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Digital-first - the modern way to organise work

Digital-first, Remote-work, Leadership6 min read

I have always taken a deep interested in how the create the optimum workplace. One of my first recollections on this topic is the concept of private offices for developers. In this post I will explore the concept of the digital-first organisation. Digital-first really resonates with me and my interest in creating an optimal workplace. And not only because it comes with a private home office.

Distributed, remote, virtual and digital

The concept of a digital-first organisation is also referred to as distributed work or remote work - others call it as virtual-fist or digital by default. I prefer digital-first as this say more about how you work, rather than from where you work. Framing it as digital-first allows for all kinds of companies to adopt the principles - without evicting the office overnight.

I actually think that the office can be a great place to be. There are often snacks, good coffee, a standing desk, co-workers to socialise with and no family to interrupt - many places have great catered lunch as well. So, I don't particular have anything against the office. But the office has some potential drawbacks. Some of my personal dislikes are the commute and limited control of the environment (noise, light, heat and fresh air) Also, co-workers have a tendency to take up more of your time than you planned for. How many times are you interrupted on average day?

For me it is very much about the actual work been done though. The above differences between working at the office and from your home are mostly of practical nature. One important part of most people's work is working together. Collaboration is an almost primal drive in humans - and our highly specialised and complex world require us working together. This is also what fosters some scepticism about digital-first. Those who are sceptical argue firstly, that collaboration via digital tools are less rich and results in lower quality work. Secondly, they argue that accidental hallway meetings and ad hoc discussions is an essential of both doing the work. Thirdly, the social element of working together must be collateral damage in a digital-first organisation. All points are valid and a digital first organisation must carefully organise the work and social relationships to counteract these, on the surface, weaknesses of a digital-first organisation.

Before I get into how I believe work should be organised, I briefly want to highlight why I believe digital-first is the way of the future for knowledge workers: Access to talent from all over the world Flexibility in the working day - pick up the kids, workout or coach soccer Control over the working environment Optimised for the important deep work and flow Better and more deliberate decisions) All of this doesn't come for free just by cancelling the office lease or even adding the Teams or Zoom link to the meeting invite. You have to carefully and thoughtfully design the organisation to be digital first.

Asynchronous communication is like superpowers

The most important concept is understanding asynchronous communication. I see this as the hidden superpower of the digital first organisation. Email, shared documents, wikis, blogposts and comments are asynchronous. Phone, video calls and face to face meetings are synchronous. Chat (e.g. Slack) is perhaps somewhere in the middle, but more skewed against synchronous communication. Asynchronous communication is the part that enables flexibility, deep work and better decisions. When communication is asynchronously you can work on different schedules, or even different time zones. You can work on hashing out that next big feature description on your own time. By using a shared document with a good feedback mechanism, you can get your team to comment when it fits into their schedule.

Writing in longform to convey your ideas, forces you to spend more time on achieving a deeper understanding of the problem space. For me writing is a great way to find flow in my work. I find the same when working on problem solving. Both writing and problem solving requires deep work, where you focus without distractions and work on you own schedule. Organising the work to be done without scheduled meetings and instead working together asynchronously is a key to getting more deep work into you day.

Of course, things slow down when a piece of work requires 2-3 days of gathering feedback and refinement. This is seen from a digital-first perspective an advantage. With multiple sessions of deep work and feedback from your team, that is also the result of distraction free deep work the quality of the work is bound to be better. Stop for moment and think about what kind of feedback you get after a PowerPoint presentation in a face to face meeting, and then contrast with a well thought out written feedback on a write up. Perhaps the process is slow, but sometimes you need to move slow, to move fast. For me longform writing will lead to better and more deliberate decision making.

I believe that an organisation primarily using asynchronously communication will be more effective and produce higher quality work. But asynchronous communication is not useful for all kinds of communication. Doist tweeted the following guidelines:

Establishing trust in a digital-first organisation

How you work together is important, but also who you work with has a big impact on your well-being and job satisfaction. It is easier to give and receive feedback when you trust your team members. Establishing trust in a digital-first organisation requires just as much consideration as the work.

Face to face time is still very important

To establish trust, I think it is still important to have real world physical meet ups - both for work and pleasure. Something as simple as sharing the same food is scientifically proven to foster trust and cooperation. Company retreats are the go-to technic for establishing trust with actual in-person meetings and social activities.

As a small aside the "company retreat" is not only for remote organisations. In my many years with Novicell, the annual "Kick-off" is beloved tradition. But in an otherwise digital only organisation, the company retreat is probably even more important. With a truly globally distributed team, meeting face to face is not possible to do regularly. The same can be said for a lot of people during the current pandemic. So, what are some of the technics to establishing trust digital-first?

Remote meetup

Getting face to face time is important, and a substitute for in person meetups are remote meetups. "Remote meetups are larger blocks of time, for a group of 3-9 people to go deep on a specific topic." Remote meetups are naturally synchronous in nature, but used with moderation, I see them as a good way to establish a connection between people who perhaps are new to working together.

I have successfully run remote workshops, and with a good agenda, some preparation and tools like Miro and Mural it can be a great format for working together.

But remote meetups are planned events, what about the accidental hallway meeting or random coffee break that plays a big role in working at an office.

Digital trust with orchestrated hallway chats

Let's get back to asynchronicity and one technic Basecamp applies: the check-in. Basecamp have regular check-ins on both work and non-work topics. The canonical check-in is "What did you work on today?" But to establish a connection - and thereby trust - another example is "How do you feel this week?" A continuous book club can be created with the question "What are you reading?" Check-ins are the digital-first team's water cooler.

Another way to create virtual spaces for social interaction is the Donut app. Used together with Slack, it automatically connects people to chat asynchronous or setup video chats. Check-ins and Donut-style meetups are just two examples of how the digital-first organisation can create human connection and trust.

Create transparency with over-communication

Asynchronous communication is a world of written communication, this presents both possibilities and challenges. Let's begin with the challenges.

With everyone sitting by themself, it's not possible see what other people are doing or pick up visual clues of peoples' feelings and reactions. Therefore, the digital-first organisation must over-communicate. Both as a company and as a person you should try to be as transparent and explicit as possible. On an ongoing basis communicate what you are doing and whagot you expect of others. For this to happen with as little effort as possible the task management, documentation and communication tools is key.

The digital-first organisation should strive to use tools that both empowers the individual to get work done, and also provides a shared co-created view for the entire organisation. For me this is the perhaps most interesting part of the story. I really believe that there is huge potential for the digital-first organisation to create a shared "second brain". I'm still working on bridging the gap from ides to concrete implementation, but I hope to explore this area more in the future.

Digital-first as the future of work

Regardless if you prefer to come into the office, work from home or something different I believe that digital-first is the future of work and how the modern organisation should be designed. With its emphasis on asynchronous communication, the digital-first organisation is an ideal way to create the time and place for deep-work. With the right set of tools and a deliberate practice, the solitary knowledge worker in the digital-first organisation is empowered to co-create high quality work in trusted human relationships.