By Becky Hancock
Before the Business: Leading at Chegg Skills
This piece of advice doesn’t come from my own business. It comes from a job I had before I ever thought about starting one, back when I was a squad lead for Chegg Skills, managing a team of thirty UX educators.
Hiring for the Real Skill
I was involved in the hiring for every one of them, which turned out to matter more than I realized at the time. I read every resume myself and reviewed every portfolio, and I wasn’t just checking a box. I was specifically looking for evidence of the exact skills we were teaching our students. If we were asking students to demonstrate strong research habits or thoughtful design reasoning, I wanted proof that the educator in front of me actually had those habits themselves, not just a resume that used the right buzzwords. By the time I extended an offer, I knew that person had the real chops to mentor a student well. That gave me something valuable before management even started: confidence in my own team.
But hiring well only gets you halfway there. The other half showed up the moment someone new joined the team, in the very first conversation I had with them.
The First Thing I Told Every New Hire
Every time I onboarded a new educator, I told them the same thing. I’d say, “Yes, I’m here to make sure you are doing your job. However, and more importantly, I’m here to make sure you like your job. So if there’s any aspect of what I ask you to do that doesn’t sit right, or that you genuinely don’t enjoy, I want to know about it so we can make some changes.”
I said that line dozens of times over the years I managed that team, and I meant it every single time. It wasn’t a script I was reciting to sound like a nice manager. It came from a real belief that a team member who dreads part of their job is going to do that part of their job worse, whether they mean to or not, and that a manager who never asks about it is choosing not to know.
Why That One Sentence Mattered
What surprised me was how much that one sentence changed things. It wasn’t the org chart or the perks or anything I could put in a slide deck. It was simply telling each person, directly and early, that their happiness on the team was something I was actually tracking, not an afterthought to whether they hit their numbers. People could feel the difference between a manager who wanted compliance and one who wanted them to genuinely like being there. Once they believed I meant it, they told me things. Small frictions, workload issues, mismatches between what they were assigned and what actually energized them. And because I heard about problems early, I could usually fix them before they turned into someone quietly checking out or leaving altogether.
What It Taught Me About Managing Teams
Looking back, I think that’s the whole of my advice on managing a team and keeping morale high. Hire carefully enough that you trust the people you bring on, then tell them, plainly and often, that you care whether they like the work, not just whether they do it. Say it, mean it, and then actually act on what they tell you. That combination did more for how I was perceived as a manager, and for how happy that team of thirty actually was, than any policy or perk ever could have.
Managing a team of your own? I’d love to hear what’s worked for you. Drop it in the comments.