Teaching Justices to Write: Cherise Bacalski

Teaching Judges: Appellate Expert Cherise Bacalski on Brief Writing and the Human Side of Law

Appellate specialist Cherise Bacalski teaches appellate writing at NYU Law's New Appellate Judges Program, and in this interview we discuss her insights from both sides of the bench and how her background in rhetoric shapes her approach to appellate advocacy.

• Training new judges: At NYU, Cherise teaches newly appointed appellate judges how to make their opinions more readable through proper structure, headings, and organization—skills that help both judges and practitioners.
• The rule is king: What is the rule in your case? Cherise explains that, whatever it is, that rule should inform every part of your brief.
• Write for a “hostile reader”: Reading your brief—your trenchant, brilliant, erudite, sparkling brief—is the last thing any judge wants to do. Forget being brilliant. Just be clear, concise, skimmable, and easy to digest.
• Lead with old information: One of the most effective writing principles is beginning each new point with familiar information to propel readers forward at the speed of thought, reducing the need for excessive explanation.
• The human element: Cherise views the law as fundamentally human. Understand you are talking to humans, not picking a lock.
• AI is an amazing tool, but not a replacement: Use AI to test arguments and identify weaknesses in briefs. But AI sometimes misses critical "smoking gun" evidence in case analysis.

Tune in for a masterclass in appellate advocacy that bridges the gap between academic rhetoric and practical legal persuasion from an attorney who's seen the system from multiple perspectives.

Transcript

Tim Kowal
Okay, I'm Tim Kowal. Jeff is out today. I think he's observing Rosh Hashanah. I hope he won't hold it against us that we get going. But I am so excited to get going with my conversation with Cherise Bacalski She is a Western United States appellate specialist based in Utah and a writing coach at NYU Law's new Appellate Judges Program. I was very interested to reach out her to talk about that.

We've been long time LinkedIn pals and I've been looking for an excuse to reach out and bring Cherise onto the podcast and introduce her to our listeners. So welcome Cherise, thanks for coming on.

Cherise Bacalski Thank you, thanks Tim. I just have to say real quick that you were the first person who helped me when I went out on my own this last year, provided me counsel and guidance as I approached a difficult issue on appeal under a difficult and maybe cloudy procedural posture. And I just have to say thank you so much for doing that. Like your friendship and mentorship was, it was...

really important to me in the beginning of starting my firm. So I just wanted to thank you for that.

Tim Kowal 
⁓ you're more than welcome. I'm so glad I be there to offer whatever little assistance I was able to give. But I am interested to talk about your new endeavor. But before we get to that, I wanted to talk a little bit more about your background that you bring to your appellate practice. And you started in the Utah State Attorney General's Criminal Appeals Division.

Cherise Bacalski 
It was pretty big, but thank you.

Sure.

Yeah.

Yes.

Tim Kowal 
And

I think that means defending the judge, defending the convictions on the defendant's appeals. 

Cherise Bacalski 
Yes, so it's

defending the convictions and it's also in large part defending trial counsel because a huge number of the criminal issues in Utah that are raised are raised under the Sixth Amendment right to ineffective assistance of counsel. And so on appeal, you're kind of a finger pointer, right? If you're raising an issue, you're pointing your finger at someone in the criminal context, you're allowed to point your finger at

trial counsel. And so when you represent the state, you are defending the court's judgment and the rulings that the court made along the way, as well as the jury's verdict and trial counsel's decisions. it's kind of, yeah, you're just, you're seeking to show that there are none of the errors that

occurred were prejudicial really. But yeah.

Tim Kowal 
Yeah, well, you're a defender of the institution in that role. You're a defender of the state, defender of the attorneys and of the judges. But now I assume in private practice, you're probably representing a lot of appellants who are challenging the judgment and challenging the system. The system did me wrong. I didn't get my fair shake in court. And you have to, we were talking about this a little bit before we hit the record button as a theme that we wanted to cover.

Cherise Bacalski (02:59)
Yes, very much. Yeah.

Yes.

Mm-hmm.

Yes.

Yes.

