How to Hire Skilled Content Strategists for Your Business

In the last four years, I scaled a content strategy team from three to 13 people. In the process of conducting dozens upon dozens of interviews and including various internal stakeholders, I quickly learned how to avoid common pitfalls.

It’s difficult hiring for strategic roles. You’re want to find a strategic thinker and someone who understands UX principles and best practices. If you’re not asking the right questions, it can be easy for someone to bluff their way into a content strategy role with reasonable surface-level responses while failing to provide enough substance to show their strategic thought process.

In sharing my tips for hiring content strategists, I hope you can hire talented content strategists who can immediately hit the ground running and make a direct impact on your bottom line.

Use a Test Project— and Scope It Correctly

The topic of test projects has become a sensitive one, and for good reason. I’m a huge fan of test projects, but I have several guardrails to help ensure I’m not taking advantage of applicants. For a position that’s highly strategic, like a content strategist, test projects can ground the abstract in the concrete, but you need to approach it carefully and thoughtfully. 

First, when you’re defining the test project, make sure you’ve defined a clear purpose for it. I decided I wanted to use a test project to test for persuasiveness, effective communication, and strategic thinking. I also wanted to use it as an easy way to compare candidates to one another.

When I started reviewing content strategy resumes, almost all the candidates looked the same on paper. I would see very similar titles and applications, namely content strategist, content manager, or content coordinator. Sometimes the words marketing or SEO would be thrown in the mix as well. And the experience described would usually be vague: managed and/or planned content, brainstormed topics, published content, etc. Those phrases can mean very different things in practical terms, depending on context, so resumes didn’t give me a real sense of the candidates’ work. I wanted a consistent benchmark to compare candidates to one another.

Second, you never want to assign a test project wherein you might use the individual’s work—unless you make that clear in the ask. This can be partially mitigated if you send a completely made-up scenario to the applicant. If you think there’s any chance you may use ideas from the applicant’s work, you should draft a contract clearly outlining that possibility and pay for the test project.

Finally, you want to be clear about the time commitment involved for the test project. You don’t want someone to spend a ton of time on something that may result in little to no return for them. When I structure a test project, I create one that shouldn’t take more than 15 to 30 minutes, and I tell applicants that expectation. That way, they won’t worry about whether they spent enough time, and you’ll get an accurate baseline for comparing candidates.

For the test project itself, you may send an applicant a user pathway for a website and ask them to make three recommendations for improving user experience. You may send a link to a website and ask the candidate for three recommendations to improve site structure. You may send a link to a blog and ask the candidate how they would approach categorizing topics. Whatever you decide, it should be illustrative of the work they’ll be doing in the role.

I send test projects to candidates before I interview them. If someone sends a promising application and I want to set up an interview, I have them complete the test project beforehand. That way, we can discuss the project in the interview, and the candidate can get a feel for whether they enjoy the work.

Structure the Interview for Maximum Efficiency

Interviews can be fun for everyone involved. If they’re not, I would politely suggest you’re doing them wrong. I love that interviews give me the opportunity to meet a lot of talented people who get to showcase their strengths and success, while discussing their best work. I also enjoy connecting with others over our shared interests and passion. A great interview can feel like a geek-out session among colleagues.

You want to go into every interview with the same structure and plan, so you’re comparing applicants against the same questions and skills. When you’re planning the structure, involve anyone else who might join the interview. That way, you’ll be aligned on what you’re looking for, but you’ll also be aligned on how the interview should flow and how much time should be spent on each portion. You won’t be rushed or trying to cram in too much.

For a content strategy interview, I typically structure it in five parts: the introduction, the content strategy questions, the test project assessment, the soft skills, and the conclusion. The introduction usually takes five to ten minutes. I ask all the interviewers to introduce themselves along with their title and how they collaborate with the role. Then I ask the interviewee to give us a broad rundown of why they’re a good fit for the position. During this part of the interview, I look for verbal communication skills and genuine interest and passion.

