot for a very short taxi ride’.  


In reality, they had to travel 25 minutes from Split to take us that short distance so I think it was pretty fair overall. Definitely a case of remembering the overall feeling and vibe I want (relaxed and enjoyable) and not being too cheap!


I highly recommend finding a good local transport company and putting everything through them. They handled all our transfers and even handled getting one of our team from another airport a few hours away.


I also hired a car for myself just so we had one for the various supermarket trips, pharmacy trips and to have that extra bit of freedom if needed. This was really helpful in the first few days when it was just the management team as it meant we weren’t reliant on taxis and being specific with our timings. 

What was the budget?


When I originally started thinking about the retreat, I did some rough numbers and hoped I could do it for $15k.


As we started booking travel and accommodation, I revised this to $20-25k and really hoped it wouldn’t go above that.


It was really interesting to me to see how expensive (and difficult to arrange) some things were vs what I’d expected.


How much did it actually cost?




We’ve been tracking the cost as we made each arrangement and I added up the last of the spending on the flight home. I was pleasantly surprised to see that even with being very free with drinks and meals out, the cost came in less than what I’d expected. 


This was helped by the fact our boat trip was cancelled due to the wind making it too choppy on that day but even with that we still would have been well within the lower end of the revised budget.


Cost breakdown:


Flights / Transport to Split: $5,259

Car Hire: $330

Villa: $5,522

Local transport/taxis: $530

Food, Snacks and Drinks for the villa: $525

Catering in the villa: $2,905 (1 x dinner, 4 x breakfasts 2 x lunches for 14 people)

Meals / Drinks Out: $2,120

Stationary: $30

T-shirts: $250


We had planned on having a photographer ($600) to take professional photos of the retreat and of the team to get some good photos for our website and also to make a short video too. I cancelled this as the weather wasn’t great so didn’t think we’d get good results for the spend.


We’d also planned a boat trip for an afternoon ($1650) which was cancelled due to weather. This was a shame as it would have been good fun but it was a pricey item and we still had a great time without it so no big loss.


What went wrong?!


Thankfully we didn’t have any really significant issues. 


The weather caused me a few mildly uncomfortable hours of having to re-plan things amidst a lot of uncertainty (weather forecasts in Split are notoriously unreliable due to the close proximity of the mountains). 


The forecast would say 80% chance of rain and in reality it was sunny and hot but we had to plan for the worst case scenario.


The most significant issue was when two team members felt ill on the Saturday evening. 24 hours after they returned home, one tested positive for Covid.


They had been sharing a room with another team member, flown home with four others and we’d all been in pretty close proximity for a few days!


Cue fears of a meme landing in Slack along the lines of: “I went on a team retreat and all I got was a t-shirt and covid!!”


In the few days after the retreat we’ve had three of the team test positive and two others not feeling great. 


Thankfully as of the time of writing this all are recovering quickly and not feeling too bad, and the rest of us are all negative and consuming every bit of vitamin C we can get our hands on! 


What nearly went wrong?


One thing that really didn’t land as well as I expected was when I talked the team through the benefits we were going to offer them. 


As we look to make sure they’re not disadvantaged through working ‘remotely’ and being ‘self-employed’ like most remote workers are, I talked through how once we hit our next key goal that would trigger us paying them $100/month towards medical insurance, $50/month towards laptop and home working equipment and 5% of their salary towards pension contributions.


This was a pretty big deal and I’d hoped for some enthusiasm from them!


I didn’t get it. 


It was all a bit flat.


After that session I had a quick huddle with my management team and we talked about it. What I hadn’t realised is that the team saw our next goal as unachievable. 


While it’s a very achievable goal, to them it was a big step up from where we are now so they were struggling to imagine it. 


Them not believing we could hit it meant that they didn’t believe they’d ever get the benefits. 


Some intervention was needed and I had to find a way to not only make them feel it was achievable but also to make them see a clear path to it and get them excited about it. 


For a bit of context, the goal in question is for us to fill 10 roles with amazing candidates every week through our Done With You service, and for us to be doing this by the end of 2022.


Not a crazy number and something I know is very achievable so long as focus on improving a few key friction points.


I had a hunch that they were all thinking very individually about the goal. 


So after a few hours of co-working, we got them all together just before lunch for a quick summary. 


I needed some props. Like in many situations, I figured beer could help so I went to the fridge and got a six-pack and a four-pack of beer. 


Ten beers in total.


I took the ten beers and gave them to one of my team, Nikola.


I asked him if he could help me out, if he could drink those beers for me.


All ten of them.


In the next 45 minutes. 


He looked a bit confused and a bit hesitant, he said he could but he’d be pretty ill.


Perfect answer! 


He couldn’t do all ten himself. 


So I split open the six pack and took one beer out and went to the person next to him and asked if they could maybe help out. Could they drink one beer over the next 45 minutes?


A positive answer and I moved onto the next team member in the circle. 


Now, this was John and I suspect he’s sunk a fair few beers in his time so I asked if he could handle two beers for us. An enthusiastic response from John and I took two more beers from the six pack and passed them to him. 


I kept going, distributing the beers amongst the team. 


A few minutes later we had ten beers split across some of the team all with 1 or 2 beers each.


Now I asked them how they all felt about drinking those beers in the next 45 minutes. 


They were all super happy. 


Some of them were smiling clearly seeing where I was going with this beer fun!


I then talked them through how us hitting our next goal of ten roles filled per week is tough if we’re on our own but if we split it across the team then it’s just 1 or 2 roles each. 


Not so scary. 


There was really great energy at this point, the team were smiling, they were all jumping in positively and it was a completely different vibe from just a few hours earlier. 


I brought up the benefits again and this time they were a lot happier. 


Phew! Crisis averted!


Out of the whole retreat, this was a key moment for me. 


Both in recognising something hadn’t landed well and for adapting quickly and coming up with a cool and fun way to get the team to think differently about something that was hugely positive for them. 

What would I do differently?


Everything worked out pretty well and the post-event survey hasn’t resulted in any major suggestions for us to change. The time we were together was about right, more choice of food would be ideal (always tricky with different tastes etc) and it would be nice to do an activity or two all together out of the villa but everyone was really happy.


One thing that I’ve realised is not a priority is having a pool.


When I was looking for villas, a pool was a must-have. 


I had visions of us all chilling around the pool, swimming/splashing about etc, a true chilled villa vibe.


In reality, we didn’t have that much time to be around the pool (apart from some late-night drinking and chats), the water was freezing cold, and so long as we have good outdoor space to hang out in this would definitely move to my optional list which would massively increase the villa options for us to consider. 


How do I feel after the retreat?


Overall, really really really good. 


Almost everything I’ve read about team retreats has included how positive the business owner feels afterwards. 


I’m no different! I feel really good for finally having met my team. I started to get to know them and crucially they’ve got to know me a little more. I made a conscious effort to have random one-on-one conversations with as many of the team as possible.


I also feel really proud of the specific things we progressed and/or completed. 


Vision, values, benefits, expectations, and goals not only completed but I feel really good about them and that they’ll really make a difference to us moving forwards. 


One of my goals is to feel more ‘professional’ and this was a big step towards that.

We also had some really interesting and deep conversations including one about prejudice in recruitment and how we handle that in a supportive and constructive way with both business owners and candidates.

I had some really surreal moments too. 


I bought JobRack back in 2018. 


It was very small. 


It had no team. 


For two years things went pretty slowly as I was working full time and had just one team member. 


Then in the past 2 years, things have changed hugely. 


I focused on it full time.


I launched a new service that offered people what they really needed


I hired more people. 


Suddenly this ‘little’ business I bought four years ago has a team of 15 smart people, who really care about what we do, and they’re looking up to and following me!








Every time the group was all together, or we took a group picture, I’d have this ‘holy shit’ moment of realisation that this is my team. 


Closing the retreat by thanking the team at dinner on the final night, I had goosebumps up my arms and I felt genuinely emotional. Pride. Gratitude. Excitement. A little nervousness! All the feelings!

Should you run a team retreat?


In my opinion…. hell yes, you should!


It can be a bit scary.


It can cost a significant amount of money.


But if yours is anything like mine you’ll feel epic afterwards, feel like you’ve got great value and be confident that you’ll get a whole ton of benefit both for you, your business and your customers. 


If you’re anything like me you’ll start thinking about the next one on the plane home!


Got questions?


Feel free to ask away and I’ll do my best to answer them. 

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