Tim Kowal 
that we appellate attorneys kind of have one foot in the institution and one foot outside the institution. We're trying to build rapport with opposing counsel through civility and engaging the justices in conversation about what the law is, what it should be. But then we are also representing those challengers who are outside the institution and feel that there's no one else outside the institution who will help them challenge the big bad institution.

Cherise Bacalski 
Yeah.

Mm-hmm.

Yes.

Tim Kowal 
How does your background working in the AG's office and defending the institution give you insight into your role in representing these outsider challenges to the institution that's done them wrong in their eyes?

Cherise Bacalski 
think that's a good question. And when I was in law school, I worked with and for a couple of judges. One of the judges told me, the more often you switch sides, the better. And so if you plan on doing criminal work, work for the state, work for the defense, work for individuals, and go back and forth. Because every time you do, you'll get a little bit better. And so I...

I knew that I was a little bit more defense focused. And so while I was in law school and after law school, I decided to focus on working for the state. So I worked for the US attorney's office here. I worked for the local government. I worked then after law school for the AG's office. And I think what that experience taught me is that it's a lot easier to defend your win than it is to get a reversal.

So if I'm bringing an attack on a judgment, I've got a win on every single prong to attest. So let's just throw out ineffective assistance of counsel since we were talking about criminal law. Ineffective assistance of counsel, you have to show error and you have to show prejudice or harm. Now the AG's office will oftentimes get an affirmance based on the fact that there was just no prejudice.

Tim Kowal 
Mm-hmm.

Cherise Bacalski 
or that there was no error. And the court very frequently refuses to reach both. They say, can dispose of this claim on one. And so however many prongs you have to win in order to get your reversal,

Tim Kowal 
Hmm.

Cherise Bacalski 
You have to win all of them. for example, and there's some strategy that goes into it. So if you're alleging plain error versus ineffective assistance of counsel, plain error requires error also that it was plain or obvious and that it was harmful. And then you're also attacking the court, right? So you've got three prongs. Yeah. And you've got three prongs to that test and you've got two prongs to the ineffective assistance of counsel test. And so.

Tim Kowal 
Yeah, the trial judge is in the dock.

Cherise Bacalski 
Who are you going to point your finger at? The one where you have to make three showings or the one where have to make two? So there's a little bit of strategy to that, but yeah, it's a lot easier to defend a win. A lot easier. ⁓

Tim Kowal 
What do you like, but

do you like defending the wins or do you like being the underdog trying to challenge the judgment?

Cherise Bacalski 
so I love both. I really do love challenging the judgment. I think there's a certain amount of creativity involved, bringing in policy arguments and really thinking about why the law exists. I think that is really important when you're challenging the judgment. But yeah, there's a lot of creativity involved. have the landscape is completely blank.

and you're filling it in. So it's pretty awesome. And then there's a lot of talking to your client and kind of strategizing, what is the ultimate remedy that you want? And making sure you're laser focused on that.

Tim Kowal 
Yeah, I like what you said earlier about it's beneficial to switch sides as often as you can to get, I guess, putting the shoe on the other foot as often as you can to be in that habit of, okay, well, this seems obvious to me, but let me stop and pause. How could I imagine the situation being reversed in such a way?

Cherise Bacalski 
Yeah.

Yes.

Tim Kowal 
that I would be on the opposite side of this and how would I feel? And it helps to isolate what are your biases? Do I just have kind of a anti-institution bias here that I think the judge is wrong? What happens with, as you pointed out, you've got to satisfy both that the judge made an error and that it prejudiced the case. that second prong ⁓ is the most perplexing for the clients, obviously, because they'll say, what do you mean prejudice? I lost.

Cherise Bacalski
Yeah.

Mm-hmm.

Yeah.

Yes.

Tim Kowal 
How could I be more prejudiced than that? ⁓ So it's a little bit difficult for them to stomach and even for attorneys. A lot of attorneys file opening briefs that just ignore the prejudicial error ⁓ aspect altogether and just assume that, well, if I proved error, then obviously I need to win.

Cherise Bacalski 
Yeah. Yeah. Yes, it's shocking.

Yeah, yeah, it's actually pretty shocking. And I've seen some briefs from some very well-regarded appellate attorneys who completely forego a harm or prejudice section.

It just goes against, I think, everything inside of me to do that. ⁓ But, yeah.

