How to Coach Remote Leaders, Remotely

From San Francisco to Singapore, companies are making remote work the ‘new normal.’ How can coaches support leaders through this transition when they themselves are working remote?

Practically overnight, the pandemic has ushered in a new era of remote work. Leaders must now reinvent themselves in this new place-less workplace. Many are turning to leadership coaches to improve their personal performance, which is fine until you realize it’s not just the leaders who have ‘gone virtual’ — the coaches have as well.

Just one year ago, leaders would be having face-to-face coaching sessions. Goals, strategy and progress under discussion, the coach as sounding board, guiding the leader with a suggestion or two in the right direction. But if that leader wanted to become truly proficient, he or she had to apply the coaching into practice with a more hands-on way, and the coach would likely not witness the leader’s actions. With virtual coaching, that’s no longer true.

How can you make sure remote leadership coaching is successful? A few things I found useful:

1. Transform the sessions

It is a mistake to try and reproduce a traditional meeting onto a screen. Attention spans are shorter with video calls and the notion of time is not the same. It’s better for the leader to have a greater number of meetings with shorter intervals in between, more bite-sized and highly targeted. The same applies to coaching sessions, which should be shorter and tied to a specific skill or moment.

Keep the attention level up by adding interactive elements to virtual meetings. For example, sharing slides or quizzes during video conferencing can elicit greater discussion. There are now many tools to help with scheduling, holding conferences, sharing information and tracking progress. Leaders can get creative with such tools to gain attention, and coaches can support leaders to grow their virtual leadership abilities the same way; using personalised, interactive support from their coach.

2. Build a culture of trust and inclusion

In last month’s article, I discussed how the loss of informal controls (corridor catch-ups, water cooler moments) in a virtual workplace can cause leaders to be less trusting of their workforce and manage presence rather than performance. I see some leaders slipping into micromanagement in a virtual environment, so it’s more essential now they find time for one-on-one conversations or small group discussions where rapport is established, where everyone feels trusted and included.

That means encouraging leaders to be open and vulnerable by sharing their personal views with the team. Random chats help teams connect and build trust. These water cooler moments can be replicated by creating non-work channels in Teams or Slack where employees can share jokes, memes or cat videos.

The need for informal connections and conversations led, Tim Malone of MIT’s Sloan School of Management and a graduate student to develop Minglr, an experimental software system developed to support informal interactions. Malone points out that Minglr or Zoom may not replicate coffee chats or water cooler conversations, but reminds us that these spur of the moment conversations should not be lost to the pandemic.

While some leaders maybe reluctant to participate in these channels the moments to laugh, chat and be together support the social connections and builds culture, more so during these trying times. This same advice applies to coaches. Good coaches are supple and smart enough to adapt their style of coaching to a situation and individual learning objectives. I try to overcome the remote barrier by sharing my ideas and real-life experiences, which has kept me in good stead of forging and maintaining trust.

3. Take extra care when giving feedback

Feedback which motivates -rather than alienate — is notoriously tough. It’s even tougher in a remote environment, where a leader cannot directly read the other person’s body language — or observe non-verbal cues.

● Leaders should keep taking the team’s pulse so any visible slip-ups don’t suddenly arise. A dedicated channel to raise issues (or to discuss solutions) alleviates the heat before a problem escalates.

● Where there is a problem, face-to-face feedback (yes, through video) is preferable to the written word, as the tenor of writing can often be misconstrued.

● Leaders must be true to their word. Trust is created through lived reliability, so when you say you’ll do something, it must be done or trust is eroded. That is the foundation of creating a strong, workable feedback culture.

This all sounds obvious. The hard part is delivering very specific, actionable feedback in a manner that maintains positivity with no physical interaction — when someone receiving feedback is unable to grab a coffee with a colleague to defuse a difficult conversations or to celebrate a successful end to a project. Language is as powerful in the virtual world as the physical, and words should be chosen thoughtfully. And, keep in mind ‘’the internet has fundamentally changed the way we communicate with each other.’’ Not only words but what words we choose to capitalize or italicize matters. As Gretchen McCulloch reminds us, in her book, Because the Internet; Understanding the New Rules of Language.

Reflecting on the past year, remote coaching now comes into its own. While coaches have worked virtually, (usually by phone) only recently has this shifted full-time to video. Together, the leader and coach work through giving and receiving of virtual feedback through the same medium the leader will be using with in-person meetings. It’s a great way to get comfortable with the experience.

4. Let go of old assumptions

The unfamiliar can cause stress or anxiety, and many of us cope by staying with comfortable habits. It’s not unusual in times of change for a leader to fall back on old behaviors or forget’ the skills they’ve developed, which can diminish their impact.

An important step in coaching is to embrace what’s changed. Remote leaders must take stock of where they are now, what new challenges are being faced, and how to act in response. Never underestimate the power of revisiting key skills like communication, flexibility and listening. The remote leader needs to reconsider such skills through a new prism.

Remote coaching is truly an exercise in leading by example. Leaders tend to work with coaches who demonstrate connectivity, support, commitment, challenge, encouragement and persistence — all of which are coaching skills which get results. Remote leaders experience the same shift; tasks which were second nature now feel awkward. For example, charisma may be lost in virtual translation.

The point is that when coaching remotely, leadership coaches can now ‘walk a mile’ in the client’s shoes and experience the disorientation of adjusting those skill sets to a new environment. That readjustment can help us to guide leaders, and make the most of their own remote delivery. Each interaction is an opportunity to develop leaders — and in doing so, develop ourselves further.