The Golden Rule of Professionals: Be Specific & Ask Good Questions

This summer, Pen + Brush is teaming up with experts in both the visual and literary arts to bring our readers a guest blogger series focused on insights, advice and information that will help artists and writers take their work and their careers to the next level.

 For our second topic, “The “Business” of Being a Creative,” publishing world expert Jane Friedman provides the following thoughts on how asking specific questions, instead of making general asks, can help further your career.

The Golden Rule of Professionals: Be Specific & Ask Good Questions

You can sabotage your writing career if you frequently engage in these two behaviors:

  1. Pitching yourself to strangers in a vague or long-winded way

  2. Asking questions of such a broad nature that you nearly disrespect the person called upon to answer

Let’s tackle the pitching scenario first. Important: While I will specifically reference editors and publications, these principles apply no matter what kind of gig you’re after. You might be trying to land a speaking engagement, a book signing, a guest blog post, a contributor role, a reviewer position. This applies to it all!

Pitching Specific Ideas vs. Being “Available”

I’d like to lay down some principles that I’ve found to be the hallmark of a professional.

Pitch Principle #1. If you have no relationship (yet) with the editor, pitch something very specific. That’s because you’re approaching cold, you’re an unknown quantity, and the onus is on you to quickly show what’s in it for them. How does your idea, concept, or product benefit the person or organization, and why will it be successful?

It’s a bad idea to assume that you yourself are so impressive (in terms of your bio or your abilities) that the editor or organization will bend over backward to find a way to work with you. You have to make it easy for them to say yes by actively demonstrating how you understand their needs.

Even if the editor or publication can’t accept your pitch or proposal, if she is impressed by your approach, she may want to keep in contact, or consider you in the future (though you should definitely ask when you should follow up, and how).

Caveat: It rarely works in your favor to criticize someone’s work as a hook for your pitch. E.g., “I noticed you have a lot of typos this month in your publication, so I thought you could use my proofreading services.”

Pitch Principle #2. The bigger the publication or company (in terms of size or fame), the more specific and succinct you should be in your pitch or proposal. No one has time to help you figure out what you should be doing. Sometimes smaller or regional publications/organizations are more willing to be conversational with you on the phone or via e-mail about how you can work together—but don’t count on it.

Caveat: If there’s an open call for freelance/writing help, then follow whatever directions are stated in that call. Don’t worry about specifics just yet. (If you start asking for specifics before you even throw your hat in the ring, you will likely annoy people.)

Pitch Principle #3. The more well-known or trusted you are by the publication or organization (or the more experience you have), the looser you can be in contacting them for “available work.”

Everything works differently when you have established relationships, or a long-term collaborative history with a person or a publication. But you shouldn’t treat cold contacts the same way.

Caveat: Don’t underestimate the power of specificity when you approach even an established, long-term contact.

 For example, many people I know ask if they can speak at a Writer’s Digest event or contribute to the magazine. But they don’t exhibit knowledge of past programming or editorial content—or pitch specific ideas. That makes my job a lot harder (particularly when it’s via e-mail), because now I have to take time to educate that person or help him brainstorm how he ought to contribute. Never assume someone has the time to do this. Plus, if it’s not obvious to you how you should contribute, it might not be obvious to them, either.

When in doubt, give your contact something specific to say “yes” or “no” to. I guarantee it will result in more frequent (and faster) responses.

Asking Good, Specific Questions

For those who read the Brazen Careerist, I am beating a dead horse, but the better questions you ask (in any situation), the more you will learn, and the more quality and helpful responses you will get. Here’s an overview on why: 

When people e-mail or call me asking broad questions like:

“How can I get published?”

“How do I market my book?”

“I keep getting rejected. Tell me what to do next?”

“Should I self-publish?”

It makes me wonder what kind of response is expected, since hundreds—if not thousands—of instruction books, courses, and videos are available on these very topics!

Such questions cannot be answered in a reasonable length e-mail or phone call, and posing such questions risks disrespecting the person you’re asking. (It calls for a significant investment of time, expertise, and energy.)

So, find out everything you can on your own—go as far as you possibly can through online and offline research. Then, when you hit a real brick wall or dilemma, ask a very specific question that will help you take the next step.

That’s the way to ask a question that respects a person’s expertise.

Finally—especially when you ask for anything that would be a favor—you need to spell out exactly what you are looking for. Don’t generally ask, “Can you help me out in any way?” Ask specifically for what you want. People who are doing the favors shouldn’t be expected to come up with what they should give you. Outline (even in a bulleted list!) things that they can quickly say “yes” or “no” to, without thinking hard about it … Because most people want to be helpful, but as soon as it becomes a complex task, they’ll save their energy for something that has far more power to impact them—like the demands of their boss or job.

This article originally appeared on Writer Unboxed.

About Jane Friedman

Jane Friedman has 20 years of experience in the publishing industry, with expertise in digital media strategy for authors and publishers. She’s the co-founder and editor of The Hot Sheet, the essential publishing industry newsletter for authors, and the former publisher of Writer’s Digest. In addition to being a professor with The Great Courses and the University of Virginia, she maintains an award-winning blog for writers at (more than 180,000 visits per month).

Jane has delivered keynotes on the future of authorship at the San Francisco Writers Conference, The Muse & The Marketplace, and HippoCamp, among many other conferences. She speaks regularly at industry events such as BookExpo America and Digital Book World, and has served on panels with the National Endowment for the Arts and the Creative Work Fund.

She has a book forthcoming from the University of Chicago Press, The Business of Being a Writer (2017).

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