Your Pitch: Go Legal, Go Short, Go Reality

If you want to master communicating and building relationships with the gatekeepers, tastemakers, potential customers, etc within your industry, the first step is to leave your industry.

About ten years ago, I ran across Michael J. Critelli’s Harvard Business Review article “Back Where We Belong.” I kept a copy of the article, surprised that a Pitney Bowes executive had mentioned the book The Sling and The Stone. I was repping the title and it was not a business book, nor one I had considered pitching to a business audience. However… Critelli’s attention to the defense world as a part of his “ear to the ground” strategy made sense. (It’s even more interesting to read now, as Critelli wrote the article during a time of great upheaval in the shipping industry, which plays into shipping today.)

A few takeaways from the article:

1) I needed to pay more attention to cross-over audiences. Who else might be interested in the projects on which I was working?

2) I needed to learn the language of different audiences. I could speak defense and history, but was not fluent in business and other potential crossover industries.

Going Legal

One of my college roommates used to tease me for saying everything twice. For example, if someone asked my opinion, I might reply, “You’re right. You’re definitely right.” If they needed to learn how to do something, I might say, “You need to go to the store and buy x, y and z first. You can’t do it without buying x, y and z first.” I didn’t pay attention to my looping dialogue until her good-natured teasing, but I’ve self-edited ever since.

Digging into the legal industry has been helpful as clarity is key within the legal world, where wordiness and poorly-thought-out letters can lead to trouble. You’ve got to get to the point and edit out the distractions.

Letter to the Stranger

From Emotions to Advocacy by Pam Wright and Pete WrightAmong the best advice I’ve read about writing letters (both within and outside the legal world) is in Pam Wright and Pete Wright’s book From Emotions to Advocacy. I’m partial to the book’s “Letter to the Stranger” section, in which the authors ask readers to:

Assume that before you mail your letter, your letter slips out of your notebook and falls into the street. Later, a Stranger sees your letter and picks it up. The Stranger puts the letter in his pocket and takes it home to read. What impression will your letter make on this Stranger?

The authors offer the example of seeing “couples arguing or parents disciplining their children in public” — something we’ve all experienced. They then ask:

What was your reaction? If you are like most people, you felt uncomfortable. Perhaps you had a stronger emotional reaction. You did not like it! You felt sympathy for the person who was being humiliated. People have the same reaction when they read angry letters.

In a previous article, “How to Pitch,” I shared a number of e-mails/letters that Steve and/or Black Irish Books have received, with examples of what to keep and what to avoid within the e-mails/letters. I didn’t include “Angry Letters” as a section, but what the Wrights wrote about angry letters applies to all categories of letter writing.

Strangers receiving your letter are viewing one slice of you/your project. They don’t have the full context, just as you don’t have the background for the couple fighting in the park. That couple’s appearance in your life is similar to your letter’s appearance in the life of a journalist (or potential customer or anyone else). It is unexpected, and often unwanted, contact. Your letter can not turn off the journalist the way the arguing couple turned off passersby. You want to engage, not push away.

Keep it Short.

A Time to Kill by John GrishamThere’s a scene in John Grisham’s A Time to Kill, when head-honcho lawyer Jake Brigance is waiting for the District Attorney to finish his opening statement. Both he and the D.A. have an hour each to make their statements. The D.A. eats up every minute, which results in his losing the attention of the judge, the jury and even the court artists. Jake Brigance decides to go short. He knows:

Most people don’t like lawyers to begin with, especially long-winded, tall-talking, wordy lawyers who feel that every insignificant point must be repeated at least three times . . . Jurors especially dislike lawyers who waste time, for two very good reasons. First, they can’t tell the lawyers to shut up. They’re captives. Outside the courtroom a person can curse a lawyer and shut him up, but in the jury box they become trapped and forbidden to speak. . . . Second, jurors don’t like long trials. Cut the crap and get it over with. Give us the facts and we’ll give you a verdict.

It’s a fiction example that is repeated in the non-fiction world daily.

