being the boss

All your questions about being the boss, answered — like dealing with low performers, lateness, weird feedback, and more.

can I teach a very disorganized employee to be more independent?

A reader writes: I have a question about helping my employee get organized. She has two pivotal job duties which are closely tied but not directly linked — I could technically have two people doing each piece separately, but the volume as a small business doesn’t warrant that number of employees. Think the relationship between […]

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my employee eavesdrops on me

A reader writes: At first I thought I was being paranoid, but on three separate occasions, I’ve wrapped up a closed door conversation others in our C-suite, only to discover my employee directly outside my door. Our office set-up is odd; we’re essentially one huge office that was cut into thirds–one side is her office […]

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my employee is hassling coworkers about their clothes

A reader asks: I hired a new team member, “Jane,” six months ago. She’s competent and diligent, but now that she’s coming out of her shell, her rigidity around her idea of professional norms are alienating her team members as well as other people on staff: * She complains about women colleagues’ workwear for being […]

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employee wants a higher raise than she earned

A reader writes: I have an employee whose yearly review I am working to wrap up. After the initial review, we usually discuss a raise, based on what was discussed in the review. We typically would expect a 2-5% raise for this person. I got an email from her requesting a 13.15% raise. I don’t […]

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is it normal to cancel days off for a resigning employee?

A reader writes: I am a new manager, though I’ve led individual contributors on project-based work for a large part of my career. My direct manager, “Sam,” said something puzzling to me last week and I’ve been chewing on it all weekend. One of my direct reports, “Drew,” put in their two-week notice on Monday. […]

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my assistant keeps arguing with me

A reader writes: I’m a new manager. My assistant was close with the previous manager who I took over from, and it’s been a bit of a challenge creating a good relationship with her. Any time I make a decision for our team, she constantly asks why and she quite often says, “That’s not how […]

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I ramble nervously when I give employees feedback

A reader writes: Whenever I have to give any challenging feedback to someone I supervise, I tend to ramble on and repeat myself. I want to be sure that I am clear and direct, but then I worry that I was too harsh so I soften things a little. Then I want to give examples […]

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