These 3 Questions Are Your Secret to a Successful Project

Landing a new writing project is always an exhilarating feeling. No matter how long you’ve been in the business, it’s always a pleasure to know your skills are wanted. Feels good on the bank account, too.

But then, what? Early in my career, the start of every new project was overwhelming. There was so much to know and learn, from elements of my own craft, to the client, and the client’s industry, and the specific topic. I would spend interminable hours bathing myself in every aspect of all of those things until finally, finally, at long last, I would feel that I knew enough to begin the work.

In the time since, I’ve learned that there are really only three questions to ask, and the answers to those will give you everything you need to proceed. Ideally, you should be asking these questions during the prospecting process, before you agree to a project. But, failing that, it’s fine to ask them as part of the onboarding process after you’ve accepted the project.

The Three Questions:

One: Who is our audience?

You probably remember this question from English classes. But this is no mere academic exercise. In business, audience is everything. If you don’t understand who you are creating a product or service for, how will you create something they want? And if you don’t understand who you are marketing it to, how will you know how to talk to them?

When you first start asking this question, many prospects and clients won’t have an easy answer. They’ll probably hem and haw a bit. That’s okay. Asking it is the most important thing. Then let them talk and try to nail it down.

You can remind them that content that tries to target too many people at once will be less effective than content that targets a specific audience. Remind them that they can always tweak the content later for a new audience.

PRO TIP: This is an opportunity to sell them additional valuable services–they’re going to need somebody to do that tweaking–but you don’t have to rush into selling them on that right away, just plant the idea.

If all else fails, let them know that you can address multiple audiences, but that you should at least have a key audience in mind. Then let them discuss and settle on a key audience.

This question does three key things for you:

  • One, it provides you with a starting point to provide valuable content.
  • Two, it sets you up in an advisory role with the client, which builds trust and a solid foundation for future work.
  • Three, it positions you for the next question.

Two: What keeps the audience up at night?

This question can be asked in a number of different ways, however is comfortable to you. You can say, “What are the audience’s key pain points?” or “What problems is the audience trying to solve,” or simply, “What hurts?”  I have found that most prospects resonate with the “what keeps them up at night?” question, but what’s important is that you help them get at the heart of the deep and troubling problem(s) that their audience wants to solve.

There are at least two levels to this question. On one level are the big bad problems that may or may not have to do with the specific content piece you’re providing. On another level are the specific detailed problems you can indeed help them solve with the content piece. It’s good to let the prospect or client talk about both, as they will impact each other and provide good fodder for both this content piece and others.

PRO TIP: This is another opportunity to lay the foundation for additional valuable services. Make notes on all the problems your prospect’s clients have, and use that to launch future conversations about other types of content related to each problem.

Pay very careful attention to all of the answers that your prospect or client provides to this. Be very quiet and listen very carefully and let them talk for as long as they want to on the topic. It is likely they will dredge up thoughts and ideas that had never occurred to them before (and you get to be the hero! Even though it’s coming out of them!). Even if they already know the answer to this, and can rattle off the answers, you once again show both your concern and your expert status by asking the question.

Another reason to pay close attention to these answers (and take notes! Or record the conversation and transcribe it later): They will tell you where the content’s main focus should be. In partnership with your client, choose one of the pain points and use it as the focal point of the piece. Organize all of the content around that one focal point to create a targeted, focused, powerful piece of content.

Three: Do I actually want this project?

That wasn’t what you were expecting, was it? I mean, OF COURSE you want the project. The client is paying, and you may have already agreed to it, and WHY NOT?

Why not: Because maybe your energy would be better used elsewhere.

You are not a hack. You are a professional with valuable skills and you are your own person, so you get to CHOOSE. Here are several reasons you might want to decline a project:

  1. The client has no idea what they want and keep changing their minds before you even get started.
  2. The client invites several people to the meeting and then they argue amongst themselves a significant portion of the time.
  3. The client wants to see your work before they pay you.
  4. The client says they’ll make your 50% payment up front, but then the payment doesn’t show up in a timely fashion.
  5. The client doesn’t want to answer your questions and says they just want you to do what they hired you to do.
  6. You simply don’t LIKE the client.

The first two problems may indicate a client that is going to be a lot of trouble and stress. You don’t need it. The second two problems indicate a client that does not value you and will always be a hassle about money. The fifth one means they don’t respect you, and they are not going to give you everything you need to do your work.

And the last one? Your gut. Trust it. Did you know that your gut actually contains the same type of cells that your brain does? Many biologists call it the body’s “second brain” for that reason. And it contains MORE OF THEM than your brain does. It is SMART. Trust.

Now. However. You don’t HAVE to fire a client because one of these six things happen. If you’re comfortable, you can ask them about it. Something like, “I sense that your team isn’t in agreement on this right now. I can’t do my best work for you without a clear direction from you. Is there something we can do to resolve this before we begin work?” Substitute the problem you see, and you can use this for any of the problems.

Except the last one. Listen. If you don’t like the client, don’t work with them. Find someone else. Maybe it’s them, maybe it’s you. If you just don’t like anyone, or most people, it’s probably you–go get some therapy, learn yoga, meditate, find God, whatever. If you like most people but just not this one, then it’s them. Let them go.

Once you’ve answered these three questions, of course you’ll still have work to do. But the answers to the first two will guide you. They’ll tell you and the client who you need to interview, and what you need to research. Instead of deluging yourself with EVERYTHING THERE IS TO KNOW, you’ll be able to focus your work on what really matters.

The end result: You’ll work faster, and the quality will be better. Wins all around, and that is how it should be.

Go forth and do, my friends. You’ve got this.


Fen Druadìn Head
Fen Druadìn Head is an award-winning freelance writer and coach. Her work can be found all over the internet in publications as diverse as Redshift Magazine and Grit. Fen's fiction is represented by Ethan Ellenberg.