Remote work can and does work. I get frustrated when organisations treat it as something they can allow and then leave to look after itself. People need context they can access, a fair opportunity to contribute and time to build relationships. Somebody has to make those things happen, and some of it costs money.
“We’ve got distributed offices, it’s the same” is a response I have very little patience for. You can have several offices, each running on local conversations, with people travelling between them to fill in the gaps. That might work perfectly well for those offices. It tells you very little about the experience of someone working remotely, outside all of them.
A person can be on every relevant call and still miss the conversation where the options were narrowed down. They can read the decision afterwards without ever having had a useful opportunity to affect it. An organisation that wants remote work to succeed has to pay attention to that experience, including when most of its employees happen to share an office.
Leaders need to experience how the organisation works remotely
Having leadership spread around helps. When leaders themselves have to wait for an answer across time zones, find the reasoning behind a decision or join a discussion from outside the room, those problems become harder to dismiss. They have some experience of the friction everyone else is being asked to work through, and the authority to do something about it.
That doesn’t happen just because the leadership team has several addresses. If the important conversations still depend on being near one particular person, everyone else is left arranging their working life around access to them. Leaders need to use the same written context and shared discussions they expect the rest of the organisation to rely on.
Making participation fair also takes judgement. Everyone doesn’t need to contribute to every decision, and we don’t need to wait for every time zone before doing anything. We do need to know whose input matters and give them a reasonable chance to provide it while it can still change the outcome. The same people shouldn’t always have to join late at night to be heard, or find out afterwards because they chose to sleep.
Write down enough for people to work without you
Ben Balter’s Open and Async is useful on this. Working openly and communicating asynchronously require habits that let people understand the work without being present for every conversation. Buying the tools doesn’t establish those habits.
Writing things down is part of the work. People need to know what we’re trying to do, what we’ve considered, where we’re uncertain and why we made a particular choice. A polished announcement at the end won’t help somebody contribute to the thinking that preceded it. Share the work while there is still something to discuss, and keep the result somewhere people can find it later.
This takes effort from the person writing. They have to explain context they may otherwise have supplied in a conversation, and make their reasoning understandable to somebody reading it later. That effort lets other people work without waiting for them to wake up or finish their meetings. It also gives new colleagues a way to understand decisions without having to reconstruct the history through whoever happens to remember it.
There’s an additional benefit now: agents need written context too. The goals, constraints and reasons behind previous decisions are useful to an agent trying to contribute, just as they are to a colleague. We already had good reasons to make that context accessible and keep it current. More of our work now depends on it.
The time between visits needs attention too. Ileanell Perez describes protecting space for connection, collaboration and discussion as her team adopts AI, including a regular team lunch with no work agenda. When more work happens in conversation with a tool, colleagues can have fewer reasons to turn to each other. An offsite every few months won’t sustain those relationships on its own. Leaders need to make room for people to talk and learn together in an ordinary working week.
Getting together helps the work between visits
I think remote teams need to get together in person every few months. Organisations should budget for it and make it reasonably possible for everyone to attend, taking travel, accessibility and caring responsibilities seriously. An invitation alone doesn’t make a trip practical.
I’ve travelled far more as a leader than I did as an IC, and I consider that an important part of doing the job. More seniority often means decisions with a greater blast radius, and relationships across more of the organisation. Sometimes the right thing is to get together and work something through. A leadership group might need that every month while the wider team meets quarterly or every six months. They don’t all need the same cadence.
At our recent company offsite, people in my org were already talking excitedly about our own gathering in January, before we’d even left. There’ll be about 80 of us, and what they were looking forward to was the face time and hanging out. Seeing the humans in the flesh! That time together matters to people, and they were already keen for more.
A lot of the value for me has come from getting to know the people I work with. I don’t need access to their private lives. I want to understand what they care about at work, what they’re trying to achieve and what success looks like to them. Time at an airport, a meal or a bar can reveal quite a lot, good and bad! There is room to talk beyond the immediate thing we need from each other.
That understanding changes how I work with someone afterwards. I can explain what I need in a way that connects with what matters to them, and find an approach that helps us both get to the outcome. I have a better sense of their usual behaviour, so I can notice when something seems off and ask about it. I’ve also got past some bumpy first impressions by spending more time with people. We all get stressed. One difficult interaction doesn’t give you a complete understanding of a colleague.
I’ve benefited from other people making that effort with me too. Some senior leaders dismiss relationship building, but it has been an unlock in my career. Knowing each other better makes the later remote conversations easier, including the uncomfortable ones. I wrote about noticing changes in how people show up before; spending time together helps me develop the understanding I use when we’re apart.
Some difficult conversations also benefit from being in person. Working through decisions about layoffs is one example where I can see a reason to make the journey. But money can be precisely why that isn’t possible, which is a fairly grim irony. Sometimes you have to work through it virtually. Leaders still have to handle those conversations well, and the relationship you’ve already built matters when you do.
Leave space in the offsite for people
I can’t necessarily persuade every CEO or CFO to value the time that goes into building those relationships. I can organise my own offsites to make use of it. That includes dinners and silly awards. A bit of levity gives people something to enjoy together, and a conversation can be useful without producing an action item. Nobody needs to drink or disclose something personal to participate.
There is often pressure to make the agenda illustrate how fast we’re moving. We need people running at a thousand miles an hour, so apparently every minute of the trip must demonstrate it. I think we model pace much more meaningfully in our normal work: what we prioritise, how we make decisions and whether we follow through.
Presentations and working sessions can be worth doing together. But if we fill every available hour, we’re using up the time people could have spent getting to know each other. A meal squeezed between an overrun session and the next obligation doesn’t offer much room for that. People also need time to themselves, especially around travel. Giving them some breathing space makes it easier to participate in the time we do spend together.
If people come home exhausted and spend the next two weeks recovering, have we actually got the outcome we wanted? And if we left no room to build relationships, how much of the agenda could have been a virtual call?
Remote work has worked well for me, and I’ve put effort into making it work for others. That has included writing things down, travelling more and protecting time for people to get to know each other. Leaders need to plan and pay for those things, and pay attention to whose experience still falls short. We can’t leave people to make it work for themselves and then blame remote when they struggle.