How I structured our *remote* senior team offsite

The agenda, the outcomes, and the feedback from a senior team offsite at Lingumi, held on Zoom

For new readers, this is my newsletter about trying to be a better CEO. You can read my pieces on writing non-fluffy strategy, writing investor, team & board updates and holding my senior team accountable from previous months. If you aren’t yet a subscriber, you can…

What a hectic month September was. I’m sitting down to write this, later than planned, on a rainy Sunday morning - an indication, perhaps, that I’ve under-performed at one or more of i.) delegation, ii.) time management, or iii.) prioritisation in the past month. More on those skills, and my work to improve them, in future newsletters.

One of my wins in September was running a successful remote Senior Team offsite. I’d normally have gone to great lengths to get everyone into the same room (and away from the office…remember those?) for a couple of days, but Covid forced us online.

The benefit of being compelled to run the event remotely was that it led us to formalise a lot of what happens (or we presume happens) informally in person: how do we get people feeling relaxed? How do we build trust in the group? How do we balance the different energies of a diverse group of thinkers?

Below, I’ll go into a lot of detail on why we needed an offsite, how I structured the offsite, the games & icebreakers we played, and the lessons learned & feedback to improve the next one.

There’s some contextual pre-amble below, but scroll down for the blueprint of each session if you want to dive into the nitty-gritty straight away.

The context: we really needed an offsite

To set the scene, we’ve built up the senior team from scratch over the last 9 months, as we’ve taken Lingumi from 10 to 50 people, spread across the UK, Singapore, Taiwan and China. As each of the senior team members arrived, we gave them a big mandate: ‘build a department’. Each function has grown headcount fast, and each team leader has focused on hiring the best talent they can find for each position, which is a huge time commitment.

I’m enormously proud of what they’ve achieved; as I looked around the Zoom windows of an all-hands ‘Wins’ meeting on Friday, I saw screens of faces I’d be pushing hard for us to hire back tomorrow if they were forced to leave and re-apply. However, the downside of this focus on team-building was that I wasn’t carving out time to strengthen my own team (the team builders!).

I don’t mean that mechanically - we’ve made a series of critical hires and shuffles that have resulted in great team and business growth. What I mean is we weren’t putting in the time together to build trust, create and buy into a shared strategy, and come to deeply respect and rely on one another.

Hanna, my coach, reminded me that this was an investment I should be making more actively when she told me “your top priority is to make your team successful. Anything else is lower priority.”

In the business, especially for product opportunities and customer problem-solving, my ‘OODA loop’ is pretty fast - I react and push for change in the product, or for customers, swiftly. I think I developed that speed over several years of being a ‘product builder’ and the principal customer service agent for several years in the seed stage. In our first couple of years, we iterated and pivoted slowly, because I didn’t notice - or was afraid to admit - that we didn’t yet have product-market fit (PMF). Gradually, I became more rational and, to some extent, “dispassionate” about change (inspired in part by my co-founder Adit’s no-bullsh*t attitude to PMF). We began to iterate faster, and developed strategic laser-focus. The OODA loop sped up.

On team building, though, my OODA loop is much slower; I’m new to the art of ‘developing a high-performing senior team’, and so am firmly in the learning phase. The critical value of having good colleagues, and a good coach, is to force me to notice things more quickly, and pay attention to them. Two themes had been emerging from my one-on-ones that I’d been slow to pick up on:

1. We hadn’t developed enough psychological safety in the senior team: we felt uncomfortable balancing support vs accountability, high-trust autonomous org vs “I’m going to jump in and fix this”. And above all, we didn’t know each other well.

2. The senior team wanted to work on the strategy together: given that my team are almost all new to the business and joined in the middle of an intense year, they were leading through their teams, with minimal time to think about the broader business. My team were seeing the strategy like the prisoners in Plato’s Cave; working with the empirical information they could see or had been told, but without the time to go outside together, create a shared context (see the “sun”), and then collectively debate and build a shared belief about the broader strategic “truth”.

Eventually (with a lot of nudging from Adit), my OODA loop reached its ‘Act’ stage and I booked in an offsite.

Running the offsite

Let’s dive into the nitty gritty. The offsite had three objectives: i.) develop stronger trust and psychological safety in the group, ii.) created a shared understanding of the business strategy, and thoroughly debate it, and iii.) begin the process of building a ‘Lingumi feedback culture’ that would move ‘giving feedback’ from an erratic and inconsistent act, to a high-BPM heartbeat in the team.

