Planning and executing a team retreat which helps your business to be better

Team retreats are exactly that: a retreat from the daily work you do as a team. We might think of them as a retreat from life and the world, the whole team staying in a remote cabin in the wilderness, playing paintball games in the woods and doing trust falls. Or a few people gathered around a boardroom table in a different office space.

We run a team retreat at least three times a year. In the early days of PF, as the company began to grow, I noticed a major difference in the team’s enthusiasm and energy after we’d gotten together in person for any reason. As a fully remote team, with no official “offices”, it was rare we would meet up, so when we got together to attend an event or exhibit at a conference, we felt the difference. We were more connected. Had more creative ideas. Casual chats when grabbing drinks or preparing food turned into “what if we” and “I’m not sure about” conversations. Things we’d been mulling over for months turned into actions within hours or days.

That was when I decided to set up an in person team retreat. Everyone would attend, and we’d spend a full day together in a location we all travelled to – London, Manchester, Edinburgh, Glasgow. As we began to bring on international team members, it became more costly to bring the whole team physically together. At the time we were doing at least two retreats a year, and I remember deciding we’d have one international team member attend a retreat, turn about. This failed spectacularly. Although the retreat was a great success, with ideas and laughter and bonding and clarifying our values and taking photographs and coming up with better ways to serve our clients, the one person who wasn’t there felt their absence from the group, and we all felt it too. The team told me the next week “That didn’t feel right; whatever we do, everyone has to be at a team retreat”. They were right, and we talked about how to make that work. Instead of having in person retreats 2 or even 3 times a year, we’d have one, and it would be longer, and everyone would come.

Then covid hit. We had our first full week retreat planned for May 2020. Every member of the team from all the different countries flying in. A huge house up north in Scotland with rooms for everyone and a big kitchen and space to go for walks by the beach. We were excited. This was going to BE OUR YEAR. And then it wasn’t. It wasn’t anyone’s year. We cancelled and rescheduled venues and flights and plans, and said no problem, we’ll do it in a few months, and let’s do an online retreat instead. When things were still locked down, we rescheduled it for a few months later. Then a few months later again. Then the next year. Now it’s 2022 and we’re hoping to hold our full in person retreat in September.

These delays have taught us even more about team retreats. Formerly we ran them in person or not at all. Now we’ve discovered how to build hybrid retreats – with online sessions and offline plans and groups of people in similar areas getting together for dinner or creative activities. We ran one team retreat fully online, but that felt like an extended team meeting and it’s tough. I wouldn’t do that again.

First, we’ll look at how team retreats help all of us: the team, me as a leader, and our clients. And then I’ll walk you through our learnings: what worked, what didn’t, what we love, what was a spectacular fail, and what we’re still learning today.

How team retreats help the team

This is the most obvious purpose of a team retreat. Our retreats prevent even enjoyable work becoming drudgery, helps us see and think differently, and focuses us all together on one purpose, one theme.

I looked back through my notes from the last four team retreats, and here’s what the team shared they loved and appreciated about them:

  • Reading a book together applied to my personal life, not only my work
  • Loved the breakouts by team groups
  • (New team member:) Getting to know everyone, the PF brand, how we communicate here
  • Being able to genuinely stop working
  • The space to feel more connected with each other
  • Sharing part of my culture (for Culture Night)
  • Downtime and time for a different kind of rest
  • Space to think about, what makes us a PF team member? Who am I as a person and as a member of this team? What things do I enjoy and why do I feel that way? What parts do I need to work on and which are only okay?
  • It’s good to laugh together
  • Inspiration & getting fired up
  • It helps us change things
  • We have the conversations we don’t normally have
  • The whole team being on the same pace
  • Permission and space to breathe, be creative, get outside

Even reading these over again has encouraged me for our next upcoming retreat, and reminded me of their importance and the humanity of the team I have the privilege of leading. These are not robots. They’re not worker bees. You don’t hand them tasks and tell them what to do whether they like it or not. As a leader, team retreats help me to lead better.

