I’m the VP of a small firm that runs entertainment for other businesses. We have about 200 part-time employees who host events and fewer than 10 full-time staff on our all-remote administrative team, most of whom report to me.
Last year, “Lisa,” a part-timer for almost eight years, petitioned us to create a role for her to manage our marketing. Knowing this would not require 40 hours a week, the owner and I negotiated a full-time role for her that includes marketing among other duties. She quit a better-paying corporate job to take our offer, citing our flexibility and character.
Nine months later, she’s doing fine at her job but is hard to work with. I give people a lot of latitude to execute their duties, but she’s so out of sync with our group’s cooperative attitude. She drags out online debates longer than necessary. She’s hard to redirect when she has an idea or opinion. She takes things personally, acting petulant or dismissive. She gets defensive about not being trusted as a “department head,” but she’s the whole department. She asks for changes without considering how much work it creates for others.
As another senior employee put it: “After a conflict with Lisa, I didn’t feel like things were resolved, even when we finally agreed.” In my own weekly check-ins with Lisa, she usually puts me on the defensive about how I give direction.
Meanwhile, I’m thinking: She asked for this! We literally created this job for her, and she’s never satisfied!
How do I set up a performance improvement plan that is partly based on vibes? It's hard to articulate exactly what I need her to change.
JobAdvisor:
Let me take a stab at articulating it based on your description: Lisa quibbles, filibusters, and lashes out at others when she feels disrespected, and you need her to stop doing those things.
I’ll even take a guess at why she’s like this: Insecurity. She’s trying to fill her needs by feeding off your group’s empathy and tolerance. Like a cuckoo laying its egg in another bird’s nest, she has made her success your responsibility.
Here’s the piece I’m missing: Why are you accepting it?
Your letter says nothing about how she has contributed to your company’s performance or even earned the deference she’s demanding. Is her “fine” work producing better results than before her position existed? Has she solved a problem you didn’t realize you had?
If not, I’m wondering what the point is of keeping her satisfied. What would the fallout be if people simply said “no” to her requests? What keeps you from letting her go?
These hard-nosed questions are admittedly out of character for me. I’m all about empathetic management, meeting people where they are, accommodating quirks, and giving people leeway to do their thing. Cultivating employees and helping them grow into their roles is a wise long-term investment. But that’s when they’re trying to meet you halfway and doing their best to contribute despite personal obstacles or cultural misalignment.
Maybe you’re grateful for her previous years with the company. Maybe you don’t want to pull the rug out from under her after she gave up her previous job. Maybe you want to give her a fair warning and an opportunity to course-correct. Those are all reasonable justifications for trying to coach her into better behavior — but they work both ways. She could stand to replace her entitlement with gratitude and recognize that you took a chance in hiring her. She’s enjoying a more flexible, cooperative work environment — which means she needs to do her part to keep it that way. Her latitude extends only as far as her respect for her colleagues’ time.
Management psychology articles, blogs, and books can provide more detail on how to handle insecure colleagues, but here’s my cheat sheet: It involves figuring out what motivates or triggers them, applauding the things they do well, refusing to take their bait and not rewarding bad behavior with appeasement. It means being okay if Lisa’s unhappy with the outcome. Sometimes it means letting her have the last word — and letting it splat on the ground, unanswered. It means someone in authority telling her, in public if necessary: “I assume you meant no disrespect, but that comment was out of line.”
The more specific and immediate the follow-up, the easier it will be to articulate what she did or said and why it was a problem.
Another thought: Has your remote team ever gathered in person? Sometimes breathing the same air can help people connect in a way that keyboards hinder.
All that said, if she can’t or doesn’t want to adapt, it might be time to part ways. If she agrees the current arrangement isn’t working, but her core marketing skills are valuable, maybe she would be happier providing those services to you as a contractor.
Also, whatever else you do: Do not put Lisa in charge of anyone. Giving an insecure person underlings to manage in hopes it will ground them is like placing kindling around someone playing with matches.
Pro Tip: If your relationship with a worker is shifting from full-time employment to contracting, make sure you follow the Labor Department’s worker classification rules. There’s more to it than swapping a W-2 for a 1099.