I see the word “ambiguous” thrown around a lot lately in Administrative job postings. Admittedly, I’m mostly looking at Executive Assistant and Chief of Staff roles, but it seems to be a common trait they are looking for. A quick Google of “Executive Assistant ambiguous” shows I’m not the first to notice this.

What does, “Comfortable with ambiguity” actually mean? Ambiguous is a mental space as vast as the word itself. It’s hard to put a finger on it and define it when you’re experiencing it, so I applaud that job listings can at least admit it for what it is:

They want a mind reader.

Ambiguity is just code for, “I’m going to give you vague instructions. Do with it what you will.”

The thing is, as maddening as it can be if you’re not prepared for it, I thrive in ambiguity. A few things happen when I’m given an ambiguous ask. My brain immediately begins to create a decision tree, considering the ways that we can make this work. I’m assessing the ways that it will affect the overall company and support the vision. I’m wondering if there is a budget for this project or I’ll need to bootstrap my way to completion. Regardless of task I’m given, I’m always going to have a dozen questions. I would rather an ambiguous idea of what success will look like more than I want to work for someone who has a defined vision.

There are two kinds of leaders who give you an ambiguous ask:

There are those that have a vision in mind, give you an ambiguous ask, and then are frustrated when you need to know more.

Then there are leaders who actually want this. They know that you will think of all the things that they haven’t. They understand that is a blind spot of theirs and they actively utilize the expertise of their team.