#21: 18 questions to help you hire a great writer (…or become one)

Welcome to contentfolks—a fortnightly newsletter with short lessons & ideas about content that makes a difference, sparks action, and truly serves its audience. Thank you for being here!


Hey 👋

This newsletter will ask more questions than it answers. That’s because I’ll share my go-to list of questions to use when hiring writers (freelance or in house):

  • If you’re the person doing the hiring, these questions can help you communicate your expectations from the start and remove (some of) your biases from the hiring process

  • If you’re the person doing the writing, these questions can help you understand what an editor/strategist may be looking for when they’re deciding whether or not to hire you


Knowing what to expect > trying to read each others’ minds 🔮

As an editor/strategist looking to hire new writers, you must be able to explain what counts as ‘good’ content and why a deliverable is, or isn’t, a good fit. Likewise, as a writer hoping for repeat work, you need to know what the hiring person is looking for and how they will evaluate your submission.

…but a lot of this stuff isn’t really made explicit at the beginning of a new writing relationship. We behave as if the other person can read our mind and inevitably get frustrated when things don’t work out.

A much easier way forward is to seek alignment from the start***. For example, if the editor/strategist is proactive and detailed about what they want and communicates this before any writing even happens, the relationship has a better chance to work out.

*** by the way, I suspect this is true of life in general.


💡 A practical example 💡

In recent years, freelance writers who come my way are given a paid task, links to useful information (e.g. style & tone of voice guidelines), and the following one-page list:

freelance writer evaluation questions

I tell each writer to keep this list in mind because we’ll use it to evaluate the final deliverable and decide whether or not to move forward.

Here’s the list:

1. Is your writing competent?

  • Did you explore both the WHAT and the WHY of a story?
  • Did you pick the parts of a transcript/story that were the most impactful for our audience?
  • Did you turn a basic outline into a specific, helpful, and actionable piece?
  • Were you concise without sacrificing meaning or clarity?

2. Did you do your research?

  • Did you read the brief closely to understand what was asked of you?
  • Did you find trustworthy, verified, up-to-date sources?
  • Did you check in if something needed clarity?

3. Were you detail-oriented?

  • Did you follow our tone of voice guidelines?
  • Did you double-check company names, interviewee names/job titles, etc.?
  • Did you proactively edit and remove typos and errors?
  • Did you avoid word & concept repetitions?

4. Can we trust you?

  • Did you meet the due dates we agreed on and the requests outlined in the brief?
  • Did you take ownership when things worked—and didn’t?
  • Did you respond well to feedback (e.g. were you willing to redraft if something didn’t work)?
  • Did you question things and challenge us/offer a different viewpoint when something in the brief didn’t work or you had a better idea?

💡 Bonus questions: if you’re looking to hire an in-house writer or build a long-term content partnership, you can include other elements you value. For example:

5. Do you care about the bigger picture?

  • Do you understand the role you play in [company’s] larger business—and if not, are you interested in finding out?
  • Are you actively interested in knowing how each piece contributes to moving [company] forward?
  • Do you have the ability and interest to get to know our audience so you can write well for them?

🔥 Pro tip for writers: these questions are written from the point of view of a hiring manager looking to find a great writer—but if you are a writer, you can use them to sense-check where you are and as a roadmap for improvement.

For example: proactively editing and removing typos and errors (#10) is a given, but there’s an art to finding trustworthy, verified, up-to-date sources (#7) and you will be a stronger writer if you learn how to do it.


Too often we act as if teammates and co-workers can read our mind—and waste a lot of time and effort as a result. This list helps writers and editors/strategists be on the same page: it’s not as exciting as actual telepathy, but it’s still a smart way to build an editorial relationship 😉

fio