Are longer lists better? — Frequent Questions

Q: Are longer lists are better than short ones?
A: [steam coming out of ears] I. Hate. Lists.

longer listsElmore Leonard said writers should always “Try to leave out the part that readers tend to skip.”

If only we could identify those parts in advance, eh?

Well, some of them we can.

Like lists.

I hate lists.

They’re just plain lazy. And did someone say boring? Oh, you bet.

Bullet-pointed lists are meant to impress the reader, I suppose. Ooh—look at all the things! But to me bullet-pointing lists is like going to a networking event and throwing a big stack of business cards at a table full of strangers.

Would you ever be impressed by that? Ooh—hasn’t she been busy collecting cards!

Reader, I’m going to answer this one for you, because I know you’re not idiots. You would not be impressed by that. Not ever. Not only is it unhelpful—just like lists—it’s also downright rude. So don’t give your reader a bunch of things—tell them what’s special about each one.

Lists disguised as sentences at least show a bit more effort on the writer’s part. But they still lump everything together in an undifferentiated mass. If something is important enough for you to mention, it’s important enough for you to tell me why you’re mentioning it.

Longer lists are not better than short

If you insist on making a list, keep it short. And use what writers call The Rule of Three:

Wikipedia very appropriately offers three reasons this rule works. And they’re not presented as a list, either, so 10 points for Wikipedia:

The reader or audience of this form of text is…more likely to remember the information conveyed. This is because having three entities combines both brevity and rhythm with having the smallest amount of information to create a pattern.[2][3] It makes the author or speaker appear knowledgeable while being both simple and catchy.

I added the emphasis there. Now let me translate it into a more readable form: Your list will be more memorable, being shorter. Three is the fastest pattern you can create, and patterns are always more memorable. Plus, you seem smart—while being memorable.

I’d add a fourth use for the Rule of Three, because establishing and quickly breaking a pattern is not only memorable, it can also be damn funny. Breaking the pattern with the third item in the list gets a laugh because the listener recognizes the pattern with the second item and before they even realize they’ve recognized the pattern, you go and break it. For instance, you might imagine a flight attendant going through the airplane asking:

“Would you like coffee, tea, or Xanax?”

I didn’t expect that. Funny!

Breaking the pattern on the fourth or fifth item will only get you a confused stare.

“Would you like coffee, tea, soda, juice, or Xanax?”


The list that ate my headline

Back in the day, I sometimes wrote press releases for a—well, let’s be nice here—an extraordinarily picky client. For a press release about a famous artist, I wrote a headline that mentioned three of this person’s most iconic works. The client added a fourth. And a fifth. Still not enough variety. Pretty soon the headline was a laundry list—one of the longer lists you’ll ever encounter. (Pro Tip: Headlines are not supposed to take up half the page.)

“I don’t like the headline,” the client whined. “It’s too clunky.”


“That’s because you keep adding things to it,” I said. “Keep it to three things and it’ll be snappier”—and I named the artist’s three most iconic pieces.

I don’t remember how many pieces we ended up listing in the final headline, but I think only one of my suggestions made the cut. When the media wrote about the release, though, guess how many pieces they cited? Yes, three. Because journalists know what they’re doing. They also know an iconic image when they see it; all three were the pieces I’d suggested to begin with.

Don’t mess with the rule of three, folks. It’s smart, efficient, and journalist-approved. Tempted to publish longer lists? Don’t say Elmore Leonard and I didn’t warn you.

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FAWTSY — maybe acronyms aren’t all bad

One of the first things I noticed on stepping into Chase Field, home of the Arizona Diamondbacks, wasn’t the very impressive ballpark. It was a button on the ticket-taker’s shirt.

FAWTSY — funny word, great concept

An acronym. I hate acronyms—usually. I hate them because they’re confusing. Because they break the flow of your writing, as readers search for their secret agent decoder rings to translate your alphabet soup into usable English. I had to see the button a few times before I could read the translation—the button I saw on Sunday was a newer design, with smaller explanatory type.

So, yes, if I came across it while reading, “FAWTSY” would confuse me. Or at the very least make me stop thinking about the ideas the writer intended to present. But that brief cognitive interruption is exactly what makes this acronym a valuable marketing tool.

FAWTSY — Find a Way to Say Yes.

“Find a Way to Say Yes” is a great commitment to have your public-facing employees make. And a fantastic promise to your customers. If United Airlines employees had been held to the FAWTSY standard, the company would have avoided several recent public relations disasters. Not to mention a meltdown in their market capitalization.

FAWTSY, coined by the club’s former SVP of Communications and curgent CEO, Derrick Hall, has alowed the Diamondbacks to put their commitment to customers and other stakeholders front and center. But would it work in a speech?