Tim Kowal 
Yeah.

So

you've switched sides, literally, you were working inside the institution, working at the AG's office, defending judgments, that was your job. And now in civil practice, many, maybe even most of your cases are challenging the judgment. So that's a very drastic way that you switch sides. Do you have any other examples or techniques of how you can switch sides? Is it?

Cherise Bacalski
Mm-hmm.

Yeah.

Tim Kowal 
Can you do it just mentally, internally, just talking with opposing counsel or talking with colleagues? What are some of your techniques?

Cherise Bacalski 
Yes. Yes.

Absolutely. Okay,

so one of the techniques, one of the things or an exercise that I gave my students, I teach at BYU Law, and I had my students write down the facts in the case in their report problem that were favorable to them. And then I had them switch sides and write down the facts that were favorable to the other side. And I think that you should do that.

I think that as an attorney, you should always have the other side's strengths in mind. That's what you're writing to. You're not writing to a straw man argument. You are writing to a legitimate judicial concern. You're up against the law. And a probably very well-respected judge who thought that their judgment or their conclusion was sound.

And so I think, you know, performing that exercise where you're, you're literally saying, these are the strengths of my opponent's side and, trying to acknowledge them and then kind of weigh the strengths of your side and see how you can possibly overcome their strengths. I think that's necessary. Also having, somebody to talk to, I think that appellate work is teamwork. It's gotta be teamwork. I'm a solo.

but I practice with a lot of people. I always bring in independent counsel. I work with a lot of contract attorneys. I call up friends. I run issues by them. So I have one case right now where there's a team of three attorneys and one paralegal working on it. So it's, you know, I think the teamwork is, leads to the best result. So definitely make sure you're not in a...

echo chamber in your head. Yeah. Yeah. And maybe even use chat GPT. Yeah. Yeah, absolutely. In fact, I have Westlaw with co-counsel and so making sure that you've got co-counsel to tell you

Tim Kowal
Yeah, get out of the silo.

I was just gonna ask you if you've ever used Chat GPT for that.

Mm-hmm.

Cherise Bacalski 
what the other side will likely say, what issues they will raise is really beneficial. So I love doing that. I love running my stuff through AI and just kind of having it tear me apart.

Tim Kowal
And if you prompt it right, it will do that. And of course, if you prompt it wrong or right, depending on your perspective, it'll tell you that your case is rock solid and bulletproof and you're certain to win. It's all a matter of what you want it to say. But yeah, if you give it your brief and say, tell me all the reasons why I lose. What are the most likely arguments? What are the strongest arguments in rebuttal to my brief?

Cherise Bacalski 
Mm-hmm.

Mm. Yeah.

Yeah. Or even, I don't

tell it that it's my brief. I tell it, I am representing the other party. How can I attack this brief? And then I give it instructions specifically under rule whatever, you know, or if it's a complaint that I'm filing under rule 12b6, you know.

Tim Kowal 
Mm-hmm.

Cherise Bacalski 
What are, or all of the, you know, rule 12. What are all of the ways that I can attack this? You know, and I just kind of, what are all the jurisdictional or what, you know what I mean? Just everything. Where's the weakest, you know, whatever it is. And I tell, I literally tell it, I am the other side. Tear those apart for me.

Tim Kowal
Yeah,

yeah, yeah, so you lie to it. And that's fair, because it's not human. Yeah, where do you get your ideas and techniques for chat GPT? Are you a creative thinker when it comes to chat GPT, or are there other thought leaders that you're following on chat GPT or AI generally?

Cherise Bacalski 
Yeah.

think

my husband started with AI a long time ago. And so when I got co-counsel, he just, mean, he's my best friend and we hang out all the time. And he's excited about technology. He's a technology nerd. And so I frequently talk to him about my searches and...

results and my gosh look what co-counsel did and look what it got me and he would always make sure that my prompts were good and he even uses chat gpt to write prompts for co-counsel that's one of his suggestions you use chat gpt to write a good prompt for co-counsel ⁓ give it all the information yeah

Tim Kowal 
Yeah,

that's a good idea. I hadn't done that. I have chat.gbt write its own prompts sometimes when I tell it what I'm trying to accomplish. So tell me how to do this the best way in a prompt. I haven't thought about having it prompt for a co-counsel search or for that if you use the Lexus AI. And probably it can do some research and find out the best techniques for prompting in these other platforms.

