10 things to Look for in a Chief Creative Officer

Once upon a time, an agency I admire was advertising for a Chief Creative Officer. So I did what everyone does: I sent them my resume, I tried to connect to key people on Linkedin, I pressured friends who knew their key people to say nice things about me in their general vicinity. You know, the usual.

But I also kept thinking – if I was hiring a CCO, what would I want to know? Where they’d worked? What they’d worked on? Who they followed on which social platforms?

Or would I want to know what the hell they thought being a CCO meant? With the explosion of platforms and the upheaval of AI, any definition you came up with yesterday will probably be out of date by tomorrow. And since this industry hands out job titles with more reckless abandon than a sports doctor handed out painkillers in the sixties, even the simple logic of “well they already were a CCO at…” doesn’t really work anymore.

So I wrote down what I thought agencies should look for in a CCO, and then sent it to the agency I admired in dribs and drabs because that’s what I was told effective CRM did.

Fun fact: I didn’t get the job. Hell, I don’t even know if they read the dribs or the drabs. But I still think that what I figured out about CCOs is valid so here it is for you to ignore like they did. It starts like this:

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Let’s begin with Presumption, which the internet defines as:

“behavior perceived as arrogantdisrespectful, and transgressing the limits of what is permitted or appropriate.”

Wait, what? 

Look, what we do in advertising is – has to – cross the limits of what is perceived as being permitted and appropriate. And to be sure, some use this as permission to just get attention. And some, just because they’re assholes. But those clowns aside, I think it’s vitally important that we really understand what the limits of any given client, project, industry, are, if they’re valid, and if they quite as universal and carved in stone as people think. My experience is that they tend not to be, and in the rearview mirror of history people recognize that.  

So you have to be presumptuous. And if, when you are, feathers are ruffled and you’re called into HR because you’re deemed “disrespectful” or “arrogant”, well, that’s a small price to pay for figuring out something for your clients that the competition – theirs and yours - didn’t.

The second quality a CCO should have is creativity.

Well duh, right? Although you’d be surprised how many don’t have it. Then again perhaps you wouldn’t be. Some CCOs are really just glorified project managers – making sure the deadlines are met and the mail is answered. And some, well, they’re sort of account people with unusual clothing choices, more adept at gladhanding the client than they are at making sure the work is great. And others are really just the art director or the copywriter with the biggest office.

And yes, absolutely, hitting the marks is important as is having a relationship with the client, as is being able to write or design. But when I say that a CCO needs to have creativity, I mean she needs to be able to be so saturated with it that she can pull it out of others when they don’t even know they have it themselves. Have enough of it so others can lean on hers when they have lost faith in their own. So fluent in it that she can translate it to clients and other stakeholders who don’t understand it. That she can go beyond the comparatively simple skill of actually DOING it to making others do it better than they ever thought they could. That’s the kind of creativity I’m talking about.

Next up: Patience

In a “have it now”, instant-gratification world, where everyone is their own version of Veruca Salt, “patience” probably seems like exactly the opposite of what a CCO should have. But a CCO needs to be able to see the long game and needs to be able to play it. Needs to be able to walk that infinitely fine line between “giving in” and “losing a battle to win a war”. Must be someone who can wait until the copywriter finally figures out how to say what needs to be said. Who can wait until the light bulb finally goes on for the client and he “gets” it. Who can wait for, well, everyone. You know who has this skill? People who really understand what they bring to the table. Who are confident in their own abilities and their own integrity – and who can instill that confidence in those around them. You know who doesn’t have this skill? Toddlers. Which is why we shouldn’t put them into positions of power. (Am I still talking about advertising? I think so….)

The fourth thing you should look for is curiousity.

Look, it’s a tough task staying curious when you’re a CCO. Staying on top of the avalanche of stuff you’re inundated with on a daily basis is almost overwhelming – the last thing you want is to open up new cans of worms that are going to bring chaos and disruption to that avalanche. Right?

Wrong, unfortunately.

