Five Critical Questions to Ask Before Hiring a Writer

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No two writing projects are alike, and the differences don’t always show up in the statement of work.

Much of what determines a writing project’s success comes from the chemistry between writer and client. Differences in personality and working style make each project unique.

You might think, then, that the most important questions to ask before hiring a writer would relate to the writer’s character, experience, and approach. While those questions are important, even more critical are the questions to ask about yourself.

As with so many life situations, the key to succeeding is that piece of ancient Greek wisdom, “know thyself.” The better you know your working style and expectations, the more likely you’ll be able to find the writer who will align with them.

Here are five “know thyself” questions worth asking whenever you’re looking for writerly help:

1. What outcomes do you expect the writing project to produce?

As with any project, start with a vision of success.

That doesn’t mean you must be able to visualize what the end product will look like. After all, you’re embarking on a creative journey, so you can’t expect to predict every step of the way or the exact final destination.

You can, though, describe specific objectives you want to achieve. For example, let’s say you’re writing a white paper to help your customers solve a specific problem. Goals for that document might include:

    • Define the problem in ways that resonate emotionally with the target audience
    • Describe in layperson’s language how our solution solves the problem
    • Differentiate our solution from other available alternatives, especially DIY alternatives
    • Attract attention through eye-catching document design that meets our branding specifications
    • Guide readers toward registering for our free webinar

Notice how each of these objectives starts with a strong verb. Clearly articulating the results you want the writing project to deliver will help energize and focus both you and the writer.

2. What writing activities do you need help with?

Getting formless ideas into written form is messy work. And it seldom follows a linear path. However, any writing process involves activities that fall into three main categories:

    • DESIGN activities include conducting research, generating ideas, brainstorming different approaches to the topic, analyzing the target audience(s), zeroing in on a key message, and mapping out a document structure.
    • DEVELOP activities include “getting the words out” as well as creating rough drafts of visuals.
    • REFINE activities include revising (improving ideas, structure, and data visualization), editing (improving the written expression of ideas), and proofreading (checking for typos and formatting glitches.

It’s important to consider the whole range of activities you really need help with because it’s easy to fall into the trap of thinking that all you need is a little “wordsmithing.”

If you’re looking for a wordsmith, you need an editor, someone whose superpower is combing through paragraphs and sentences to make writing more cohesive and lean. But is that the only skill you really need?

Many writing projects also require someone who can help clearly define ideas, consider counterarguments, and serve as a sounding board for emerging thoughts. If that’s your situation, then you need a writer who can become your strategic communications partner, not just “polish up” a near-finished product.

3. What’s your working style?

How do you prefer to collaborate? What’s your team culture? What assumptions do you bring about how the writing process should work?

Questions such as these are critical because collaborating on a creative project requires a high level of synchronicity. When you’re considering potential writers, ask yourself such questions as:

    • Do I prefer a highly structured development process that starts with a clear plan and proceeds step-by-step, or do I prefer a more iterative, agile approach?
    • Do I like to communicate primarily via email or Zoom?
    • Do I like to respond to drafts through written comments or by talking through my reaction?
    • Will I need to pull other people into the creative process as it unfolds?

4. How much time do you have to devote to the project?

I mean how much time do you REALLY have to engage in planning and reviewing the writing product you want to produce. It’s easy to overestimate how much capacity we have to respond to drafts or squeeze in a quick meeting.

A writing project can run into trouble if the amount of time you truly have for collaborating doesn’t match the amount of creative control you want to exert over the writing process.

5. How much control do you want to have over the process and product?

Of all the questions we’ve explored, this might be the most critical.

Creating a piece of writing is a lot like shooting a movie. On a movie set, you need a director or else each actor could bring their own quirky interpretation to the script. In the worst case scenario, the actors might just start wandering randomly over the set.

On a writing project, you also need a director, someone who takes responsibility for articulating the intent of the project, defining the approach to achieving objectives, and monitoring execution.

Some writers work best when they sit firmly in the director’s chair. Others prefer to co-direct, and some thrive when they receive explicit instruction. There’s no single best approach—the key is to align your expectations with the writer’s at the start of the project.

Be clear about areas in which you feel confident to direct and areas in which you would like the writer to provide guidance, based on their experience and expertise. Think of yourself as the producer—the person with the Big Vision—and delegate roles and responsibilities strategically.

When you choose a writer, you choose a new member of your team, so it pays to do some self-examination first. Recognizing your genuine needs will enable to find the right colleague who, over time, could become a long-term partner to help your business reach its full potential.

Curious about how coaching and authoring together could help you get the communications support you need? Book a free consult.


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