The tells that reveal you’re not ready for the next level in content marketing
In the last decade, I’ve managed and mentored many Content Marketing Managers. It’s one of my absolute favourite things to do, and mentorship is something I continue to carve out time for even when I feel full to the brim with my own client work and deliverables.
Most of the people who come to me are hungry for growth. They’ve probably been operating at the manager / senior manager while for a while now, and they’re starting to feel a bit stuck. They come looking for help getting into director roles, pivoting to other kinds of marketing, or pursuing some other advancement path.
But they also want to be better content marketers. They’re often not getting what they need from their leader. Many content marketers are 1-2-person teams reporting to a CMO or even CEO. That often means your leader is not going to dig into the ins and outs of your work.
Through those conversations, I’ve seen some patterns emerge: These are my ‘tells’ that you’re operating in a manager mindset rather than a leadership-ready one.
And I’m listing them today in hopes that it will help some content marketers who’ve been frustrated by their inability to break through to the next level. This might be a little lightbulb moment that helps you break through. Because you can’t fix what you’re not aware of…
Tactical execution tells:
1. ‘Human Grammarly’ editing
Over the course of my career, I’ve worked with some amazing editors. Between my time in academia and later in media, I know the difference a great editor can make to a final piece.
Here’s what really great editors talk to you obsessively about:
Structure: Is the argument building logically? Are you burying the lede? Does the conclusion actually follow from what you've presented?
Conceptual gaps: What assumptions are you making that readers won't follow? What context are you skipping? What counterarguments aren't you addressing?
Flow: Do paragraphs connect to each other? Are transitions working? Does each section earn its place in the sequence?
Tone: Is this the right voice for your audience and purpose? Are you being too formal/casual/technical?
Human connection: Are you bringing the ideas and experiences to life in real, deeply visceral ways or just disseminating information?
Clarity of purpose: What's the single takeaway? If someone only reads the first and last paragraphs and skims the Hs, will they get it?
Evidence and examples: Are your points supported? Do your examples actually illustrate what you think they do?
Reader journey: Can someone who doesn't live in your head follow this? Where will they get confused or lose interest?
Stakes: Why should anyone care about this? What happens if they don't act on this information?
Fact-checking/substantiation: Are your claims actually true? Where's your evidence? Are you making sweeping statements without backing them up? What sources are you citing, and are they credible?
I think a lot of content marketers are quietly in love with the ‘idea’ of being an editor, but actually haven’t cultivated these skills at all. Instead, they jump into the piece and act like Human Grammarlies. My two cents? Enough of the em-dash/passive voice obsession already…
2. Content calendar obsession
Every few months in content marketing communities, someone starts a passionate thread about content calendars. The tools, the formatting, the tracking systems. It just lands with me like busywork masquerading as strategy.
A content calendar is a planning tool. Nothing more. It doesn't make your content better, generate breakthrough ideas, or create dramatic efficiencies. It keeps you organized and helps other teams know what's coming.
You're not a newsroom. You're not breaking stories. Beyond the occasional product launch or seasonal campaign, most content marketing isn't time-sensitive. Yet managers obsess over their calendars like they're running the NYT.
Leaders understand the difference between operational tools and strategic thinking. When you conflate your calendar with your content strategy, you're revealing that you think logistics are leadership.
3. Desktop writing
If you want to lead any area of marketing, you HAVE TO talk to people, whether they’re your internal SMEs, the people building your product, your sales, or customer success teams. As a rising content marketer, more of your energy should go into Case Studies and Thought Leadership pieces, not the desktop writing stuff that can be handled by anyone.
You have to get out of your building and talk to your market. And no matter how deep you go down Reddit or how much time you spend on Answer the Public, you’re never going to get that visceral connection through your laptop.
I get the discomfort; I’m an introvert too. But I promise you, you’re going to be a better content marketer if you do these things. And what you learn will propel you out of that channel manager mindset and into one of an integrated marketing leader.
4. Following tools too faithfully
Ten years ago, writing content was like taking shots in the dark. Then along came tools like MarketMuse, Surfer, Frase. Suddenly, we got immediate feedback and guidance. But then the tail started wagging the dog: Many content marketers let their own better judgment fall to the wayside and just checked those boxes. It resulted in so much grey goo.
But the best content marketers? They always stay in the driver’s seat. Because no matter who (or what) is doing the writing, when you lead the responsibility is yours, and the reflection is on your brand.
People who are ready for leadership roles have a much more balanced, less codependent relationship with the tools they use. Because leaders understand that tools are meant to inform decisions, not make them. When you defer judgment to a tool, you're essentially saying a piece of software has better strategic thinking than you do… not a leader-potential look.
Strategic tells
5. Thinking a ‘to do’ is a strategy
It’s 2025, and I’m still meeting content marketers who pull up an Excel sheet with a list of keywords and/or topics to show me their strategy. Ooof. It hurts every time.
Sorry folks. This is not a strategy. A strategy is your WHY and HOW, not your WHAT or to-do list. (btw, I wrote about Goals/Objectives/Strategy/Tactics over on Digital Sisco’s blog if you want to dig into this more.)
