Top 10 things to look at to get remote working, working.

Owen Evans
February 3, 2024

We’re lucky at CTO Academy to work with tech leadership coaches around the world and this week we’ve got a great article from Owen Evans based down in New Zealand which looks into what can go wrong with remote working, and how to make it right.

“A lot of us have spent 2020 adapting to the new normal and a lot of us have found remote working for the first time. I’ve been there for a few years and worked in organisations that have embraced remote first mentality before it was cool required by a pandemic. Here are the top ten things my teams work on when working remotely ….

1.Learn to write

One of the core competencies of teams working well remotely is being able to write well and persuasively. You need to rely on ideas and information purchasing through the organisation without relying on cooler chats and coffees, or serendipitous meetings.

But the amazing positive from the whole organisation writing things down to communicate is there’s a great breadcrumb style trail of how decisions got made. Everything is easily recorded and archivable as it’s already in written form.

Get used to how to get ideas from genesis to development in a written form, work on brainstorming in the open, writing down half formed ideas and opening them up to collaboration.

2.Embrace Asynchronous Decisions

This leads from good written communication, but when you’re remote working you can’t always be 100% cognisant of all the distractions everyone else is going through. As such communication should be on a more asynchronous nature. Ask yourself if you need an answer to that question now, or just need an answer. Do you have other tasks you can work on while you wait, is the urgency you feel just your own psyche playing out. If you can embrace asynchronous decision making you can open yourself to moving many things forward at once, including more diversity in decision making (a lot of people need more thought than you might realise to make a good case for their thoughts on decisions and as such get crowded out of realtime, meeting based, decisions)

3.Set clear goals

Clarity of goal making is one thing that sets productive teams apart from those that aren’t. with remote working you can’t rely on a carrot and stick mentality and force people to align to certain work, you have to be clear about what good looks like for their own output so they can make decisions themselves.

Team owned OKRs work well (as long as the team gets to make them and buy into them themselves) and invest in data driven dashboards. Also make sure there’s someone accountable for setting and reviewing goals for the team (in an engineering team this should be a primary function of the engineering manager)

4.1 on 1 meetings for growth

Remote work can feel disconnected from an organisation. You need to work hard to reconnect individuals to a whole. It’s also a reinforcer for the idea that you need to repeat a message 4 times to ensure everyone’s heard it. Make sure your managers are empowered and trained in good 1 on 1 practice, that they’ve understood how to grow teams and team members and are able to convey messages from their own managers to their team.

5.Repeat the message

This is stated above but worthy of it’s own point. If you’ve read the seminal parable “five dysfunctions of a team” you’ll know that your primary team is not the team you manage but the team of fellow managers around the organisation. Your role is to help disseminate information to the team you manage alongside this group. Repeat messages many times. Lean on tools like All Hands to get a core message across to a wider organisation without it having to be in realtime. Repeat, repeat, repeat.

6.Agenda is key to a productive meeting

On top of 1 on 1s remote work tends to overload people with meetings when a company first switches to remote work, if you haven’t embraced asynchronous decisions yet you end up overly worrying about check ins and catch ups on projects, you fill people’s calendars with Zoom meetings and burn everyone out.

Instead you should set the challenge that if you can’t set a meeting agenda then the meeting shouldn’t happen. You should default to shorter time and add follow ups if they’re needed (they rarely are). Embrace optional attendants and make it clear your letting them know the meeting is happening but not expecting them there. People will burn out if you let them or inundate them with meetings so stop it.

7.Remote working is not working from home

OK so the pandemic is slightly different, but usually remote working is not actually working from home. I vary my schedule to make sure I can work from Cafe’s or co-working spaces or the beach (it’s summer here is a write this so I’m looking longingly at the sea). The real reward for good remote working is that it can be “work from anywhere”. The only caveat to that I have is that time zones are still hard, and I don’t have a fix for that sorry.

8.Be OK with not being OK

It’s important to allow people to bring themselves to work, their real selves. Remote working breaks down a bunch of the usual barriers to work vs home life and it can be a real struggle for some. You also don’t get all the social queues that people might be struggling unless you give them space to make sure it’s ok to express it. As such you should model this vulnerability from the top. I try and coach CTOs or mangers to occasionally admit when they’re lacking motivation and be ok with it. Admit that the sun is shining and they want to go get an ice cream, or they have kids that just need them for a couple of hours and so need to check out. If you don’t admit this from the top down, no one will feel safe to express these things

9.Celebrate the wins

Sometimes you don’t get to celebrate or see the wins as well as you would in an office, you don’t see a cake turn up or donuts or everyone wearing silly hats. I make sure I take time for frivolity and celebration within the teams I manage, silly hat Friday’s, making sure people take time out to have a dinner if the team has done well, enjoy a well earned break if the team has been crunching through a project a bit. It’s more important than ever to celebrate every win you get as a team as it can help break the isolation

10.Trust the process

Getting a team used to all these things takes time, there are going to be road bumps along the way. Trust your team, trust in those who you’ve hired to do a job, trust that you’ve got this. It’ll take time to be smooth but the payoff is amazing”

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