When (and how) do I learn to lead?

It’s a really common story in creative industries, most especially advertising, that no one teaches you how to be a boss.


Creatives climb the ranks because they make amazing work. They’re phenomenal at doing the doing. But at some level of seniority, you’re tasked with overseeing younger creatives. You’re suddenly thrust into this situation where your job is to help make someone else’s work better, to push and feedback and advise until the work is where it needs to be. You have to solve the brief loosely enough to know what you’re looking for, but stay open to what someone else might bring to the table. Not fall in love with your own notion of how it should be, but also not get so disconnected that you can’t shape the bananas ideas that might come back.

And that’s not even talking about the mentorship bit — because in addition to being responsible for shaping someone else’s work, you’re now responsible for shaping their career. For making sure they’re on the right path, that you’re giving constructive feedback and helping them grow and giving them more responsibility than maybe they’re ready for, but in a compassionate and trusting way.

And no one’s taught you how.

If you’re lucky, you’ve had a couple of mentors or bosses in your past that have shown you what this can look like. Or you stumble into doing it perfectly right away. If you’re like me, you’ve had a lot of bad examples of what not to do.

I exited the womb little-miss-do-it-myself. A “born leader” as my primary school teachers might have said. I was determined and independent and confident. Commanding a room with an outsized vocabulary from a very young age.

When my career got started, this same attitude served me well — I pushed and pushed for a seat at the table. I took on too much. I stretched my understanding of what I could do at every turn. I excelled. I was trusted by clients and colleagues much more senior than I.

That scrappiness, that determination found me in charge of many projects at a very young age. Found me changing careers at 25 and running shit in that new direction within a year. I knew how to bare-knuckle it. I knew how to say through my every action “I can do this. I swear I can do this if you just give me a chance.”

And it worked.

But the thing is, there’s a difference between forcing your way into having a seat at the table and pulling someone else up to it. And no one teaches you the second bit.

The first time I struggled to manage someone I was smack in the middle of a really tough professional lesson. For a long time I’d resisted the notion of feminism — I thought it wasn’t my fight, those issues didn’t exist anymore, I was doing just fine on my own as a woman thankyouverymuch.

Turns out, there’s this shift that happens when you become senior in your career. The precocious, smart, driven 22 year old in the room isn’t a threat to the patriarchal power structure of the office/world. The smart, confident, emotionally adept, powerhouse 28 year old in the room is a massive one.

Suddenly the traits I’d had my whole life — smart, born leader, creative, verbose — were reframed in a way and then used against me. I was a know-it-all, difficult, stubborn, scary. And that was among my peers and supervisors.

So when I began to struggle to lead a new junior hire, fresh out of school, epitome of millennial entitlement (it would turn out), I also struggled with where to turn for advice. My no-bullshit approach, and assumption that everyone has integrity in the work that they do, really floundered in this situation. I was confronted with someone that wanted constant praise for the effort he put in, didn’t understand (or want to learn) the implications of the mistakes he made, and didn’t seem to have a real interest in listening to everything I was trying to teach him. It was a shock to my system. Realizing that not everyone is like me. Not everyone responds to a sink-or-swim mentality where you learn immensely precisely because you’re out of your depth. Not everyone would respond to feedback, no matter how compassionately and carefully it was delivered.

I was learning that my approach wasn’t working, but had nowhere to turn for a different one. Should I read books? Take a seminar? Talk to my shrink? Realize that it was not, in fact, fully my fault and you can’t lead someone who doesn’t want to be led?

I never found the answer to that question, but I think it’s partly to do with how this industry manages women. What traits are groomed, which are squelched. How we support women with “leadership skills” and teach them how to lead the various types of people she’ll encounter. Without calling her difficult, or telling her to quiet down, or to watch her tone.

This industry has a massive woman problem. Not the least of which is how many of us are in leadership roles. Part of that is opportunity. Part of that is being treated badly by the men currently in power. But a big part of that, is that this industry doesn’t know how to teach people how to lead.

To cut a long story short(er), I’ve since left that job and gone back to freelancing. Partly to sort out what type of work I want to do, but also to sort out what type of worker I want to be. I’m at a level where any full-time gig I take on will amount to a lot of management, and I need to find a way to do that that suits my style.

I’ll let you know if I ever figure it out.

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