After you write your letter, identify the adjectives and then delete, delete, delete. Same with repeating sentences. Get your point across in the first try. Just when you think you’ve finalized your letter, read it out loud to make sure it is a letter you’d want to read yourself — and then try to cut it in half.

What’s the Skinny?

Many of the e-mails we receive include embellishments, such as calling a workshop or seminar a summit, or using other words to fancify reality.

Reality can be painful and it can lengthen the process, but it often leads to open-minded people who value the truth. The most extraordinary people I’ve met have been the ones who are open and honest about their personal realities.

In the comments section, following my “How to Pitch” article, John C. Thompson shared the content of a letter he wrote years ago:

Dear Jack Knopff, I just got out of prison. I accepted Christ as my Saviour and I am turning my life around. I have the rudimentary skills of a bookkeeper. Based on your expertise, what would you recommend I do. Respectfully, John C Thomson.

It was an extraordinary letter to write, so I asked John for more information. The following is an excerpt from what he sent. It’s an equally extraordinary story.

I was 13 when I was first arrested, I would be 33 when I was last released from prison (a 19 year period). I had spent 17 ½ years in confinement. What would I have learned that was transferrable to the job market? I wasn’t skilled, disciplined, nor did I have the wherewithal to conduct a successful job search. . . .

I had read several books on job hunting. While I learned how to prepare a resume, I was extremely lacking in the job experiences to put in it. I walked out of D. Wm Berry and Associate and headed to the newspaper stand on Chicago and Main St. A Crain’s Business Report headline grabbed my attention. “The Top 100 Privately Owned Companies in Chicago.” An idea slowly developed in my head, and I purchased the magazine. I would write a letter and address it to the CEO’s and presidents of companies and bypass the Human Resources Department. At first I thought I would test my plan and contact the bottom of the 100 list, but hey, why would they hire me any more than the top ones on the list? I would start by contacting the top 20 on the list, and include several local large companies in Evanston, such as Northwestern University, Evanston Hospital, Washington National and American Hospital Supply.

Now for the letter. I had nothing with which I could impress them, so I altered my approach. It was entirely opposite from what anyone else would do. In the body of the letter, I told them three things.

1) I had recently been released from prison.

2) I had accepted Christ as my Saviour and had turned my life around and was starting a new life.

3) I had the rudimentary skills of a bookkeeper.

I closed the letter with a question. “Based on your expertise and experience what would you suggest I do? After I wrote the letter, I passed it around to three English majors and my wife. I asked them to edit the letter for grammatical perfection, but don’t change the letter itself. We prayed and then mailed the letter.

Of course there is the rest of the story, but I was hired by Leo Burnett Advertising in Chicago and six months later hired away from them by Northwestern University.

I admire how honest John was about his past and how he didn’t ask for pity/sympathy. He stated the facts, kept it short, and stuck with reality. (John, if you’re reading this, I hope you’ll share the full story with all the readers).

Go legal.

Go short.

Go reality.

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Steve shows you the predictable Resistance points that every writer hits in a work-in-progress and then shows you how to deal with each one of these sticking points. This book shows you how to keep going with your work.

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A short book about the writing of a first novel: for Steve, The Legend of Bagger Vance. Having failed with three earlier attempts at novels, here's how Steve finally succeeded.



Steve shares his "lessons learned" from the trenches of the five different writing careers—advertising, screenwriting, fiction, nonfiction, and self-help. This is tradecraft. An MFA in Writing in 197 pages.



Amateurs have amateur habits. Pros have pro habits. When we turn pro, we give up the comfortable life but we find our power. Steve answers the question, "How do we overcome Resistance?"



  1. Erika Viktor on April 22, 2016 at 6:26 am

    I think we value reality because its part of growing up. The wizard behind the curtain is perhaps the best metaphor for this. He’s just an old guy with fancy gizmos. In other words, human.

    Selling a fantasy works on younger people and inexperienced people, sad and desperate people. But the truly learned, wise and experienced have the ability to cut through the bullshit and even grow to resent it when its offered on a silver platter, billed as gold. Maybe that’s why reality is so refreshing to them.

