Travel Planning

Effective delegation is not a static skill — it’s an evolving process.

As you work with your assistant, your delegation style should evolve from basic task assignment to a more sophisticated approach where you primarily provide high-level direction and final approval on nearly finished work.

Let's explore this evolution using a common scenario: travel planning.

Beginner Stage

At this stage, you're still doing most of the heavy lifting in terms of decision-making and direction. Your delegation is stream-of-consciousness, delegating as things come up. Oftentimes, you have already searched for flights and hotels, and the delegation to your assistant is only in booking them and putting it on your calendar.

Example: "Book a flight to New York for next Tuesday. I prefer morning flights on Delta. Also, reserve a room at the Hilton Midtown for three nights. Make sure it's a non-smoking room with a king-size bed."

Intermediate Stage

You're now reviewing and editing rather than creating from scratch, but still providing significant guidance. You delegate recurring or trigger-based projects that repeat indefinitely.

You may have established some general preferences, but you're still involved in key decisions. For instance, you might ask your assistant to research flight options and hotels based on your criteria, then present you with a few top choices for final selection.

Example: ”Every time I have a business trip:

1. Check my preferred airlines (Delta, United) for flights departing between 7-10 AM.
2. Book a hotel within a 10-minute walk of my meeting location. Preferred chains: Hilton, Marriott, Hyatt. All of your preferences are documented in your preference docs.
3. Arrange airport transfers with our usual car service.
4. Add the itinerary to my calendar and send a summary to my email."

Advanced Stage

At this stage, your assistant is so knowledgeable about your goals, preferences, and personal algorithms that they can proactively suggest tasks that you simply approve. You are often so in sync that your assistant surprises you by making the exact same observations as you.

You've given your assistant so much feedback and have built up so much trust that they feel confident to act autonomously on your behalf, even if that involves making small mistakes.

Your assistant now manages the entire process with minimal input. They might proactively book your preferred flights and accommodations as soon as a business trip is confirmed, only reaching out if there are unusual circumstances or if they need to choose between equally suitable options.

Example: "My goal is to make my business travel as smooth and productive as possible. I want to arrive refreshed and prepared for my meetings, with minimal disruption to my work schedule."

Based on this goal, your assistant might:

• Proactively book flights and accommodations for upcoming meetings as soon as they're scheduled.
• Adjust your travel plans based on weather forecasts or airline disruptions without prompting.
• Prepare a pre-trip brief including:
  • Local weather and appropriate attire suggestions
  • Restaurant recommendations near your hotel, with reservations made if needed
• Any relevant cultural norms or business etiquette for the destination
• Arrange for your preferred amenities (e.g., specific snacks, a portable standing desk) to be available in your hotel room.
• Schedule buffer time before and after trips for preparation and catch-up.

Your assistant might say: "I've arranged your upcoming trip to Tokyo. Based on your preference for adjusting to time zones, I've booked an evening flight arriving two days before your first meeting. I've also scheduled a light day of remote work for your arrival day to help with jet lag. Let me know if you'd like me to adjust anything."

Tying it all together

Becoming a skilled delegator takes time and practice. To speed up this process:

1. Write down your preferences: Keep a list of what you like and how you make decisions. Update it as you learn more about your work style.
2. Ask your assistant for ideas: Encourage them to suggest solutions, not just point out problems. This helps them learn to think like you.
3. Give and ask for feedback: Regularly discuss what's working and what needs improvement. This helps both you and your assistant get better.
4. Let your assistant do more over time: As you build trust, allow your assistant to make more decisions. Start small and work up to bigger tasks.

The goal is to have an assistant who can easily extend what you can do, and in some cases surpass your own ability.