Horse Race Method

Effective delegation hinges on your assistant understanding your explicit and implicit preferences, tastes, and thought process.

The Horse Race Method is a rapid way to transfer this context by completing the same task side-by-side and trading notes until your assistant consistently matches or exceeds your own output.

It's called "Horse Race" because you and your assistant are essentially running the same “race” (i.e. completing the same task) simultaneously. You can directly compare your outputs and thought processes.

Here's how to implement it:

1. Set the Track: Define clear parameters for an upcoming travel need. For example: "Non-stop flight to San Francisco, leaving Tuesday afternoon, returning Thursday evening. Preference for aisle seats and hotels within walking distance of the convention center."
2. Start the Race: Both you and your assistant independently book a trip to San Francisco for an upcoming conference. Parameters include: non-stop flight, Tuesday departure, Thursday return, hotel near Moscone Center.
3. Compare Results: Review both itineraries side-by-side. Your assistant found a cheaper flight, but you secured a better hotel rate. Discuss the trade-offs: "The $200 flight savings is great, but the hotel you chose is a 20-minute walk from the venue, which could impact my tight schedule."
4. Give Specific Feedback: "I prefer the 2 PM flight you found because it allows for a morning meeting in our office. However, I always choose hotels with 24-hour gyms for jet lag workouts. The hotel I picked has this, which offsets the higher room rate for me."
5. Refine and Repeat: Conduct the Horse Race exercise for a specific task until your assistant's choices consistently match—or beat—your own. The goal isn't speed, but deep understanding of your taste and thought process.

This method's power lies in its real-time, task-specific training—which unfolds over several cycles until you reach a high level of trust with your assistant.

Let's see this in action with a travel booking example:

Round 1

• Task: Book a day trip to Chicago for a client meeting.
• Your approach: You choose a 7 AM flight to arrive early, book a hotel room for day use, and schedule a car service.
• Assistant’s approach: They book a 9 AM flight, don't book a hotel, and assume you'll take a taxi.
• Feedback: Explain your preference for early arrivals, the need for a day room to freshen up, and why you prefer a car service for reliability.

Round 2

• Task: Book a three-day trip to London for a conference.
• Your approach: You book a red-eye flight to arrive in the morning, choose a hotel near the conference venue with a 24-hour gym, and schedule gaps between meetings for jet lag recovery.
• Assistant’s approach: They book a daytime flight, choose a cheaper hotel further from the venue, and pack your schedule tightly.
• Feedback: Discuss the importance of maximizing time in the destination, your specific hotel preferences for international travel, and why building in recovery time is crucial for productivity.

Round 3

• Task: Plan a week-long, multi-city European trip combining client meetings and personal time.
• Your approach: You create a detailed itinerary balancing business and leisure, book flexible tickets for potential changes, and include detailed notes on local transportation and dining options.
• Assistant’s approach: They create a similar itinerary but miss some nuances about your preferences for mixing business and personal time.
• Feedback: This is where you can really dive into the finer points of how you like to travel, work, and relax. Discuss how you make decisions about when to extend trips for personal time, how you prefer to navigate in foreign cities, and your strategies for staying productive on long trips.

By the end of this process, your assistant will have a deep understanding of not just your travel preferences, but your overall approach to balancing productivity, comfort, and cost. They'll be able to book trips that feel like you booked them yourself – or even better.