Newsletter #6 - The Shadow Training Technique

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.

The 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:

It immerses your assistant in the nuanced context of your decision-making process
It showcases your communication style and priorities in real-world scenarios
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.

School Delegations for Parents

Now that your kids are back in school, there are some new work-streams your assistant can help with.

Here are two starter delegations to help you stay organized:

Calendar

Have your assistant add all important dates and events from your school calendar(s), along with other kid-related activities, onto your family calendar.

This way you’ll won’t be caught off guard when things come up, and this delegation can turn a static list of dates into action. Instead of a 1-2 page school calendar, you can now:

Plan for predictable dates, events, and purchases driven by:
- School activities
- Birthday parties
- Big tests
- Sports
- Clubs and extracurriculars
Make plans (childcare, family vacations, etc.) for when schools are closed during:
- Holidays
- Teacher trainings
- Parent conferences
- Early dismissal days
Decide what level of participation you want and what purchases need to be made:
- Assemblies
- Conferences
- Performances
- Fundraisers
- School/community building events

Once everything is in one place you can be confident you won’t miss anything important and stay on top of what’s coming up.

Comms

Setting up your calendar initially is one thing, but schools send 3-6 messages per week, on average (with even more during busy periods). Have your assistant summarize school-related comms for you and create a weekly “digest.”

Example structure:

Key dates/events of the week:
- i.e. upcoming field trips or special assemblies
Action items / requires your consideration:
- Mandatory participation (Parent-teacher conferences, surveys, consent forms)
- Decision points (Opportunities for extracurricular activities or school programs)
- Volunteering (Participate in school events or committees)
Admin updates:
- i.e. Policy changes, safety alerts, and reminders about deadlines. Make sure your assistant knows to alert you right away if one of these is urgent.
Classroom or teacher updates:
- i.e. Insights from teachers about classroom activities or student progress

Without a system to collect and triage these tasks, adapting your schedule to school events will take up mental energy that’s better spent with your kid(s).

Notes

Now that the kids are back in school, hopefully the burst of activity and to-do’s have subsided. How do you work with your EA to offload the ongoing mental load and stay on track of things?

Some ideas:

Calendar —> Have your EA make a consolidated school calendar that integrates dates and events across all sources (school, extra-curriculars, sports, etc); have these then inputted into your gCal or family cal, but surface to you:
- All days that school is closed (holiday, teacher training, conferences, etc) or when there is early dismissal —> helps you plan for finding childcare (early dismissal) or plan for vacations (holiday school closures)
- Important events to attend (assemblies, conferences, performances, etc) —> EA to schedule based on your input
- Social events (fundraisers, school/community building, etc) —> helps you decide if you want to participate, schedule
Ongoing communications from school, teachers, PTAs, coaches, etc. On average, schools send 3-5 weeks a week; this increases during busy periods. Have your EA read and summarize for you each week. Sample structure:
- Important dates / happenings this week
- Requires action from you, ordered by what is likely most relevant
  - Your attendance or action is required (parent conferences, intake surveys, etc)
  - Decisions need to be made (Sign up for extra-curriculars, etc)
  - Do you want to volunteer or participate
- Admin updates - policy changes, safety alerts, impending deadlines
- Classroom or teacher updates

No time for the details? Just have them surface to you things that require your action or attention: