One of the common objections I hear when discussing the benefits of hiring a remote Executive Assistant (EA) is, “I think this person really needs to be a boots-on-the-ground person.” It’s a valid concern, but today, I want to challenge this perspective by juxtaposing the roles of boots-on-the-ground vs. wings-in-the-cloud.

Boots-on-the-Ground

Boots-on-the-ground refers to roles that require a physical presence. These are tasks and responsibilities that necessitate being on-site, interacting directly with people, and managing in-person activities. This could include things like:

  • Overseeing physical office space
  • Handling deliveries
  • Setting up for events and meetings
  • Greeting guests and offering drinks

Wings-in-the-Cloud

On the other hand, wings-in-the-cloud roles are those that can be efficiently managed remotely. These tasks often involve strategic planning, administrative support, digital communication, and coordination. Examples include:

  • Calendar and email management
  • Research and data analysis
  • Project coordination and follow-ups
  • Creating reports and presentations

Smashing Two Roles into One

When you try to combine these two distinct roles into one, you risk overloading a single person with a diverse set of responsibilities that may not align with their strengths. A boots-on-the-ground role requires physical presence and face-to-face interaction, while a wings-in-the-cloud role demands strategic thinking and digital communication. Expecting one person to excel at both can lead to burnout, inefficiency, and unmet expectations.

The Case for Wings-in-the-Cloud

Let’s consider the advantages of hiring a remote EA (wings-in-the-cloud) alongside your on-site team (boots-on-the-ground):

  1. Specialization 🎯
    By separating the roles, you allow each person to specialize in their area of expertise. Your on-site team can focus on managing physical operations, while your remote EA can handle administrative and strategic tasks. This division of labor ensures that each role is performed with precision and efficiency.

  2. Increased Efficiency 🚀
    A remote EA can streamline your workflow by managing time-consuming administrative tasks, allowing your on-site team to concentrate on core activities. This results in a more efficient operation where each team member is working to their strengths. Plus, they never get pulled into random projects or sideways conversations by other team members, making them more effective at the projects they work on.

  3. Flexibility and Scalability 📈
    Remote EAs offer flexibility and scalability. As your business grows, you can easily adjust the level of remote support you need without the logistical challenges of expanding your physical office space. This adaptability is especially valuable in today’s dynamic business environment.

  4. Cost-Effectiveness 💰
    Hiring a remote EA can be more cost-effective than adding another full-time, on-site employee. You save on overhead costs like employment taxes, benefits, office space, equipment, and utilities while still gaining access to top-tier administrative support.

Conclusion

Next time you find yourself thinking, “I need a boots-on-the-ground person,” consider whether you’re trying to merge two distinct roles into one. By recognizing the unique strengths of each role and leveraging the power of a remote EA, you can create a more efficient, flexible, and scalable operation.

Embrace the wings-in-the-cloud approach to support your boots-on-the-ground team, and watch your business soar to new heights.


Micah Foster headshot, Co-Owner of Dream Support for executive assistants

Micah Foster, Co-Owner

Micah Foster is a partner at Dream Support LLC who has been providing remote executive assistants to busy leaders who need administrative and organizational help for over five years.

He has a passion for creating and maintaining positive and productive work environments and empowering people to reach their full potential.