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Marketing Showrunners

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By: Jay Acunzo on November 27th, 2019

Marketing Leaders Get Blunt: Hard Truths You Need to Hear If Your Boss Is a Barrier

November is Make the Case Month at MSR. Every week, we’ll load you up with the big-picture ideas and tactical tips you need to sell your  branded show concept to the “powers that be” within your organization. We know that shows are the best vehicle to help grow brand affinity among your customers; this month, we’re helping ensure everyone else at your company understands that, too. If you’re as pumped as we are, catch up on the content we’ve already published and subscribe for exclusive bonus content and conversations here.

I’m driven by what others think of me. 

Yup. It’s tough just writing that sentence, and I know all the platitudes about not caring what others think, but I do care. I really, truly do. It’s like the classic bit from John Mulaney’s standup special, Kid Gorgeous

When my wife walks down the street, she does not give a shit what anyone thinks of her in any situation. She’s my hero. When I walk down the street, I need everybody, all day long, to like me so much. It’s exhausting. My wife said that walking around with me is like walking around with someone who’s running for mayor of nothing.

At first, that feeling that I share with my fellow Catholic-schooled, skinny white guy Mr. Mulaney actually helped me. It helped me develop manners as a kid, helped me study hard and participate in class and get good grades. It drove me to join clubs and seek leadership roles for them, to apply to internships and work hard over the summers between school years. I was hell-bent on succeeding using the path we were “supposed” to take because, well, that’s what successful people looked like … to others.

Then, what should have been The Job: Google. Right out of college, I worked as a digital media strategist at Google, advising brands and agencies on how to use AdWords to grow their businesses. It was everything the path I was “supposed to” take promised to yield when I graduated. Apparently, I’d made it. 

Ha. Right.

I was miserable.

I hated working for Google, with a burning passion I still don’t like to revisit. At first, I blamed the company. But now? 

I blame myself.

I remember a crystallizing moment that snapped me out of my 22-year sleepwalk of trying to make others happy instead of myself. I’d just seen some funny, inspiring, viral YouTube video while at the office in Cambridge, MA. (Google set up shop in the heart of MIT to attract engineering talent — and some of Google’s redheaded step-children, i.e., us sales and marketing folks, were there too.) I’d watched that YouTube video five or six times in a row at work, and, once home to my apartment and three roommates, I hyped it up to them.

“You GOTTA see this, guys!” I placed the laptop on the table. I opened it. I navigated to the URL on YouTube. I sold them on the amazingness of this video all the while. Then I clicked play and … BAM! A pre-roll ad smacked us in the face.

I felt like an idiot. I felt frustrated. We wanted that great content. We got an obnoxious car commercial instead. We didn’t ask for this, nor did we enjoy it. In fact, we despised it. 

Someone scoffed. “Ugh, aren’t these the literal worst?!”

Wait a sec.

The thought slowly rolled over me like a thing that is really heavy and sucky rolling over you, a person who dislikes very heavy and sucky things rolling over you.

That car brand is … wait just a second. Their ad agency is … oh no.

Shit. This is my fault. I’m responsible for this.

I’d sold this campaign. I’d convinced this agency to start using YouTube ads for their client. There I was, sitting there with three friends, hating the very work I was responsible for doing in this world. And by the way, with the scale behind Google and YouTube, it wasn’t just me and three buddies who felt frustrated. It was thousands of people, or hundreds of thousands. Hell, if I was succeeding at my job, millions of people were having worse moments in their days because of something I did for a living.

THAT … is the literal worst. 

I should have quit right then and there. But, of course, that’s not how life works. We don’t live in a dramedy. (Tell that to my single friends, amiright? Eh? Ehhh?) Reality is messy. I was too caught up in how Google looked on my resume and on LinkedIn. How could I quit a job that was supposed to be the best-ever in tech? Surely, I thought, something is wrong with me, and I can make something work by staying.

Nuh uh. Eighteen months later, after thrashing and hating the bulk of my waking hours … I finally quit. It’s been (mostly) creative, self-directed, fulfilling work since.

