10 Ways to Manage a Remote Team During the Summer and Holiday Seasons


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Since 2020, many companies have transitioned to fully remote or hybrid work models — recognizing the immense work-life benefits that remote opportunities provide in the form of balance and flexibility for employees.

As the founder and CEO of a fully remote team at my company, ZenToes, I’ve found that my team has flourished in a scenario that recognizes and allows for individual autonomy and scheduling flexibility year-round while prioritizing productivity, community and a commitment to company goals.

Managing a fully remote team can, at times, be challenging. It’s important to maintain a sense of company culture while also regularly checking in with employees individually. Especially during holiday periods — whether it be summer, Thanksgiving or winter holidays — remote management strategies should adjust to suit the needs of employees and the organization to ensure goals are met and employees can still enjoy the season.

Related: This Remote Worker Spends 300 Nights a Year on a Cruise Ship

Below, I’ve included the top ten tips that I’ve found crucial in managing my fully remote team during the summer and holidays.

  1. Prioritize communication — Foster an environment of regular, open communication to ensure employees understand the importance of clearly requesting time off in advance. Supporting employees’ enjoyment of time off is essential to helping employees achieve work-life balance. Instill confidence in your team that you’ll be supportive and receptive to PTO requests and establish a standard amount of notice required to ensure mutual respect.
  2. Stay organized – Organization is key to ensuring you stay on top of tasks and all team members stay on track to meet individual and team goals – especially when working remotely. At ZenToes, we host weekly team meetings via Zoom to keep all departments up to date on priorities, progress, milestones and new goals.
  3. Utilize technology and available tools – Technology can be incredibly useful in helping your remote team manage their time, stay organized, coordinate scheduling and ensure timely completion of tasks. From Slack and Trello to tools like Notion and Calendly, more tools are available today to support remote teams than ever. Find what works best for your team and ensure everyone feels supported utilizing each platform. We use Asana, Slack, the Google Suite, and a few design-specific tools.
  4. Allow for scheduling flexibility – We can all understand that sometimes things come up. Establish core working hours for your remote team. When things do come up, and an employee requires last-minute scheduling flexibility, ensure that the rest of your team is aware and covering. During holiday periods at ZenToes, for instance, the time between Christmas and New Year’s, we have our office closed with key team members maintaining an “on call” status – ensuring no one needs to work unless there’s an emergency and everyone can enjoy time with family and friends.
  5. Focus on results – Results should be the core measurement of your team’s work and success. During holiday periods, people may need to account for the scheduling of family visits, children’s camp schedules, vacations, and more. Ultimately, as long as the work gets done and is done well, people should be able to make the most of these holiday periods and precious time with family and friends.
  6. Establish clear goals – Define clear goals and objectives for your company, teams and individual team members. Understanding and unifying around a desired outcome supports team camaraderie and gives work a clear sense of purpose to help motivate remote employees.
  7. Have regular individual and team check-ins – This one might seem obvious, but check in with your team. Beyond our weekly team meetings at ZenToes, we also have regular individual check-ins to support employees’ work, growth and happiness.
  8. Make time for face-to-face time – Set aside time to actually see each other each week – even if it’s via Zoom, Google Meet or Teams. As great as remote work can be, it can sometimes get lonely. Seeing your team’s faces will support overall team building, company culture and connection.
  9. Establish effective reporting mechanisms – Clearly define how you want your team to report and track progress each week and on each project so that they can come to regular check-ins prepared. The company can ensure progress towards individual and company goals.
  10. Empower employee wellbeing – Ultimately, employee wellbeing should be paramount to every business leader and company. Make sure your team knows that you truly respect and care for them as people, not simply at work but in all aspects of their lives.

Related: Minority Entrepreneurs Face More Economic Disparities — and More Money Trauma. Here’s How to Stop the Silent Struggle With Financial PTSD.

Everyone’s remote management style is slightly unique, so of course, pay attention to your own needs and the needs of your team members. As long as you’re able to foster a supportive remote work culture and organized system for tracking and commitment to all achieving company goals, all remote employees can get the most out of the holiday period, personally and professionally.



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