I think you’d need the right audience—and the right speaker. Someone who could commit to the joke of making a nonsense word the centerpiece of their speech. And someone equally committed to the business message behind the “nonsense word.”

And it couldn’t be a one-off. You’d need to commit to this word for at least several months, rolling it out several times in speeches to diverse groups of stakeholders. You’d need some collateral, too—buttons, tennis balls, posters—whatever made sense for the company and the message.

If the message is important enough, and the company committed enough to it, then I would FAWTSY to a request to write a speech centered on an acronym. Now I wish someone would ask me: It sounds like fun.

Facts need stories, but only if you want them to be remembered

“I think this time we’ll cut down on the stories and just give them the facts.”

“Noooooooooooooo!” I didn’t actually scream, but you could definitely hear the italics in my voice. And then I remembered I was talking to my client.

“I mean, I’ll write anything you want me to write,” I said. Which is true; in the end, it’s their work. “But I’m just giving you the benefit of my expertise here. Facts need stories if you want anyone to remember them.”

Shortly after I got off the phone, I came across a blog I wrote a couple of months ago on Dr. Oliver Sacks, who excelled both as a scientist and as a storyteller. Lawrence Wechsler wrote in his Vanity Fair profile of the good doctor:

“He recently attended a conference on Tourette’s syndrome. Ninety-two specialists gave papers on EKG readings, electrical conductivity of the brain—all kinds of technical subjects. Sacks, the 93rd, got up and said, ‘It’s strange. I’ve been sitting here all weekend and heard not one sentence on what it might be like to be a Touretter.’”

Ninety-two researchers, not one mention of a patient. I’m sure their research contained an excellent array of facts, but nothing to make them memorable. Nothing to anchor them to the human experience. And even scientists are humans, so I’m told.

facts need storiesFacts need stories to transport them

If you want your reader or listener to remember what you have to say—and why are you wasting your time saying it if you don’t?—you must encase your facts in the colorful candy shell of a story.

Sorry—perhaps M&Ms are the wrong metaphor for scientists: You must encase your facts in the quick-dissolving capsule of a story.

A good story gamifies facts. Listening to a story may seem like a passive behavior, but inside—where it counts—stories activate our minds. We want to figure them out. We imagine different outcomes, look at them from various angles. Facts without stories just get filed away in a dusty corner of our brains. Why should we waste a minute on them? They contain no mystery, no possibility. Facts just “are.” Stories…well, stories “might be.”

Listen, I’m about as Type A as they come. When clients make with the small talk, they nearly always take me by surprise. But when I’m writing, I understand there’s no substitute for stories. They’re the only currency that matters.

I mean, write whatever you like; in the end, it’s your work. Still, if you don’t care about being memorable, you might as well just read your audience the phone book. It requires much less time and preparation. No one will be able to recall a thing you said. But you’ll definitely make an impression.

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Cutting remarks — when clients edit (sigh)

When clients edit, the result is often not prettyStrange things can happen to speeches when clients edit them.

I’ve been writing speeches for over 25 years; you’d think I’d be used to this by now. And largely I am. I don’t let myself get too attached to any piece of work. I’m very clear that it’s my clients’ work, not mine. So when they ask me to shorten, I cut with a razor blade, delicately: It’s amazing how much you can tighten up writing by taking out a word here, a sentence there.

But when clients edit a speech themselves, they whack through it like Indiana Jones in the jungle. Was Indiana Jones ever in a jungle? Well, if he were he wouldn’t care what foliage he ruined; he’d just be trying to clear a path. And I have to confess, if I were escaping Nazis I would probably not be worried about aesthetics either. But as far as I know, no one’s ever shortened a speech to escape Nazis.

When clients edit what they don’t understand

I recently wrote a speech for a new client. Heard back from the staff person: the client loved it, the people who’d booked the client loved it, the audience loved it. Hooray!

And then I opened up the final remarks. All the facts were there. But the story I’d constructed around them was nowhere to be found. And I have to say, I was sad.

The event organizers requested a shorter piece. If I had been there, I would gladly have wielded my razor blade. Instead, someone used a machete. They cut out all the story, leaving only a jagged trail of facts.

Look, facts are essential. The provide proof; they give your story weight. But facts alone do not tell a story.

Analogies are not just the poetic bits that hold the facts in place. They are the mechanism that transports facts into the listener’s brain. They help us synthesize information—something we have to do before we can draw on it. There’s a reason our elementary school math teacher made us figure out how many apples Joan had ended up with if she started with four and Johnny gave her two more. Yes, you may get the same answer just by adding the numbers (did everybody get 6?), but it gets stored into a different part of your brain. Because: story.

