Probing questions to expect from a sharp freelancer

What’s the secret to success in outsourcing writing projects? How do you get the greatest value in the shortest time for the lowest cost? Obviously, one of the most crucial things you can do to ensure your ultimate satisfaction is to engage the most effective writer available for the project.

meetingPicking the best content creator is more art than science, but there ways to improve your odds of success. I’ll pass along some hints below…but that isn’t really the point of this post. The point is this: Hiring a writer means entering into a creative partnership, and both partners have legitimate questions and concerns about it.

You can get the greatest leverage from this arrangement by asking smart questions of each candidate writer before you engage him or her. But an effective writer will have some pointed questions for you too. It’s really those questions I want to address here. An effective partnership begins with frank, straightforward answers to those questions – even if the frank answer is, “I don’t know yet.”

What To Ask a Prospective Writer

A colleague – another writer who generates white papers for technology companies – recently posted, in a group, a link to a helpful article called “7 Questions to Ask When Choosing a White Paper Writer.” The article is from the blog of still another creator of marketing content. (It’s no secret that there are lots of capable writers; we compete with each other, but we cite each other’s stuff when it’s smart and serves a purpose.)

The article suggests a series of questions that a marketer seeking to engage a writer should ask, to pre-screen each writer’s qualifications for the project – the specific focus here is on white papers. It’s worth clicking through to read the full exposition, which is quite thoughtful. But the author winds up the piece by reiterating the seven proposed questions, and the insight each question is intended to secure for the hiring manager:

1. Could you tell me a bit about your career background?
Is this writer capable of understanding our offering and our audience?

2. What experience have you had writing for technology companies?
Is this writer’s experience relevant to our needs?

3. What kind of white papers have you written?
Does this writer have experience in writing white papers?

4. Could you send us some samples of white papers you’ve written?
Is this writer capable of keeping our readers engaged?

5. What kind of white paper would you suggest for us?
Is this writer able to propose the right kind of white paper for our objectives?

6. What’s your process, and how do we work together?
Is this writer able to deliver what we need in a reasonable time?

7. What else can you offer us once this white paper is complete?
How can we get more for our money, using this writer?

It’s a useful litany. You may have additional questions that address issues that are important to you, but this is a great start.

But, as I indicated earlier, there are legitimate questions on both sides of a contractor relationship. Consider what is on the mind of the content professional you’re looking to hire.

What a Professional Writer Will Want to Ask You

A freelance creative is a rational business person. He or she has personal pride in the quality of the work. The writer also wants to be paid, fairly and promptly, and has internalized (often through painful experience) the basic business principles of cash flow management and the time value of money. The writer is at least as interested as you are in generating the content you want, as quickly as possible – in meeting your requirements with diligence and professionalism, but also in “getting to done” as expeditiously as possible.

With that in mind, here are “7 Questions” you can expect from an astute creative pro. Expect them regardless of whether the project is a white paper, web site copy, a press backgrounder or a video.

1. What is the objective of the project we are discussing?
Your project is typically one element of a more comprehensive program, and addresses one particular issue your customer will encounter on his “journey” to adopting your offering. The writer wants to provide the right words to accomplish the goal you have in mind. Help her understand that goal.

2. What is the scope and urgency of the project?
What kind of product do you have in mind? If it’s a white paper, what exactly do you mean by “white paper”? The term has been applied to many kinds of documents, but clearly it means to help your customer with a specific decision or concern. Can you provide an example of a similar piece that you felt was successful – against which you will measure success? Was there a precedent you want the writer to emulate?

When and how will the content be used? Is it needed for a specific event? If this is a longer term need, can you at least specify a deadline? Let’s be frank: Your writer legitimately needs to know when you expect the project to be completed, not just when the first draft is due, so she can avoid conflicts with other clients’ projects, and know when to anticipate any milestone payments that are tied to completion.

3. What have your experiences been with other writers?
If you can identify any features of past contractor relationships that were especially satisfying – or if you have had recurring frustrations with freelancers – an astute writer will want to know. Help him succeed by sharing these experiences.

4. What is the approval process for the project?
With whom will she be collaborating? How many collaborators and approvers will there be? These are fair questions – the writer needs to budget her time, and needs to know whether the review of each draft is going to require days, weeks or months.

5. Are there any known, specific budget constraints?
If the writer is likely to incur expenses on your behalf, are they capped? Is the project going to be paid for with money you have in your current budget, or are you depending on your ability to draw from funds that will be allocated later? These questions may feel awkward or intrusive. But they’re legitimate.

6. What follow-on work are you likely to want when this project is completed?
A contractor is interested in a relationship that goes beyond the immediate project. A professional will ask: Do you need help repackaging this content for leverage? Do you need help promoting this content? An effective writer can do both for you.

7. What do you need from me to get started?
Typically, a project will begin with a proposal and statement of work, including a payment schedule, with advance and milestone payments. What the contractor needs to know is: What is your sign-off process for engagement? Once sign-off is completed, what is your onboarding process? If you require a nondisclosure agreement (atypical for writers, but not unheard of), the freelancer will want to know in advance.

A freelance contractor is your wingman on an important mission. Both of you will benefit from a partnership marked by candor and common interest in a successful outcome, not just for the content to be generated but for the relationship you are building. Expect probing questions at the outset; in fact, if the freelancer neglects to ask them, consider that a red flag in itself.

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