How to Hire Content Strategists

May 21, 2019

Recently, I scaled a content-strategy team from three to eight people. In the process of conducting dozens upon dozens of interviews, while involving various internal stakeholders, I quickly learned how to avoid some common pitfalls of hiring for strategic roles.

It’s challenging to hire for strategic roles—neither as easy nor as straightforward as hiring for other skill-based positions. Ultimately, you’re looking for a strategic thinker who understands UX principles and best practices. If you’re not asking the right questions, it’s all too easy for candidates to bluff their way into a content-strategy role by saying what superficially seem to be the right things, without providing enough substance to show their strategic thought process.

In sharing my tips for hiring content strategists in this article, I hope to help you avoid these common pitfalls so you can hire talented strategists who can hit the ground running.

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Send Candidates a Test Project

Asking candidates to complete test projects during the interview process has become a sensitive issue and for good reason. While I’m a huge fan of test projects, I rely on several guardrails to ensure that I don’t take advantage of applicants. For a position that’s highly strategic—such as a content-strategist role—test projects can ground the abstract in the concrete, but you need to approach their use carefully and thoughtfully.

First, when you’re defining your test project, make sure you’ve clearly defined what you’re looking for. You should have a clear purpose for using a test project. For example, when scaling my team, I decided I wanted to use a test project for a couple of reasons:

  1. To assess a candidates’ persuasiveness and strategic thinking. Both of these characteristics are essential in a content strategist. However, in reviewing the test project, I would not fault the candidate for anything beyond the lack of these two things. (For example, if they had made small typos, I would ignore them—giving them the benefit of the doubt.)
  2. To differentiate between candidates with similar resumes. Most candidates looked very similar on paper. I saw the same titles in their resumes and applications, including content strategist, content manager, and content coordinator. Sometimes they would throw the words marketing or SEO into the mix as well. The experience they described was usually vague—for example, “managed and planned content,” “brainstormed topics,” and “published content.” These phrases can mean very different things, depending on the context, so they gave me no real sense of the candidates’ work. I needed a consistent benchmark for comparing candidates to one another.

Second, you should never assign a test project in cases where you might use the candidates’ work—unless you pay candidates for completing the test project and make your intention clear in your request. You can partially mitigate the impression that you’re asking for free work if you base the project on a completely made-up scenario. But, if you think there’s any chance that you might use any of the applicants’ work, you should simply pay them for completing the test project.

Finally, be clear about the time commitment the test project should require. You don’t want someone to spend a lot of time on something with potentially little or no return. When you create a test project, ensure that completing it won’t take more than 30 to 45 minutes and communicate that expectation clearly. Then, candidates won’t worry about whether they’ve spent enough time on the project, and you’ll have an accurate baseline for comparing candidates.

For a test project for a content-strategist role, you might send candidates a user pathway for a Web site and ask them to make three recommendations for improving the user experience. Alternatively, you might send candidates a link to a Web site and ask them for three recommendations for improving the site’s structure. You could send them a link to a blog and ask them how they would approach categorizing its topics. In any case, the candidates’ work should be illustrative of the work they would be doing in the role.

Different hiring managers use test projects for various reasons. As I noted earlier, I use test projects to compare candidates to one another and to understand how their skills would apply to the work they would be doing. Therefore, I send test projects to candidates before I interview them. If someone’s application looks promising and we want to set up an interview, we first have them complete the test project. That way, we can discuss the project during the interview.

Structure the Interviews

Interviews can be fun for everyone who is involved in the process. If they’re not, you might be doing them wrong. I love that interviews give me the opportunity to meet a lot of talented people who get to discuss their strengths and success, while showcasing their best work. I also enjoy connecting with them over our shared interests and passion.

You should try to approach every interview with the same structure and plan, so you’re comparing applicants’ answers to the same questions and assessing the same skills. When planning the structure for the interviews, involve anyone who might conduct interviews with you, so you’re on the same page. You can align on what you’re looking for, as well as on how the interview should flow and how much time to spend on each portion of it. Make sure you won’t feel rushed or try to cram in too much.

