Lessons from a failure: Ghost writing pitch

When I pitch myself for a freelance writing or editing job, I almost always win. Why? Because I am selective about the gigs I pursue, have sterling qualifications, and typically come recommended by someone the potential client trusts. But I just lost out on a job — a big one that I really wanted. I usually write about success, but I thought you might benefit from hearing about my failures, too.

I was invited to pitch a ghost writing gig. The prospect was a prominent CEO

Several weeks ago, I heard from contacts at a ghost writing agency I had worked with. The owner of the agency wanted this business, and thought I was an ideal writer for the job.

Before I go on, you should get used to the way ghost writers describe themselves and their clients. The client is referred to as “the author,” and their name goes on the book. The ghost writer is referred to as “the writer,” because they’re the ones doing the assembly and writing of the words.

In this case, the potential client author was the CEO of a prominent company. While I can’t share the name of his company, you absolutely would have heard of it and have likely used its products. This CEO had an amazing personal backstory, and his ideas on management were fascinating. Not only that, he had already pitched the book to publishers and made a publishing deal. Taken together, those qualities made the job irresistible to me.

Ghost writing a whole book at this level is a commitment of six to twelve months. Given my qualifications and track record, I’d be charging a six-figure fee. That level of commitment and compensation comes with risk, and a big job like this crowds out other work, so I’m very selective. But this job looked ideal to me, and seemed like a great challenge that I was well suited to take on.

How I pitched this project

I did all of the following to prepare to win the business:

  • Assembled a resume and list of projects, tailoring the latter to demonstrate particular skills that would be useful for this project.
  • Reviewed media about the author, to become as familiar as I could with his story. There was a lot of it, and it confirmed that the author was a fascinating person.
  • Interviewed with the author on Zoom, and shared what I knew about the challenges he was facing and about my previous ghost writing work. I’ve ghost written two business books and edited a whole lot more, including the soon-to-be published autobiography of another prominent CEO.
  • Realized that, in an incredible and fortunate coincidence, one of my most treasured professional friends, who was also an editing client of mine, already had a trusted business relationship with the author. I worried it might violate the author’s confidence to tell my friend he was writing a book, so instead, I suggested that the author contact my friend to hear more. Even without speaking to my friend first, I knew that the author would receive a strong recommendation for me, and I was right.
  • Sent the CEO a followup email the next day. He responded positively.
  • Asked his admin for his home address, and sent signed copies of books I’d written and ghost written by overnight post, along with a cover note about my desire to do the project.
  • Worked with the agency on how to price the job. (The agency insists on doing all the financial negotiations, but the agency and the writer usually collaborate on a pricing proposal.)
  • Sent another followup email to the author a few weeks later. Again, the CEO responded positively, telling me I was “top of the list so far.”
  • I got indications from the agency that the author wanted to negotiate the price. This was a positive sign of real interest.

The interview

The author’s admin set up a 45-minute in-person meeting for me with the author. At that point, as I learned from the agency, it was down to two people, me and one other writer.

What would happen in that meeting? I felt it was important to prepare. I did the following:

  • Requested a copy of the book proposal that the author had used to land the publishing contract, which the agency shared with me. The author had since parted company with the writer who worked on the proposal, because that author couldn’t capture his “voice.”
  • Had another, more focused conversation with two people from the agency, to get as clear an idea as possible about what the author needed and what had changed since the proposal.
  • Reviewed my notes from the previous Zoom conversation to get a bead on what the author needed.
  • Decided to focus, not on my qualifications, but on what I though the book needed, which was a clearer definition of the main idea.

I also got a haircut and beard trim, since I haven’t had an in-person business meeting with a potential client — or anyone else, for that matter — in the last three years of the pandemic. For good measure, I took a COVID test and assured myself that I was negative, in case the author asked.

One good thing about my background as an analyst is that I’ve met with many CEOs of big companies and other prominent leaders, typically in a position where I was going to provide advice. Your attitude in such meetings is key. You cannot be obsequious, or they will not respect you. You cannot be arrogant, or they will be offended. You must be clear and truthful, and if necessary, respectfully challenge people when you think they are wrong. This was the approach I would take with this potential client.

I arrived at the meeting carrying a few of my books, including the two I’d ghost written, and a copy of the author’s previous proposal.

The CEO was very hard to read in the meeting — I think that’s just the way he is. He did ask some questions.

  • He asked what process we would use. I mentioned the very different processes that I’d used with other authors and said it would depend on how he preferred to work. Later in the conversation, once I got a bead on the content he’d already created, I described a clearer potential process.
  • We talked about his ideas, and how we could work on refining them, as I’d planned. I talked about the shortcomings of the organization of the book that the proposal included, as well as the voice in it.
  • He asked about whether the books I ghost wrote were New York Times bestsellers. I told him they weren’t, but said the book I had cowritten on the topic of social media was a bestseller. He asked what it took to be bestseller — I said that it took a great book, a prominent author, great promotion, and luck in timing.
  • Of the two books I ghost wrote, one had not been included in the package I had sent to him. He picked up on that, took the copy I’d brought, and asked if it was any good. I told him that it was an interesting idea, but not really practical to implement, which was my honest opinion.