Cherise Bacalski 
Mm hmm. Yeah. Yeah. Yeah.

Yeah.

Yeah, yeah. And he does that for co-counsel. So, or I'm sorry, for ChatGPT, yes, ChatGPT generate his questions. And so it's just a, know, application of that principle to co-counsel, yeah.

Tim Kowal
Now, can you share a formative experience that has shaped how you think about the law? You suffer any stinging defeat, or a soaring victory, something that gave you either hope or despair about the practice of law?

Cherise Bacalski 
I think the thing that I've learned, so I've been practicing for, I don't know, 11 or 12 years. And the thing that is my main takeaway after this much practice is that the law is...

It's human. It was created by humans, it's enforced by humans, and it's limited by humans. And so because of that, it's very imperfect. And I don't think we have a broken system necessarily, but I do think we have room for growth. And if you want, I can share some stories. ⁓ One, judicial training. I think that...

victims in the system are victimized by the system frequently. For example, victims don't behave the same way that non-victims behave. And so if a trial court is making a credibility assessment of someone who's been abused, know, that victim will oftentimes stay by the perpetrator, will allow the abuse to continue.

will keep going back and will even because of the abusive situation will support and prop up the abuser. well, there's none of that makes sense to somebody who hasn't been abused. And so you get credibility assessments of victims that don't take into account their victim status, if that makes sense.

I'm working with quite a few victimized women right now who are in the process of being victimized by the system. And I think that judicial training would be really helpful.

Tim Kowal 
Can you give me an example of the kind of judicial training that would help that situation?

Cherise Bacalski 
I think you can bring experts in and have experts, expert witnesses even, people who are experts in psychology, talk to judges on a regular basis about the kinds of behaviors that victims will participate in willingly. It's, you know, I think it's really, it's really...

easy for a judge to say, don't find you credible, and I'm not going to ⁓ weigh this in your favor. And they've then been victimized by the system. And as you know, as an appellate attorney, credibility assessments are virtually untouchable on appeal. So what do you do with that?

Tim Kowal 
Yeah, right. the

Cherise Bacalski 
So if

you've got a victim, are you then tasked with hiring an expert?

on victims to testify about credibility and just so that the judge can take their testimony seriously. I mean, it's a really high bar to get like good credibility findings with victims who have gone along with the abuse.

Tim Kowal 
Yeah,

yeah, yeah, well, I guess you could file that under the broader heading of, it's like an epistemology problem. Like what do we believe, who do we credit as being credible or not credible? I think the flashpoint, the major national example in our country's recent history was the O.J. Simpson trial or.

Cherise Bacalski 
Mm-hmm.

Mm-hmm.

Tim Kowal 
Everyone

knows, you know, OJ did it but he was acquitted. What do you do with that fact? Is that a dysfunctional ⁓ credibility of that that jury or dysfunctional incredulity of that of that jury or in the case of domestic abusers? Yeah Yeah was there, you know ⁓

Cherise Bacalski 
Yeah.

Or was there just reasonable doubt?

I mean,

here's where you've got poetry working in your favor. If the glove don't fit, you must acquit. So it's one of those situations where the defense did a really good job of showing the reasonable doubt and making it physical and palpable right there for the jurors. So I mean, was it jury nullification? I don't know. Maybe the glove just didn't fit.

Tim Kowal 
Mm-hmm.

Yeah, maybe. ⁓

Cherise Bacalski 
Maybe

that's reasonable doubt. As defense attorney, I like thinking that there's a jury out there that conclude that there was reasonable doubt because the physical evidence didn't align.

Tim Kowal 
Yeah, well, and that's that's that the jury system is part of the magic of our system. It is it is what keeps it human, as you say, that there is there is no ⁓ it's not a, you know, brooding platonic truth, you know, ⁓ out there. It's just whatever. ⁓

Cherise Bacalski 
Mm-hmm.

Yeah.

Yeah,

it's whatever these people agree upon. Really. Yeah.

