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Why this matters:

There are dozens of different kinds of copy and content writing, each with its own set of criteria for success. For example, a landing page or piece of sales collateral requires a different set of skills than copy for a creative ad, caption, or commercial — or an article for thought leadership. This question allows the candidate to showcase experience and versatility — especially as it’s relevant to your role.

What to listen for:

  • Familiarity with the copy or content types you need most
  • The ability to learn to write other types of content
  • Cues that the candidate will investigate past samples, ask the right questions, and approach the process with a sense of quality and excellence

Why this matters:

The process itself can vary across copywriters and formats. But in general, the best written copy won’t be effective unless it’s aligned with several things: your objectives and your strategy; your brand voice; your audience persona, mindset, and journey; and other key factors.

What to listen for:

  • Evidence that the candidate seeks to gain a clear understanding of the request, including the intended objective and audience
  • A strong information-gathering process, especially for long-form content — including necessary interviews, research, data, and insights

Why this matters:

No matter how much your new copywriter understands, now or over time, about your subject matter, topic, or industry, your needs will undoubtedly require them to learn something new down the line — a new voice, new sub-topic, new product, etc. It’s imperative that they’re not intimidated by the learning process. It’s even better if learning new topics is par for the course for them.

What to listen for:

  • A systematic process they use for exploring new subject matter
  • An indication that the candidate’s process is thorough and efficient — the last thing you want is someone who’ll unnecessarily linger in the information-gathering phase

Why this matters:

Writing can often be challenging, but what can sometimes be even more challenging than the original assignment is seeing a proud piece of one’s best work get covered with comments and reactions — not all of them favorable. This question is key to learning how a copywriter processes constructive feedback, and whether they can leverage it to learn and improve.

What to listen for:

  • Signs that the candidate treats respectful feedback as a stepping stone to learning more about the topic or the stakeholder audience — or to improving their skills
  • A willingness to ask clarifying questions
  • An ability to read between the lines during stakeholder communication

Why this matters:

Depending on the time sensitivity in your work environment, you may want to make sure that your future copywriter places the utmost importance on deadlines. This question will help explore your candidate’s sensitivity to deadlines — and can shed light on their work values in general.

What to listen for:

  • The willingness to be accountable
  • Any issues around time management or perfectionism — and, ideally, details about what they’re doing to minimize these issues
  • Other work values that are important to the role, such as quality, research, and discovery

Why this matters:

Even the most well-crafted writing doesn’t always perform optimally. This question will give the candidate a chance to reveal how they define success personally — and to showcase work that hit or exceeded objectives. Consider it a bonus if they give credit to other team members where due.

What to listen for:

  • The ability to easily recall an example and describe their approach to the project in detail
  • A strong sense of business value — with a knowledge of how it’s quantified as a result of their work
  • Enthusiasm and passion for their work

Why this matters:

Every copywriter has those moments where the words just won’t come. At the same time, great copywriters have a strategy or two ready for when the creative tank starts to feel drained. The right candidate will show a high degree of self-awareness in this area, and be able to articulate their approach to dealing with the occasional bout of block.

What to listen for:

  • Specific examples of actions they’ve taken to get unstuck on a project
  • Signs that they’ve experimented with various tactics — and landed on the best fit for their unique work style
  • Acknowledgment of the reality of writer’s block

Why this matters:

Time management is absolutely fundamental to copywriting, especially in fast-paced environments where new work is assigned on an ongoing basis. Every writer’s process is different, as are their strategies for managing time and deadlines effectively. The ideal candidate will possess a strong awareness of their working style, habits, and strategies for managing themselves on the job. 

What to listen for:

  • Signs that the candidate is able to switch gears fluidly when necessary, if that’s needed in your work environment
  • Self-awareness about their own best practices
  • Mentions of apps and other technology tools that can help with productivity and workflow

Why this matters:

Talent is definitely a factor in great copywriting. At the same time, talent can only get writers so far — practice and a strong drive for growth are key. Look for candidates who describe some method of keeping their skills fresh and their personal growth engines running, whether it’s reading (books or good copy), telling stories, or just embracing feedback and writing as much as they can. 

What to listen for:

  • The general desire to embrace learning and achieve some sort of mastery
  • A sense of openness toward feedback and other ways to improve
  • References to specific books and other resources they’ve used in the past
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