Because in the modern advertising agency – or whatever it is we’re calling where we work these days - unless the CCO is leading the curiousity charge, where else is it going to come from? Of course, everyone contributes and everyone is important, but the CCO is the one who has to constantly be thinking about the next, about the what if, about the why not, about the why this. Has to constantly endure the “oh jeez, not that, can we please just finish what we’re doing before we deal with that?” and the “we don’t have time for that right now” and all the very legitimate complaints and concerns of the rest of senior management. Because if she’s not curious, no one will be. Not the rest of senior management, not the rest of the creative department, not the rest of the agency. And if the agency isn’t curious, it’ll be dead before lunch time.

Five – is um… charm.  

What are we, beauty contestants? Used car salesmen? Gameshow hosts? No, of course not. But also, yes. Look, sometimes the client doesn’t understand the work right away. It’s not love at first sight. It’s not a slam dunk. Because let’s face it – the best work isn’t logical. If it were, we could all hang up our laptops and let AI run the show (spoiler alert: coming soon enough, thank you very much).

But no, the best work is a left turn – the memorable work has an element of “what the hell was that?” and for that the client often needs your help. Oh and by the way, the number of clients who will articulate it that way are few and far between. So you have to be charming. You have to woo them a bit. You have to help them get there. And when you do, and when the work works, they will be eternally gratefully. Well, maybe not “eternally”, but “for a long time” which in advertising is basically the same thing.

Oh, and charm is also useful when trying to convince the creative department to come in and work the weekend – as it is when trying to convince accounting to approve the bar tab for said weekend work.

Six is persistence.

Maybe you’re sick of this list. Or maybe you’re not sick of this list because you stopped reading it up there around patience (ironically…). Or maybe you haven’t stopped reading and you’re not sick of it, but you’re not emailing me as you read it and so how the hell should I be able to tell the difference? I don’t know. There’s a fine line between being persistent and just being crazy. And annoying. I get that. Honest. But I’m not sure you can really be creative if you’re not persistent. If you don’t have the ability to just keep writing even when you don’t know what you’re writing. To just keep brainstorming even though no one in the room has said anything for hours; I don’t mean ”anything of value” – I mean literally  ANYTHING AT ALL. If you don’t have the faith inherent in persistence that eventually you’ll figure out the answer, that eventually you’ll come up with the solution, then I don’t know how you can actually create anything consistently. And frankly, delivering this stuff consistently is what clients are paying us for, really. 

Because the times when it just flows out of you (and doesn’t suck), are few and far between. Maybe that’s just me. But my experience is that it’s not. And being able to create a team that is consistently great requires persistence – if nothing else, being persistent in telling them to be persistent.

Before I get to the next one, a diversion.

So there’s this story that George Lois told me about himself (of course). He said he was on the top floor of the tallest building in Newark presenting a campaign to the Matzoh king, who was like a thousand years old. Well, to the Matzoh king and about 17 of his kids and nephews and nieces and cousins and god knows who else. And they were dithering about the campaign George was presenting, you know the way clients do. “What if you did this…?” and “I don’t know, maybe it won’t be understood by…” and so forth. And finally George walked over to the open window next to the Matzoh king’s desk and began to climb out of it, yelling “If you don’t buy this god damned campaign I am going to jump out of this window!” And everyone started to freak out (a reasonable response) and pulled him back in from the ledge and the thousand year old Matzoh King said “okay, okay, we’ll buy the campaign! And Mr. Lois, if you ever leave the ad business, there’s a job here for you selling matzohs”

Now, most people’s takeaway from that story is “Oh those were the golden days of advertising!” and “Oh that George Lois! What a character!” But most people are wrong. Because what that story really illustrates – as George and I argued about in his house in Manhattan - is that people need your passion in order to believe in something that scares them. To believe in something that they don’t understand. That they’re not sure about. George had passion for the campaign and that’s what the Matzoh king needed.

A CCO who doesn’t have passion isn’t worth throwing out a window. And that’s why it’s number seven.

Number eight is Resilience.

Wait, how is this different from persistence?

It’s as different as indifference is from failure. Persistence is about punching until you knock the other person out where resilience is about getting up off the floor after someone cleaned your clock. And the latter happens a lot in this business. Most of what we write or design or concept never gets to the brainstorm, let alone to the presentation or god forbid the client. We kill our own work, we hire people to kill it for us, we seek out people to pay us so they can kill it. Not letting it make you crazy – or said another way, being resilient – is vital. Some call it “a thick skin” – but the best people I’ve ever worked with are incredibly thin-skinned. How else could they be sensitive to the nuances that will resonate with customers and other humans?