Tim Kowal 
Yeah, whatever happens. also

that constitutional phrase, case or controversy, you're not asking what is right or wrong in the abstract. We're applying it to this specific scenario. So it's almost like you're forging a new thing. It's like truth that is going to be incarnate because of the application to the parties in this particular circumstance.

Cherise Bacalski 
Yeah.

Yeah.

Yeah,

Tim Kowal 
⁓

Cherise Bacalski 
very much so.

Tim Kowal 
That's one of the vexing difficulties of the law is applying all of these holdings from finite specific, party specific, fact specific, history specific examples and trying to suss out some broad abstract notion of what is the law based on juridical principles that have been just forged in one case after another, after another, after another.

Cherise Bacalski 
Mm-hmm.

Do you find? have a question for you.

Tim Kowal 
Anyway,

yeah.

Cherise Bacalski 
Practicing so much in California. So I've practiced a little bit in California. I think I've done 12 appeals there, 12, 13 appeals there. But the majority of my like 100 plus appeals have been here in Utah. And I do feel like they're...

Whatever there's an appetite for, generally is what happens. Do we have an appetite to rule in this person's favor? And I'm wondering if you sense that in California as much. I do feel like there's a huge hurdle when you're on appeal. You don't get to put new evidence before the court, right? You're stuck with the closed universe of the appellate record and the narrative that played out below.

Tim Kowal 
Mm-hmm.

Cherise Bacalski
And so.

Just wondering if...

If you get the sense from the appellate court in California, or the appellate courts, the many, many, many appellate courts in California, that...

Tim Kowal 
You

Cherise Bacalski 
that outcomes are more difficult to change than they should be.

Tim Kowal 
don't know how to answer that specific question more than they should be. your first question, which was about, you well, now I forget how you put the first question that I did have an answer to. Basically, that, you do judges want to rule a certain way in a case? I was going to answer by referring to my first impression reading the first page of the Rudder Guide. You know, the Rudder Guide is like the practice Bible.

in California and in many other states and federal jurisdiction as well. The California Civil Writs and Appeals Rudder Guide, authored by the illustrious John Eisenberg, says, the most important question that any practitioner needs to ask him or herself at the outset of an appeal is, did the right party win? And that was the line, did the right party win? And that's so graded on me for quite a long time, because I thought, there is a right answer.

Cherise Bacalski 
Yes.

Yes.

Tim Kowal 
There is a platonic right answer and a wrong answer to every case. And it grates on me the idea that, the judge can just decide that, I think the right party basically won here. So we're just going to kind of fudge it here, fudge it there, and make the right outcome come out the way we think it should. But after, I don't know, just the softening of years, and I become compromised or something. But I do get that sense now. Whenever I look at a case, I just get a sense that

Cherise Bacalski 
Mm-hmm. Yeah. Yeah.

Tim Kowal
that yeah, there were some screwy things that happened, but it basically came out right. And I think it's, like to think that I'm not just compromising values. I like to think that maybe I can't articulate the entire, what will come out in the appeal in a moment, but it is compressed into a hunch that I think that these errors are not enough to overcome what happened in just the momentum of

Cherise Bacalski
you

and

Tim Kowal
Powerful arguments that do in evidence that do support the outcome here It's just not going to be enough to overcome that maybe it's just kind of a wang that okay Here's yeah, there are some errors and they were substantial but but gosh, know Everything else that supports the judgment is just too much to to overcome And we like the result I remember I shared once there's a there's a law review article written by Where is he? Is it Washington? You or George Mason? It's a

Cherise Bacalski 
Mm-hmm. Yeah.

Yeah, but we like the result. Yeah. Yeah.

Tim Kowal 
maybe Georgetown, it's John Hasnes and it's called the myth of the rule of law and he shares this anecdote that always stayed with me from reading it. He teaches contracts and first-year contract students and so he'll give a case to a student who's going to be tasked with at the next class of arguing for the plaintiff's position and then to the students who's going to argue the defendant's position gives a different case and each case perfectly supports the position.

plaintiff should win based on this binding precedent. But under this other binding precedent, equally binding, the defendant should win. And he says that you can give example after example like that. And he says after years of teaching the law, he's come to the position that there is probably in any given case a binding precedent or at least, know, persuasive precedent that governs, that could support completely opposite results in every case. And what

Cherise Bacalski
Mm-hmm.

side.

