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Remote and hybrid team leadership

5 min read

Remote and hybrid team leadership

In this session of Conversations at Work, we talked about what works, what doesn’t, and what people need more than ever from their leaders in the changing landscape of work.

Workplaces have changed forever (and likely for the better) since widespread remote work became a reality in 2020. That means the old leadership playbook needs to be thrown out the window. So, how do we ensure individual, team, and business success when all or some of our people are remote? In this session of Conversations at Work, we talked about what works, what doesn’t, and what people need more than ever from their leaders in the changing landscape of work.

Our guests brought contrasting perspectives to the table. Kerry Wekelo, COO of Actualize Consulting, has over 15 years of remote leadership experience, whereas Bretton Putter, Founder of CultureGene, leads a company that helps organizations with culture development and transitioning to a remote or hybrid model.

Learnings from the past year

We all took away some lessons from 2020, but a common one is how we had to convert our living rooms (or bedrooms) into an office. Working from home means that we no longer rely on the bricks and mortar of our offices for connection and maintaining our organizational culture.

Although we experienced difficulty replicating the serendipitous conversations and water-cooler chats, some found that remote work helped us be more upfront and honest. Brett mentioned that because our personal lives are more exposed (on camera) and through the collective suffering caused by isolation, people are more open about personal struggles and show more empathy. This helps the workplace become more human and strengthens psychological safety.


Even with more than 15 years of experience working remotely, Kerry also came out of 2020 with some memorable lessons. She described her increased appetite to figure out ways to connect with people, including experimenting with virtual events to emulate physical connection.

What’s essential for remote work?

By now, a lot of us have experienced some form of working virtually. While studies found that 65% of people can focus and be productive at home, there are a few prerequisites for effective remote work.

Trust: Everybody is responsible for building trust. When an organization is focused on results and outcomes rather than hours worked, individuals take ownership of their work and arrangements. Which leads to...

Offering flexibility: If there’s one thing we take away from the sudden transition to remote work, it’s that we have to rethink the traditional ways of working. The time has come to fuse different modes of working and design offices and policies that can accommodate the various ways people want to work.

Overcommunication: In the virtual world, you’re no longer a chair swivel away from asking a question, and everything feels much more transactional. Over text and emails, the meaning behind words is more frequently misinterpreted and we’re missing expressive aspects such as non-verbal communication. That’s why intentionally outlining the context of the task or sharing specific project details is good practice. Add on the worry of job insecurity from the pandemic, communicating the company’s stability is often an overlooked part; leaders should always be keeping tabs on how people are doing and showing care. Think more communication, not less.


Defining processes: The removal of in-person collaboration means that defining and adopting processes takes priority. Solid documentation and regularly maintaining them is so necessary to enforce transparency, especially when onboarding new employees. A great example of this is the Gitlab handbook, which plays a prominent role in keeping everyone informed about how things work across the growing company of 1,200+ employees. Extensive documentation like this may be overwhelming for smaller companies, but it shows how deliberate the company is about establishing its culture.

What do leaders need to focus on in remote or hybrid teams?

Don’t micromanage: When coworkers are no longer all next to each other, some leaders cling to monitoring every step of the way. Forcing longer and harder workdays on employees can lead to burnout; many people are already concerned about “proving” their presence, threatening psychological safety. The bottom line is, remote work and micromanagement don’t mix.

Be a living example: Employees model the behavior of leaders. That’s why leaders have the critical responsibility of creating an inclusive culture and intentionally uplifting teammates. It also helps when a leader shares failures and lessons learned, deliberately creating a culture of reflection within the team.

Give thanks and care: You don’t have to switch to a four-day workweek to show that you care about your employees’ wellbeing. People will appreciate any show of gratitude and kindness; simply asking people how they’re doing can make all the difference. Try and provide extra care and support, such as a budget for equipment upgrades and a wi-fi allowance.  

Be open and available: It’s never been more important to let your teammates know you’re here for them. An open-door policy can extend virtually so people can access leaders whenever they need them, on top of scheduled group check-ins and 1:1 conversations.


Show authenticity: We talk plenty about showing up as your genuine and whole self. Vulnerability might be scary as a leader, but you’re allowed to be self-aware and upfront about your limitations. And don’t forget that your personality doesn’t disappear just because you’re behind a screen—introduce your kids or talk about the unique cactus you have on your desk. Embrace the things you actually can’t do in the office!

Remote and hybrid is the way forward

While this working style might not be for everyone, there are definite pros and cons of working remotely. The hybrid evolution is even more fascinating! This transition to remote work revealed more opportunities for us to grow our communication and leadership skills even through the stress.

Let’s learn together to build connection in this new world of work that’s here to stay—and remember to have fun along the way. We need to continue to grow and adapt through all the hurdles thrown at us, from 2020 all the way to the future ahead.

Want to rewatch the whole conversation with our guests and attendees? Head to the recording below:


About Conversations at Work

Leaders, we’re here with you.

Leaders need all the help they can get. That’s why leadership is our focus for Season 2 of Conversations at Work. So much has changed at work this past year, with themes of inclusion, remote work, authenticity, psychological safety, and more becoming pressing for leaders. But how are we helping leaders make sense of this and take action? It starts with talking, learning, and sharing with others. This is a space for leaders to do just that—let’s come together and then get to work.

Next event

How is remote work making people feel (and what leaders can do about it)?

Join us on April 29 @ 10AM PT where we reveal everything we found out through a research survey on the impact of remote work on inclusion and connection. 

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Faye Wai

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