If you’ve worked in content marketing in the past 10 years, you’ve watched the best practices (and what actually works) shift dramatically. When I first started as a writer-slash-marketer 10 years ago, I had to be really scrappy. I learned everything I could and constantly experimented. As a marketing team of one, I was the in-house “expert” on everything from YouTube tutorials to blogging to website architecture.

While the experimenting hasn’t stopped, the attention around content marketing has definitely amplified. Content marketing is a professional practice now. The adults arrived, and the business started paying attention to content. I’m glad that content marketing is getting the attention and structure it deserves, but I still love talking to people who started in the same place I did — as scrappy DIY marketers, fresh out of college, when “content marketing” was a new term.

That’s why I was excited to connect with Andrew Littlefield. He’s managing editor at Convene, a fast-growing network of meeting, event and flexible workspaces. But as he shares in the conversation below, he took a winding path to get there. As his LinkedIn profile says, “If ‘make cool things for the internet’ was a major in college, I would’ve chosen that.”

Keep reading for Andrew’s take on how to stay scrappy as a content marketer and a leader of creative teams.

Tell me about the arc of your career so far. It sounds like you’ve taken a different path from most.

I actually studied music therapy in school. I got into it because I didn’t know what I wanted to do when I was 18 years old. I knew I liked band class and so I thought that’s what I should do.

But, out of college, I started working for a small private health care company. My role was partially working with clients but also helping with the business side of things, including running our website and on marketing. We didn’t have a lot of money to spend on traditional advertising, so we were doing a lot of blogging and social media to build an audience.

I realized that I got most of my energy from making things and it should be a career, so I applied for every kind of startup job I could. The one thing I liked about the startup world is that they don’t really care about your background or what you studied as long as you can do the work.

What was that first startup role like?

First, I was a marketing team of one at WeDidIt, a fundraising tool for nonprofits. Then I got a job at Ceros, a company that makes design software. I took a chance on writing some things that weren’t necessarily about marketing our product. They were just creative stories, and they did really, really well.

The more we talked to our audience, the more we realized they liked those things more than the traditional marketing advice articles that we were writing.

Our customers don’t go home and talk about marketing advice with their families. They talk about interesting stories they heard on NPR. We wanted to be in that conversation, so we shifted our strategy. I got to hire a team and focus on creative stories. From there, I ended up at Convene.

How do you keep up that creativity and refine your approach in your current role?

I think a lot of conventional wisdom for content marketing is that you need to be really focused subject-wise on the audience. That’s definitely true for a lot of businesses. But I think it kind of sells content short, because content can be more than just a direct-selling, direct-response tool.

Your content and editorial strategy can be the mouthpiece and point of view of your company. It’s the chance to have a perspective and let that personality come to life for people.

If a customer walks into your office and sees your team’s character, you don’t want them to read your content and say “Who the hell is writing this? This doesn’t match what you guys are.”

When you come into our space at Convene, it’s very evident what we’re about, and I think an editorial strategy gives us a chance to let that come out online as well. It’s like the editorial page of a newspaper.

So you’re saying that marketers are missing a big opportunity to say something new.

A good brand shows what you have to say that’s different than anyone else.

Doing super-tactical stuff can be effective for some. But it can turn your content into a commodity. That’s something easy for others to replicate.

If you’re building a unique tone, a voice, and perspective, it’s not easily replicated by somebody else.

How do you help the team at Convene share their unique perspectives?

We have a set of very highly respected executives at Convene. They have very prominent voices in their fields. So I’m kind of a back-seat driver. I need to amplify their voices a little bit more through guiding and coaching. I’m teaching them what a good hook is, what a good story is and how to discover where we can get these great ideas.

They come with a lot of seeds of interesting ideas because they’re at networking events where something is said and spurs a good conversation. They bring those seeds back, and then I focus on how to translate it into a great headline that someone’s going to click and read, with a coherent argument they understand.

It’s about asking the right questions and just telling people straight up: “I need you to write a headline for this, because right now it’s just an idea. What’s going to make me click on this?”

We’ve tried creative writing prompts too. Our head of marketing had the idea to think about how someone would write a book review about our content. We say, “In the future, if someone reviews this thing you wrote, what would their headline be? What would they say? What are they going to criticize? And what are they going to tell people the three takeaways were?”

I really like that. How has that exercise helped you improve your content?

Here’s another way we think about it. When freelance writers pitch me something, they have to tell me their title, a little brief, who their sources are going to be, and they also have to fill out something called the “how could we screw this up.” It’s basically identifying what would make this a really weak story from the beginning so that we can avoid it.

It’s really helpful. It’s not time-consuming, and it doesn’t add a lot to the process. It’s just a one-sentence thing that I have writers identify. The exercise has been really helpful in making them think about what they’re going to need to factor in before they get started. Everyone’s always excited about a new idea, and they don’t necessarily want to think about the roadblocks.

You’d be surprised how helpful it is to sit and think before you even start, “What’s the weak point here?” It might be something like “I want to write this design feature, but we could screw this up if we don’t get good photography.” Now we know this story has to have good photography, or it’s not going to happen.

So you need to be thinking about that from the beginning.

What have you learned about hiring creatives?

When I was hiring staff writers, I was amazed at how many were applying for a creative writing job with the most boring, standard cover letter that you could imagine.

One of the writers I hired opened her cover letter with something like, “It’s 3:30 a.m. I’m standing on a corner in Queens, and I have a deadline at 8 a.m. for a story, and I still don’t have a subject.” And I’m hooked. You’ve got my attention. Those are the type of people who are easier to coach, too, because they want to push themselves. They want to try new things.