My friend, I’m not saying we should all suddenly quit our jobs the moment something gets hard, nor can some people afford that. I’m also not saying finding the next job will be easy, nor am I guaranteeing it will be better. But that shouldn’t stop us from stomaching a hard truth: Sometimes, it’s the right call to leave.

My problem at Google wasn’t a boss so much as the organization and the very job itself. It simply wasn’t for me. Today, I hold no grudge, because I was so focused on trying to impress others that I forgot what would bring me joy and fulfillment in this one life I get (and sure, a boss or two at Google didn’t really help).

Because this isn’t an easy thing to say publicly — “time to quit” — I want to share some of the most blunt responses we got to a survey of top marketing minds below. We sent this survey to these folks to learn how they make the case and get buy-in for better content internally, or how they’d want their teams to pitch them as executives. The survey was part of Make the Case Month on MSR, dedicated to equipping you to getting resources and planning the right strategies for your branded podcast or video show. (All that content can be found here.)

The team at MSR and I really do want to help you make the case for a great show. We know you have a vision, or at least an inkling, of what could be better content to build a better brand and a more passionate audience. All month, we’ve been trying to help you get your boss and your whole team as excited about the possibilities of this stuff as you are. 

But sometimes (and I hope these times are few and far between), all the prep and data and creativity in the world aren’t going to matter. Because sometimes, you’re working in the wrong situation entirely. And if you find yourself in that situation, the best advice I can give you is the very same advice I struggled to accept back at Google: leave.

Without further ado, some motivation to bid that boss adieu. 

What do you say to a marketer who claims their boss is the biggest barrier to doing better work (and it’s actually true)?

“Any marketer who has the unfortunate position of working with closed-minded executive should think long and hard about leaving the job. Time is fleeting, and your ability to hone your craft is severely hampered by a skeptical manager. I’d also encourage them to fully understand why the boss doesn’t want to do X, Y, or Z. There may be alternative reasons that could be overcome by a deeper conversation. Seek to understand and then act.” – Kyle Lacy, CMO, Lessonly 

“If you care about the work your department/company/you are putting out there, you’ll either find a way or you’ll find a new job. Life’s too short to be in a position that doesn’t allow you to try different things. Marketing is changing too quickly to not be constantly testing.” – Vincenzo Landino, CEO, The Landino Group, 

What’s a grave mistake marketers need to avoid making when grappling with internal politics, and what should they do instead?

“They let go of high standards in favor of increasing volume of output. At the fundamental level, brands are simply what companies churn out consistently. Every thing you put out there adjusts brand perception up or down — even minutely. If you put ideas or efforts against this backdrop, you might give everything just one more pass before it goes out the door. ” – Camille Ricketts, Head of Marketing, Notion

“They focus on the significance of the idea rather than on the substance of the case for it. Specifically, they make the case that makes sense to THEM, rather than the case that will make sense to whomever they need to convince.” – Tamsen Webster, Founder and Chief Message Strategist

“Not getting buy-in for the right amount of time. I always believed I didn’t start creating good content until after 1,000 blog posts. Creating great content is a process. You generally don’t catch lightning in a bottle. Sell, upfront, the time to your executive team so you can find your voice, your audience, and continuously improve your storytelling.” – Joe Pulizzi, 6x author of Killing Marketing, Content Inc, The Will to Die (fiction), and more

Marketers spend a ton of time educating their stakeholders about why they’re doing what they’re doing. (‘Let’s talk about Content Marketing…’). Instead of teaching executives WHAT content marketing is, or why you’re doing a show, invert your presentation: Tell them what we’re doing now, what we’re going to do instead, and what results we can expect. IF (and only if) they ask how does this work, do you need to start teaching them.” – Andrew Davis, bestselling author and keynote speaker

“Before a meeting with any high-ranking executive, you should know their motivation. What has their boss tasked them with this year? What are their must-do mandates for the quarter? Your ideas will be better received if they directly tie back to that leader’s goals. It’s about how you can help them, not how you can pile more random acts of content on their plate.