Same reason so many of us learned French by following the travails of a young man as he encountered the world. In the textbook’s first chapter, he made a phone call. Feel free to recite along with me:

Allo. C’est Philippe LeDoux?
–Oui, c’est moi.

Memorize all the vocabulary words you want; they’ll fly out of your head as soon as the test is over. But put those words in the context of a story, and they stick with you for life. C’est vrai, n’est-ce pas?

Our brain organizes information in story form. But why make it do all that extra work? Tell the story your way and your listeners’ brains will store it your way. People will not only remember what you’ve said; they’ll act on it.

If you’ve got too much to say in the time allotted, don’t cut out the story. Cut down on the content. Audiences can only take in two or three ideas per speech. You can force feed them more, of course. They’ll sit there politely and listen. But they won’t remember a thing.

The client was happy; the organizers were happy; the audience was, reportedly, happy as well. But I know they could have been happier. My client could have had more of an impact. A missed opportunity. Tant pis.


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A New Client: Frequent Questions

Q: How do you write for a new client you’ve never talked to?

A: Usually badly.

I should probably expand on that.

Everyone who’s ever started a new job knows that you’re not going to do it perfectly right out of the starting gate. I always tell my clients that’s why the first draft says DRAFT at the top. But I’m not just talking about writing jobs. Think about any new job you’ve had—whether it’s your high school gig flipping burgers on Saturday or your most recent move into the Chief Development Officer’s chair. You got some training or orientation. Someone talked to you about expectations, gave you the tools you would need to get the job done.

I already know how to write—you know that, or you wouldn’t have hired me to craft speeches for the CEO. But to do my job properly, I need some other tools. And if I’m writing for a specific person, one of the tools I need is access to that specific person’s voice and way of thinking.

Getting to know you: new client/new writer edition

You don’t have to buy your writer a steak dinner—as one new client recently did—but if you expect the writer to convey a sense of your personality and what’s important to you, plan to invest some of your time in a conversation. (Phone and Skype work just as well as steak, with less fuss and fewer calories.)

That dinner yielded a story idea neither of us would have thought of if we hadn’t had that conversation, as well as three op-ed pieces my client loved. We built the foundation of a solid, hopefully long-lasting, relationship. And a couple of days ago, the client sent me the kind of email you don’t usually get so early in the game: “I love it! You really get me, Elaine.”

And then there’s my friend Sam, who started writing for a new client about the same time I did. Sam has still not met—or even spoken to—his client. He’s making do with watching videos and reading things his client wrote.

Of course, most of those things were probably ghost-written for the client by Sam’s predecessors. At this point, it’s like reading a copy of a copy of a copy. (Ooh, add that one to the heap of analogies that no longer work in the digital age. Gather around, kids: Back in the 20th century, if you wanted to share something you had to “copy” it. Sort of like scanning, but the quality of the image degraded with each generation. So the first copy was fine, the copy of the copy was less legible, and the copy of the copy of the copy was…Oh, never mind.)

The bottom line is, if you don’t have time to speak to your speechwriter, don’t hire a speechwriter—hire a psychic.

Name-Dropping: Not just pointless—annoying, too

Name-dropping is a fantastic way to make sure people stop listening to you. But—wait—that’s not what you want? Oh. Well. Then stop dropping names.

Even if you’re not dropping a whole list of, say, client names—and we talked about avoiding lists just the other day—even dropping one name without substantive context in turns people off.

I wish I knew someone who could explain this to you. Let’s ask my friend Jack Dorsey, founder of both Twitter and Square. No, I do not actually know Jack Dorsey. But I do know how to search the internet. And a Google search of “name-dropping annoying” took me to this email he sent to his employees at Square. Apparently they were too young and too enthusiastic to realize how pointless the habit is. So he spelled it out for them:

“Using someone else’s name to sell an idea does two things:

  1. It diminishes your authority.
  2. It diminishes the idea’s merit.”

Dorsey sums up everything I have to say about name-dropping in this one lovely sentence:

“Authority derives naturally from merit, not the other way around.”

That deserves repeating: Authority derives naturally from merit.

In other words…

It’s not just about who, it’s about what and why

While you may feel super-special to have worked with 487 of the Fortune 500 companies, listing them does not show us why you deserved to get that work. What did you do? What problems did you identify and/or solve? How did the client feel about your work?

Now, please don’t answer those questions 487 times—that’s as bad a list. Maybe even worse, because it’s longer. Look for ways to categorize the names you want to drop:

“I’ve written for a number of leading business executives, including Warren Buffett.”

And then I might write a bit about the work I did with him. Certainly Mr. Buffett is not the only “leading business executive” I’ve worked with. But he is the one that arouses the most curiosity when I talk with prospective clients. Boil down the list to the most interesting elements—and if you must cite more than one, force yourself to stop at three.

