Lemme tell you about the best manager I ever had.
I met Heather randomly during my in-person interview at ESPN (a grueling 8-hour day jammed with 30-minute interviews and almost no toilet breaks). I remember nearly running face-first into Stephen A. Smith at the lunch line and getting my picture taken on the SportsCenter set, but that's about it. Although she wasn't on the official itinerary, I happened to swing by Heather's desk where she worked as an Art Director. She was kind and welcoming, as were most people. Little did I know she would go on to play a major role in hiring me.
Although I was promised the job, I didn't end up getting that specific role (thanks to a department-wide reorg); however, Heather (and others) remembered me and when a different position opened up four months later, it was Heather was the one who sent me my "Congratulations, you're hired!" email.
All new hires at ESPN go through "Rookie Camp," a two-day onboarding session which includes a download of benefits information and an in-depth campus tour. At the end of day two, everyone's manager comes to pick them up and walk them (or drive them, since campus is humungous) to their designated cubicle where they get their equipment and meet other teammates. It was kind of like junior high, where all the parents retrieve their kids after school is over. Or maybe it was a little too much like junior high, because Heather was the last manager to show up. Actually, I sat awkwardly in a conference room all alone until one of the Rookie Camp leaders asked if she could call someone for me (yeah, it was just like junior high). Finally, Heather showed up (apologizing). I must have looked silly waiting all alone because we joked about it for the next five years.
I quickly figured out that Heather was someone I could trust and rely on. She was empathetic and protected me from all the stuff you want a manager to protect you from — office politics, unwarranted design critique, time vampires, etc. It's probably not fair, but I've compared every manager I've had to her and nobody comes close.
I soaked up every lesson I could from Heather. She taught me how to write code, how to get the most out of meetings, and how to hold people accountable. With the exception of coding and some administrative how-to's there was never any lesson plan, which meant most of what I was picking up from Heather was via observation. Of all the things she unknowingly taught me, the most valuable was how to ask questions.
Heather is the kind of person that you want on your side because every decision she makes feels like the right one. I remember watching her (politely) grill editors who had flippantly filled out a project request form. Whether she approved or rejected assignments, it was always a thorough process — almost like she had written an entire Yes/No flowchart just for that single instance.
<aside> 📄 Project Request Forms were the original method for assigning projects in our department (when I arrived). How editors and designers collaborated matured over time. It went from an open-door policy (where ideas weren't vetted that closely) to a weekly brainstorm (with designers and editors pitching ideas to each other). The former was tough, as editors had a tendency to show up last-minute and ask for some art to go along with a finished piece, making design feel like an afterthought.
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Heather's line of questioning made her the perfect communicator. I never left a conversation wondering if we were on the same page. She often used phrases like "Just so we're clear…" and "What I'm hearing is..." to make sure we were in sync.
I lost count the number of times I was caught by a surprise follow-up, "What do you mean?" from Heather. Almost immediately, in every case, I'd feel like a deer caught in the headlights with absolutely no clue what I'd just said. Even after working with her for five years, I just couldn't get used to the level of authentic curiosity she had.
On a professional level, it forced me to justify my design decisions and support them with evidence, like user experience research and my understanding of code. I had to show my work. It was always helpful. It was also annoying.
<aside> 🤝 Something worth mentioning about Heather: everybody loves her. As intense as her meticulous question-asking could be, the admiration I witnessed from our coworkers never wavered. Project kickoffs could get awkward, especially when she painted someone into a corner, but it never felt contentious. She always ended meetings with a smile and a warm "Thank you!" The questions were a skillset, not a character flaw.
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Personally, if I'd had a bad day or was experiencing a problem with a co-worker, she wanted to know the specifics. Not only did the questioning catch me off guard, her kindness was disarming. She helped me recognize that most issues could be solved with better communication and perspective. This was annoying, too.**
I eventually picked up on the importance of asking questions and it formed how I led projects. Understanding the intent of every request, the root of every problem, the process for every design decision — I became obsessed with knowing the why as well as the what.
As for the what, it's probably time I get specific. Allow me to share a few of my favorite questions with you, as well as some tips for how to ask them.
I'm starting here because this may be the most important question of all.
It's also the hardest one to ask.