I followed up with an email describing the process I thought was best for the project.

Why I lost

The day after my meeting with the CEO, he emailed to tell me he had selected the other writer.

I was bitterly disappointed, of course.

When this happens, it’s tempting to invent comforting reasons why you lost the business. I considered such reasons, as anyone would. Here are some of them, along with why they are false:

  • The agency didn’t pitch me well enough. [In fact, the agency selected and promoted me and answered all my questions in detail. They were an excellent partner, and I’d never have had this chance without them.]
  • The guy doesn’t understand what it takes to get a book done. [Of course he doesn’t. It was my task to explain that, and I didn’t do a good enough job at that.]
  • He’s too fixated on the New York Times bestseller thing. [Probably. But if that’s what’s important to him, I should have had an answer for that.]
  • He must not be all that hot shit of a guy as he appears to be. [Nothing changed except that he turned me down. I thought he was amazing before, and he still is.]
  • I used his product recently and it wasn’t so great. His company isn’t so wonderful. [That’s just self-justifying bullshit. One experience with his product doesn’t change the great management job he was doing.]
  • He wasn’t serious about me as an option, I was just a fallback. [He had interviewed ten writers and despite a busy schedule, had clearly reviewed my books and spent time in person with me. I had a fair shot. CEOs like him don’t often schedule meetings that are a waste of time.]
  • He already dumped one writer, I’m probably dodging a bullet. [Maybe. But the reasons I wanted this job hadn’t changed. If I were given the chance to work with him now, I’d still take it.]
  • I guess I suck. [Nah, I’m pretty good, actually.]

These statements are all self-serving, self-pitying excuses. If I let myself off the hook by believing lies like that, I would never grow and learn anything. After four decades as a writer, I know who I am, I know who clients are, and I know how business works. I’m way too experienced to wallow in self-deception.

Looking back, all of things I did leading up to the in-person interview were just right. I wouldn’t change any of it.

I believe I failed in the interview. I should have concentrated more on the process I use to turn authors’ content into books, which is what he was focused on. I should have more clearly explained how my extensive editing work was highly relevant for structuring the ideas in his book. Once he said he was ready to completely move on from the existing proposal, I should have stopped talking about the shortcomings in that proposal. And I never should have criticized a book I ghost wrote. I was too honest and naive and was not thinking strategically about my answers.

I can chalk it up to being rusty at in-person meetings, but in the end, I should have been more focused on what his real problems were. (Salespeople reading this are probably saying, “Duh, of course,” but I’m not really a salesperson, I typically focus on my abilities and how they apply. That has worked because usually the person is sold before they even connect with me.)

I also found out, secondhand, that the other writer has ghost written multiple New York Times bestsellers. If I’d known that, I would have focused on what I believe the author’s real objective should have been — namely, making the biggest impact, not getting on the New York Times list. It would be easy in hindsight to say, hey, how could I compete with another writer with those qualifications? But I still think I am extremely strong on writing and ideas, and I bet the other guy wasn’t an analyst for 20 years. I had a case to make. I didn’t make it. That’s not on the client, the agency, or the competition. That’s on me.

What I learned from this

In my sixties, with seven years freelance experience, I’m still learning useful things about my trade. At this point, I am pretty adept at what I do, but not as adept as I need to be at selling what I do. Here’s what I learned — and I hope these lessons may be useful to to you as well.

  • Making excuses for your failures is counterproductive. Wallowing in them is worse. The only question worth asking is, “What did I do well, and what could I do better next time?” Come to think of it, those are the same questions you should ask when you succeed.
  • I have grown used to winning these bids easily. In the future, I will assume that there is choice between myself and someone else well-qualified, and will put a level of effort into preparing that is appropriate, given that they might pick someone else.
  • I am most comfortable talking about ideas, which is a strength. And I’m certainly good at talking about myself. I should put equal or greater emphasis on talking about what my potential client is concerned about. In this case, that was process and becoming a bestseller — both of which I can address, but failed to address clearly.
  • I focus on being honest. (It’s the easiest way answer questions.) I will also focus on understanding why clients ask particular questions, and on which of my potential honest answers would best address their core concerns.

One more thing, dear reader. Please don’t waste time responding to this post with “You should have won, you are talented,” or any of that blah blah blah. I don’t need comforting and I am not lacking in confidence. But if you learned something from this post — or have additional insights on these sorts of failures — I’d love to hear about that.

Have you failed lately? What did you learn?

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  1. This was highly instructive and I appreciate you sharing the story and your honest reflection. I had a similar experience. I was crushed because I thought I had the work. When I was passed over I took the high road and wished him success. Two months later his first choice failed and I got the call. It turned out to be a great project and a big lesson about behaving with grace.

