It turns out it’s not that easy to talk people into letting you spy on them.

I learned this when trying to convince creative folks in leadership positions to let me shadow them for a day. It doesn’t sound like a big deal, but there are a lot of reasons for people to say no: top secret client projects, too little bandwidth, nervous people in the chain of command wondering what your motives are. And that’s assuming your prospect even cares enough to give you a reason.

When you’re early in your career, resources for professional development abound. You know so little that any level of exposure is a learning moment. After 20 years in the design trenches, it’s a different story. Decades deep in the hustle, I found myself in need of some Executive Realness. I’d been to the conferences. I’d read the books. I’d worked my way up the ranks. I was looking around, realizing that edification opportunities weren’t all that obvious anymore. In recent years, growth had come from self-imposed stretch projects and collaborations with interesting people. But in my capacity as a Creative Director at a digital agency, I was feeling the need for actionable insights.

Most people in the creative industries learn about their preferred style of leadership by jumping around from agency to agency. They work with various leaders and learn from different mentors. My work history is a bit of an anomaly, in that I’ve been working with these FINE folks for the past 15 years. That’s 75 percent of my time as a creative professional. A couple of years ago, I was promoted to Creative Director, but I had only worked closely with one human being doing that work. When I took on the new role, I was plagued by imposter syndrome, and I wasn’t confident that I was doing a good job. I wanted to know how other people were doing the damn thing.

So I started wondering: could some of the strategies used for professional development at earlier stages of a career be tweaked to become useful for senior level positions? The one I started obsessing over was the humble job shadow. Though it’s often used as an orienting tool for students, it seemed ripe for a hack. I set out to find other CDs doing work I respected in the digital space to see if I could convince them to let me follow them around. I wanted to observe how they led their teams, which tools they were using for internal and client communications, how they approached client presentations and collaboration, and how the culture of their studio affected their work.

I crafted a pitch that tried to get ahead of some of the concerns I knew people would have. Here’s what it looked like:

Hi So and So,

I have kind of a weird pitch for you, but you seem down for weird pitches.

I’ve been working with the same crew for a long time, and I’ve begun to feel insulated from how other folks work. I’m wondering about the plausibility of embedding with you for a day to see how you roll.

My goal is to apply lessons to how I work with my team — not to do anything that would encroach on you. I would happily oblige any required handshakes and/or legalese. Besides which, I think you know and I know and the American people know that there’s no secret sauce. It’s all sweat in the trenches, at the end of the day.

If this is successful, I think we could do some fun stuff around it — maybe a think piece about professional development for senior talent/leadership?

Thanks for considering,
Tsilli

There were a few things working in my favor: I had deep history and trust with my employer, such that they weren’t nervous about a flight risk. I had a reasonable project load, allowing me to schedule a day out of the office. I’d built a good amount of social capital within the local design community. And I had a specific outcome in mind — i.e. this piece you’re reading right now.

As expected, plenty of people declined. But thrillingly, my first “yes” was from Joe Stewart, one of the partners at Work and Co. He and his partners started their agency in the spirit of removing a lot of bullshit from the design process. True to form, he was down for my weird pitch. I signed an NDA and was shielded from any project work that would have been too sensitive to share with an outsider. But otherwise, I was given an amazing level of access. I sat in on creative meetings, was paired with several different partners throughout the day for Q&A, and saw everything from project resourcing to concept iteration.

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“Your design needs more truck nuts.”

This is real feedback I gave a designer once. In general, I try to be more constructive in critiques, but I couldn’t think of a better way to say it in that particular moment. It’s a tricky thing when you’re the arbiter of what’s worth showing to a client, and someone on the team isn’t getting where they need to go. My mentor, Kenn Fine, has Jedi-level skills when it comes to guiding a creative team with patience and a light touch. I can’t tell you how many times I’ve seen a designer feel ownership over something that I would consider 75 percent Kenn’s. He’s so humble and skilled that his feedback is like invisible fairy dust — it doesn’t compromise a designer’s sense of authorship. It’s been no small task to try to cultivate this skill, as his disciple. I idle somewhere between impatient and cantankerous in my natural state.