I booked in two full mornings, 8am to 1pm, to accommodate a team member in Singapore. I set up 4 sessions:

1. Trust building (Tuesday 8:30am to 10:30am) (moderated by me)

2. Strategy (Tuesday 11am to 1pm) (moderated by me)

3. Feedback (Weds 8:30am to 10:30am) (moderated by someone from the People team)

4. Competitive advantages (Weds 8:30am to 10:30am) (moderated by someone from the Finance & Strategy team)

Before each day kicked off, we spent 30 mins from 8am having our breakfast or a coffee, and playing some ice-breaker games. If you’re British, and thinking ‘Christ that sounds cringey’, then trust me and bite the bullet; the games I outline below are fantastic for changing the mood of a day, injecting energy, and building trust.

The Ice Breakers & Games

My other half works in the theatre world, where these sorts of games are bread and butter for building trust quickly: throw a bunch of actors into a room and ask them to work together to enact passionate narratives of love, lust, death, tragedy, or conflict, and you realise you need some trust-building exercises. So, with a hat tip to the pioneers of stage and screen, here are the games we played over Zoom. They may sound really silly to a serious business person like you 🤨, esteemed reader, but trust me - they’re great fun, and very effective at bringing people out of their shell…or early-morning stupour:

• Commercial 📽: person A chooses an object and acts out a TV commercial of it silently for 30 seconds. Person B has to narrate the commercial. Funny, and builds improvisation skills!

• Uncover 🙈: everyone covers their heads with something and mentally counts to 60. The first person to uncover loses, anyone who misses the buzzer loses, and those in the middle win. The moderator watches to declare the winners, and can confuse people's ability to count by not revealing exactly when they’re starting the timer, or by trying to distract people from their mental count 😇. Surprisingly tense and funny!

• Body parts 🦵: Moderator calls a number of body parts ('two heads' / 'three feet' / 'ten shoulders'). That number of that body part, and nothing else, need to be on screen before moderator calls 'we're there' and moves to next one. Quick and fun for Zoom…gets people moving too.

• I like cheese 🧀: Person A turns away from the screen. The group silently decide who should say 'I want cheese' in any voice they like, trying to disguise who it is. After the speaker says it in a silly voice, Person A turns and guesses. If right, person A joins the group and the speaker is person A. If wrong, Person A gets another turn. Remarkably difficult, and very funny!

The Trust-Building Session

We kicked off day 1 with a trust-building workshop. This felt long overdue: to state the obvious, a team needs to feel a high level of trust in order to operate effectively under pressure, while maintaining autonomy, which is our goal.

We started the session by each reading a list we’d pre-prepared, containing our strengths, weaknesses, areas we wanted to work on, and how the group could support us. This began to move us into the territory of being openly vulnerable with one another, but didn’t get us all the way there; especially with a group of Brits, there was a tendency to under-state strengths, and be reserved.

The next step helped move us into a vulnerable, open space. I took the group through a cycle of ‘one liners’, where each team member could say a line to someone else in the group. They followed this format:

• “You are extremely”: in turn, we’d each tell someone else what they were ‘extremely’ good at (“Jess, you are extremely calm under pressure….not just ‘quite calm’”). The goal here was to move from a reserved expression of strengths, to an open recognition and celebration of excellence.

• “I agree that”: this was designed to validate weaknesses; each of us would acknowledge a weakness someone else had identified, moving weaknesses from modest expressions of personal imperfection, to objective realities that the group agreed upon (“Tom, I agree that you give critical feedback too infrequently to your team, so are stunting their growth”)

• “I would push you to”: in turn, we’d push someone else in the group to recognise and work on an unexpressed weakness. This was designed to bring to bear weaknesses that we ourselves had omitted in our self-reflections (“Tim, I would push you to talk less in meetings - you can be long-winded or ebullient when expressing your views, and so junior voices aren’t given space to express theirs”)

Sounds tough, and I was nervous about how ‘raw’ this session might become. However, the results were wonderful; the open sharing of strengths and weaknesses, and natural equality of the meeting (one line each, cycling through the group), meant everyone bought in, accepting the praise and criticism graciously and warmly. As both moderator and participant, I was delighted, and learned more about some of my own strengths and weaknesses, too.

