being the boss

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

how much should I hand-hold a disorganized employee?

A reader writes: I am a new manager struggling with how to handle one of my employees. He is a smart guy but super disorganized. For example, he is in charge of ensuring all internal audits in our company have been set up and executed. We discuss this in our one-on-ones, and invariably, every time […]

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should I say something about my assistant’s messy desk?

A reader writes: My administrative assistant’s desk is atrocious. It is covered in not just piles of paper, but trash, food items, and all sorts of miscellaneous junk. She is a good employee and appears to get her work done. How would you handle this? I answer this question — and three others — over […]

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I’m the boss who’s always late

A reader writes: I’m part of the senior management of a small company I’ve been with for several years. While I’ve consistently been a stellar performer, I do have one major flaw — I am always late. Doesn’t matter if it’s in the morning, the afternoon, or the evening. I am what you’d call a […]

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employee treats coworkers as if they stink

A reader writes: I work with a group of people who are public-facing in a building (retail/public service type environment) and we rotate people on different desks on a set schedule throughout the day. I have a few coworkers who are sensitive to fragrances, and our policy was recently updated to be a “fragrance-reasonable” workplace. […]

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my employee talks about people’s weight

A reader writes: I’m a female manager of a team. I’m significantly overweight. One of my direct reports has repeatedly made derogatory comments about overweight people to me during the course of conversations, such as “____is a big girl, I mean, she’s really big!” I think that’s rude in general, and I also sense she’s […]

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my employee keeps coming to work sick

A reader writes: Now that the pandemic is “over” ( /s) and all the rules and restrictions have pretty much been lifted, I have a question: as a manager, what can I do to make people stay home when they’re sick? I’m the director of a mid-sized public library, and we have a librarian, “Brian,” […]

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I made a bad joke about my new hire

A reader writes: I have a new hire who’s coming to the end of his probationary period. Chris is conscientious, smart, and has gelled well with the team. He’s completed his probationary objectives with time to spare, and in our most recent catch-up, I suggested that he start considering his longer-term goals for career redevelopment […]

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someone emailed me about my employee’s behavior outside of work

A reader writes: I recently got an email from someone with screenshots concerning an employee of mine. They were of a personal nature directed to an organization outside of work using her personal time and her personal equipment. They didn’t concern work at all. They weren’t racist or hate-filled rants or anything of that nature. […]

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