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How to Navigate the Challenges of Managing a Distributed Team

How to Navigate the Challenges of Managing a Distributed Team

How to Navigate the Challenges of Managing a Distributed Team

Managing a remote team comes with its unique set of challenges. To help you navigate this, we’ve gathered insights from 12 top CEOs and Founders. From starting with effective onboarding to fostering informal social interactions, discover the strategies these leaders have found most effective in leading their distributed teams.

  • Start with Effective Onboarding 
  • Balance Communication Frequency
  • Promote Transparency and Team Interaction
  • Avoid Micromanagement
  • Use Videos for Team Communication
  • Accommodate Individual Working Styles
  • Establish Rules and Monitor Progress
  • Empower Teams with Autonomy
  • Ensure Clear Communication and Expectations
  • Prioritize a Healthy Work-Life Balance
  • Cultivate a Supportive Culture
  • Foster Informal Social Interactions


Start with Effective Onboarding

I run two businesses with almost fully remote staff, own a co-living company in Venice Beach helping 150 global nomads, and built technology for distributed workforces.

The strategy that always works for remote hires is effective onboarding. To be successful (I’ve had a lot of failures) is by nailing the first two weeks of the hire. Training and setting expectations are crucial. The best tactic I’ve found to instill the goals and objectives of the team is to do a Zoom or Google Meet for at least 4 hours per day for the first 2 weeks. 

Even if the manager is working on something else, the face time during that time is crucial. It sets the environment up for success, and if there is a big discrepancy, a bad fit is easily noticeable.

Robert O’Neill, CEO, Thatch


Balance Communication Frequency

I found it far more effective to foster a culture of trust and autonomy. I remember how COVID-19 made us move toward a hybrid work format. Initially, I made the mistake of constant check-ins, causing unnecessary stress and hampering productivity. 

What I learned is that good workers will suffer from frequent calls and check-ins. And ghost employees are easy to detect if you review 1-2 weekly sprints but not only their KPIs. So now, every time I want to make sure that everything goes smoothly, I open an online course, do pushups or simply go and make a coffee.

Vladislav Podolyako, Founder and CEO, Folderly


Promote Transparency and Team Interaction

We have never had an office, and our team started and then grew as a remote team. For many years in a row, it wasn’t a big deal: we were in direct contact with each team member. Over the years we reached a point where some employees didn’t feel attached to the team. We had burnout issues. 

On the management side, it also became challenging to set tasks, control, train, and motivate. We hired a project manager whose one of many responsibilities would be to have one-on-one conversations with each team member. Next, we also aimed for more transparency: we introduced dedicated channels for sharing what everybody has achieved over the last week and how they contributed. 

A major problem for the development team was a feeling of isolation: certain tasks were taking a lot of time and effort to accomplish, and they were coding by themselves without much communication with the team. We started to jump on team calls to work together on some chunks of work, to give them a “buddy” feeling.

Daria Erina, Managing Director, Linked Helper


Avoid Micromanagement

The worst way to manage a virtual team is through their micromanagement. My goal is to stay in touch with employees to monitor their progress, not to check if they are working. Micromanaging and setting unrealistic expectations can lead to employees feeling frustrated, resulting in low work morale. That’s why I don’t worry about every little detail and instead show faith in my hires to do their job well.

Stoyan Mitov, CEO, Dreamix LTD


Use Videos for Team Communication

Pictures are worth a thousand words. Videos are worth a million. On our team, we make a very regular habit of sending around Loom videos to demonstrate all kinds of activities. In addition, we encourage Loom videos for standard operating procedures and long-term documentation. 

As the process has spread through our organization, everyone has become less timid and more likely to send videos to walk their teammates through processes.

Trevor Ewen, COO, QBench


Accommodate Individual Working Styles

That’s been the biggest thing I’ve learned over the last five or so years. I have a way of working that works best for me but, despite me being the boss, I should not impose that way of working on my employees. 

I should instead be a facilitator, seeking to understand how each of my employees would prefer to work for maximum impact and then finding a way to mesh that in with existing processes for the best results. 

