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Traditional coaching relies on face-to-face contact, so how can we adapt coaching for our remote-first companies?

Distributed work (‘work from anywhere’) has entered the mainstream. In this new way of working, our definition of ‘productive’ is no longer simply being in a specific seat for a set amount of time. Rather, it's the output and engagement of the person in that seat, regardless of how many hours they're there.

The distributed environment introduces new considerations – such as time zones and virtual communication styles – that aren’t present in an office-based environment. Distributed organizations are often asynchronous, text-based, and designed for self-starters who enjoy a balance of deep reflection and thought, alongside collaboration with others. Actions have to be intentional in order for the organization to succeed.

Coaching is no different. It requires intentional thinking and action in order to be effective in a remote-first company. But when implemented successfully, it allows us to support and grow the people on our teams. This has a positive effect on productivity, quality, retention, and our engineers’ career prospects (in other words, everyone wins).

As an engineering leader, coaching has been transformative for how I approach my day-to-day. Here I’m describing my experience of coaching and being coached in a distributed company, outlining why it’s important, and sharing how virtual coaching tools and approaches can unlock your and your team’s potential.

Practicing compassion, empathy, and kindness in our organizations can significantly ease these problems. As engineering leaders, a great way to do this is by drawing on the wisdom of coaching and incorporating a few key coaching skills into our daily interactions.


The importance of coaching in distributed companies

Coaching, at its core, is about holding a space for the coachee to take a wider view of what’s possible, and to look inward to determine what might be fueling their current situation. In an asynchronous world of digital tools, common experiences such as imposter syndrome aren’t easily visible through our laptops. The autonomy afforded in a distributed environment can also bring about feelings of isolation and overthinking. Coaching creates a bridge between remote employees, allowing coachees to see beyond their problems and realize they’re not alone.

Coaching is especially powerful in fast-moving organizations, where teams are built around what’s most important for the company at the time. When a new team is built, it often means other teams are split or changed. This was the case for me. For several years, it felt as though I had a new role and team every nine months. That’s because I did! As the organization’s priorities evolved, so did the team I worked with.

Change management is nuanced and complex. Working with a coach enabled me to see beyond the immediate change, and to look toward the horizon to see the wider view.

Today, I’ve translated my experience as a coachee into how my current team operates. When somebody joins or leaves the team, or we make any structural shift, we view ourselves as a new team. This approach acknowledges the skills and perspective a new team member brings, while also acknowledging the new gaps we have to fill when someone leaves. Continuous coaching for everyone involved supports this process, allowing the team to develop change management as a strength.

Tools and approaches for distributed coaching

Coaching in a distributed environment requires more intention than traditional one-on-one, in-person coaching. But it also provides an opportunity to have an even greater impact. Here are a few tools and approaches to help you get there.

Video and voice calls

In an asynchronous environment, communication happens across time zones, and not always in real-time. Holding a coaching space for someone across time zones may seem impossible at first. The solution is to hold a coaching session virtually.

A video or voice call is a great place to build a container (a coaching session with an agreed-upon beginning, middle, and end, taking place within a certain time limit). With the power of technology, we can set the stage with the team member and conduct the session in a safe and private space.

Embracing asynchronous communication

Virtual spaces create an incredible opportunity to interact across continents, time zones, and lifestyles. Having a balance of tools we use in real-time (synchronous) and tools we use on our own schedules (asynchronous) is important when coaching across a distributed team.

For my own coaching and while coaching others, I’ve found a balance of setting the stage via a video or voice call and then continuing the conversation in a shared private Google Doc and Slack chat to be a good balance. This approach also preserves the container over a longer period of time, enabling a richer coaching experience for the team member.

Coaching is like an iceberg; as coaches, we see what happens above the surface, but the main breakthroughs happen below the surface through self-reflection, patience, and emotional work. By incorporating text-based communication, such as email and Slack, we can allow our coachees to consider what they’re reading before they respond. They can also re-read parts of the conversation at a later date, opening up space for reflection.


Journal-based coaching involves the coachee writing up what they’ve learned or observed about themselves. Writing is a powerful way to clarify your thinking. If a person’s thoughts are clear, they can begin to see the possibilities ahead.

Susan R. Horton’s Thinking Through Writing describes the ‘back to basics’ approach of using writing to bring our best work to life. In a distributed organization, writing is the cornerstone of communication. When done effectively, the notes, decisions, and all of the thinking which went into an outcome are clearly written and documented. Writing as a default enables others to read your thoughts, and encourages everyone to write, review, clarify, and publish, in that order.

Distributed organizations should have journaling baked in. At Automattic, we commonly say ‘P2 (our internal blog) or it didn’t happen’. Encouraging this type of regular journaling has a significant impact on helping folks unlock their potential.

The more you normalize writing as a day-to-day activity, the more natural it will be for your team to journal about non-technical subjects, including personal development and their areas for improvement.


Assessments and frameworks are another impactful way to clarify one’s thinking. You can use these to structure a coaching activity. Many assessments can be done online, providing a way to learn about your team members, for your team to learn about you, and to create a shared experience to bring you all closer together.

One example is 16Personalities. This assessment includes a lightweight set of questions and opens up a conversation about how we each approach the world. Reading the results allows your coachee to see a new perspective on themselves, while also enabling you to learn more about them beyond what they describe.


Distributed work requires intention. When we approach coaching with that same intention, we can use it to build, develop, and support the people that make up our organizations.

A distributed work environment brings with it several new tools and added benefits that can enhance coaching. By embracing these remote and text-based tools, we can go beyond traditional coaching methods and find new ways to create impact at a greater scale.


Using coaching skills to grow compassion, empathy, and kindness
Episode 01 Using coaching skills to grow compassion, empathy, and kindness
How coaching can help you become a better leader
Episode 03 How coaching can help you become a better leader