How team retreats help me as a leader

Planning and executing a team retreat is a massive amount of work. For the first few years of retreats, it all fell on my shoulders. Partly because I took it on. I needed to go through the process to understand what I wanted, what they want, and what we collaboratively want and need to help us work together to serve our clients. We’ve started a team retreat committee, and the team members are responsible for more and more each time, and this reflects the work we’ve been doing to scale and “de-karen” the company.

On reflection, this is how retreats help me:

  • I’m reminded what a creative, fun, talented group of people I have the privilege of working with and leading. This helps me lead better and listen better.
  • It’s a lot of work to plan. This reminds me we achieve more when we plan for it instead of letting things happen or waiting for an outside circumstance to take action. It’s also a reminder to plan almost obsessively: really think about what’s going to happen and when, how people will feel, what we’ll achieve.
  • In person retreats especially are a big investment of both cash and time, and it reminds me what a worthwhile investment it is. People first, team first. I need to put our money where I say it matters.
  • Inviting others on the team to lead expands our capability as a team, and prevents bottlenecking. It helps with our scaling and systemising process. It helps me to listen.
  • I’m not the only one with good ideas. The more involved the team are, the better ideas we have collectively, and the better we are able to serve the clients we love working with.

Team retreats remind me my job as a leader is not to tell people what to do: it’s to invite people into a space where we can collectively agree what is best for the company, each other, and for our clients. And team retreats not only help us serve our clients better, it helps our marketing to better reflect us so we reach the kind of accountants who have the same kind of philosophy as we do. As someone said recently on Twitter, “have meetings only with people who make me want to greet them with ‘Yay!’ instead of ‘Hello.’”

How team retreats help our clients

  • We are more refreshed, more creative, and better able to serve with enthusiasm and energy. We have better ideas and this flows into the work we do
  • What we learn in the book we’re reading helps every team member understand our clients’ businesses better. Those who haven’t run businesses themselves, learn more about what this is like, and how it feels
  • A retreat introduces deadlines which pushes clients to get back to us on things which have been sitting on a back burner
  • When we run one, it reminds our clients to take care of their own team members and consider how they might run retreats

Everything is better in our company after a team retreat – the impact is felt for days and weeks and months and even years after. Even when we’ve organised it in a way we’d never do again, we learned from it. After the retreat in which we read “No Rules Rules”, about the way the Netflix business is run, we recognised the need to learn from mistakes and fails and share these with each other. At PF our approach is more positive, so we focus on the learnings rather than the failure aspect. We’ve even started a Slack channel called #learnings which we use to share observations on anything in the business – a call we felt didn’t go well, a deadline we missed, a mistake we made which cost the company money, an idea we tried which flopped.

Specifically in relation to team retreats, my two biggest learnings are:

First, planning is everything.
Second, plan for things not to go to plan.

The more you plan, the better the retreat is and the more people enjoy it and the better ideas you get. The book which changed my thinking on this was Creativity Inc. Here was a company the size of Pixar, with over a thousand employees, who planned in great detail for the better part of a YEAR to make a ONE DAY event a success. They created committees. They sent out surveys. They asked for input. They identified leaders and created breakouts and started conversations online and in person. They didn’t simply have a one day event: they had a year of small events, which made this one day effective and rejuvenating, managing to stay on task whilst also being open to new things. It’s taken me years to really understand this – not only for team retreats, but also for our weekly team meets, divisional meets I’m not in, client meetings, Lab sessions, Accelerator sessions…the more you plan, the more structure you create, the more ideas flow. The more creativity there is. The more room there is. It feels backwards. I used to think I didn’t want to over-plan, but it turns out that’s the best thing to do. As well as planning for things not to go to plan, which is a part of any planning.

The practical things: how our team retreats work (now anyway)

I’ll share our learnings after this, but first here’s how our team retreats work. I’ll use the example of a hybrid retreat because those are the ones we’ve been getting better at over the last few years, and because we haven’t actually held the full week in person one for the entire global team yet! (We’ll report back once it happens.)