And frankly, being allegedly “thick-skinned” also doesn’t give people the credit that being resilient does. If you’re resilient you can take the punch, feel the pain, accept the wound, and not let it stop you. Absorb, learn, and move forward. “Ever tried. Ever failed. No matter. Try again. Fail again. Fail better” as the fella says. That’s what it means to be resilient. Learn it, and you can do great work. Fail to, and you either give up on the business altogether or you stick around but are embittered and angry. Neither of which are useful for an agency.

 For number nine, another story:

My friend Gideon Amichay has founded agencies and won awards. But his lifelong dream was to have a cartoon appear of his in the New Yorker magazine. So he worked at it for years, sending them effort after effort (all while running an award-winning agency) and eventually it happened. And when he did, he wrote a very good little book about it, called No No No No No Yes, (which I reviewed here if you’re interested). When the book came out, the store at the Museum of Modern Art took a couple of copies, which, as you might imagine, thrilled Gideon to no end. He had a book in the bookshop of the Museum of Modern Art. How many other advertising people – hell, how many other people OF ANY KIND – had done that? What an accomplishment!

But then he thought – okay, my book is in the bookshop of the Museum of Modern Art. What doors does that fact open for me?

THAT’S entrepreneurialism. Looking at every action not as an end, not as an accomplishment, not as a mountain peak summited, but as an opportunity to do something else that you never had before. Most people don’t look at life that way, don’t perceive it as a series of doors opening, as a series of opportunities. They look at it as starts and finishes, races run and won or lost. Entrepreneurs, in my experience, don’t. CCOs who are entrepreneurial are invaluable because they’re figuring out how every win, every award, every campaign – and every loss and failure as well – are new opportunities. Which keeps your agency running long after others have shut down. 

Next is  – A sense of humour.

You don’t have to be the life of the party and you don’t have to know the latest jokes or jokesters. But if you don’t have a sense of humour – about the work, the industry, the agency and more importantly yourself – then god help you all.

And while I’m a big believer in comedy in advertising – not just because it’s a great way to cut through all the other bullshit people are hearing, but because it’s an insanely great way to create a kinship and relationship between strangers (you know, like your brand and their customers) – that’s not what I’m talking about here. I’m talking about jesus christ you can’t take this shit so seriously. It’s fun. It’s advertising. It’s not brain surgery. And tho I am very very serious about doing absolutely brilliant work, I know that if we are not having fun while we are doing it then we are doing it wrong.

And you know what? Clients are desperate for fun. Every client I have ever had has looked to the time they spend with their agencies as the best part of their days. Not because we were “wacky” or “goofy” or “crazy”. But because we were enjoying what we were doing and there was – is – something contagious about that.

And the last thing on my list of things you should look for in a CCO is – courage

You have to be willing to break the mold. You have to be able to say you were wrong. You have to have the courage to stand up and say – we’re doing this, come hell or high water. Even if that means losing the locker room. Even if that means losing the client.

You have to have a healthy disrespect for the rules. Even – especially - the ones that you yourself laid out originally. Now, you can’t be arbitrary and ridiculous because that’s not courage, that’s just crazy. And it will make everyone around you crazy as well. Which is not good. But you have to be aware that things change, and also, guess what, sometimes you’re wrong. So you have to be willing to change. Because… wait for it – change takes courage. The courage to say “yeah, that was a bad idea, let’s do something else.” The courage to say “I know we’ve been working on this idea for a week and the presentation is on Tuesday, but I think this over here is a better idea, let’s go here”. The courage to stand up when everyone else is sitting down and say “conversation over. we’re doing this, and you can fire me if it doesn’t work.”

You also have to have the courage to ask for help. Within the agency (which can be hard) but also outside of it as well (which can be almost impossible). And you have to have the courage to let others succeed – maybe even succeed more than you. You have to have the courage not to be the star. You have to have the courage to be shot at and to take the hits, because you know you’re going to be proven right in the end. Or you think you are. You have to have the courage to let people around you fail – because if you don’t, they’ll never accomplish the things no one ever accomplishes because they’re too afraid of being punished for failing.

You have to have courage. Even the courage to provide 11 things to look for in a CCO when you originally said you were only going to provide ten.