Or you might group clients by industry or product:

“I’ve written for companies that make everything from consumer products to steak dinners. And some that have made waves. The New York Times praised the honesty of the annual report I wrote for Bankers Trust in the aftermath of its derivatives scandal.”

As in the Buffett example, I’ve named one company. It’s perfect if I were pitching to a financial services-oriented client. If I were pitching a nonprofit, I’d swap out the last two sentences for something that would better resonate with them.

And that’s the key. Whether you’re writing an article or a speech, you want the things you say to resonate with your audience. If you want to reach an audience wider than your mother, or that hottie you’re trying to pick up in a bar, that list won’t do the trick.

Give us context, and we’ll give you our attention.

“That’s not what I wanted to say!”

One of the first lessons I learned as a speechwriter is that the first draft often serves as a whipping boy—the poor unfortunate member of the court who received the corporal punishment it was illegal to give the prince. Seeing another person suffer on his royal behalf, was supposed to make the prince feel chastened. I doubt it ever did. But I digress.

I remember the first time I wrote a speech for a CEO. I sat in his regal presence for an hour, dutifully copying down his words. I turned those words into a typescript of the appropriate length, and took them back to him. He looked at the paper and bellowed, “That’s not what I wanted to say! I wanted to say…” and he reeled off a bunch of data points, none of which had figured in our previous conversation.

That’s when I learned first drafts can be disposable. Sometimes people need to see what they don’t want to say before they can articulate what they do want to say. That’s an important lesson for a corporate writer to learn, and I think it’s one reason I have an easier time absorbing edits than my peers who write under their own names. I’ve always been clear that it’s not my work, it’s my client’s; when they’re happy, I’m happy. And I build that into the fee, of course—I base my rate on 2.5 drafts per speech: first draft, major revision, minor revision. Works almost every time.

Knowing first drafts are disposable allows me to take creative risks. And I’ll tell my new clients that, reminding them not to expect perfection on the first pass: “That’s why it says ‘draft’ at the top.”

Still, occasionally it’ll get to me. Like when a client gives me a very detailed outline and instructions to write only what’s in the outline—”don’t add a thing, because we want to keep this very lean.” So I do. And…you know what’s coming, don’t you? They returned the draft saying, “Why isn’t X in here? What about Y? How could you leave out Z?”

[That soft thudding sound you hear is my head meeting the desktop. Repeatedly.]

Half of my frustration stems from my clients’ indecision, or re-decision; the other half is me wondering how I can possibly be surprised by this. Clients change their minds. That’s their right. And, hey, at least on this project they’re paying me by the hour.


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What you don’t know

“We can absolutely turn that around for you by tomorrow,” my then-boss told the client. “Right, Elaine?”

I had no choice but to agree. Our client, riled up by something in the news that day wanted an op-ed. I had to write it that night; I understood that. I also understood that when you deal with clients, you occasionally encounter unreasonable expectations, ditto deadlines.

What I didn’t understand was…well, anything at all about the subject. And in those prehistoric, pre-Google days that was a problem.

Now, I’ve written about many things I didn’t initially understand: like derivatives, back in the 1990s when even some of the people selling them didn’t quite know what they were. But at least then I had colleagues who could educate me. This…well, I didn’t fancy discussing it with the ladies in the office, and certainly not with the men.

My client wanted me to write about the evils of circumcision. Male circumcision. Just about the only person less well-suited for this assignment would be a nun. But there we were.

My boss knew she was throwing me into the deep end. I think she enjoyed the idea that her lesbian writer would be stuck in the office all night, thinking about penises. (She was that kind of person.)

Eventually I called my partner, who used to deal with them on a professional level (get your minds out of the gutter—she was a paramedic). She explained it, referencing various items of clothing, and I managed to bang out 600 or so words.

“Write what you know,” they say.

When you work for other people, sometimes you have to write what you don’t know, too. Do I need to add that the piece never got published?

Seth Godin is a Brilliant Man

I have read several books either written or edited by Seth Godin, but I only recently discovered his blog.  It’s fast become one of the first emails I open in the morning.

A few days ago, Godin blogged about the business variant of my mother’s old admonition, “If you can’t say anything nice, don’t say anything.”  His contention – with which I am in violent agreement – is, “If you can’t say something, don’t say anything.”

I still remember the time I interviewed the CEO of an investment fund that hired me to write a marketing brochure.  “What’s different about your fund?” I asked him.

“We are value investors and liquidate our positions at a premium.”  He paused to let the majesty of this statement sink in.

“Oh,” I responded.  “Buy low-sell high.”

I loved watching his face crumble.  And a few questions later, he finally abandoned the b.s. and gave me something real.