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WorkScripts: I’ve Been Asked To Manage My Friends — And It’s Not Going According To Plan 

Eliot Kaplan  |  September 20, 2019

Being a manager isn’t easy.  Being a manager to your friends can be worse.  Here’s how to wade into uncharted territory without losing your pals. 

HerMoney’s WorkScripts tells you in detailed, measured fashion exactly what to say in every office situation and how to respond no matter how the conversation turns. It takes you all the way through the interaction, leaving you feeling confident that YOU are the one steering the conversation. And confidence is at least half the battle. This week, we’re tackling the topic of what to do when you find yourself managing friends. 

Q: I’ve just been promoted to oversee three colleagues who are peers, whom I am friends with. Two of them are dealing with it just fine. But the third — not so much.  She’s constantly trying to push my boundaries and is pushing my buttons as a result. First, she belittled me in front of the group. Then she skipped out early on a project and left me to clean up the mess she left behind. Most recently, she told me she is planning a vacation next week even though company policy is to clear your vacation several weeks in advance, and another key member of our small team already put in for the same days months ago. How should I deal with this?

A: In many cases, being promoted over a peer can be even more of a minefield than being promoted in favor of older, more experienced colleagues. Veteran workers may tend to be more content with their roles and accepting of a rising superstar in their department. 

Clearly, your friend (and direct report) knows she’s provoking you, and the longer you let it continue the worse it is going to get. Perhaps she resents you getting promoted instead of her. (Was she expecting to get a title bump? Worse, had she confided in you that she thought she might be promoted?) Maybe she thinks your friendship merits her special treatment. But it’s not your job to psychoanalyze her. It’s your job to get her in line. You have already let too many things slide, so it’s important to act now, or her bad attitude is going to spill over and contaminate the whole team.

What you say: “Lily, you know our company policy about vacation. We can’t let you have that time off with such short notice. Julia is already taking those days, and we can’t spare both of you at this critical time, with our biggest presentation in years due soon.  Look at the calendar and please come up with a different set of days. I’m happy to work with you to make it as soon as possible.” 

The answer you’re hoping for: “This offer of a trip came up last minute, but I understand. I’ll see if I can postpone it for a few weeks when the office schedule is more clear.”

Great work… Now just work on her overall attitude over the next few weeks, and your working relationship may be not only salvageable, but stronger than ever. The friendship is still to be determined.

The answer you’re dreading: “Ever since you got this job, you think you’re better than everyone else. And you love bossing us around. What happened to my old friend who would sneak out for a vape? This company policy is stupid. You can spare a couple of people for a week. Besides, I already laid out money I can’t get back.” 

What you say:  You’ve got to stand your ground, or you risk coming off as the jelly-est of jellyfish. It’s best to do all this in a private setting, but even if she’s calling you out in front of others, you have to respond. You don’t have to say you’re the boss, show it, with something like this: 

“I’m sorry you feel that way. But our roles have changed, and I hope you understand that. That said, I respect you, and I would appreciate it if you would show me the same respect. You’re escalating this way beyond where it has to go… I’m happy to work with you on an alternative date.” 

Chances are she’ll be scouring LinkedIn for job opportunities the minute she gets back to her desk — and that’s okay. It won’t be a big loss.

The answer you never saw coming: “I’m taking that vacation. I’ve already paid for it and I can’t cancel.  Do what you have to do.”

What you say: “If you don’t come in to work next week after being told you have to, it will be considered an unexcused, unpaid absence and HR will have to deal with the next steps.”

As one of my former colleagues liked  to say, “I’m not the bitch boss, I’m the boss, bitch!”

About Eliot 

Eliot Kaplan spent 18 years interviewing over 5,000 people as Vice President of Talent Acquisition at Hearst Magazines. He now does career coaching at coacheliotkaplan.com. He knows there’s a WorkScript for every office dilemma, so send your problems to workscripts@hermoney.com for Eliot’s expertise.


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