The Value of an Illuminate Offsite

Rachel Townend
Illuminate Financial
8 min readNov 7, 2023

As I enter my tenth year of organising our Illuminate offsite I can’t help but reminisce about why we started these annual team gatherings and why today we value them more than ever. ‘Post covid’ company offsites & retreats are becoming much more commonplace and have thankfully evolved from alcohol-fuelled financiers on all expenses paid ‘jollies’ to a core part of a company’s strategic planning and engagement.

For companies who have moved to fully or partially remote working these quarterly or annual get-togethers are essential and for those of us working between multiple geographies the chance to get together face to face should never be underestimated. In turn, the choice of companies to help host and plan these offsites has multiplied since I first began and there is an abundance of support from companies such as Worktripp, Ten80events, Nomandic escape & TeamHappily to name just a few.

Whether it is a few days’ relaxation in a boutique hotel as a ‘thank you’, a purely working agenda in which everyone congregates in one corporate location globally or more recently a focus purely on wellness and employee wellbeing, the importance of a company retreat is on the rise.

Cycling 2022 The Mitre Hampton Court (Ginette Allen at The Merry Pedaller)

Surprisingly, since starting the Illuminate blog posts in 2018 we have not written a single piece about our team and culture, however, I can assure you this is not reflective of where our focus lies and for those who don’t already know, it is firmly at the heart of everything we do. I have lost track of how many times we discuss with our team the importance of holding back 20% capacity to allow everyone to contribute directly back into our team and culture. Why does this matter … because it is one of the main reasons why we prioritise an annual offsite and why we started organising them from the onset.

Illuminate offsites have always been about forging deeper connections within the team, looking inward at how we can improve all aspects of our model and of course pausing for a moment to reflect before rushing headlong to the next opportunity. Fun & team building is essential but for Illuminate, not in a structured or forced manner if we can help it.

In September 2015 (having not yet finished the close of our first fund) we made the bold decision to jump on a plane to Ibiza and host our first Illuminate Offsite. The ease of booking a 6 bedroom villa one week prior to travel with the simple specification ‘accommodation with a communal lounge with a television to tether our laptops to’… what a breeze!

Ibiza 2016 — Villa Rosa, San Antonio, Ibiza

The majority of our network assumed we were off to party but how wrong they were. Two eager ex-Bain & McKinsey consultants on the team may have helped (Alexander & Rezso, now Partners) but from day one we had a structured agenda and goals & objectives that we adhered to. Looking back on those first 2 days in 2015 we created guiding principles that we still use today alongside discussing topics such as the power of our network, high-touch interactions & relationships, respect for each other, professional development & growth, the impact of timing, the importance of sector understanding & data quality and thematic analysis. Don’t get me wrong, we are not perfect, and some may have gotten carried away on an impromptu whisky tasting resulting in heavy chastising in the morning or deciding to take the agenda to the pool on occasion, but we were aligned as to why we were there and what outcomes we desired.

In 2016 & 2017 we continued to visit different locations in Ibiza and were still small enough to be largely self-sufficient. Priorities included hiring a car the founder would deem appropriate (he is a car guy!) and getting the shopping list correct (Baked Beans, Cooked Chicken and a lot of bottled water in litre bottles. Like 36 litres). From then onwards we have travelled to Barcelona, London and Berkshire and much to my delight I finally organised a ski offsite to Val d’Isere in France this year thanks to VIP SKI. Despite our growing numbers, the format has stayed largely the same in which we create a business-led agenda, make time for team activities and create free time together whether that includes dinners, a swim or having a coffee.

We want our team to attend our offsites to work & play hard, build deeper relationships, challenge anything and pause to share and celebrate a moment in time in Illuminate history. For example, London 2022 at The Mitre Hampton Court was a particularly memorable one for Illuminate in which we finally emerged from a start-up to a fund returner in our own right! Each year we will be celebrating our wins and learning from our losses. We choose a theme that is applicable to the business and adds an element of fun — previous themes have included ‘Back to the Future’, the Olympic sport ‘Biathlon’ and ‘Fat Boy Slim’!