    1. I’m very glad to see your comment. I too wished the potential prospect well. It is never a good idea to make an enemy just because you were a sore loser. And as you learned . . . it often pays off in the end.

  2. You prepared extensively. You have relevant experience. Your emphasis was just slightly different than what the executive was looking for. For a failure, it was a pretty honorable one.

  3. Josh

    I assume you’ll read this book and mentally compare it to what you think you might’ve written. Other than possibly feeling that your book would’ve been better, are there any specific things you might learn from such a comparison? Also, do you think you’ll learn anything about the author/writer relationship? Is there scuttlebutt of this type in the ghost writer community?


    1. I’ll read the book. But I’ll do it because I want to see how the CEO tells his story (or how the other writer tells it, I guess). I won’t be mentally comparing myself to him.

      If there’s a community of ghostwriters, I’m not in it.

  4. Loved this post. Very informative and instructive and productive. I’ll still say you probably should have gotten the job; however, your “failure” is probably more instructive than your many successes. Thanks so much for sharing.

  5. Josh, I think I would describe this post as (and I use this verb in the kindest possible way) “Failing without bullshit.” 🙂

    Bravo for your honesty, and kudos for having the guts to share it with us.

    Clearly, you wanted this job very badly. It would have been good for your portfolio, your bank account, and maybe even your soul.

    So I have only one question: how can you find and win more gigs like this one? You’ve learned some good lessons here – how can you apply them to create better relationships with agents, editors, and maybe even CEOs? How can you help *them* get what *they* want?

    You have the writing skills – that’s not the issue. And now your people skills are even better than they were before. So I guess I’m suggesting that you lever your newfound wisdom to create more soul-fulfilling opportunities like this one!

    1. It’s not just people skills — that’s not enough by itself to win over the most senior potential clients. Let’s just say I learned a lot about preparing for and operating in interviews! Since I already think strategically as a matter of habit — a legacy of 20 years as a strategy analyst — I think the biggest thing I learned is “Pause, and understand what’s driving the question you’re hearing.”

  6. Thanks for sharing. Very instructive (and impressive!). A few comments from a sales & marketing perspective:
    – when a new requirement (“write a bestseller”) comes out at the end of the sales process, it’s a good bet it’s the key differentiator of your competitor. And that it is offered to you in the spirit of (often) asking for help to overcome it (i.e., tell me why you’re better / how I can get this thing and get you, too).
    – “I turn business leaders into best selling authors” is a fantastic differentiator / elevator pitch. But there are others. I would imagine yours would be something about creating a compelling vision of the future (vision / future-proof / story telling / ???). At any rate, it might be a good exercise to develop your own elevator pitch for this type of opportunity, or look at yours and see if it still serves you at this level.
    – Sometimes people just want a formula. Especially if they haven’t done something like this before. I’ve always been fascinated by the different approaches of analysts vs. consultants, who often have a much more prescriptive approach. Maybe there’s a similar analogy here.
    – The homework you put into this is truly impressive. The one question I have (which may not be relevant here) is if you tried asking who the other finalist was. I am amazed at the things people tell sales people because they ask. 🙂
    Congrats again on what seems like the start of a new chapter.

    1. That’s a really high quality set of questions you ask, Erin!

      Nobody can promise to make a bestseller. It’s dependent as much on marketing and promotion and the client, not the quality of the writing. I should have said “Good writing is an important element of becoming a bestseller, but that’s actually much more in control of the author/client, not the ghostwriter.

      I didn’t ask who the other finalist was. I could have — but I doubt they would have shared that. I think I do have a better answer on the process question.

      And I think my differentiator is “I help make your ideas better and catchier, and help you express them as powerfully as possible.”

    2. I echo Erin’s thoughts and include another factor: risk aversion.

      “Make it a NYT Best Seller” also came across to this bruised and battered sales-guy-to-execs as a trumping criterion. I think all the things you prepped for and presented were absolutely necessary to get you to the final round. All of those things you discussed with him likely impressed him, and he will quite possibly recommend you to his peers as somebody to consider.

      However, when selling something that the prospect has no personal experience living through, risk aversion prevents them from choosing the option that has never delivered that one thing their heart feels they need. The competition had *several” best sellers, not just one. That “proof” was just too overpowering that the other guy would deliver the one goal that motivated his entire effort to make the book happen: fame & respect. IMO there was nothing you could have done to overcome it.

      And I love your “after-action review.” Very helpful! Thanks.

  7. Thanks for writing this post! One thing that stood out for me and I’ll probably be using it everytime I send out a pitch from now one was the set of questions you used to not fall in the comforting reasons trap. I have just started out as a writer and it’s easy to find an excuse than digging deep & coming out with a conclusion.

    I’ll be using that section as a self-reflection template. Maybe I’ll get a printout and pin it on my wall.

    Anyways, thanks again for the share 🙂

  8. “I have grown used to winning these bids easily” resonated with me. From now on, anytime I propose some work, I’m always going to assume I’m competing against the toughest competitors.