    Thanks, Callie! I’m really enjoying these segments.

    • Callie Oettinger on April 26, 2016 at 10:24 am

      Thanks, Erika!

  2. David W Arndt on April 22, 2016 at 7:09 am

    Just read Publishing House Spy piece on your site. Well played. -d

    • Tina M Goodman on April 22, 2016 at 1:53 pm

      I also read the interview with Chaz.

  3. Mary Doyle on April 22, 2016 at 7:53 am

    This is a terrific series Callie! Making those links to cross-over audiences is not something that comes naturally to me, but I’ll be paying more attention and challenge myself to think outside the box. Thanks also for mentioning “From Emotions to Advocacy.” Self-editing is an art well worth cultivating. I field a lot of email inquiries in my work and am continually amazed at the level of (barely disguised) BS. As always, thanks!

  4. Michael Beverly on April 22, 2016 at 1:33 pm

    When I read “keep it short” I thought….oh,,she’s talking to me…

    Ha ha.

    I find curbing my writing very difficult.

    So, my latest struggle: I’m trying to decide whether to create a female pen name for my WIP romantica series or not.

    Standard procedure is to to this.

    However, I’ve received conflicting advice, and one of those advisors said something that you’ve mirrored here:

    I don’t know what cross over audience I’ll lose by creating two platforms.

    After reading this, I’m leaning towards branding the series differently, but keeping them all under the same pen name branding.

    In other words, if you like my thrillers, you might like my romance. If not, no worries, but you’re smart enough to read the genre categories and decide for yourself.

    I think that’s where I’m landing. Not 100% yet.

    Final thought: Gladwell’s book Blink had an explanation about how humans make fast and early decisions about things, ie looking at a two pictures of tribesmen, people could accurately pick out the peaceful from the cannibals.

    So, this “Letter to a Stranger” conveys the same idea:

    The reader can pick up on hidden clues and form an opinion right away.

    That opinion will cloud everything, good or bad.

    So make it good.

    Me: I love bunnies, flowers, and puppies. World peace and friendship and love.

    So, yeah, can I borrow the car?

    • Callie Oettinger on April 26, 2016 at 10:23 am


      Your first line launched a laugh!

      I’ve always understood the reasoning behind authors going with different pen names for different genres, especially if the genres run to extreme opposites. For example, I have a friend who has been trying to break into children’s music and television for years. She does adult comedy, too, and at one point was given the advice that she can’t be branded for both, that parents won’t trust someone who does an adult act, too. But… Then there’s George Carlin. The majority of his work was on the “R” rated side, yet he voiced the engineer for THOMAS THE TRAIN television series. How did I feel when my kids watched Thomas w/Carlin on board? Made me smile every time I popped in the DVD.

      So I’ve understood the reasoning, but I’ve not been sold on it being the right route, because it means artists spend a lot of time recreating themselves for different audiences, which pulls from the time needed to do their work.

      Another example:

      When Steve released THE AFGHAN CAMPAIGN, he did a book signing event at the Naval Academy. By the time we arrived all of the books had been sold in advance, so I pulled a few boxes from my car for the store to sell. Those, too, went fast. At the end of the line were the students who hadn’t thought to buy the book before the signing. Two students from this group remain cemented in my mind. The first one looked panicked when he reached the table. THE AFGHAN CAMPAIGN was sold out and the only other book on the table was THE WAR OF ART. Steve apologized and held up THE WAR OF ART saying it was the only book left, but he understood if it wasn’t something of interest to the student. The young man mumbled something in return and stumbled away from the table. The second student had his own weathered copy of GATES OF FIRE. He’d ran back to his room to claim it when he realized there weren’t any other Pressfield books in the store for signing. Steve signed it as the student said how much the book meant to him and then asked Steve what he was planning to write about next. Steve said he had a book set in WWII on the horizon. Words failed the student for a few seconds, then he spit out, “No ancient world?” Steve said, “No,” and repeated that the next one would be set in WWII. The second student channeled the previous student’s mumbling and stumbling ways and left. In his mind, Steve’s work existed in one realm.

