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What to do with a bossy direct report

Can you not?

Hi friends! I just watched the DCOM (Disney Channel Original Movie, of course) Brink, and I was reminded of just how much I wanted to be a Soul-Skater in middle school. Not sure if my 6’4” self would be the most agile on blades now…but a guy can dream.

Today’s Tunes: Looks like Kelis isn’t the only one being bossy these days…


How to Handle a Bossy Direct Report

When I was new to my job, I was paired up with a coworker (who now reports to me) to show me the ropes, specifically the operations and processes of our team. Now that I’m six months in and super confident in my position, that same coworker/my direct report is acting as if they’re my manager instead of the other way around. What would you do here? —K.

Anyone with a sibling has probably had to have a conversation along the lines of this: “I know I used to let you walk me around on a leash and pretend I was a dog when we were little, but we’re both in our late 20s now and I need you to respect the fact that I’m both not a dog and not five years old anymore.” Time to have the same kind of talk with your coworker (but maybe skip the colorful examples this time around) so they know who’s who and what’s what. Here are two steps I’d recommend taking to draw some necessary boundaries:

1. Talk to them honestly. Open and transparent communication goes a long way. Your coworker may not even realize what they’re doing, and you cluing them in could really help. Start the convo with something along the lines of:

  • “I really appreciate you taking me under your wing when I first started. Now that I’ve been here six months, I’m confident in my role and ready to lead this team in the way I was hired to lead it. I’d really appreciate the two of us working to tackle our tasks in the way our company structure dictates.”

  • It may feel a little icky, but wouldn’t you want someone to tell you if you were making their jobs harder for no reason?

2. Bring in the boss’s boss. If you tried talking to your coworker but they’re still asking you to “follow up” on something that they very well should follow up on themselves, it may be time to bring in the big boss to lay down the law (read: gently and diplomatically remind everyone of the org chart).

Because organization is the key to life (that’s a direct quote from my grandpa). Sometimes hierarchy is no fun—like picking teams in dodgeball. But other times, it’s a lifesaver—like at work, especially these days when roles often overlap and intersect.

If you, like me, have worked for a company that hasn’t updated the org chart since Olivia Rodrigo’s first album came out, I recommend taking things in your own hands to make sure that 1) your responsibilities and 2) your direct reports are clearly laid out and communicated.

One way I’ve gotten to know the organizational structure of a company when the employee handbook is useless?

15-minute meetings! I know, I know, another meeting? But hear me out.

Scheduling brief meetings with your coworkers throughout the company and all over departments can help you 1) learn your coworkers’ roles and responsibilities (which probably go beyond their job title) and 2) get to know their work style, including the best way they work together with others. Look at you, perfecting company hierarchies and having tough conversations.

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Things To Send Your Work Besties

…before you block your calendar off for the rest of the day.

As if I needed another reason to choose mashed potatoes over the gym. Over half of 2,000 adults surveyed by eBay in the UK believe that daily tasks can be more relaxing than meditation or yoga. Walking around the supermarket, vacuuming, and mashing potatoes (iconic daily task) were some of the stress relieving activities named by survey respondents.

If me having a mustache-themed birthday party in 2014 doesn’t scream millennial, I don’t know what does. Reply and let me know what’s the most millennial thing you did back in the day. That you definitely don’t regret daily…

The theater kid in me can’t even. I was the Gleek of the Week on Glee stars Kevin McHale and Jenna Ushkowitz’s podcast And That’s What You REALLY Missed! We chatted about everything from the most unhinged moments of the show to taking care of our mental health to making friends when you’re an adult (which feels as impossible as the gas leak in the choir room storyline, IYKYK).

Thanks for reading. Wishing you a speedy week to Friday. TTYOW (talk to you on Wednesday)!



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