Get Away to Get Ahead

The many benefits of a strategic offsite
(and how to not screw it up).

Fast & nasty, or slow & nuanced?
{illustration by dangerlam
}

 

Making time for the things we ‘don’t have time for’—like refreshing our business model, strategy, vision, purpose and values to ensure enduring relevance—can be a frustrating challenge. Everyone is busy. ‘There’s just no time,’ we hear ourselves saying—even though we know that's a myth. 

Of course it’s all about prioritisation and so on. But knowing that doesn’t change the fact that there are much more immediate and insidiously demanding deadlines that perpetually syphon your focus and attention. And so we jump from one task to the next, ticking all the right boxes while constantly playing catchup to the ever increasing complexity of our work. 

Many teams convince themselves that the path to liberation lies within increased efficiency—which is quite reasonable. It follows a simple logic: if we can take less time to do x and y, then we’ll have more time to do z

But what tends to happen is that the time saved through new efficiency wins on x and y gets filled up with even more x and y busyness. 

Just as the smartest and most efficient people only seem to attract more work, the smartest and most efficient teams become known for their capability—and so expectations and demands placed upon the team scale in proportion.

Again, this makes a certain kind of sense. I mean, why not? It’s good to be efficient and productive. And if you’ve got an ace team, you’ll want them to be ‘firing on all cylinders’ and ‘driving at full throttle’ and [other performance analogies].

Being efficient and productive is fine. But when it comes to leadership teams, it’s far better to be effective and progressive. 

Efficiency is the silent killer of good leadership

Woah, okay that last sentence was a bit dramatic. But if we don’t deliberately (and periodically) disrupt our patterns of efficiency and busyness—particularly amongst leadership teams—three things happen.

1. We miss out
Without ample time dedicated to developing, reviewing and renewing our strategy, we miss out on opportunities to unlock new value and growth (and therefore attain strategic advantage). Ironically, our focus on efficiency and 'getting things done’ can serve to hasten our descent into irrelevance.

2. We burn out
Busyness displaces the things we value most. We cancel going to the gym, because we are busy. We skip dinner with our partner, because we’re busy. We cancel catch ups with friends, because we’re busy. And we don’t nurture the projects that enrich our life, because we’re busy. 

Unless we are refreshing our relationship with our work—pausing to question what is most important, and why—this can lead to burn out.

At a team level, busyness reduces our capacity for empathy. We don’t have/make time to care—and this has a cascade effect. 

We forget the #1 rule of email (respect recipients time), which makes for poor communications. Our colleagues are also busy, so they do the same to us. This, in turn, eats up more of our time (while elevating irritability), meaning we have even less time to communicate effectively, and so on. The same thing happens in meetings. And because everyone is struggling with their own priorities in their own world, we miss the cues that indicate (our own, and others') impending burn out.

This can be fine for a defined 'season' of work*—but our connections (to each other, our selves, and the things we value most) need periodic refreshing and renewal.

* In my world, there are distinct periods of busyness in which I’m overseas or interstate with clients at a level that would be unsustainable if it were ongoing. But, we’ve gotten better at identifying when these peaks are, and in the future we’ll brace for them, bracket them (with ‘time off’ before and after each ‘season’), and unburden them (in other words: we won’t have me writing a book {or a similarly involving project} at the same time). 

3. We sell-out
Reduced empathy from unrelenting efficiency and busyness has an external effect too—we sell-out.* We stop listening and empathising with the needs of existing and emerging customers, and instead rely on established products and services (which is much more efficient).** We become overly reliant upon past successes, streamlining our systems in order to ‘deal with’ our customers. The bigger (and more efficient) an organisation becomes, the more likely we will experience this empathy-disconnect.

* Sell-out [noun]: a betrayal of one's principles for reasons of expedience. 
** We see (hear) this happen in music and movies, which is why many sequels are so horrible.*** Producers see a ‘formula’ for success, and do what is reasonable: they replicate it (rather than continuing to explore).
*** And by sequels, I mean the ‘afterthought’ types (not movies that were made with sequels in mind before the first film was produced—like Kill Bill vol. 1 & 2, glorious).

In my world, ‘selling out’ is the insidious threat. Perhaps a third of my activity sees me speaking at conferences and events.* Within these keynotes, it is very easy to default to established Intellectual Property (IP—such an odd concept). Stuff that you know ‘works’ (in the sense that the IP is distilled to a point where it is both palatable and digestible). This stuff works because I’ve spent enough time immersed in the complexity, doubt and paradox of these ideas to be able to form a level of conviction around them. Therefore, it is much more efficient to keynote on these, than to spend months in preparation for each and every new keynote. But—if I do this for too long, I’ll turn into a ‘pull-string speaker’ with a finely practiced and polished keynote destined toward irrelevance.**

* The rest of my time sees me researching, facilitating and advising on pioneering strategy and leadership development.
** I haven’t settled on the solution to this yet, but the model I try to work with is ensuring I integrate at least 20% ‘new’ material into everything I do (with the remainder being the core/foundational IP people pay me for—which is constantly evolving). That, and the periodic questioning and disruption of any patterns I establish (see below).