      Same thing happened when THE PROFESSION was released and Steve did an event in Pinehurst, NC, which had a number of copies of THE LEGEND OF BAGGER VANCE available, too, for the Pinehurst golf crowd. Two soldiers from Ft. Bragg arrived early and stayed late to talk with Steve. One picked up a copy of BAGGER and asked, “What’s up with that?” as if Steve had been out of his mind for writing a book so different from GATES OF FIRE and the books that followed it. I cringed, while Steve remained gracious, smiling and shrugging his shoulders as he replied something along the lines of, “Just something different.” The soldiers put the book down and quickly transitioned into how they wish he’d write more like GATES OF FIRE.

      The decision Steve made was to be available to all audiences for his books, knowing that some people will like them and some won’t. This is where “the crossover” comes into play. There are fans who love the military fiction, other fans who are into the art/Resistance nonfiction books, and then fans who like everything.

      Sooo…. How’s that for NOT keeping it short, Michael? 😉

      It’s a lot, managing different pen names for different books. I get it, but because of everything above, I wonder if it wouldn’t be better for more authors to keep to one name. If a reader of romance isn’t into your work because you also write thrillers, that reader might not be one you want to focus on anyway. The readers who become life-long fans don’t tend to care. They know you work in different genres and their interest is in your work, not in judging you on the genres in which you work.

      Letter to a Stranger: The Gladwell example you gave is a good one — same with the car example. Think of the teenager wanting to borrow his parents’ car. If he’s a complete jerk, doesn’t do his chores, etc., his parents aren’t likely to hand over the keys. However, if he behaves, helps out around the house, etc… His parents are more likely to give him a yes.

      Thanks, Michael!


      • Michael Beverly on April 26, 2016 at 10:53 am

        My favorite Steven King book is Dolores Claiborne.

        Flashing on that, I realize how much what you’ve just written above is my answer.

        “Thank you,” I said. Proving I can keep a post short and to the point.

  5. Tina M Goodman on April 22, 2016 at 1:52 pm

    I communicate like a lawyer. I was told that it makes people not like me. It’s nice to know that my style could be beneficial when pitching. Thank you.

    • Callie Oettinger on April 26, 2016 at 9:35 am

      Tina, Thanks for your comment. If their definition of communicating like a lawyer is someone with to-the-point and void-of-bias-in-messaging, then yes, communicating like a lawyer has its upside. Best, Callie

    • Sean Crawford on April 26, 2016 at 3:21 pm

      “Like a lawyer” if you mean concise, is terrific in meetings and groups and teams. If I do so, if I think before I speak, then I am considerate of the group.

      If I’m with only one or two people, then being considerate could mean paying attention to the other people’s speech rate, intensity, depth, loudness…

      To put it in metaphorical terms, the best long joke in the world will fall flat if the others are doing quick snappy jokes. To put it in writer’s terms, they say the New Yorker likes to meander for the first page of an article before getting to the thesis or topic. That’s what those readers want.

      I think, Tina, you and I and some writers I know would socialize well together.

  6. amy cygan on April 28, 2016 at 5:53 am

    Just a note on letters.

    In 1999, I graduated with an Electronics degree and was looking for my first job in that industry. I found a company to submit my resume to, only I decided not to follow the advice that the campus lady from Career Services offered, namely: Don’t tell them you’re a mom with children (no one will hire you; they’ll assume you’ll call in every time your child is sick) and make sure your resume is typed.

    When the hiring coordinator was shuffling all the resumes, my handwritten one fell off the table and caught his eye. He read it, called me in for an interview, and hired me.

    The “handwritten” letter was “different” to him, which made him read it. The part about the “with children” appealed to him as well, as his best workers in the plant were the mothers; they were committed (i.e. when you need money, you work).

    Of course, nowadays there is such a big push toward online recruiting that it is becoming an art form to stand out from the crowd. Sad face for us old-schoolers … or maybe not; I’m certain there’s some ingenuity still to be had!

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