The Case for Empathetic Drafting

By Katie Lane

©2018. Published in Landslide, Vol. 10, No. 4, March/April 2018, by the American Bar Association. Reproduced with permission. All rights reserved. This information or any portion thereof may not be copied or disseminated in any form or by any means or stored in an electronic database or retrieval system without the express written consent of the American Bar Association or the copyright holder.

As attorneys, our job is to represent our clients’ interests and advocate for them as best we can. This is something we all knew even as we studied for the LSAT. And it was drilled into us as we developed our careers.

As a young transactional attorney, I also learned that representing my client meant ensuring that all of the terms my client might need for the transaction were included in the agreement, and that they were tailored to mitigate my client’s exposure to risk. But I have since learned, as many of us have, that if that’s all I focus on when drafting, my representation may be professionally adequate,1 but it won’t be “good.”

It won’t be “good” because I would not have taken into account how my client will use the document. Who will need to enforce it on a day-to-day basis? What are the situations in which the need to enforce it will likely arise? I will not have considered the relationship the document represents, or how that relationship impacts my client’s business, nor will I have been privy to how the parties talked about their venture before the agreement was introduced, the language they used, and the trust established with those words. I may have put myself in the client’s shoes to draft provisions that will help them navigate disputes so I can ensure the proper tools will be available, but it’s likely that I will not have considered how the client would feel to be facing that navigation alone.

In short: my representation will lack empathy. And because of that lack of empathy, my representation will also lack creativity, flexibility, responsiveness, and relevance. The representation will be robotic, making it harder for a client to see the difference between me and a “fill-in-the-blank” template agreement. While my work may readily fulfill the client’s demand to provide them something that “just works,” if they can’t see themselves in what I provide, they may not realize that I have done what they asked. I have found that if I ask myself certain questions while drafting or reviewing a document, I am better able to represent my client.

Does This Document Support the Image the Client Projects of Itself?

“I don’t know. I really liked the publisher when I talked to him on the phone, but this contract is bananas.”2

My client was considering a publishing agreement with a respected imprint of a major publishing house. The imprint was based locally and known for being selective about the authors it published. She liked her potential editor and had had several productive conversations with the publisher. She had heard only good things about the imprint from her peers: it was fair, it was transparent, and it was supportive.

We had just finished going over my review of the agreement that they had offered. The numbers were right, but the rights were not. For one thing, although this was a knitting book, the publisher was obtaining film and television rights pursuant to the agreement. The language about delivery and acceptance was harsh, which my client found a bit insulting because the imprint had approached her with the idea for the book. A handful of things that she had been assured in conversation that she would have a say in were, according to the agreement, emphatically the sole purview of the publisher. The contract did not reflect the image the imprint portrayed of itself—so much so that my client was ready to walk.

I told her all of the things I tell clients who get spooked by beefy template agreements: the imprint has to use the parent publisher’s standard terms, which are written to cover a lot of different types of books; it’s in a company’s best interest to write a template agreement so they get the greatest number of rights and are protected against any potential risk; this is part of the negotiation process, and they know we’ll come back with lots of changes.

My client nodded at my explanations and repeated some of what I said as if she were trying it on for size. But she still hesitated and asked me not to spend any more time on the project until she decided what she wanted to do.

This contract, like many of the contracts I review, was well drafted from a legal perspective. But from a usability perspective, it missed the mark. The terms didn’t fit the imprint’s reputation, or even what it said about its own business practices. The publisher had spent a lot of time and effort to give my client a clear idea of what she could expect if she signed with them, and most of that work had been undone by a 10-page contract.

Whether we like it or not, the legal documents we draft for our clients are, in part, marketing materials. They tell the reader what he or she can expect from our client when doing business. A good legal document protects the client’s interests, and supports how the client is marketing itself to potential customers. An “okay” legal document protects the client’s interests and doesn’t contradict its marketing. A legal document that protects the client’s interests but contradicts the image the client projects for its customers is a disservice. Such a document wastes the client’s money, squanders its efforts to promote its business, and makes it more difficult for the client to gain the confidence of its customers and partners.

Documents that don’t “look like” the client are also harder for clients to use, both at the negotiating table and when enforcement is necessary. If your client, through its marketing, is literally telling its customers and partners to expect something different than what is represented in the deal memo or sales agreement, it is a red flag. And once one red flag is spotted in a negotiation, more will be anticipated. A simple negotiation can spin out as the other party anxiously protects itself against a perceived duality between how your client presents itself and how it behaves.

If staff don’t recognize their company in the document that you have drafted, they won’t enforce it as you intended. In this case the publisher at the imprint acknowledged some of the disconnects we had found in the publishing contract and waved them away with “I don’t know why it’s there, it has nothing to do with us. I’ve never done that with any of our authors.” That was comforting news for my client, but not great for the parent company.

I am not suggesting that an attorney “dumb down” legal documents to mirror the marketing whim of the month. Letting marketing dictate what’s in a contract or demand letter is foolish. The point is, though, that letting a contract or demand letter dictate your client’s image is equally foolish. Marketing and legal efforts should be aligned, each helping enhance the effectiveness of the other.

