The art of asking questions

Backstory

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.

The perfect kind of questioner

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.

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.

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.

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.

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.

What do you mean by that?

I’m starting here because this may be the most important question of all.

It’s also the hardest one to ask.

Asking someone what they mean establishes that you’re not on the same page. It’s a clear indicator that the person explaining has to start over, or at very least backpedal. A good colleague will respect your question and a bad colleague will roll their eyes or take a long pause and look at you like you’re stupid. Unfortunately it doesn’t matter which one you’re dealing with, it’s still really hard to ask this question.

It’s embarrassing to be out of the know. Sometimes you can brandish an excuse:

“Sorry, I’m new here.”

“Catch me up, I was out of the office during your last presentation.”

“My internet cut out. Can you repeat that?”

But even then, nobody likes to admit that they’re confused while everyone else is nodding their heads. Having the guts to ask someone what they mean will help you grow in two ways:

1. It makes asking follow-up questions easier. As soon as you ask one question the rest will start flowing. And it will be easier to ask the question again the next time this happens. Practice makes perfect in this case.
2. Leaders aren’t afraid to embarrass themselves. How many times have you almost asked a question, balked and then regretted it as soon as someone else asked the same question? If you can be the first person to admit that you don’t understand, it’ll be easier for someone else to chime in.

Questions enable others to prove their understanding. If you’re the only confused person in a group, asking questions alerts everyone else to the varying levels of understanding. Sometimes they can clarify what a presenter means and/or shed light on where you’re getting hung up. Multiple interpretations always help.

“What do you mean?” was always the most disarming question that Heather asked me. Too many times I’ve nodded along with someone in agreement while simultaneously thinking I have no clue what they’re talking about. Asking this question means never fake-agreeing again.

Can we put this on a story page?

This one is pretty specific to ESPN, so allow me to explain:

Anytime the design team had a project request, there were really only three possible outcomes:

1. Deny the project. Nobody liked this option. Sometimes saying “no” meant the person making the request (usually an editor) had to bring something else to the table — more time, a better hook, larger budget, etc. Most of the time, we didn’t have the bandwidth. You can’t say “yes” to everything, especially when stories were likely to get buried during busier news cycles.
2. Accept the project and build a microsite. This was what editors always hoped would happen. The theory was that throwing more money and resources (developers, illustrators and photo editors) at a story elevated it to a higher spot on the news feed. But even if it didn’t receive higher traffic, a microsite looked cool and felt important.
3. Accept the project and put it on a story page. This was the most common outcome. The editor would pitch a story and if there weren’t enough design elements to elevate the content (ie: make data more interactive or provide visuals only possible with some custom javascript), we’d let the editor build it out on the traditional blog-style format most readers were used to. The design team would art direct a custom illustration or two and that was about it.

Story pages (option 3) were actually my favorite type of assignment. They usually got more traffic than custom builds (option 2) and art directing some of my favorite artists in the world remains to be the highlight of my career.

As I mentioned, during my first year on the content team, we accepted just about everything that came through the door. It didn’t matter how complicated a pitch was, we found a way to make it work. I had no problem with this (I didn’t know any other way), but as we evolved, departments merged, and priorities changed, the team was forced to be more deliberate in how we accepted (and rejected) projects.

It felt like every editor’s goal (with very few exceptions) was to land a custom project with the design team. The vetting process was intense, and rightfully so — custom project lifecycles were usually 10+ weeks. A story page felt like a kind of compromise: we’d devote some resources to it — anywhere from a couple days to an entire month — but it didn’t really merit the full arsenal.

I’d love to know what the ratio of custom builds to rejected ideas was over my five years. I was shielded from more requests than I saw, but I’d imagine for every project we accepted there were two we turned down. That’s just a guess, but feels accurate?

Here’s how I see the question applying everywhere else:

That three-tiered approach has stuck with me since I left ESPN. I don’t design as many microsites or art direct as many illustrations as I used to, but I still employ the same line of questioning when accepting a new project: What’s the budget? What’s the timeline? What type of auxiliary resources (photography, development, etc.) does it require? Ultimately, I can place all incoming requests into the same three buckets:

1. Deny the project. Whether you’re self-employed or not might determine if you like this answer or not. A lack of resources, interest or ability to take on the work makes for a pretty quick answer. This is something I’ve been working on a lot lately.
2. Accept the project and give it the highest priority. This should make people pretty happy. It’s more of a “Yes!” (emphasis on the exclamation point) where you move resources and time around to make it work.
3. Accept the project and get it done. This might still be the most common outcome. It’s more of a “sure” than a “yes,” to be honest. Stakeholders (clients, executives, etc) shouldn’t feel any lack of enthusiasm, but you’ll know exactly how much energy this one will take.

Being able to prioritize my time is a result of effective question-asking. I can’t devote equal parts of myself to everything I do, so it’s become extremely important for me to categorize different types of skillsets and place client asks into different buckets. One of the first questions I ask myself when a new project crosses my desk is, “Would I be asked to put this on a story page?”

Am I forgetting anything?