The world’s bullshit detectors are more attuned to 'sellouts' than ever before.* And what’s more, we're looking to do business with companies that are driven by more than just profits—we want to work with those that are driven by a higher purpose.** Companies that actually give a damn.

* Or at least, I’d like to hope so. It still baffles me that get-rich-quick internet marketing hacks work on a large number of people.
** We’re on a quest to become a B Corp. These are businesses that strive to not simply be the best in the world, but rather: to be the best for the world.

This is perhaps the ultimate cost of busyness—we forget the bigger why, and the opportunity we have to contribute to the betterment of the world. We go for the cheapest, quickest and most efficient options—even if they’re unsustainable or potentially unethical—rather than leaning into the challenge of discovering the best option.

Unrelenting busyness is the gateway to irrelevance

The only way to liberate leadership teams (and anyone) from the clutches of unrelenting busyness, is to make it (periodically) relenting.* This is why—in addition to your daily, weekly, monthly and quarterly rituals—an annual or bi-annual strategic offsite is so important.

* Relenting [verb]: become less severe or intense.

Of course, to do this well takes time.* Which is hard because everyone is busy, and ‘there’s just no time’. But let’s—for a moment—assume that we have a leader or group of leaders who prioritise the enduring relevance of their business, and are willing to make time to ensure this. Here are some of the benefits they can enjoy:

* The efficacy of a strategic offsite is largely determined by the thinking and work that happens before it convenes.

The benefits of a strategic offsite (if done well)

Sometimes you need to get away in order to get ahead. It sounds counter-intuitive, I know, but doing this yields many benefits—the ultimate of which is perspective. 

With any strategic offsite we get to refresh, redefine, and/or reconnect with the purpose of our business. At a functional level, this purpose is inherently linked to current and emerging market needs. Your business model may be optimised to meet current market needs* but the real question is: how equipped is it to meet future market needs?

* Although usually this is not the case. Strategic review will identify unnecessary friction points, ineffective partnerships, neglected customer segments, and so on. The challenge here is to balance the demands of operational urgency with the opportunities of pioneering leadership.

The process of answering this question is beyond the scope of this article (and something I cover in my new book). But the result of this exploring translates into better decisions. This, in turn, influences the direction of your business—which ultimately determines the future relevance, value and impact of your work.

This means we don’t miss out. 
By removing ourselves from the busyness of our everyday context—and by holding a context that allows for slow/thorough thinking—we can arrive at new strategic pathways and initiatives that would be impossible to generate otherwise. 

This also means we don’t sellout. 
A well designed strategic offsite allows us to empathise with our customers, and what they really want and need. We get to question those default operational decisions that are really—when you stop to think about it—just cheap, tacky and lame. 

And it also means we don’t burn out.
There’s something about gathering a team together in a naturally beautiful location to share a meal and a glass of wine—our work facades drop, and we become (more) human. A side effect of being human, and relating to one another as people, is that we connect more. This translates into greater empathy and care for each other, and in turn makes for a greater place to work. 

This also enhances the likelihood that we will be comfortable to conduct progressive experiments, as we know that the team understands that we are operating with the best of intentions. On the contrary: we’re much less likely to see experimentation and innovation in teams where personal connection, trust and empathy are low. What we instead see is politicking and ‘ass covering’.

We had a strategic offsite recently, in which our small team had a couple of nights away at an eco-retreat in the forest with good food, fine wine, long walks, a moth attack, and deep thinking. It helped to reconnect us with each other, rather than just with the infinite work ahead. We also had time and space to explore and unpack our personal values, and their associated fulfilment factors (more on how you can do this in a future museletter). Suffice to say, the strategic offsite was so enriching and effective that we’re now doing it quarterly.

Strategic offsite? Easy! Right?

Alas—there is more nuance to this than simply booking a venue and sending out a calendar invite.

I’ve worked with leadership teams in which the strategic offsite has completely elevated the team's strategy and cohesion. But I’ve also been the token ‘external’ for offsites that are simply expensive junkets that offer no strategic value. 

And so, if you’re thinking about doing a strategic offsite with your team, here are a few traps to avoid.

7 easy ways to screw up any strategic offsite

1. Doing it cheap
Strategic offsites should serve to elevate our aspirations and thinking. Much in the same way that putting on a comfortable but flash suit influences the way we conduct ourselves (thanks to Enclothed Cognition), the context in which we do our thinking has an influencing effect. 