Drafting a document that supports the image your client projects of itself doesn’t mean drafting a weaker document, a more colloquial document, or even a “friendlier” document. It means that the document fits your client. The document’s demands and promises match what the client’s been telling others to expect from them.3 Where appropriate, it uses words that your client uses when describing its goods or services for potential customers, and not the leverage-y, world-class, disruptive ones. It puts the reason the parties are doing business front and center, not buried on page eight after 14 paragraphs about rights and confidentiality obligations. And it describes that reason with the same concern and appreciation that the parties have for it.

Does This Document Accurately Express How the Client Values This Relationship?

“Yeah, but won’t that make us look like jerks?”

I was talking with a client, a small entertainment company, who needed an option agreement. The client was in a rush. They had been talking for some time with a writer whose story they wanted to option, and they were anxious to finalize the contract quickly. They had a pitch meeting coming up and wanted to be able to feature the story in the pitch. I had made some quick modifications to their standard agreement and sent it over for review.

“What would make you look like a jerk?” I asked.

The client pointed to the language about the term of the option, which I had drafted as longer than usual because they were acquiring rights well before the story was published.

“Part of the reason I started this company was to help make sure writers, many of them my friends, have someone looking out for their interests, protecting them from those crappy shopping agreements we all get. And now I’m going to go to my friend and say, ‘Gimme the rights to your story for longer than either of our kids have been alive’?”

I had underestimated how the legal terms could impact my client’s relationship. I assumed that the strength of my client’s relationship with the other party could withstand some less than ideal, but reasonable, terms. And while it may have, I learned that my client didn’t want to risk potential harm to the relationship for the sake of those terms.

Most of the documents we draft will eventually be read by another attorney. I think that’s who most of us write for, with the assumption that the attorney will be able to explain to his or her client anything that may read as harsh. But the attorney is rarely the one who reads the document first. The inaugural reader is usually whomever our client has been building a relationship with: the owner of the business, the project manager, or the rights holder. If our drafting doesn’t properly reflect, or at the very least anticipate, the relationship, the harm caused is personal. It’s not that the document doesn’t appreciate the relationship, it’s that the client doesn’t appreciate the relationship.

The other party’s attorney will likely be able to assuage some of the initial anxiety by explaining the culture of legal writing and the practical implications of the document’s terms. But he or she will be responding to a reaction rather than framing the issue—mitigation instead of presentation.

It may not be cost-effective to craft bespoke documents for the unique qualities of each and every party who may sign a sales agreement, but we can improve templates and boilerplates by understanding where this particular relationship fits into the client’s overall business plan.

For instance, it costs more to acquire a new customer than to keep a current one. The agreement that a new customer signs might acknowledge this investment by providing more in-depth information about the service and the practicalities of working with our client than a renewal agreement does—not because the service each customer receives is drastically different, but because the new customer’s relationship with our client is different. If the new customer is scared off at the contracting stage, it’s a significant loss for our client. The renewal contract doesn’t need to carry quite as much weight in the decision-making process because the current customer’s experience with the client’s service can serve that role.

I am not suggesting that lawyers need to put the “sales” back into sales agreement, but that we take a document’s audience, and the importance of that audience to our client, into account when writing.4 What information will be important to the inaugural reader? What does our client absolutely need that person or entity to understand? If keeping confidences is essential to the relationship, the confidentiality promises should be (1) easy to find, (2) easy to understand, and (3) easy to apply. A definition of “confidential information” that is a single sentence spanning 10 lines and three subordinate clauses fails at each task.

I see this drafting disconnect most prominently in independent contractor agreements. My client has been courted and told how important their contribution will be, only to get a contract that assumes they don’t know how to do their work, that they can’t behave professionally, and that ceding ownership of everything created “during the term of this Agreement” makes sense. (Unless the client is paying extremely well, a designer, illustrator, or other creative consultant will be working for several clients, and likely on their own projects, during the term of the agreement. The definition of “Work” can temper this, but is often defined so broadly that it doesn’t.) The contract that works well for those filling the role of temporary employee does not properly represent the relationship between your client and someone hired to lend their expertise on a project. While no one needs their contract to make them feel loved, an agreement that is so misaligned can erode trust and put the working relationship in peril before it has the chance to truly develop.

Occasionally, when I have talked to other lawyers about the importance of relationship in drafting, I received pushback that our role is to be competent in legal skill, not the psychology of business, and if we stray too far outside “our lane,” we run the risk of providing less effective legal services. I disagree with both points. If the services we provide thwart our clients’ goals, we’re abusing our authority5 and directing rather than enabling our clients’ objective. Part of effective representation is providing the best advice and service for each client’s particular needs. Just as we have the creativity to tailor documents so they can adequately represent a huge corporation or a sole proprietor, we have the creativity to tailor documents so they adequately represent our clients’ relationships. Doing so is solidly in “our lane.”

Will the Client Be Able to Use the Document Without Me?