Then I dig deeper. First, I cover content strategy questions, which usually takes about 15 minutes. If I can, I’ll tie my pre-written questions to things they mentioned in their introduction. After discussing content strategy and UX, that nicely dovetails into the test project, which I spend 10 minutes on. I ask them to give an overview of their test project, and I give them both positive and constructive feedback on their approach and suggestions. I’m not expecting perfect answers. I’m just looking for reasoning—and an ability to respond to feedback in stride.

After discussing the skills needed to do the job, I tell the candidate that we’re switching gears to talk about soft skills. We typically spend about 10 minutes digging into collaboration, communication, and self-awareness. An important thing to note is that we’ve pre-defined and aligned on the soft skills we’re looking for in candidates and why they’re important for the role. We’re not asking generic, canned interview questions or throwing around the term “culture fit.”

At the end of the interview, I leave 10 to 15 minutes for the candidate to ask questions. Leaving this time at the end is important. Sometimes it’s the best part of the interview, because the candidate can showcase curiosity and critical thinking. You can also get a sense for what they care about and what they’re looking for in their career and employer. Even if you have to keep the rest of the interview at a brisk pace, I would recommend doing so in order to leave time at the end for questions.

Ask the Right Questions

In interviews, I try to give all applicants the benefit of the doubt and to root for them, while simultaneously asking tough questions and giving both positive and constructive feedback. Sometimes rooting for people while simultaneously being critical of them may feel counterintuitive. However, in my 12 years of leadership, I’ve realized that people genuinely want feedback, especially from interviews. 

Candidates want to know how they did and where they stand. If they’re not being offered a job, your constructive feedback could help them improve their interview skills for their next opportunity. So, being an honest and clear is the kindest thing you can do.

In the spirit of giving candidates the benefit of the doubt, if someone doesn’t answer a question to your satisfaction, ask follow-up questions. Give them a chance to clarify their response. Make sure they understood the question and why you’re asking it. Be direct and tell candidates when their answers go off on a tangent rather than answering the question. Reframe the question and try again. If you still don’t get a satisfactory answer you can move on, confidently knowing you’ve been clear.

Plan your questions ahead of time, and stick to open-ended questions that allow candidates to draw from their past experience and describe their thought process for approaching work.

Content Strategy Questions

  • How do you measure the success of content?
  • Share an example of when you learned new information about users and applied it to a project, initiative, or campaign.
  • If you were to step into this content strategy role tomorrow, how would you go about creating a content plan for the short-term and long-term?

Test Project Questions

  • When you were completing this test project, what additional information did you wish you had?
  • Walk us through your reasoning on your suggestion X.
  • If you learned that customers were behaving in X ways, how would that change your recommendation?

Soft Skills Questions

  • Tell us about a time when you had to navigate conflicting communication styles or opinions.
  • Describe a piece of feedback you’ve been given more than once.
  • Tell us about a time when you made a mistake.

It can be difficult to resist asking leading questions. With strategy-related questions, you want to keep questions broad and open so you can get a sense for the candidate’s thought process. For the same reason, I try to avoid giving much context for our current content strategy up-front and instead focus my questions on the candidate’s past experience.

Pay attention to your content strategy candidates. The title means different things at different companies, which can be challenging, but it’s also a huge opportunity. Sometimes you’ll find candidates who struggle with strategy but who could make strong candidates for other roles. In fact, I’ve found many talented writers who originally applied for content strategy roles. So, focus on building relationships in your interviews and getting to know people while truly listening. Be genuinely curious about others.

Hiring for content strategy roles takes time and patience, but it’s also fun. If you’re planning ahead of time and asking the right questions, your process should go smoothly. If you focus on building relationships, giving people the benefit of the doubt, and being honest, you’ll unquestionably see positive results from your hiring efforts.

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Published by Ashley Walton

Ashley has 15 years of experience in content, she has led teams of 80+ content creators, and she has taught numerous university courses on media. She's the founder of Content Maven, and at the end of the day, she hopes to make the world a better place, one piece of content at a time.

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