Tim Kowal 
what makes the law work is not that the law requires a certain outcome in every case, it's that there's an overall culture of law that's fostered in our institutions, fostered in our law schools that create certain kinds of lawyers. And then that kind of ephemeral, inexact culture of law is what makes our law

Cherise Bacalski
Mm-hmm.

Tim Kowal 
more or less consistent. It's not the black and white

Cherise Bacalski
Yeah, it's the

Tim Kowal 
So I think it ⁓ was last year that you founded your new appellate firm, Lotus Appellate Law. Can you tell us about that?

Cherise Bacalski 
So.

Yeah.

Yeah. So maybe what I'll do is I'll kind of take you on a journey of, I feel like as a woman in the law, I'm always yearning to hear other women's stories about how they make it work. So I think maybe I'll just kind of take a walk through, you know, if you don't mind. It's kind of tangential, but. ⁓

Tim Kowal 
Please do.

Cherise Bacalski 
I had my first child in law school and I didn't even think about getting a job. Truly I didn't. I was so busy. had, I think, 200-

Tim Kowal
I can't imagine.

Law school took everything out of me. can't imagine having, and then having a child took everything out of me and I didn't, I had a very small role in it.

Cherise Bacalski 
Yeah, was.

Yeah,

I had like two or three externships. I think I did 250 hours of pro bono work my last year while I was, while I, my, I had a newborn. It was a lot. It was a lot. And so I took the bar and, had an opportunity to do a public interest fellowship at the AG's office. And so I went to

Tim Kowal 
Yeah.

Cherise Bacalski 
the AG's office where I did criminal appeals for a year, realized that it would be really great to do an appellate clerkship, applied, got an appellate clerkship lined up. And then the Court of Appeals, while I was waiting for my clerkship with Justice Pierce, the Court of Appeals called me and said, we've got a vacancy. Can you come in and do that? So I clerked then for the Court of Appeals and then went and clerked with Justice Pierce on the Utah Supreme Court where I got

pregnant with my second pregnancy, my second baby and, took the California bar that same year. So I took the California bar, I was pregnant, I was not on caffeine, which was a whole thing. I would just wake up at like 4 a.m., like hit the books, take the train into the clerkship. And then I started my own firm after I was done clerking.

and after my new baby had come. I think it was, I don't even remember what was called. I had my last name in it. And I focused exclusively on appeals. And I met a woman named Emily Adams who also focused exclusively on appeals. And then we practiced together for a couple of years as solos, but kind of practicing together and building up kind of a reputation. And then our,

I founded the appellate group with Emily and someone named Freya Johnson, who had just left an appellate firm in town and grew that and then started, you it was there for five years and then was seeking out a different kind of work and started Lotus Appellate Law, where I'm now a solo practitioner, but I build for my cases, I do build communities of attorneys. I've got one of my cases, I've got

three attorneys and a paralegal on the one case. So I don't practice in an echo chamber, which is nice. But I love the kind of work that I'm doing now. I am doing exactly what I want to be doing. you know, and I love it. So yeah, I'm I am. I don't know what else to say about Lotus Appellate Law. I have a law firm. It's an appellate law firm. So yeah.

Tim Kowal 
And this is the, I think the third law firm that you started. So you must be getting good at starting law firms.

Cherise Bacalski 
Yeah, just from a career standpoint.

yeah, I'm getting amazing at it now. From a career standpoint, yeah. So I started my own solo practice. I started a larger firm, started with the three of us. And then I think there were 11 or 12 attorneys when I left the appellate group and went back to solo practice. And I'm kind of looking to hire an attorney right now, which is...

been a fun journey.

Tim Kowal 
Do you have an idea of how large you want to grow lotus?

Cherise Bacalski 
not that large. I think something very manageable, something, you know, two or three attorneys maybe. don't, I would, you know, at the appellate group, were three partners and we each managed an aspect of the firm. And so here at Lotus, I am the founding partner and, you know, I'm managing the whole thing. I'm doing the marketing.