I worked in the IT department of a midsized utility for about three and a half years. I was responsible for managing the company’s software, hardware, and IT professional services contracts, but I wasn’t part of the legal department. I supervised IT employees, reported to an IT manager, and negotiated contracts from an IT cubicle.

For the very first time, I got to see what happened when a client left a meeting armed with my advice and applied it. It was disheartening, to say the least. Statements of work I had sweated over were rewritten and agreed to on the fly without consulting me or the legal department. Project managers who were desperate to save a project’s timeline waived terms they didn’t understand, dutifully capturing the waiver in an e-mail. Managers would come back from lunches with salespeople to tell me about the great deal they’d negotiated where we got to pay more for the thing we’d just bought. In other words, it was a perfectly normal company.

It was during this job that I learned I couldn’t draft agreements assuming that I would be involved in enforcing them. I could not assume that clients, even the ones who really liked me and valued my advice, would come to me when issues with a project popped up. More likely, they would come to me after they had tried to deal with the issue a handful of different ways based on how they read the contract.

Legal documents are better when clients can use them without our assistance and when the client knows the difference between a DIY issue and a “come see me” problem. I don’t think any lawyer reading this article sends their clients off with a document they think the client doesn’t understand. But understanding what a document does generally and knowing how to use it are very different things.

Because of my experience in the IT department, when I started my own practice and drafted template agreements for clients, I provided them with a blank document to use and an annotated copy of the agreement that told them how to use it. The annotated copy uses the commenting feature to explain terms, highlight areas where I think the client is likely to get questions, and provide alternative language for situations that are likely to come up. The comments help me identify for the client what they can do on their own, what’s “safe,” and what is better to let me handle.

My initial motivation for this practice was selfish. I wanted to avoid the last-minute “I’ve tried to handle this on my own” crises. What I have found over the years, though, is that clients value my advice more when they have clear guidance on when to use it. I have learned that part of the reason clients don’t ask for help earlier is because they don’t always know if they should. Clients have told me that, in addition to trying to save money, they held off calling because they didn’t want to bother me. As a sole practitioner, I very much need my clients to bother me. I try to ensure that every client has a clear idea of when to bother me, what I want them to do before they bother me, and how we’ll address things when they bother me. I will take being bothered over dealing with a crisis any day.

Letting your clients know what they can do without you can feel dangerous, but I find it to be a more efficient division of duties. In my experience, when a client feels like they have to come to you for any and all questions, they don’t turn to their attorney more often, they do so less. When your questions are nails and all you have is a $400/hour hammer, you’ll use your shoe, a book, or a frozen burrito before you pick up the hammer. By empowering clients, I get questions that are less messy and clients that are more focused on the solution to the question than the cost of my services.

Empathy Builds Better Tools

Empathy has become a bit of a buzzword in the last few years, and it can be easy to discount advice to “be more empathetic when you _____.” I get it. I hope I’m never asked to leverage anyone’s synergy ever again, no matter how efficient it might be.

If “empathetic drafting” feels too jargon-y, I also think of this approach to drafting like building a tool. Before you build it you need to know how it will be used, make sure it fits the person who will be using it, and make sure that it is properly designed for the required job and the role it plays in achieving your client’s goals.

If you think your documents already do this, ask your clients what they think. Do they feel like the documents use the right voice? Properly represent the relationship? Are easy to use? As deeply as I believe in the importance of documents that do these things, I’m blind to my own assumptions at times. When a client comes and asks me to make the work for hire agreement I drafted “cooler,” it gives me the opportunity to stop, listen, and become a better lawyer.


1. Model Rules of Prof’l Conduct r. 1.1 (Am. Bar Ass’n 1983) (“A lawyer shall provide competent representation to a client. Competent representation requires the legal knowledge, skill, thoroughness and preparation reasonably necessary for the representation.”).

2. For purposes of this article, details of client interactions have been modified to protect client confidentiality and in certain situations similar events have been combined. All events relayed are taken from my practice as an entertainment lawyer serving the needs of individuals and small businesses.

3. Of course, sometimes the contract is right-sized but the client’s representatives have been misrepresenting who the client is to potential customers. While not something you can fix, it’s important to identify and help your client address this issue.

4. A cease and desist letter from Netflix to the proprietors of a Stranger Things-themed bar is a fine example of this. The letter more than adequately protects the company’s intellectual property interests while respecting the value of the show’s devoted fans. See Jeff John Roberts, Netflix Cease-and-Desist to “Stranger Things” Bar Is an Internet Hit, Fortune (Sept. 20, 2017), http://fortune.com/2017/09/20/stranger-things-bar/.

5. Model Rules of Prof’l Conduct r. 1.2 (Am. Bar Ass’n 1983) (“[A] lawyer shall abide by a client’s decisions concerning the objectives of representation . . . .”).

Katie Lane

Katie Lane is an attorney and negotiation coach in Portland, Oregon, helping artists, freelancers, and creative small businesses protect their rights and get paid fairly for the work they do. You can read her blog at WorkMadeForHire.net or follow her on Twitter @_katie_lane.