my assistant doesn’t know how to prioritize — Ask a Manager

A reader writes:

My team recently hired a part-time assistant, Jane, to help with my work. The problem I’m running into is that Jane either doesn’t know how to prioritize or doesn’t understand that certain things need to be prioritized even if I explicitly tell her “this task needs to be completed before you do anything else.” She continues doing tasks that she finds enjoyable without working on items that have hard deadlines. For example, I asked her four weeks in advance to pack up a big shipment by the end of month – she had plenty of time and she’s done it successfully before – and yet when I asked her what was going on a week before the shipment was due? She hadn’t gotten to it yet. She had spent three weeks working on other tasks instead, like emailing leads. With such a short amount of time left for the shipment, the rest of us had to pitch in to help complete the task, when really she could have done it by herself if she had started earlier.

I tend to be a person who prioritizes any tasks with a deadline – even if the deadline is two months later just so it’s done and dusted. I get that there are some people who function very differently, and that’s fine within reason! I don’t want to dump my work style on her by prioritizing for her, but I’m at a loss for how to better manage completion of the tasks I assign to her. Help?

I answer this question over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.