This is the fourth in a series of five essays focusing on how people have navigated difficult times in some of their closet—or most critical—relationships. In this one, the writer discovered the key to communication with a team of much-younger colleagues.

By Sandy M. Fernández
Illustration by Lauren Tamaki

When I saw the name of the book at the store, I may have snickered. Titled something like Managing the Unmanageable Employee, it felt like a book that already should’ve been stashed in my desk drawer, dog-eared and highlighted. By then, I’d been at my job at a website for a year. It paid less than I’d made before, but I felt lucky to have weaseled my way in, given that I had zero tech aptitude or experience (at the time, I think I was still using a flip-top cell phone). 


A former manager of mine was heading it up and clearly wanted some support with his Gen Y staff. “You can edit the younger writers,” he said to me at the perfunctory interview, and the deal was done. Yet I was somehow surprised when I arrived and found I shared the same title with five other staffers, at least two of them young enough that back when I was buying my first Ann Taylor career wear, they probably weren’t even eating solid food yet.

I tried to do what my boss had asked. I gave feedback. I parceled out advice. I took people to coffee and had earnest talks with them about office decorum. But The Youth seemed not to want my advice. They disagreed with my edits—and said so. They went around me to our boss when I gave them tasks they didn’t like. (Good luck finding him—he generally hid from them and did his messaging through me.) When I pushed back, chats with The Youth tended to get circular, like a whirlpool, sucking away work hours and my congeniality. These felt like the conversations I used to have with my kid when he was a toddler and no amount of reasoning could convince him to wear his rain boots. I started spending too many hours smoldering at my open desk, wondering what exactly was so hard about changing one measly sentence. Sometimes I felt like the tension was physically on my skin, obvious and sticky. 

Against that backdrop, the book seemed like too good a dark joke to pass up, so I bought it. But I was also desperate, so I started reading it. And it was a revelation. 

Pretty much all office conflict, it said, is predicated on a misunderstanding of roles and goals. It hit me that I was running around trying to manage coworkers who, no matter the duties my boss had whisper-granted me, were actually my peers. They had a boss—and it wasn’t me. No wonder they kept trying to appeal to him when the office busybody started bossing them around. I did have more experience and hard-won skills, but these were tough to appreciate when I was barking from my office chair. I’d come up in a work culture where, especially at entry level, you did as you were told. But my Gen Y cohort worked collaboratively: When they repeated themselves over and over again, it wasn’t because they were stubborn; it was because they wanted me to hear them. Meanwhile, I wanted them to respect me—which, in my mind, meant a quick acquiescence. The unmanageable employee, it turned out, was me. And I needed to start managing her.

I took The Youth out to more coffees—but this time to listen rather than to give advice. I asked them how I could help them, and what they thought could be going better. If that sounds easy, it wasn’t: It felt vulnerable, humbling—enough that, though I felt like a dork, I did as the book advised and practiced exactly what I would ask beforehand, trying to get my questions under eight words or less so they’d be direct and clear. I didn’t totally succeed, but it did force me to think through and finesse, and saved me from rambling when I got flustered or uncomfortable (which happened). 

As expected, The Youth did feel like I was overstepping my bounds. And they felt a little uncomfortable, but mostly with how clearly uncomfortable I felt. Not as expected, they also straightforwardly appreciated my help. “I don’t always agree with everything, but I know you’re really good at what you do,” said one of my toughest adversaries. “You make my work better.” A sentence I never would have heard if I had just kept sitting and glowering.