If your aspirations for your business are world class—don’t host your strategic offsite in a B-class venue. If anything, punch a bit above your weight. Aspire, and find somewhere inspiring.*

* This is not to say it has to be expensive. Just don’t make it cheap (in a tacky/nasty ‘polystyrene cup’ type of way). 

2. Doing it convenient
Ah, so tempting. It’d be so much easier and efficient if we just went down the road. It’d save us having to worry about accommodation for most folks too. Amirite?

But convenience can quickly become a threat to your offsite. People might multitask the offsite with a quick 'ducking into the office' to finish up a few things—which means their thinking, contribution and presence won’t reach the depths that a remote offsite will take you to. I know several teams that do their offsites ‘onsite’—and it just looks and feels like a long meeting.

No: you want your offsites to be in a location your people otherwise wouldn’t normally venture to. This is all about context. 

By venturing into a new context, you open up the possibility for new thinking (see the next point). The journey to the offsite is an important element, as it acts as a kind of ‘third space’ between our normal work context and the offsite context. This allows us to prime ourselves for the offsite. 

By having to stay overnight, you’re creating a new shared experience for the team. They can stay back late, and partake in those rare but oh-so-special conversations that only ever occur after a good dinner. You also create space for people to process and reflect at night and in the mornings (opening up even better thinking in subsequent sessions). If you were to do this in a convenient/local location, many folks would be returning home at night, where they may be distracted by family and established routines. 

3. Doing it boring
Another temptation would be to hit up a big hotel. You know: the usual suspects. You probably have corporate rates with them. They’re a safe option.

But safe is boring. Safe is what everyone does, which means that safe is the default. And what this looks like is default rooms with default notebooks and default mints and default everything.

By all means: if you want default thinking to be the theme of your offsite, go for it. But most of the folks I work with are seeking something that’s much more inducive to new, pioneering thinking.

If you don’t want more of the same—choose something different.

4. Doing it quick
Someone will be looking at the costs associated with an offsite: the accommodation, the catering, the transportation—not to mention the opportunity cost of pulling leaders together and away from their work. In order to maximise the ROI, some folk will seek to create a dense, tight agenda: breaking things down to 30 minute blocks.

This is precisely not the point.

What we are attempting to disrupt is busyness (and the fast, default thinking it favours). The best offsites have loose agendas, with plenty of room for organic and emergent conversations. Rather than covering off on content, they’re focused on creating context.

5. Doing it diluted
There are two very easy ways to dilute the efficacy of a strategic offsite.

The first is to do it without diversity. If you don’t have diversity of gender, age, culture and—most importantly—thinking baked into your team: you’ll want to remedy that. For example, the digital literacy on many senior leadership teams is woeful. Including someone with the savvy will enhance the quality of your conversations.

But we don’t want to go inviting everyone. That’s the second way we can dilute the impact: by inviting too many people. There’s a quality of conversation that can be achieved with a team of 7±2 people. With too many people, we begin to see factions form. This can be managed by a good facilitator, but when it creeps beyond 12–15 people, we're in trouble.

6. Doing it discreetly
You don’t need to keep your strategic offsite a secret. That only heightens suspicions that you’re doing a junket, and it widens the gap between leadership and the rest of the team. Rather, you want to involve the wider team: in consultation in the lead up to the offsite, and in the followup communications that occur soon after.

In fact, a very similar trap to doing it discreetly, is doing it discretely. This is where we treat our offsite as a singular, isolated event—rather than a key element of bigger strategic momentum. Let’s not do that.

7. Doing it... with a specific objective to achieve
That’s right. You don’t want to have a clear objective to achieve as a result of your strategic offsite. Stay with me.

It’s one thing to design, develop and do a strategic offsite with a specific intention (and a process to support it). It’s quite another to do it with a specific objective you are striving for. 

The issue quite simply is: you’ll probably achieve it. 

But—and it’s a big but—in your fixation to achieve this predetermined outcome, you’ll miss the unique opportunities inherent within a strategic offsite. Namely: the opportunity to cultivate emergent discussion, new exploration, new thinking and new perspective.

So: save your goal-driven conversations for the boardroom (a place much much more appropriate for narrowed focus and thinking). 

With a strategic offsite, we can do better. 


Of course, there are more mistakes than the seven I listed above. You could use an internal facilitator that favours particular factions or politics, or hire an external facilitator who’s a numpty. You could subscribe to some archaic ‘proven process’ and slave the offsite to that. Or you could miss important nuances in the lead up to the offsite, or have people arrive unprepared. Or—and this is common—you could do a wonderfully effective offsite… only to have nothing change when people return to their roles.

So many opportunities to stuff up!

But one thing’s for sure—the biggest mistake would be to not do any offsite at all.

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