If there’s one task that most entrepreneurs and high-achieving individuals despise, it’s managing their calendar.

Managing your calendar isn’t just time-consuming—it’s exhausting and frequently feels complex and inefficient. Between coordinating schedules, anticipating conflicts, and calculating time zone differences, it’s a task that often feels never-ending.

Calendar management responsibilities include:

• Coordinating with stakeholders to find a suitable meeting time: The back-and-forth communication required to align schedules can quickly become a tedious and time-consuming task, especially when dealing with multiple stakeholders with different time constraints.
• Tracking and following up on unanswered scheduling requests: It’s easy for meeting proposals to get lost in the shuffle, and having someone to ensure nothing falls through the cracks is invaluable.
• Scheduling complex meetings across time zones: For many of our clients, managing time zone differences has been a significant challenge. Delegating this ensures meetings are accurately scheduled without the stress of juggling global clocks.
• Incorporating buffer times for travel: A well-planned schedule includes the necessary cushion to get to and from meeting locations, preventing last-minute scrambles or delays.
• Anticipating and resolving scheduling conflicts: One of the most critical yet often overlooked aspects of calendar management is proactively identifying potential conflicts. An assistant can monitor your schedule, identify meetings that may no longer align with your priorities, and reschedule them well in advance—whether that means shifting the time, moving them online, or reorganizing your day to avoid disruptions.

Your calendar is a reflection of your professionalism. Missed appointments, last-minute cancellations, overlooked conflicts or time zone errors send a poor message to clients and partners. A streamlined calendar not only enhances your efficiency but also boosts your credibility.

• Grant your assistant calendar access and include them in relevant correspondence: Start by sharing your calendar and cc’ing your assistant on emails related to meeting scheduling. This ensures they’re in the loop from the start.
  PRO TIP: When adding your assistant to the email loop, add relevant notes to the correspondence. For example, “This is John, based in New York, and Dave, in PST.” This allows your assistant to propose meeting times without needing to ask stakeholders for information you already know, minimizing back-and-forth.
• Provide context during the initial weeks: As your assistant familiarizes themselves with your stakeholders, it’s helpful to introduce participants and highlight key details. Clarify who’s who in your calendar: Offer insights into your contacts. Who are the key stakeholders whose meetings must be prioritized? Who can be rescheduled with greater flexibility?
• Discuss your time preferences: Share your scheduling boundaries. What are your preferred hours for meetings? Are there time blocks that must remain uninterrupted? Should a lunch break be built into your day, or do you prefer to work through? Do you have a “no meetings” day in your week?

Now that you’ve delegated the time-draining activity of calendar management, take a moment to appreciate the freedom you’ve gained. Enjoy a well-deserved break—sip on your favorite coffee, stroll by the beach, or unwind in the park. Enjoy this beautiful day now that can eliminate from your brain tedious things like “Did I end up scheduling that meeting with Joe?”.

If you travel frequently, you know that planning a trip—whether for work or leisure—can be a logistical nightmare. Travel planning involves navigating a sea of options—flights, trains, hotels, car rentals, and activities. All come with different budgets and timelines. The sheer amount of choices can be overwhelming, and the details often slip through the cracks. It’s fun to travel. It’s not fun to plan it.

Travel Coordination responsibilities include:

• Booking your travel: Whether it’s flights, trains, or a mix of both, one-way, round trip, or a multi-city journey, your assistant can look through the options to craft the most convenient itinerary for your trip.
• Reserving accommodation: Between hotels and Airbnb, there are so many accommodation options to choose from with varying budgets, locations and amenities. You need to find one that checks all the boxes and is available during your stay time.
• Local Transportation: Making sure you have a taxi waiting for you at the airport, or a car rental reserved.
• Researching activities: What are the best restaurants in the area, is there a good music concert taking place during your stay, or maybe you are looking for something fun to do with the kids? Finding those hidden gems can take hours to research.

Booking activities: Tickets for that museum you’ve always wanted to visit or a reservation at the hottest restaurant in town? It’s done!

Business travel can become a regular part of your routine, and understanding your habits and preferences can remove a lot of the friction, making it much smoother. Personal travel, on the other hand, often requires more detailed planning and research. Having someone dedicated to spending hours sorting through options means you don’t have to, delivering only the most relevant information and saving you time.

• Provide your assistant with all the essential details to book your travel: passport information, frequent flyer numbers, and credit card details.
• Discuss your flight preferences: Do you typically fly economy or business? Do you need a suitcase, or is a carry-on enough? Are you a fan of row A or F (We are not even going to bother with the other rows. Nobody likes to sit in the middle, and aisle preferences are a myth! We all know that.) ?
• Share your preferred flight times: Do you lean toward red-eye flights, early departures, or daytime travel? The more precise you are about your preferences, the easier it becomes for your assistant to independently find options that match your needs and present only the best choices for your review and approval.
• Let your assistant know what kind of activities you generally enjoy and look to do. Are you an extreme sports fan? Do you like to try the local cuisine? Do you like tourist traps or do you prefer the hidden corners?

Savor the incredible wine at that charming seaside restaurant your assistant discovered for you, and hey, Surprising them with a little souvenir won’t hurt either.