I'm doing the finances, I'm the admin, just everything. And so if I were to have, and then I practiced some law on the time, yeah, or on the side, yeah. So I can't imagine having just a 10 or 15 person firm that I'm also managing, you know, all of the attorneys, it just seems like a lot. I'm sure that it's scalable. I'm sure you can do it and I just don't know how, but right now I imagine it being a small, cozy little appellate shop.

Tim Kowal 
Yeah, and then when you have some spare time, practicing some law.

Yeah. Well, that's to be continued because I have some questions for you about maybe we can talk shop offline because I'm trying to decide how large I want to grow my own firm. And I have some of the same questions about, ⁓ know, when you get bigger, I would like to have enough attorneys so that ⁓ enough help so that I can take some of the other stuff off the plate.

Cherise Bacalski 
Yeah.

Tim Kowal 
So I can get back to actually practicing law, but I'm wondering if maybe that is counterintuitive that the larger you grow at the less law you're actually going to practice.

Cherise Bacalski 
Yeah. Yeah.

I think that's true. I think the larger

you grow, the less of all you practice and the more you're handing over the job you really started out wanting to do to someone else so that you can do the building. Yeah.

Tim Kowal 
Hmm, well, that's a little bit

sad. I guess if you want to practice, you have to go work for somebody.

Cherise Bacalski 
Yeah, yeah it is. mean it.

Yeah, yeah. I mean, right now, so when I left, I'll just say this, when I left the appellate group, I thought, okay, if I do four appeals a year, that'd be perfect. And I think I have something like 15 or 20, it's been less than a year. Right now, it just, I've got a large, which is why I have so many contract attorneys working with me and for me. But I've got my hands in everything, right? I'm the only attorney here, I'm the only one signing anything. So.

It's a lot. It's a lot. So that's why I'm trying to bring on an attorney. think it would be awesome to have somebody who can take a case start to finish with me so that the entire weight of all of the cases isn't on me, but I am enjoying it and I get invigorated by the practice of law.

Tim Kowal 
Okay, well, I need to move on to talking about the NYU Law School gig teaching new appellate judges. But I did want to weave in ⁓ your background in rhetoric. So I'm just going to give the audience a little bit of a taste of your background there. And then I'll ask you maybe to kind of weave in some of the lessons that you learned there and how that's integrating with your teaching of new appellate judges.

Cherise Bacalski 
Yeah.

Mm-hmm.

Tim Kowal
So you're formally trained in rhetoric. You hold advanced degrees in writing, rhetoric in the law and teaching. You've taught college level writing courses in advanced persuasive writing, rhetoric and creative writing at BYU. You've also taught appellate brief writing and you've led the appellate practice clinic and moot court. And so I wanted to ask, what do all of your background in formal rhetoric and writing

Cherise Bacalski
Mm-hmm.

Tim Kowal (32:01)
How does that coalesce into your own practice and then your teaching of new appellate judges?

Cherise Bacalski 
Yeah. So I think that my rhetoric background, what it does is, I mean, I've got these two kind of mantras that inform my practice. And one is that the rule is king. So just the rule that you're working with, whatever it is, if you can show an error, an application, you you've got to go. 

Tim Kowal 
So in legal writing would be like the rule

of law or the rule that the legal standard is king. Is that the idea?

Cherise Bacalski 
Yeah, whatever rule it is

that you're working with, it should inform every section of your brief. It should be present and show up everywhere. So whatever rule you're working with, it should inform your headings and subheadings. It should inform the way that you introduce your narrative. It should inform everything. And then,

Tim Kowal 
Yeah, it's kind of like your tie

should match your socks and your belt should match your shoes. It's like it all needs to be integrated.

Cherise Bacalski 
Oh yeah,

yeah, the belt and the shoes. It's like the belt and the shoes. Exactly. The belt and the shoes. It's like you start with the shoes and then you say, what else should I wear? You know, the, so the, yeah, the rule is king, right? It really should show up everywhere in your brief. Also the judge, and I'm writing to judges.

Tim Kowal
Yeah.

