Oregon State Bar Bulletin — DECEMBER 2014

The Legal Writer

Difficult Conversations:
Talking About Bad Writing
By Suzanne E. Rowe

What do you say to a writer whose document doesn’t meet your expectations? If your goal is to avoid conflict, or if you just don’t have time, you say nothing. But if you are a foot soldier in the never-ending battle for better writing, you have to say something.

Any conversation about bad writing is bound to be difficult. Writers tend to form immediate and lasting attachments to their own words — whether those words fly from an iPhone, leap from a laptop, flow from a fountain pen or result from scrawls with a nubby pencil. Telling the author of such beloved words that they don’t measure up is uncomfortable. But the only way that writer will improve is with honest assessment, clear guidance and another chance.

After laying some background, I’ll suggest some opening lines. Don’t try them in a bar.

Getting Started

Of course, before you can have the conversation, you have to identify the problem. Some problems aren’t strictly about writing; the grammar and punctuation might be perfectly fine, but the document might fail because it doesn’t serve its purpose (you wanted a letter, not a memo) or because the analysis is too thin or flat-out wrong. Other problems are mainly based on writing; the writer has helpful ideas but can’t put them into a helpful written form.

Once you identify the problem, think about where your conversation with the writer should take place. A new colleague might be more comfortable in his office or a conference room; being summoned to your office could add stress that could make the conversation more difficult. A walk to the nearby coffee shop might be easier still, but only if you’re unlikely to be interrupted.

And consider the tone you’ll use during the conversation. If a colleague is about to get fired for sloppy writing, the “mad mom face” might be appropriate. But treating the writer as an equal partner might keep the conversation from becoming too depressing and even more difficult.

“I appreciate your effort.”

Regardless of the problem you’ve identified, your conversation will likely get off to a better start if you recognize that the writer really, truly tried to produce a good document. I remember getting a document back from a supervisor who had drawn a single line through an entire page—from the top left to the bottom right—with a note that said simply, “Sorry.” My little heart sank. But the supervisor began our conversation by saying, “I appreciate your effort.” Then he told me why the analysis we had discussed was flawed, which of course I should have realized as I was writing the document. His acknowledgment that I had worked really hard on that flawed analysis motivated me to fix it and gave me the confidence that I could.

“Let’s just talk.”

If you can’t make heads or tails of the analysis in a document, the writer may have an analytical problem rather than a writing problem. It’s very hard to write clearly about something that is still fuzzy conceptually.

To determine whether the problem is in analysis or writing, set the document aside and tell the writer, “Let’s just talk.” Investing a few minutes in a conversation can show you the problem, leading to the next part of the conversation.

If the writer can’t explain what he was trying to write, he has an analytical problem. Your choices here are to invest time teaching the writer about legal analysis or to assign the project to someone else.

But if the writer knows exactly how to explain the analysis orally, then he has a writing problem. You might suggest he use software that transcribes his oral summary, which could provide a good basis for a better document. Alternatively, you could take notes as you listen and then hand them to the writer at the end of the conversation as a rough outline. If the writer grew up without Saturday morning “Grammar Rock,” he might need a crash course in fundamentals. I suggest one of the following: Megan McAlpin,Beyond the First Draft, or Richard Wydick, Plain English for Lawyers.

“I got lost.”

When you can distinguish heads from tails in the analysis of the document, but the tails came before the heads, try telling the writer, “I got lost.” Beginning this way shifts the focus from “You’re a bad writer,” which is just going to make the conversation more difficult, to “I got lost and you can help me find my way.” The writer who wants to improve will be happy to help you find your way, while realizing that the document failed to meet its objective. The writer who just wants a year-end bonus might conclude that you’re dumb (how did she get to be a partner when she got lost in my perfectly clear document?) — ensuring no year-end bonus and probably a short stay in your office.

“Omit needless words.”

One of the many marvelous quotes in Strunk and White’s The Elements of Style is the simple advice to “omit needless words.” Concise writing is often clearer than verbose writing. Short sentences are easier to digest than long ones. Simple sentences are more straightforward than those with twists and turns that require multiple commas and semicolons.