Flower arranging with Adam Garrett at Devine Flowers

I often read that offsites must be run and designed solely by Senior Management, however at Illuminate we have always built our agendas in a collaborative and inclusive manner and although alignment is key, we want to know what is at the top of our team’s agenda … not just ‘management’s’. Our Interns and Executive Assistants (EA) have run sessions that are just as valuable and well-received as our founders. For example, on our last offsite, Katie Karlsson, our fairly new New York EA valiantly put herself forward for a session on giving feedback which resulted in a brilliant & memorable practical session searching the chalet for our team mascot ‘Einstein’ using varying types of feedback.

When I look back on the past ten years I smile … I remember 2016 when Mark Whitcroft caught the evening easyJet flight to Ibiza in which the passenger next to him proceeded to be escorted from the plane for their bad behaviour before they had even taken off (not anyone from Illuminate I might add!). His face = priceless. In 2017 I recall Luca Zorzino’s realisation that he had left a suitcase belonging to our new head of finance in the back of a taxi after volunteering to look after it since it was Andrew Patey’s first day at Illuminate (fear not we got it back!). In 2021 we played a fiercely competitive game of Taboo I will never forget (I’m not sure I will ever laugh that hard again either) and Tim Frost, to this day is still trying to work out how the Magician outfoxed him multiple times by the side of the River Thames in 2022.

Do my favourite memories directly link to our business agenda? No. Have they created a bond, an arena to regale stories, laughter amongst colleagues and a personalised history specifically to Illuminate? Yes! For Illuminate our offsites are as much about connection, taking time away from the normal routine, energising and sparking creativity as they are the work agenda (which runs alongside all of the above).

Val d’Isere 2023 - Altitude Biathlon. Crossing the landscape at speed whilst targeting with great accuracy.

I appreciate some of this has been a rather self-indulgent trip down memory lane but perhaps a few insights if I may:

  • There is huge value in just being together face to face (no agenda needed). Building Trust comes from real connections.
  • Things always take longer than you think- especially as your team grows. Design the agenda and then allocate more time! Herding cattle comes to mind when arranging activities but when it comes to meetings, we use a phrase called ‘parking lot’ to keep conversation on topic. Any discussion that is of interest but not relevant at that exact moment gets noted down and resurfaced at the end should time allow.
  • If you can enforce a ‘no device / no external meeting rule’ then do so but also make sure you build time into the agenda for people to check their emails & deal with absolute priorities. (be aware in particular that the EAs will still have incoming emails from their executives and the build-up can cause anxiety!)
  • Make sure you have a comfortable and well-lit meeting room — it's easy to cut corners here but you may well regret it post a full day's agenda! Decent wifi is a must and don’t forget to factor in that you may end up with team members who have to dial in due to unforeseen personal circumstances closer to the event.
  • Smaller breakout sessions in which people open up about their challenges, learnings from the year and/or motivations are often the most valuable (especially with larger groups) and in our experience are the things people take away and remember for years to come.
  • Make it personal. I am still lucky enough to have arranged these offsites singlehandedly and I can offer ‘above & beyond’ but even if you do outsource don’t underestimate the meaning behind a personalised letter from the founder or a location-specific gift to keep as a memento from the trip.
  • Have a strong opening act (for us it is our Founder who is a motivating & engaging speaker) and don’t be afraid to ask external speakers to join or mix up the agenda to keep the energy levels high.
  • When you decide on your offsite dates do put a follow-up session in 2 weeks later to keep momentum and hold people accountable for the follow-up actions.

The main challenges I now find myself faced with are around whether to outsource the offsite project to an external company (yet keep that personalised approach), whether to add a facilitator or external party to the agenda planning and how to keep all our team engaged and included as we start to break down into geographies, departments & specialities.

What is my overriding takeaway from 10 years of arranging offsites you may ask? That’s easy … if you are the one arranging them then make sure you book a week off after to recover! (Something I have never done but one can dream, right? 😊)

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Rachel Townend
Illuminate Financial

Rachel is Chief of Staff at Illuminate Financial Management. Rachel brings a wealth of experience and expertise to her leadership role.