If you’re making this mistake, know you’re not alone. But if you start to distinguish these things, you’ll never make the same mistake again. And I promise, your tactics will be smarter and more effective because you’ve taken more measured steps to get there.
6. Bravery with change
The beautiful thing about AI right now is we’re all actually in the same boat. We’ve all had these tools for the same amount of time, and we’re all overwhelmed to the same extent.
What’s more, in many ways, AI is leveling so many fields. While performance marketing favoured those who were data-driven, AI may perhaps favour those of us who are more creatively inclined. High EQ introverts may even have an advantage.
And yet, I see two camps forming:
Those who are digging in. Making shit. Breaking shit. Forming constructive criticism.
Those who are waiting like little baby birds with their mouths open: Feed me.
The second group relies on prompts / prompt libraries / GPTs that other people wrote instead of finding their own way. And they’re missing the crucial moment to become AI literate, to build a relationship with these new tools where you feel out their contours and get to know their quirks.
If you work in digital, you’re going to have to constantly figure out things you’ve never done before. And if you’re going to be a leader, you’ll have to simultaneously lead others there, too. If that idea is scary, maybe you’re not ready…
Leadership tells
7. Over-adherence to playbooks
Playbooks can offer wonderful support when you’re learning the ropes. Whether it’s playbooks for case studies, ebooks, webinars, thought leadership, blog post structures, whatever—sure, study all the playbooks.
But what’s missing for many is the moment when you discard the playbook. They continue to slog to them precisely when they should start questioning them. And when those playbooks stop performing, instead of writing their own playbook, they wait for somebody else to give them a new one.
Real leaders know the playbooks, take elements from many of them, but play them the way a jazz musician would. Ultimately, they write their own playbooks continuously. And they’d probably never do something the same way twice.
8. Passivity with authority
When I hear the second or third “that’s what my CMO wants…” I instantly think, “and that’s why you’re where you are.”
Passivity in the face of authority is how you signal you can't lead. And BTW, that authority figure never disappears—everybody has a boss. Even when you're at the top, you're still in the middle.
To be clear, you won't win every battle or even most battles. But shrugging and disowning responsibility reveals you're not thinking about influence and persuasion. Which is unfortunate, because that literally becomes the job when you're a director. The title doesn't give you magical buy-in. It just gives you the opportunity to fight for better outcomes.
9. Title obsession
Is a ‘Content Strategist’ better than a ‘Content Marketer’? What about ‘Content Producer”? There is so much hand-wringing over titles. And, sure, you should give them some thought. But ultimately, I think they’re often a huge red herring.
I’ve had people tell me their titles are holding them back from getting jobs (but they’re getting interview, so that doesn’t feel like the complete explanation…) And I’ve interviewed and hired countless people and never really considered the actual titles they had in past jobs.
Plus, we all know the politics of titles: Sometimes they’re given to distract from salary, sometimes it’s a retention play. Sometimes you just work at a company that’s small enough that everybody gets to be a VP (heck, I half ironically gave myself the title of Chief Content Officer at Digital Sisco).
And, look, I know titles are one of those things that are easy to dismiss once you get them. But they’re really not worth losing sleep over. Put that energy into the work and your monetary worth instead.
Still feel stuck? Get a mentor…
If you’re serious about leveling up, my advice is to seek out a mentor (external to your organization) who’s just ahead of you, not the most senior person in the room, but someone who remembers what your next leap felt like. They’ll have the clearest advice on what you need to build next.
You can have a formal mentor you meet with every month, or do a series of ad hoc coffee dates. You’ll probably be surprised how many perfect strangers are willing to give you an hour of their time if you offer to buy them a coffee.
Finally, think about what you need more broadly. For example, I mostly mentor women in tech because I understand the challenges and culture, and it’s also important to me to support other women. Look for somebody who will understand your unique situation and experience in a full sense.
My main advice if you’re asking a stranger to step up and help you is don’t be an ass about it. You’re not entitled to their time or knowledge. Come prepared, show up on time. The basics. And if you are full-time employed and have an education stipend, pay for their time (especially if they’re sharing resources with you).
And not to turn this post into an awkward pitch or anything, but if this post resonated with you and you feel like you could use some guidance, don’t hesitate to reach out. I may not have the capacity to commit to full-on mentoring, but I genuinely love meeting other content marketers, and 1:1 conversations are more my jam than networking-type events.
🍓Sweet treats before you go!
If you read one thing…
I cleaned up some bookmarks this week and revisited this piece on awe. “Experiencing awe can make people feel small, shifting their attention away from themselves and towards the people in their communities.”
I’ve been thinking a lot about wonder and curiosity lately, about how narrow and selfish marketing and branding have become (pain! agitate! solve!), how jaded and exhausted we all are. And how we’re reacting to AI as if it’s just One More Thing to learn and game. But maybe we could also make room for awe too—just sitting with it and not trying to turn it into anything else… How might that change things?
If you buy one thing…
Most of us have an old handwritten recipe knocking around that’s very dear to us, whether a beloved family recipe or something long ago transcribed and tucked into a stained and tattered cookbook. I love the idea of turning that special recipe into a decorative keepsake to treasure, whether for yourself or as a special gift. From Alice Funge Ceramics.