Extreme Outsourcing - Too Many Questions

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The Pain

If you've ever hired an assistant (particularly from a culture like the Philippines), you've experienced some form of the below:

1. Hire an assistant to help you save time

2. Ask for their help on a simple request, like "schedule a haircut for next Tuesday at 4 PM"

3. Get six questions upfront, or have your assistant hit a small roadblock and then ask six questions:

• They're closed on Tuesday

• Is it just a haircut?

• Did you have a barber you wanted?

• You have a meeting at 3 PM, is that too close together?

• How do I put it on your calendar?

And on and on and on, until you just say, "F it, I'll do it myself - this is 60 minutes of questions for something that would have taken me 3 minutes!"

Why does this happen?

My experience suggests this is caused by a combination of a few different factors.

A mix of inexperience, a lack of systemization, business culture, and bad management (yes, you).

Here are three things that I do to reduce these questions to a dull roar.

Recognize the Cultural Context

Many of the folks you'll be hiring aren't used to a boss that is both demanding and kind.

I've had overseas talent tell me that this throws them off - and is unique to Westerners.

Often, your assistant's only work experience is with dictatorial bosses.

Culture tells them to say "Yes" without fully understanding what the task is (and, therefore, costing you time later).

By asking you lots of questions, your assistant may feel as if they are making sure they do a good job, when in fact, it's the exact opposite!

This is largely cultural!

If you've ever read the "One-Minute Manager," you'll understand this phrase that I use a lot.

"You are expected to learn about my business and me, make decisions, and overcome hurdles ... without my specific input. "

"I'll never blame you for making a judgment decision that I disagree with. I will blame you if you ask questions that you could have found the answer to in Google, Notion, or that I have answered before. "

Your Job is To Learn, Get Better, Solve Problems, and Save Me Time

Be specific during hiring and onboarding.

One of the easiest ways to build this habit is to have a policy of the following:

"Whenever you have a question, I want you to make a judgment as to the best solution and provide me with options."

Here is an example:

Instead of sending me a message that says:

"The barber doesn't have time at 4 PM on Tuesday."

My expectation is that you send me a version of this message:

"The barber doesn't have time at 4 PM on Tuesday. He is available at 3 PM or the next day at 4 PM. I suggest 3 PM since your Wednesday is full. Please let me know, and I'll confirm that time."

Part of Your Job, Is to Document Your Job

Answering questions, in the beginning, is inevitable.

Answering the same ones over and over isn't!

Part of your onboarding should be showing your assistant how to use Notion, and how you want it organized.

"Any piece of information I give you, I expect you to file in Notion and reference in the future."

Here's an example of my "Family" notion board, which my assistant is responsible for populating and maintaining.

Whether it is my shirt size, shipping address, or my wife's health insurance information - I send it once, and she is responsible for filing it and referencing it forever!

Here is an example of the nested structure that is in our family Notion - for how to take care of our pet bunny.

Happy outsourcing!

Any questions, comments, work, need help, or whatever - just holler.

Jon