Preparation: 3 months ahead

We run retreats 3 times a year, so we start planning for the next one immediately after the current one has finished.

To keep our retreat focused on a theme, we choose a book for the whole team to read together. Deadlines are identified, and the books are purchased for the team. I recommend physical book copies, but team members can request audiobook versions as well. The book is chosen based on what we are focusing on right now as a team. (More on this in our Learnings)

Each team member reads the book by deadline, and submits a video with their thoughts and notes about what struck them and how it applies to PF. As we’ve grown, we’re now experimenting with the team discussing these in their divisional meets, and submitting one video per division (ie the Designers Collective, the Writers Guild, the Council, which are our names for the team divisions).

The team retreat committee (3-4 people) meets to review observations from the previous retreats, and meets once a month to make sure everything is going to plan – venues are booked, sessions are organised, books are being read. Starting a team retreat committee has helped me not to bear the entire burden of planning, and it reminds us how quickly it comes up!

We create an agenda with specifics about how to prepare, why we’re doing this, and how to use the time well. This is finished and distributed to the team at least 4-6 weeks before the retreat begins. Here are a few pages from our upcoming retreat agenda (it also includes session times and topics, and zoom links).

For hybrid retreats, each region plans their own in-person get togethers. For example, we have 8 team members in the UK (6 team members in Scotland and 2 down south), so for some regional meets we’ll gather the whole UK together, or depending on restrictions and lockdown requirements, it might be only the Scottish Contingent or only one or two people. Again, planning is key. We’ve learned the hard way not to plan too many activities in person close together, because as a remote team we can forget how much time it takes to travel and arrive and greet each other and catch up and then get to where we need to go!

Our USA team members might get an Airbnb and stay together the whole retreat, or they might attend from their own homes and get together for an evening. The hybrid retreats are flexible depending on the locations, people, and any relevant health restrictions. Some of our further flung members in Argentina and South Africa will plan their own rest times, like arranging a massage or booking creative time at a pottery shop. All of this requires planning, or else we come to the retreat days and realise we didn’t buy train tickets, or didn’t book a restaurant, or didn’t have the materials we need for a creative exercise.

Retreat time: 3 days (Hybrid)

For a hybrid retreat, we take three full days away from client work. We find this works well Wednesday to Friday, because as enjoyable as these days are, it takes a lot of energy and it’s a lot of focused time with our co-workers. We need downtime with ourselves or our families afterwards.

During the retreat, we include:

  • All-team sessions (2 hours max): These are held on Zoom to allow everyone to attend, for no longer than 2 hours, with moving/stretch/fresh air breaks every 30 minutes. We only hold one of these per day. We tried running two or even three of these and found them exhausting.
  • Breakout sessions (10-30 mins): We either break out during an all-team session, or schedule these separately. These include 3-4 people in each group and have a specific topic to work through. Each group comes back with ideas or actions, depending on the purpose of the breakout.
  • Action sessions (30-45 mins): This is usually on the last day of the retreat. We review everything we’ve talked about and the actions we’ve written down, and identify who’s doing what, and by what deadline.
  • One to ones: These are scheduled by individual team members amongst themselves. We encourage them to choose at least one person from the team they don’t regularly talk to, and have a phone call (or FaceTime). Ideally this is held whilst walking or sitting outside (not sitting-in-office-zoom), and there is no restriction on topic, or length of call. Team members can arrange as many as they like, or only one or two. (Observations we had after several retreats was that quality is better than quantity in this case.) They’re encouraged to prioritise team members who are on their own and aren’t able to join regional meets.
  • Fresh air breaks: This is a specific time to take at least one full hour outside. We encourage doing this without a phone, or with the phone in airplane mode, to help get head space. This could include going for a walk, a run, a swim, or just sitting outside in the sun (if the person happens to live in a country that has some).
  • #restpillar time: Rest is one of the four character pillars of PF, and it means being intentional about getting refreshment for your mind, soul, and body. It doesn’t mean naps (although sleep can be restful): it means space. Openness. Quiet. Release. Rest looks different for different types of people – for one person going for a run is restful, and for another it’s sitting in a chair reading. Rest time is spent on your own, because it involves listening to yourself and to messages you may have missed from being so busy. We encourage rest time during retreats.
  • #creativitypillar: Creativity time means an activity or exercise which stimulates you creatively. Usually it includes something different from what the team would normally do: our designers might try writing poetry, or our content writers might do some painting. Creativitypillar means there isn’t an “outcome” to be displayed or sold. Examples include:
    • Visiting a museum
    • Painting or sketching (digital or paper, chalk or paints)
    • Writing fiction or poetry
    • Trying a new app or tool (like AdobeFresco or Canva or TikTok) and playing with it, with no planned outcome
    • Building Lego or blocks from a pile of random bricks
    • We suggest blocking out 1-2 hours for this time, and after they’re done they share their #creativitypillar exercise with the team in slack, so we all get to enjoy the creativity and get ideas for our own exercise.