I typically structure a content-strategy interview in five parts:

  1. Introduction—This usually takes just five to ten minutes. I ask all interviewers to introduce themselves, including their title and why they’re in the interview. Then I ask the candidate 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 or passion.
  2. Content-strategy questions—Then I dig deeper by asking more questions and discussing candidates’ answers. Covering my content-strategy and UX questions usually takes about 15 minutes. If I can, I try to tie my prepared questions to things candidates have mentioned during their introduction.
  3. Test-project assessment—Our discussions about content strategy and User Experience usually dovetail nicely with the test project, on which we spend ten minutes. I bring a copy of the candidate’s test project for review and provide positive, constructive feedback. I ask candidates about their reasoning—why they approached things the way they did—and try to offer new information that challenges their original answers. This lets me get a feel for their real-time, strategic thinking and problem-solving ability. I don’t expect perfect answers. I just want to understand their reasoning.
  4. Soft skills—After discussing the skills the candidates would need to do the job, I tell them we’re switching gears to talk about soft skills. We typically spend about ten minutes digging into collaboration, communication, and self-awareness. It’s important to predefine and align on the soft skills you’re looking for in candidates and why they’re important for the role. Don’t ask generic, canned interview questions or throw around terms such as culture fit.
  5. Conclusion—At the end of the interview, I leave ten to 15 minutes for the candidate to ask questions. It’s important to reserve this time at the end. Sometimes this is the best part of the interview because candidates can showcase their curiosity and critical thinking. You can also get a sense of what they care about and what they’re looking for in their career and employer. Even if you must maintain a brisk pace for the rest of the interview, I recommend that you always leave time for candidates to ask questions.

Ask the Right Questions

During interviews, I try to give all applicants the benefit of the doubt and root for them, while asking tough questions and giving positive, constructive feedback. Sometimes rooting for people while simultaneously being critical of them can feel counterintuitive. However, in my nine years in leadership, I have realized that people genuinely want feedback, especially during interviews.

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

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

Plan your questions ahead of time, sticking to open-ended questions that let candidates draw from their past experience and describe their thought process.

While it can be difficult to resist asking leading questions, when you’re asking strategy-related questions, you must keep your questions broad and open so you can get a sense of the candidate’s thought process. Therefore, I try to avoid giving much context for our current content strategy up front, instead focusing my questions on candidates’ past experience.

Content-Strategy Questions

Here are some examples of content-strategy questions:

  1. How do you measure the success of content?
  2. Share an example of your learning new information about users and applying it to a project, initiative, or campaign.
  3. If you were to step into this content-strategy role tomorrow, how would you approach creating a content plan for the short term and the long term?

Test-Project Questions

These are examples of test-project questions:

  1. When completing this test project, what additional information did you wish you had?
  2. Walk us through your reasoning on your suggestion______.
  3. If you learned that customers’ behaviors were ______, how would that change your recommendation?

Soft-Skills Questions

Here are some examples of soft-skills questions:

  1. Tell us about a time when you had to handle conflicting communication styles or opinions.
  2. Describe a time when you received feedback with which you initially disagreed.
  3. Tell us about a time when you made a mistake.


The title content strategist means different things at different companies. This can create challenges, but can also be a huge opportunity. Sometimes you’ll find candidates who struggle with strategy but could make strong candidates for other roles. In fact, I’ve found many talented copywriters who originally applied for a content-strategy role. So focus on getting to know people and building relationships during your interview process by truly listening.

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’re sure to get positive results from your hiring efforts. 

VP of Content & Creative at Clearlink

Salt Lake City, Utah, USA

Ashley WaltonAt Clearlink, Ashley oversees more than 50 copy, design, content-strategy, and video-marketing professionals. With over ten years of marketing experience, Ashley develops frameworks for creating user-friendly, best-in-class content and creative deliverables.  Read More

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