This works best for smaller teams and small businesses, but if you are a small business owner then there is little reason for insisting your team works your way besides ego. Put it aside.

Kate Kandefer, CEO, SEOwind


Establish Rules and Monitor Progress

When managing remote employees, providing the appropriate technological resources for communication is only half the battle. You should establish clear rules and standards for remote work efficiency. I start with the delegation of various errands to whoever is bound to complete them proficiently in a given time span.

The next step is monitoring their progress on a given project. Teamwork is the platform I use to closely follow the work process. As a result, workflow is optimized, communication issues are resolved, and employee performance is evaluated. Knowing each team member’s strengths and weaknesses allows me to train them accordingly.

Stefan Chekanov, CEO, Brosix


Empower Teams with Autonomy

While cooperating with a remote team, you need to competently organize each person’s working day, sometimes even adapting to different time zones. I’m strongly sure that a very effective strategy is to specify the duties of each team member for a week or two. 

Yes, I’m of the opinion that it’s not necessary to limit people to a list of daily tasks and clear figures, such a framework can contribute to burnout and reduce a person’s attention during a working day. 

We tested two tactics—the designation of one-day goals and 2-week goals for all team members. As a result, employees saw that they were trusted, and had the opportunity to plan their working days independently. They understood what result was expected from them, without stress, strain, and haste. 

Such a balance definitely positively affects both the company’s results and the mental and physical state of employees.

David Kemmerer, Co-founder and CEO, CoinLedger


Ensure Clear Communication and Expectations

As the CEO of a company specializing in property management, including BnB and hotel management, navigating the challenges of managing a remote team distributed across the world has been a priority for me. One strategy that I have found highly effective is fostering a culture of clear communication and setting transparent expectations. 

With team members located in different time zones and working on various property management projects, it is crucial to establish open channels for collaboration, such as regular virtual check-ins and dedicated communication platforms. 

By ensuring that everyone is aligned with the company’s goals and objectives, we can maintain a cohesive and productive remote team, ensuring the success of our property management endeavors regardless of geographical boundaries.

Johan Hajji, CEO and Founder, UpperKey


Prioritize a Healthy Work-Life Balance

I’ve faced the challenges of maintaining a healthy work-life balance for both myself and my employees. When working from home, it’s easy for work to spill into personal time. To address this, I prioritize setting clear and healthy boundaries. 

We establish defined working hours, allowing for flexibility, while also ensuring reasonable response times. We establish designated communication channels for the team and outline procedures for urgent situations. By setting these boundaries, we create a supportive work environment that respects personal time and fosters productivity.

Tobias Liebsch, Co-founder, Fintalent.io


Cultivate a Supportive Culture

The transition to managing a remote or distributed team brought about its unique set of challenges. Asynchronous communication, maintaining a sense of unity, and ensuring productivity across different time zones were some of the hurdles I faced. Among the various strategies I employed, the one that truly made a difference was fostering a culture of trust and autonomy.

Ensuring that team members had the flexibility and independence to manage their own schedules, coupled with clearly defined goals, proved invaluable. This approach not only increased overall productivity but also elevated job satisfaction levels. However, it required substantial effort to clearly communicate expectations and provide regular feedback. 

Ultimately, building a culture of trust and autonomy was not just about shifting responsibility; it also involved nurturing an environment where team members felt valued, understood, and confident in their roles. This, I found, was the cornerstone of successful remote work.

Vikrant Shaurya, CEO, Authors On Mission


Foster Informal Social Interactions

Managing a remote team has its own set of challenges. One thing I’ve learned is how important informal, social interactions are, just like those we have in physical offices. So, I started creating virtual water cooler moments. 

We’d meet online just to chat, joke, and share personal stories, not work-related stuff. It’s a simple way for us to connect on a personal level, despite being in different locations. I found it really effective. It helped us bond as a team and understand each other better. This, in turn, made our work interactions smoother and more productive.

Even though it seems like a small thing, these casual chats have been a game-changer in managing my remote team.

Irina Poddubnaia, CEO, Founder, TrackMage


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