A generic pitch won’t win a big contract. Here are 5 tips that will.

Photo: Paul L. Dineen via Flickr

I’m affiliated with a ghostwriting agency. The way they work is simple: they send an opportunity to their mailing list every week or two, and anyone on that list can respond. I’ve snagged the opportunity every single time I’ve pitched them, but I recently communicated with a woman who’d failed every single time. Reviewing her pitches — and her strategy — helped me to see what it takes to win when pitching big opportunities.

These ghostwriting opportunities are significant contracts. I’ve pitched to ghostwrite five proposals and two whole books, to edit three books, and to do writing coaching. I am almost always the highest-priced alternative, and I almost always win.

These jobs are significant, generating $10,000 to $120,000 each. And they’re competitive — often 5 or more writers or editors will be vying for the same gig. The contraction in the publishing industry has generated a glut of freelance writing and editing talent.

My approach is instinctive, but my friend and her failed attempts made me think more carefully about how I approach these challenges. For what it’s worth, here are some general tips for freelancers pitching major gigs, whether they’re writing gigs or any other kind.

1 Be selective

My ghostwriting agency might share 30 to 50 opportunities a year. I only pitch two or three. My niche is very clear: I write fact- and case-study-based thought-leadership books and articles about marketing and technology trends. I can realistically claim that I am the best writer and editor available to do jobs like that. I am not the best writer to ghostwrite a memoir, write about politics, do a rah-rah self-help book, or write about investing. So I let those opportunities sail right by.

If I pitched more, I’d have to put less effort into each pitch. As I’ll describe here, that doesn’t work.

2 Research clients carefully

The research starts with reading the opportunity email carefully. Who are these people who want to hire me? What are their objectives likely to be? These are blind opportunities — the ghostwriting agency does not reveal the name of the client, because they don’t want you contacting the client directly. Even so, I can usually get a clear idea of what kind of people I’m pitching — Silicon Valley CEOs or high-end consultants, for example — and make reasonable guesses what their mindset would be.

In one case, I had a feeling I knew exactly who the company was based on the description. This enabled me to make a highly tailored pitch. I still didn’t go around the ghostwriting company, because that would likely not win the business, but would rightly get me blackballed from all future opportunities. Integrity matters more than the agent’s fee.

3 Customize everything you send

Start with the resume. My ghostwriting and editing resume is completely different from the resume I would use to get a job. It has no “objective” at the top. It is focused exclusively on my work on books. I portray my experience as a Forrester analyst primarily in the light of the five books I wrote or edited there. It makes me look like a book writer and editor, rather than an ex-analyst and technology executive.

My friend’s resume was her generic resume — it included a long list of projects as a writer, including articles and editing positions and an earlier gig as a copy editor. Most of those projects were irrelevant to somebody hiring a ghostwriter, and the length of the list of projects is not nearly as important as the quality and relevance of the things on it. Her resume inadvertently communicated something else — “I don’t know how to focus on what matters.” That’s not a good quality for a writer.

In addition to the resume, I send a one-page project list of books (not articles) I’ve written and edited. It describes, for each one, what my role was and what notable success the books have had (blurbs or sales, for example). Each one includes a link to the Amazon page for the book so the prospective client can look them up. The roles I list are simple: author, coauthor, editor, proposal writer, ghostwriter. Everyone in the industry knows what they mean.

I also include a cover letter that describes, in a page and half, why I am exactly the right writer for this particular project, based on specific work I’ve done in the past. When I pitched an innovation management CEO, I described how I’d written about innovation in past books. When I pitched an AI startup, I listed the AI-related projects I’d done for other clients. I also address potential objections. For example, I got one of the book ghostwriting gigs despite the fact that I’d never ghostwritten a book before then. In my cover letter, I explained why I was ready to ghostwrite that based on my other collaborative book projects.

My friend wondered why I didn’t just put the cover letter content in the email responding to the opportunity. I think a 400-word email is a little unwieldy. I also feel like the agency and the client are looking at packets of content attachments, and including the cover letter in that packet is stronger than just putting all the text in the email.

You might wonder if I focus on the needs of the ghostwriting agency or the client. I focus only on the client. And I know the agency does, too. If I send the right package for the client’s needs, I know the agency will send it through to the client along with a few competing bids. At that point I’m confident I’ll win our over the other people who made the cut.

4 Choose writing samples carefully

I send two or three writing samples along with the resume, project list, and cover letter. I choose these samples carefully. I sent innovation-focused samples for the innovation management gig and marketing-focused samples for marketing writing gigs. I always make it clear if I wrote, cowrote, or edited the sample.

Some of my writing is good. Some of it is great. (I imagine some of it is weak, but I try to forget about those bits.) I try to send the writing I think is great, but again, only if it’s directly on point. I might send one great sample that’s a little off topic and one good sample that’s right on target. There’s no penalty for sending two or three samples.

There is, however, a penalty for sending samples that are too long. I send pieces that are 500 to 1000 words long. If they are so intrigued that want to know more, they can easily buy the books.

5 Be consistent and don’t budge on price

If I’m lucky (and I have been), the next step are conversations with the client. Everything I say in those conversations is absolutely consistent with everything I put in the pitch. I don’t pretend I’ve ghostwritten what I’ve only edited, and I know the details of every project since I lived through them. If they contact my past coauthors, editors, or other clients, they will hear exactly the same things I am telling them. This is the advantage of telling the whole truth — there’s no need to keep the story straight.

Once we get into more detailed discussions, I estimate the time the project will take, multiply by my hourly rate, and create a quote. Then I don’t back down. I am worth what I am worth and this is not a price negotiation. I have quoted editing jobs that I missed out on because they wanted somebody cheaper, but if they want somebody cheaper, they don’t want me.

I do craft the quote so there are milestones with payment throughout, where I accomplish specific goals (like drafting half the chapters). This ensures I don’t get held up waiting for payment for a project that drags on. On book writing projects, the first part of the project is typically creating a book proposal, including a sample chapter. I put a mutual option in the contract so either party can cancel after the proposal is done and paid for. This gives me a chance to parachute out if the client is awful (hasn’t happened yet), and gives them a chance to opt out and get another writer if they’re not happy with my work (that hasn’t happened yet either).

I recently heard about a pricing strategy that I will adopt in the future: a retainer arrangement. One of my projects has dragged on far more slowly than I’d imagined, so I ended up doing the work and getting paid much later than I thought. In a retainer arrangement, you get paid every month, and then when you hit milestones you get paid for those, minus the money already paid on the retainer. This encourages the client to move a little faster since there’s a cost to waiting around.

Pitching is work. Do it with energy, integrity, and intelligence

It would be a lot easier not to do the work I’ve described here. If you created a generic resume and generic pitches, you could send a lot more of them out. You would have reach.

The most likely outcome of that is that you wouldn’t get the work. Twenty generic pitches are less effective than two carefully focused ones.

But you might get the work. If you did, you’d get clients who were focused on price and not very selective. They wouldn’t appreciate the special skills you have, and they wouldn’t pay for them.

But you would have saved a day’s effort in crafting the pitches.

I think this is an easy choice. But hey, it’s up to you.

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  1. Great stuff, Josh. Given that so many media and PR pros are experiencing layoffs, might you write an article about getting started freelancing? You mention a few examples of pitching when you hadn’t yet done what was asked of you (ie ghost written a book), but the tips you offer seem mostly those of an experienced hand. Thank you.