With this in mind, it was instructive to observe Joe in the wild. He went full “truck nuts” with his team. This was a culture of meritocracy, in which everyone had equal skin in the game. It was a breath of fresh air to watch his team’s spirited arguments over big decisions like the best way to code a user test in time for an aggressive deadline. Ideas came from everywhere, disagreements were taken in stride, and the developers ultimately talked Joe into letting them try a route he warned might be too involved for the time available. He may have been direct and outspoken, but he didn’t have his boot on anyone’s neck. It was a good reminder that leadership has its flavors.

But as much as it was cathartic to experience a room full of skilled seniors with assured opinions go at it, I kept thinking about how the softer spoken folks on my team would have fared in that room. As an aggressive communicator, it’s taken me a long time to learn how to make space for people with different communication styles. The more I thought about the experience with Joe’s team in the weeks and months afterward, the more the catharsis of it worried me. I resolved to reconcile their commitment to rigor with the way of the Jedi.

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Over the course of my day spent at Work & Co, I saw some quick progress being made on several fronts: that user test got fleshed out, new team members got plugged in for their specialized skills, and design and copy came together in real time. None of this was particularly remarkable from an agency standpoint, but the heavy focus on UX helped me see some tools in action that I hadn’t seen before.

My dirtiest secret, working in this industry, is that I’m a Luddite at heart. This is an admission no one wants to make in the digital space, where it’s all about innovation, disruption, and the new-new thing. I remember taking a seminar in college about mass media. Everyone in my class was writing breathless papers about CDROM technology (dating myself!) and how it was going to upend everything as we knew it. I wrote a screed about why I believed Hollywood needed to commit to original content from fresh voices. I’m into evergreen takes.

It will probably come as no surprise, then, that up until my shadow day, my team was working in flat design files like it was 2006, not 2016. It was getting more and more difficult for us to communicate behavioral ideas with our development team and our clients. Our only experience with prototypes had been costly in time and effort. In the rare instances we used them, we would build in code only to scrap our work.

Seeing things in action with Joe and his team was a crash course in the landscape of design prototyping. I got the complete rundown of the tools they had tried and used, their various strengths and weaknesses, and when and how they deployed each. By the end of the day I had a plan for how to implement prototypes within my team. They’ve become indispensable for getting client buy-in, and have reduced documentation when projects go into production. Another tool in the toolbox.

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Since completing this exercise, I’ve continued haranguing a few other targets of interest. When I can’t quite align with someone for an entire day, I sometimes downshift to another humble mainstay of professional development: the informational interview. I don’t call it that, obviously. That’s not sexy. I call it a POWER LUNCH, in all caps. (I wish I could take credit for that, by the way, but I stole it from George Thorn.) I tell my victim that lunch is on me, and I ask aaaaaaaaall the questions I can think of. I also offer counter-information, to make it useful for both of us.

I’ve had conversations over lunch about everything from whether it’s right to get into designers’ files to show them what you think they should do next (helpful or dictatorial?), to how to handle certain tricky client situations (show them your full hand, or curate heavily?). I have my own biases about such matters (it’s dictatorial/curate heavily). But there have been some situations where I’ve tried the thing I think is wrong because another CD swears by it, and hey — sometimes, it’s the right thing to do.

A single insight — from a POWER LUNCH, or a day of senior shadowing — is priceless. After so many years of having a small, trusted circle of mentors and a loyal cadre of long-suffering collaborators, it’s important to get new insight wherever possible. I’m not one to downplay the importance of putting one foot in front of the next and making your own mistakes, but there’s something to be said for studying someone else’s playbook. You know and I know and the American people know that it’s all sweat in the trenches, at the end of the day. Let’s make it easier for each other, right?