The Shadow Training Technique

Advanced delegators know an assistant's effectiveness depends not only on their grasp of explicit context, but also on their meta-knowledge — such as knowing where to find info, who to ask for help, and unwritten rules that guide their decision-making.

Shadow Training is a technique that naturally teaches both types of context as you work in real time.

Here’s how:

• For the first few months, schedule regular 30-60 minute sessions during varied work periods. For example, 9:30-10:30 AM might capture your morning email triage, a client call, and strategic planning. If it feels natural, include your assistant in calls. Otherwise, host open screen-sharing sessions to provide a comprehensive view of your workflow.
• Optimize your calendar together. Pull up your weekly view. Make real-time changes and provide as much context when you can: "Let's move this partner call from Friday to Thursday. It aligns better with our weekly planning rhythm."
• Work in real-time, think out loud. Narrate changes you’re making and provide deeper rationale. “I'm comparing our Q2 marketing spend to our customer acquisition numbers. The cost per acquisition seems high for our social media campaigns, but email is outperforming expectations.” As you switch between different tasks and contexts, explain your process: "I'm switching to our financial dashboard now — I always check our burn rate and runway before making any resource allocation decisions”

This method achieves multiple goals simultaneously:

1. It immerses your assistant in the nuanced context of your decision-making process
2. It showcases your communication style and priorities in real-world scenarios
3. It trains your assistant to anticipate your needs by exposing them to your regular workflow patterns and thought processes

Shadow Training fast-tracks your assistant's context in a way that no manual or template could. An upfront investment of a few months compounds their knowledge of how you operate.