If you get a document that is filled with verbose, long, complex sentences, your conversation could be as simple as “Omit surplus words.” Of course, then you’ll need to sit down with the writer and show her which words are surplus and how to omit them without sacrificing meaning. Or you could refer the writer to a text on good writing. In addition to the McAlpin and Wydick, you might even suggest Strunk and White’s.

“Careful editing suggests careful analysis.”

Whenever I see a sloppy document — misspelled words, confusing grammar, bad formatting, yucky citations — I assume that the analysis is just as sloppy. That means I’m less likely to trust the writer’s analysis. While I admit that I’m a curmudgeon, I suspect that most attorneys agree with my assumption.

You might begin this difficult conversation with these opening lines: “Thank you for your analysis of this problem. You’ve moved us closer to a solution. But when I first read the document, I was suspicious of your analysis because the editing was sloppy. Careful editing suggests careful analysis. The reverse is also true, and you weren’t very careful.”

“We have a client.”

Even a document that is clear analytically and well written might still fail. Attorneys tell me that one of the biggest problems new law clerks have is solving real-world problems. The newbies forget that the document isn’t an exam or a class assignment, but a tool that needs to help the client get closer to the desired solution. So while in law school it might have been fine to conclude that the hypothetical client didn’t have a claim under one cause of action — and then stop — in the real world, the writer needs to look for other causes of action or for alternative approaches to the desired end.

While getting this piece of writing is frustrating, the resulting conversation with the author might not be too hard. Begin with “We have a client, who is relying on us to solve problems. I agree with you that this approach won’t reach the solution the client wants, but that just means we have to think more deeply or creatively about how to do that.”

“This project deserves more thought.”

Another frequent problem with new attorneys is that they mistake speed for effectiveness. I heard recently of two summer law clerks who were racing each other to complete projects. They seemed to think that only one of them could get an offer of permanent employment (which might have been true) and that the most important factor was who could produce documents the fastest (which was absolutely wrong).

Unfortunately, the speed-demon projects that they wrote did little more than skim the analytical surface. The clerks’ supervisors were increasingly concerned that they were not getting deep, thoughtful responses. A quick answer is only beneficial if it provides sufficient analysis for good decision-making.

I suggested beginning a difficult conversation this way: “I appreciate that you tried to complete this project quickly, but it deserves more thought. We can’t sacrifice deep analysis for speed.” The writer might have spent so little time on the project that she didn’t realize that her surface analysis wasn’t enough. In that case, you might need to double back to “We have a client,” or “Let’s just talk.” If the writer realized the complexity but prioritized speed over thoroughness, try this: “When you realized that the project was more complex than I anticipated, you should have checked in with me.”

What NOT to Say

Trying to sugar coat the message isn’t going to help the writer at all. Lavishing false praise, followed by constructive criticism, is likely to confuse the writer. Is it good? Is it bad? Do not say any of the following unless every word is true:

You’ve done a good job. The writer might not hear the criticism that follows. The document’s good, right?

This is almost there. The writer will think that the problems you are raising are just minor polishing points or your personal quirks.

This was so helpful. Most writers really do want to help. And if you say they have, they’ll be mentally celebrating rather than listening to your concerns.


The opening lines offered here work well in a mix-and-match world, so you might select a few that apply to the document at issue.

1. Acknowledge the effort. “I appreciate the time you spent on this project.”

2. Show specific examples of the problem and explain why the problem made the document ineffective. If possible, show places where the writer got it right. “I couldn’t follow your analysis here on page four. But see on page three how clearly it unfolds?”

3. Suggest what to do next. “Let’s just talk through the analysis on page four.”

4. Most of all, show confidence that the writer can improve. “You’ll be writing documents like this frequently, and I’m sure you’ll be able to do so independently in the future.”

One difficult conversation can put a colleague on the path to better writing, while saving you from reading lousy documents in the future.



Suzanne E. Rowe is the James L. and Ilene R. Hershner Professor at the University of Oregon School of Law, where she directs the Legal Research and Writing Program. You can write to her at srowe@uoregon.edu.

An archive of  The Legal Writer articles is available here.

© 2014 Suzanne E. Rowe

return to top
return to Table of Contents