My First Management Role Didn’t Go As Planned—Here’s What I Learned

How old were you when you managed your first direct report? Was it your high school job at the frozen yogurt shop? Your second or third job out of college? Maybe you haven’t even gotten to that point in your career yet. For me, unofficially at least, I fell into my first management role a few months after college graduation—but my first official opportunity didn’t come around until I was a 26-year-old director in the middle of The Great Resignation prompted by a pandemic.

Let me back up a bit. After I secured my journalism degree (go Hoosiers), I interned for a smaller company in Chicago. There weren’t too many of us, and I was soon promoted to a full-time, non-intern position. What I didn’t expect was to somehow end up (mostly) in charge of the next intern when I had held that very position just a few months prior. That intern wasn’t my official direct report, but I showed her the ropes and served as her first-round editor and general go-to gal.

Cut to after a few jobs, and I finally got the chance to fully and officially flex my managerial skills with a direct report—an intern dedicated to my department (AKA my mighty team of one) for three whole months. What was interesting was that just as she was learning the ropes of the intern position, I was also finding my own way. How hands-on did I want to be as a leader? How could I build rapport while still maintaining our boss/report relationship? There were times when I probably should have just picked up the phone instead of DMing on Slack or prepared more details with clearer direction before handing over an assignment. And everything—from the hiring process to remote onboarding to getting things across the finish line—definitely took much longer than I originally expected as we both found our footing in our new roles.

That internship period has since come and gone, but I find it helpful to reflect back on the highs and lows of being in charge during such a strange time for the professional workforce. Did I expect my first leadership role to entail managing someone halfway across the country? No. Am I late to the management game? I’m not sure. Did I learn a lot? Absolutely. So for all of the other first-time managers out there (and myself), here’s what I’ll try to remember next time:


Know that hiring takes time

Finding the right person won’t happen in the blink of an eye. Not only do resume reviews and candidate interviews take time, but so does the proper prep work. In order to ensure equitable hiring practices, my company lists job descriptions in a 30/60/90-day structure that outlines what the candidate will do once hired instead of requiring specific experience. We also prepare a list of questions to serve as a guide through each and every interview—we still have our own unique conversation with each candidate, but this strategy gives us a standard baseline for all candidates. TL;DR: If you’re hiring from outside your organization, it takes more work than you expect.


Source: Color Joy Stock



Once you’ve given your direct report a start date, you’re on the clock. Onboarding is usually a key indicator of company culture, so you want to leave a good first impression with a smooth, educational process. Along with HR materials like an employee handbook and a W-9, gather as much relevant information for your direct report ahead of time. Be ready to hand over a packet of introductory information like links to important documents, usernames and passwords, and the original job description. Don’t forget the not-so-obvious things like your work style, schedule, and any other preferences that are important to share up front—and don’t forget to have your direct report share the same.



Seriously. Explain absolutely everything, and then explain again. This applies to in-person work too, but it’s especially relevant in remote situations where a lot can get lost in translation. Is your direct report comfortable with the technology you’re using? Did they hear you clearly? Maybe they prefer to review things on paper instead of over a screen—are you both on the same (digital) page?

One of the biggest lessons I learned was that if my direct report didn’t understand something, it wasn’t really on her—it was probably on me. What information had I shared with her? Did I give her enough direction? Did I give her enough feedback? I’m not suggesting micro-management, but in my opinion, it’s better to over-explain than under-explain. Either way, do your best to clearly articulate the task at hand, then make yourself available for questions just in case.


Source: Social Squares



If you’re working remotely, it can be easy to Slack someone a to-do list and call it a day. We’ve all had those days when turning our camera on just isn’t going to happen, but try to set aside some regular “face time” to check in with your direct report. And while touching base on specific assignments is great, a recurring 1:1 meeting dedicated to overall progress, career growth, and some casual banter will go a long way in getting to know each other and building rapport.


Listen to Them

Just like you probably encourage your direct report to ask questions, make sure to ask them some too. See what they’re interested in and, if possible, take their career goals and growth areas into account when mapping out tasks and assignments. Are they interested in analytics? Have them pull next month’s numbers—better yet, have them present them to you and your boss. Take it even further and see if there’s a hands-on project they can call their own or a department they can shadow for a day or two to get a sense of what the work is actually like.


Listen to Yourself

I’m not going to sugarcoat it: Managing someone else in addition to your own responsibilities is a big undertaking. It’s probably going to take more time and energy than you think—your direct report will have off days, you’ll have off days, and deadlines will creep up before you know it. Throughout your role as a manager, have a serious conversation with yourself about your work style, communication preferences, time management skills, etc. You’ll learn things about yourself that you’d never expect, and it’ll make everyone’s experience that much more worthwhile.



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