Why ‘on sites’ really, really matter in a remote first company

As most of you probably know, I work for a remote-first company, and I recently had the opportunity to attend my first on-site/off-site meeting in Silicon Valley (I can’t decide what to call it given that my ‘site’ is a dining room and the company office is a co-working space…). There are a bunch of articles you can find about the virtues and perils of the off-site meeting, and they tend to cover all the usual stuff around team building, morale, blocking out time etc. Today though I’m going to write about why I think they can be so important through the lens of the Stockdale Paradox, of my favourite concepts from of my favourite books, Jim Collins’ Good to Great.

The Stockdale Paradox

The Stockdale Paradox is a very simple idea, named after Jim Stockdale, the highest ranking officer who was held prisoner at the ‘Hanoi Hilton’ prisoner of war camp during the Vietnam War. It’s one of the most surprising findings from Good to Great (or at least it was to me), and it goes like this:

”Retain faith that you will prevail in the end, regardless of difficulties, AND at the same time, confront the most brutal facts of your current reality, whatever they might be” - Jim Stockdale, Good to Great, pp86

Before reading the book I thought that it was important to be optimistic. To assume the best. To not lose hope. But, as Admiral Stockdale is quoted as saying in the book, it was the optimists that didn’t make it out of the Hanoi Hilton because, by denying the reality of their situation, they were unable to cope when they were eventually forced to confront it.

The lesson here for companies who are seeking to make the transition from good to great is that you have to find ways of managing this paradox. Of having absolute faith that you will, as a team, prevail in the face of the competition, whilst at the same time being able to be brutally honest about your current challenges, be they internal or external.

My recent experience of participating in an offsite amongst the engineering and product leads at Tetrate makes me think that an off-site provides a unique opportunity for you to do just that.

Finding the faith

Let’s address the softer part of the paradox first, the ability to find and retain faith that you will prevail despite the circumstances. Faith can be a tricky thing to come by in a remote company, where work can feel very transactional. At the core of all of us is a very basic need to belong, as it’s belonging that ensured our genes’ survival back when being cast out from a group meant near certain death.

When the majority of your interactions with people come via text or task-focused video calls it can be hard for people to really feel like they belong to something that’s worth belonging to. This is a problem for both individuals, and the companies that they work for. Individuals for the reason mentioned above, companies because retention becomes difficult, especially for in-demand roles like software engineers.

As an individual, there are certain things you can do to help you find your own sense of belief in what you’re doing. On-site meetings provide a qualitatively different way of interacting with people, a way that is much more likely to inspire a feeling of belonging as you get to know people as people, beyond their job roles. There’s more to it than this though, as you also get to see the way people work. The way they think and interact with other people as you get to spend far longer blocks of time working with them than you do day to day.

Perhaps I’m fortunate in the professional company I keep, but when you see just how good everyone is at their jobs it’s inspiring. You can’t help but be impressed at the clarity of thinking on show, at the willingness to really dig into a thing and come to a decision. Watching (and hopefully taking part in) the sheer amount of stuff get done really helps create that sense of faith that, no matter what, this group of people will prevail.

I think there’s also something to be said for the sheer inconvenience of an off-site, which might seem a weird thing to say. The fact that people are willing to disrupt their everyday lives and potentially travel thousands of miles to be there speaks to their level of commitment to the group. We all want to know that the people that we are working with are invested, because we all know that otherwise the enterprise is doomed to fail. Nothing kills morale faster than sloppy, half-assed work, so this very visible demonstration of commitment means a lot.

Allowing the truth to be heard

My experience of an on-site is that it also provides a unique way of fulfilling the second part of Stockdale Paradox. There’s something that’s psychologically very difficult about writing down hard truths and pressing the ‘send’ button. It can lead to endless second guessing and overthinking, and half the time not pressing the button at all. My personal feeling is that it’s down to the asynchronous nature of the communication and the lack of non-textual cues as to whether you’re still accepted by the group (or your boss) afterwards.

Being in a group setting, where you hopefully already feel accepted by the group in a very natural way, makes it easier for people to say the tricky things that have been on their mind for a while. This might take place in the context of a formal meeting, but it just as likely might happen during one of the many serendipitous chats that seem to happen at things like this. Informal access to the leadership of a company is something that doesn’t happen naturally in remote-first companies, so this has a value that is hard to replicate any other way.

The way that these meetings tend to come with a formal agenda also helps here. This is because it creates a wonderful combination of progressive disclosure and the creation of commitment. When you add an item to the agenda, knowing full well that the discussion is potentially difficult, all you have to write is the title. That’s, psychologically, a pretty easy thing do it. There’s no danger there, you can write it in such a way that no one is going to read it and immediately reject you, thereby satisfying the lower-brain need to be accepted.

Once you’ve put the item on the agenda though, you’re committed to actually talking about it. There’s no longer any getting away from it. You know the time will come, and so you prepare as best you can, and when it does come all the good things about the group setting that I’ve written about already come in to play.

It’s the combination that’s magical

For me the paradox has another layer once you combine both halves. In the end, it’s the confronting of the brutal facts, and seeing that people are willing to really apply themselves to fix it, that helps fuel your faith in the team around you and your ability to prevail.

The format of being together in person makes a huge difference to a team’s ability to really dig into a problem and its implications. It’s easy for an in-person meeting to take as much time as it needs (especially if you’ve done it right and not completely packed the agenda), whereas a video call rarely runs more than a few minutes over because people either have another meeting to go to or Life Things like needing to go pick up kids from school. This really is one of the key functions of leadership, and the format of an offsite meeting gives you the opportunity to fulfil it in a hard to replicate way.

In the end, all organisations and teams have problems to solve, and there are things about on-site meetings that make them great forums to solve them in. I’m interested now in what ways people have for addressing the same problems/paradox when on-sites aren’t possible, but this post is long enough so it’s a topic for another time.