One extra note here: in each round, we did several cycles, so each person could praise or push several others. However, there was a ‘pass’ option at every stage, for anyone who didn’t have a piece of feedback to share in the moment. This kept things moving along, without putting pressure to arbitrarily praise or criticise.

The Strategy session

The focus of this session was ‘the Lingumi flywheel’. Inspired by reading Jim Collins’ ‘Good to Great’, and, subsequently, his 30-page monograph (available on Kindle) on ‘Turning the Flywheel’, I wanted the team to work on a Lingumi flywheel that we built and owned together, to represent the naturally compounding elements of our business, and how they snowball.

Amazon’s example is below, and was built after a workshop with Collins. It beautifully illustrates the business’s compounding, interlinking advantages:

I built a Miro board with some suggested ‘flywheel elements’ to spark thought, breaking the group into pairs or threes to build their own versions of the flywheel. Each was distinctive, but shared some core elements that are central to Lingumi: delivering a great, human feeling teaching experience, improving the core economic ‘engine’ by selling courses and reducing churn, building engaged communities of parents, and several others.

We then spent an hour together, wrestling these into a flywheel, debating its construction, and agreeing what was, and what was not, core to the flywheel.

After the offsite, I spent another two hours boiling down this down to a finalised flywheel, and taking that through another review loop with the team. If this is going to define how the entire team understands the business, it needs to be really good, and requires a single ‘owner’ to finalise it. But the collaborative wrestling and debating was enjoyed by all:

I can highly recommend going through this exercise. The finalised flywheel feels like a succinct, potent expression of the power of our business, its underlying economic engine, and the compounding improvements to how we deliver value to Lingumi families.

Guest sessions: Feedback, and Competitive Advantages

For the second day, I brought in two team members to guest host sessions. The first was on defining a feedback culture for Lingumi, and the second on Competitive Advantages.

My key learning here was to spend time with the hosts reviewing the agendas and helping them prep for the desired outcomes of the sessions. I failed to give them as much time as I could have done here, but the outcomes were nonetheless positive.

In the first session, we used a Miro board to define and debate our personal feedback preferences, then practised feedback styles in breakout rooms, before returning to update the board if we’d changed our views - this set the stage for work being done in our People team on standardising and training the team on models for giving and receiving feedback.

I’ve zoomed out to render them invisible, but each card had the initials of a team member on it:

In the second session, we used two strategy models to rigorously analyse our business model at Lingumi: Michael Porter’s ‘Five Forces’, and the classic ‘SWOT’ (Strengths, Weaknesses, Opportunities, Threats’ model. Again, we used a Miro board and breakouts to focus in on small groups, before coming together to compare and debate.

This stuff is the nitty gritty of our business, so I’ve craftily zoomed out far enough so you, dear reader, can’t see everything, but I hope this gives a broad sense of how the Miro board was structured. To the left, Porter’s forces, and to the right, SWOT, with its various intersections:

Learnings and Feedback:

The group gave positive overall feedback, with some excellent detailed points made in the follow-up survey:

My key takeaway from the whole offsite was ‘do these more often’. We’d all been so focused on building our respective teams, that I’d sacrificed the time required to build mine. “A fish rots from the head”, as the Russians say - and a senior team who don’t trust each other and work effectively together is a risk of not running these deep, personal, and vulnerable sessions with my team.

I had a lot of specific and targeted feedback on my own style as a moderator, too:

The form yielded lots of ‘quick win’ type learnings: more and longer breaks, longer sessions (“we were just getting going when we had to wrap”), more pre-reading, and some feedback that I should “moderate more loosely” (allow more time for people to consider and comment on topics before whisking us along the agenda). All useful stuff to work on for next time.

I’ll wrap this up with my key learning: when I get lost in the week-to-week operational and management weeds, I fail to spend enough time planning these longer-term, key events. This is classic short-termism; overweighting the importance of the ‘urgent’ in lieu of spending time on high-leverage, important work. Lesson, I hope, duly learned. Finding the balance of time in my week-to-week is another area for improvement, one I work on very actively with my coach, and one I’ll cover soon.

Until then! — Toby

(p.s. hit reply with any comments…many thanks to the many of you who did so last time)

Not a reader? Hit the button below to subscribe.