r/managers•
sweetdoggieblue

Freelancers: what not to do when you get a gig

We had layoffs at my small office in early November, I was put in charge, and my boss gave me a budget to hire freelancers to get through the end of the year. A former colleague said she was having trouble finding freelance work (we're in journalism), and I asked if she would like to work temporarily.

The first week she was on duty (remotely), I asked at the end of the day, where are those two stories you edited? I needed her to share the links (which I've repeated several times). Her response: When can I send you an invoice?

We are now three weeks in. She is still struggling with tech issues (we're both in our 60s) so she took the initiative to come to the office to get some assistance (good). She is still not sharing links with me, though she can see this is how the other freelancers work. At this point, I'm simply thinking, when can I cut this woman's hours? I took a short break for lunch, and there she was in the lunch room asking me how to use the office coffee machine. I'm doing my best not to be overwhelmed, and I can't even get a quiet lunch!

At the end of the day, she said she was disappointed that my boss hadn't come into the office because she wanted to ask him about a job opening. I'm thinking, you really think you're getting past me? That I would recommend you?

Afterward, she began complaining again about how hard it is "out there." And I thought to myself, when someone like me gives you a chance, maybe you can make it worth their while. Don't make it so damn hard to manage you.

Posted Dec 3, 2025, 1:36 AM UTC

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