Scenario Planning

You have unique, highly nuanced preferences, and there are many cases where your assistant won’t know what to do. It’s not their fault — they simply don’t know how you think or operate without you telling them.

For example, imagine they found themselves in one of these two scenarios:

• Scenario 1 → Rescheduling a  massage
  • It's 6:15 PM. You have a 7 PM massage, but you're in a meeting until 6:30 PM.
  • The massage place messages your assistant, saying they need to move it an hour later or to tomorrow.
  • Should your assistant: a) Call you as soon as your meeting ends? b) Not call, assuming you'll check messages before leaving? c) Accept the later time if they know you're free?
• Scenario 2 → Gift-buying dilemma
  • Your assistant researched gifts around $100, and you chose one.
  • The chosen gift is now sold out.
  • Should your assistant: a) Buy one of the other options without asking? b) Wait to reconfirm with you?
  • What if the same gift is available but now costs $250?
  • What if waiting until Monday means the gift won't arrive on time?

In both cases, your assistant might be worried about making the wrong decision because your preferences are nuanced or not immediately obvious to them.

Instruct your assistant to proactively surface gray areas to you as they come up or, ideally, proactively. When replying, be overly thorough with the nuances of your thought process and preferred action.

Here’s a simple message format you can have your assistant use when they hit a roadblock:

Regarding [task], I’m running into a roadblock. [Explain roadblock].

I recommend [recommended action] because [reasoning].

Walk through as many as possible with them — it’s the fastest way to eliminate your assistant’s uncertainty and will save you time that would be spent on trial and error later.