Post retreat

In past retreats we’ve used the final day to hold an all-team session to talk about what we loved, what worked and didn’t work, and anything we’d change. However, with team members in multiple countries, the timing of the session meant most of us were giving observations on a retreat which wasn’t over yet. We’ve decided to change that, and following the retreat, we’ll use our normal team meet time (Tuesday afternoon) to have this conversation, including:

  • What did you love?
  • What worked really well? What didn’t?
  • What would you change for next time?

We also use this time to confirm actions we’ve already taken (the easy ones we can implement straight away), and confirm who’s responsible for other actions we agreed on in the Actions session.

The observations and review of team retreats have taught us a great deal about what works and doesn’t work for us.

Learnings: what we’ve learned worked and didn’t work for us

As you build a team retreat, you’ll have your own learnings, and not all of them will match ours. If any of these can help you avoid struggle or exhaustion, please use them!

  1. Have a theme. Our way of choosing a theme is to select a book for the entire team to read together the 2-3 months before retreat begins. We choose this book based on what our current focus is as a team and as a company, and what will inspire conversations and change in this area. The books we’ve read in the past are (in this order):Traction – when we were beginning to consider what scaling and systemising the business looked like
    Rising Strong – when i was processing as a leader what transparency and vulnerability are, and how those fit with running a business and the team working together as a team
    24 Assets – Exploring what it means to build assets for our company (like the marketing map, concentric circles, the Buyer Progression Model) and how to use them well
    Creativity Inc – when we wanted to lean into our creativity as a team and recognised our growing team presented new challenges and we didn’t want to get stuck or stay stuck
    No Rules Rules – how to maintain a good healthy culture as the team grows and we continue to add team members every few months
    Deep Work – Recognising the temptation to get distracted by little things and attempt multitasking. How to go deep , stay focused, and achieve more and do better individually and as a team
    Atomic Habits – what we’re reading now, as we have Wildly Important Goals (WIGs) for the company and for each individual person. We’ll talk about how we achieve these by creating good daily habits.The book is usually a “business book”, and so far I’ve chosen the book each time to direct conversation and make sure it’s something I want every single team member reading every word of. It’s always a book I’ve either already read, or spent time reviewing and understanding what’s in it. I always buy a copy (if I don’t own it already) and flick through it to make sure it’s a good use of time for the entire team.
  2. Don’t have too many sessions (online or offline). We’ve settled on only ONE session per day, 2 hours max, with everybody. Some days we’ll have another breakout session with a few people in it, and people do one to ones throughout the day. But a full day, with the whole team, all day, is overwhelming. It doesn’t deliver what we thought . We think it’s great and get excited….and then we are exhausted and don’t have energy to implement our great ideas. And there is so much work to do when we get back.
  3. Adding extras adds complexity. Trying to add things, like professional video recordings or taking team photographs or inviting guest speakers, is tough. It always takes longer than you think and it detracts from the other things you’re trying to achieve. If you have an extra item like this you want to achieve, set aside an entire day for it and focus entirely on that and do it well. If there ends up being extra time, use it to do breakouts or eat together or do a creative activity but these are a bonus extra.
  4. Focus on connection, rest, and open conversation. If you need a team retreat to plan new services or sketch out your onboarding process or create content, you might be missing an opportunity to be doing this daily in the business. To be fair, our early team retreats were entirely about this. We used every minute to discuss services and review client lists and plan marketing actions. Over time, the better organised we got with our weekly team meets and divisional meets, the less we needed retreats to figure out pricing and services and systems, and the more we realised we needed them for focus and sharing and ideas and banter and connection. If you do need to use your retreat to focus on services and systems and finance, think about how you can begin to incorporate these into daily and weekly rhythms. You’ll achieve more in the long run.
  5. Plan for downtime after. For short team retreats, we use Wednesday – Friday (or Thursday – Friday). For full week retreats, we use Monday – Friday (with travel time on the weekends). No matter how well you plan, it takes a different kind of energy to participate in a team retreat and everyone will be exhausted and in need of rest and family time afterwards. Once we ran it on a Tuesday/Wednesday, and everyone had piles of work to start in on the next day. It derailed all our enthusiasm and great ideas and we all lost momentum from what we’d spent two days discussing and working out. It took a good three weeks for us to regroup.
  6. No client work, no meetings, no coaching groups, no trainings, at all. This takes planning and setting expectations – letting clients know it’s coming, setting deadlines, not arranging meetings. It took us years to finally get right. We run several intakes of the Accelerator coaching group every year, and the sessions run on a Thursday afternoon. Every Accelerator group we’d realise we couldn’t move a session because we’d already calculated out the whole 12 week plan, and it would throw it off to cancel or move one. So during every team retreat I’d run a session, then rush off to deliver a 1.5 hour session with Accelerator members while the team were resting or doing creativity time or having breakouts. We made it work, but this year for the first time ever we are having a team retreat in which there is no Accelerator session on a Thursday, because we planned it that way.
  7. Leave empty space. One of the things which annoys me about most conferences and live events is the way they are absolutely crammed in. Breakfast session at 7am. Second option at 8am. Conference start at 9am with a talk until 9.10am and then another one from 9.10 to 9.30am. Breakout from 9.30 to 10am. And on and on and on the entire day until everyone is exhausted, rushing, and with brains so full they aren’t really taking it all in. It’s as if we think more stuff means more learning and more growth, whereas sometimes more is just more. Empty space allows people to talk. Think. Process. Wonder. Be curious. Consider. Leave options for the empty spaces – creativity time, rest time, food time, walking time – so people don’t default to their phones or client work or emails or running errands. Set expectations about this. Help people to understand how to be intentional about their creativity time or rest time.
  8. Pay for everything. The team’s travel, the Airbnbs, the food, the whisky distillery tour, the dinners, the drinks, the books, the creative tools, the venue, the swag, the gifts. This is one of the single best investments you’ll make as a company in your people, and the more you plan for it the better you will be as a result. Still create a budget and invite the team into choosing how and where that budget is spent (more creative options); but think about how this will build a team who love working together, whose opinions and input are valued, and who know they are worth investing in, in a big way.

We’ll have many more learnings along the way. Our next retreat runs in a month’s time (from the writing of this article) and we’ll have new observations and suggestions based on who we are as an agency, who our team members are, and what kind of company we want to be.

I’d love to hear about your team retreats. You’re welcome to connect with me personally on LinkedIn or Instagram to ask questions, or share what you’re trying.

You can also join your fellow accountants in PF Lab – we hold live sessions and share resources about team retreats, remote working, managing a team, building a culture, book reviews, andmore! See you in there!