One of my favorite moments at ESPN came just a few weeks after arriving.

All of the latest hires were gathered for a presentation featuring president, John Skipper. He spoke for about twenty minutes on company priorities, outlining three main goals for us as new employees. He got through the first two, seemingly omitted the third and then opened it up for questions.

My hand flew up before I’d really thought about it:

Me: “You said there were three things we should be focused on as new employees.”

Skipper: “Yes. And?”

“Me: “Well… what was the — “

Skipper [cutting me off]: “OH! I forgot the third thing!”

There was scattered laughter. Before he answered, Mr. Skipper asked me my name, job and where I was from. He’d already revealed he was a Tarheel, so we had a fun exchange about Roy Williams and KU’s record against UNC (in front of 200+ people) and then he finally answered.

Ironically, I have no memory of his answer. What did stick with me was his ability to bounce back after making a mistake (remember: leaders aren’t afraid to embarrass themselves), as well as how he wrapped up the third point. Whatever his answer, he looked at me and asked, “Am I forgetting anything else?” I shook my head in mocking approval and he went back to taking questions (and ribbing employees about their hometowns).

John Skipper suddenly resigned from ESPN on December 18, 2017. I was at my in-laws house for Christmas when I found out via Deadspin (a pretty common occurrence with news from work). I’d been at ESPN for two and a half years and had a few more choice encounters with Mr. Skipper, including a catered breakfast (along with other employees who had August birthdays). He always impressed me and I was proud to work for him.

Sometimes there are people who definitely want to ask a question, but don’t feel like they get their opening. It always helps when you can look at someone directly in the eye and confirm you’re both on the same page. One of my favorite ways to do that is to leave the door open and let someone else close it for you.

“What else have I missed?” or “Am I leaving anything out?” provide those open and shut opportunities for people less likely to interject on their own. These types of questions were coincidentally used all the time during project meetings on the design team. I always appreciated walking away knowing everyone had a chance to speak.

Another trick Heather unknowingly taught me was the art of sharing the floor. It wasn’t uncommon for large meetings to leave quieter folks completely silent and I always admired when she would look at someone and say, “What do you think [name]?” Rarely did anyone just nod their head; it felt like every time a person was given opportunity to weigh in, they had a lot to say. That “permission” could last throughout the rest of the meeting, and often carry over into other meetings throughout the week.

Be kind and open-minded

Even if I somehow became better at asking questions than Heather, she would always have the upper hand because of the biggest difference between us: she’s kind.

Something I’m always working on is my demeanor. Among those that work closely with me, I have a reputation for pushing back. Hopefully, it’s not unwelcome (I’m an 8w7 on the enneagram scale so it’s in my nature to play the devil’s advocate), although I’m sure I could offer up more smiles and gratitudes.

I only lasted six months at my last job (an advertising agency in KCMO) so I didn’t get a chance to outgrow my, “Sorry, I’m new here,” phase. Unfortunately, it never felt like my How, What or Why questions were welcome, despite being encouraged to ask them. Others were visibly annoyed when they had to explain things to me and any pushback I was used to giving was met with a lot of frustration. It made me even more grateful for Heather and my colleagues at ESPN who seemingly welcomed my challenging nature.

Warmth isn’t completely necessary when asking hard questions or pushing back on a coworker’s ask, but it helps a ton. There was a sharp contrast in my exchanges before and after I started taking emotional intelligence courses. Since working on my EQ, I’ve definitely noticed traditionally difficult meetings staying pretty even-keeled when I ask a lot of questions.

Fielding questions can be just as difficult, and that’s where empathy plays an even bigger role. I’m constantly reminded of Heather’s patience with me as a young designer; her open-mindedness kept me comfortable. She didn’t dismiss dumb ideas and never made me feel stupid, even when she had to repeat herself (which she did a lot while teaching me to code).

Book recommendation: Emotional Agility by Dr. Susan David. This book changed how I approached nearly every relationship in my life. Halfway through it, I bought a copy for my wife because it perfectly articulated my personal issues with sharing my feelings.

I credit Heather with a lot of my growth at ESPN. She oversaw my promotion and made time for us to speak one-on-one, even after I moved under a different manager. To this day, I find myself asking myself What would Heather wanna know? when kicking off a new project. Her influence outlasted our proximity. I hope everyone has a person like that in their life — a manager who mentored them without knowing it or a coworker who went out of their way to elevate others.

I’ll always be grateful for her leadership and I’m so jealous of anyone who continues to work with her. I hope they’re picking up on everything she’s sharing, especially the art of asking questions.

Heather is still at ESPN, except now she’s a Creative Director. She’s still asking questions, though. When I told her I was leaving — my hardest goodbye — she made sure to find out exactly what I was doing next and if I was happy with my decision. As always, her questions helped me out and confirmed I was on the right path.

Author’s note:

I actually started writing this in September 2020, only a couple months after leaving ESPN. I let it sit for a while (pretty normal with these articles) until I was ready to refocus on the theme and wrap it up. It might seem a little convoluted with me picking it up almost an entire year later, but I’m gonna run with it.