“At Salesforce, I’m fortunate that all individuals draft a document listing their vision, values, methods, obstacles, and measures for all coworkers to see. We call this document a V2MOM, and it’s super helpful to reference when meeting with others. Don’t know your leader’s priorities? Just ask. Any busy executive should be glad to share their goals with you in exchange for a more tailored meeting agenda.” – Heike Young, Director of Content Strategy, Salesforce

“If you want people to think about you, give them a fact. If you want them to care about what they think about you, tell them a story […] There’s a concept in storytelling called the ‘B story, which is also sometimes called the ‘subplot.’ But it’s usually neither secondary, or any less important than the main story theme. The B story is what carries the emotion of the entire story, and it’s usually what carries the entire change that the hero goes through. In conversations with the CMO, we not only have to illustrate why our disruptive new thing will help the business (numbers, metrics, performance etc.), we also have to tie in the larger emotional hook that makes the CMO care deeply about the change.” Robert Rose, Founder/Chief Strategy Advisor, The Content Advisory

In conversations with the CMO, we not only have to illustrate why our disruptive new thing will help the business, we also have to tie in the larger emotional hook that makes the CMO care deeply about the change.

Identifying a good or bad boss is often about how one feels about the work, rather than the results. What’s a simple habit you’ve developed or that others possess to get unstuck and regain momentum to start feeling great about the work?

If your content sucks, you’re not getting inspired. Get out of your day to day, get off the computer, get out into the world, wherever inspires you, and just observe. Write down what you see. What people say. What conversations are being had. ” – Vincenzo Landino

Understanding the situation so well from the other person’s position that you could argue for it effectively yourself, even if you don’t agree with it. That allows you to not only understand their current position, but also respect it — and THAT means you can validate what they’re feeling right now, which is a necessary step before they’d be willing to listen to a different or opposing view.”  – Tamsen Webster

Do a survey of your team to understand what podcasts they listen to, shows they watch, and get a sense of the diversity of content that is already consumed within your organization. This will help make the case to your team about the opportunities that exist out there for you to make better content if you can focus on the right niche. ” – Chris Savage, co-founder/CEO, Wistia

“There is a secret about proposing disruptive change, and it’s that it’s much harder to get someone to change when they have to admit that what they’ve been doing is wrong. So, the first place to start with proposing change to finicky, skeptical or close-minded execs is to start from a place of evolution from the ‘right’ things we’re doing, rather than correction from the ‘wrong’ things.” – Robert Rose

Since leaving Google, everything has been better…

…is something I wish I could say to you. The truth is, progress is a zig-zaggy line, full of peaks and valleys. The problems are twofold: First, we often obsess over those ups and downs at the expense of zooming out and seeing the full picture. After all, temporary peaks and valleys matter far less than the trajectory of the entire line.

Second, we often can’t decipher the difference between a temporary downturn … and the entirely wrong trajectory for our careers. I hope this post helps, and I’d like to leave you with one final thought: redefining what it means to “make it.” 

We think it’s about resources, or about climbing the ladder in one place, or in one industry. I thought I’d “made it” when I got a job at Google. I was wrong.

“Making it” has nothing to do with anyone else’s perception of you. It’s not public at all. In truth, the people who are thriving are more proactive about their work. They’re not constantly reacting, and they’re not stuck in a stagnant state. When things get hard, they try to make the case for something better, but ultimately, they decide to leave if they’re truly unable to be proactive.

We get one life, and therefore one career. We get one shot at this, before it’s all over. The one thing worth striving for — more than titles, or logos on our profiles, or public acclaim — is the feeling that you’re actually striving for something. Don’t be reactive. Don’t stagnate. Find a place — and by that I mean, people — who will help you get proactive in your work.

That’s when you’ll know: You’ve made it.


Subscribing to our newsletter is a good idea any time, but particularly exciting during November 2019. During MSR’s Make the Case Month, subscribers will receive weekly newsletters with exclusive invitations to chat live with the MSR team. What are you waiting for? Subscribe now!


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Founder of Marketing Showrunners, host of 3 Clips and other podcasts and docuseries about creativity, and author of Break the Wheel. I’m trying to create a world where people feel intrinsically motivated by their work. Previously in content marketing and digital strategy at Google and HubSpot and VP of brand and community at the VC firm NextView. I write, tinker, and speak on stages and into microphones for a living. It’s weird but wonderful.

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