Cherise Bacalski 
a lot, but the judge is human. And I know this is, people are probably wondering like, what does it have to do with rhetoric? Well, rhetoric is very audience focused. And my reading, my writing style is, is one informed by reader empathy. I know that my reader does not want to be reading the thing that I have written to him and her. I have a very hostile reader who has way better things to do.

So it's got to be clear. It's got to be good. It's got to be short. It's got to be you know as as easy to digest for a human as possible and So that's the type of brief that I write. I try to spoon feed. I try to make it skimmable I try to make it easy. So those two things because because I'm trained in rhetoric and I know that I'm trying to persuade a human

distracted judge who is very busy and has much better things to be doing, even though that's the judge's job, but really truly has much better things to be doing than, you know, putting together my confusing brief for me, right? So I've got to make it easy for them to rule in my favor.

Tim Kowal 
You've got a hostile reader. I think that should be a mantra. I every attorney needs to have that burned into their brain as they're writing. I know sometimes trial counsel will ask me after we filed our opening brief, and we're still waiting for the respondents or appellees brief, then we're still in the nascent phase of briefing. the last, do you think the court is going to read it immediately?

Cherise Bacalski 
got a hostile reader. Yeah.

Yeah.

Tim Kowal 
as if like they don't have anything better to do. They're just sitting around, you know, waiting at the bottom of the chute for our brief to come in so that they can read it, hop off the presses. No, they're a hostile reader. They're going to read it as an absolute last resort. They're praying that your case gets settled and dismissed before they ever have to read page one.

Cherise Bacalski 
Yeah.

Yeah.

Yeah. Mm-hmm. Yep.

Yeah. It's true. So I think my rhetoric training probably informs my writing and my teaching that way. And I also just try to make the genre of an appellate brief really easy for my students to follow. I try to unpack it for them. I'm trying to alleviate the stress of trying to figure out this big, huge, you know, the big question of like how to write a legal brief. It's like, ⁓ this is how you write.

very easy actually. It's like Mad Libs. Fill in the blanks. You know the blanks are already there. They're in the record. And you're just you're just doing it in a way that is reader friendly and that is very strong and easy to get through. So as far as the NYU Law School, what I learned, so I've only done it one year, but what I learned about the judges was that they are so eager to get it right.

Tim Kowal
first tell me who are the judges? these federal judges or state judges?

Cherise Bacalski 
Yeah, yeah, they're federal and state high court judges, courts of appeals and state supreme courts. Federal and state, yes. And ⁓ they've been put on the bench in the last three years on the appellate bench. They're all appellate judges. And they're, I think, seeking to understand how to draft their rulings in a way that is clear to the reader, to the legal reader. And

They have a lot of questions about how to do that correctly. What I got from them when I visited with them was that they love their job. They really love their job. They love what they're doing. They love working with their clerks. The actual job of being an appellate judge is one that they love. And they're trying really hard to do it really well.

Tim Kowal 
Do these judges, mean, appellate judges already know everything that there is to know about judging, don't they? what is it that, do you notice that there's something that they're lacking or do they, do the judges ask questions? Are they insecure about something about the appellate job? they're being, presumably most of these appellate judges are being elevated from the trial court bench. What are they most eager to, what is the gap they're most,

Cherise Bacalski
Hmm.

Tim Kowal 
eager to bridge.

Cherise Bacalski 
Well, I'll tell you what I did. What I did was I found some opinions and it could have been literally, it was literally like randomly, like any opinion will do. And I applied my writing checklist to it, to these opinions. And I showed the judges, look, here are the inconsistencies in this opinion. Here are the ways where the headings are not aligning with the body paragraphs.

or with the roadmaps. Here are the ways that you are confusing your reader in the facts. Here are the ways that this judge really walked me through this. What are the rhetorical strategies that she used in order to make it so that I was encountering old information first the whole time so that I understood what she was doing the whole time? Some judges do a lot of meta work.

They tell you, is what I'm about to do and here I'm going to do it and this is why. And they'll kind of lead you through their opinion. And some, some judges kind of like just throw the opinion at you. So just showing them the impact of all of those moves and making the structure explicit visually. ⁓ you've got to, we're coming from a place where, and let's just pick a year, 1910. Judicial opinions in the 1910.

What did they look like when you compare them to just judicial opinions in 2010?

Tim Kowal
they just look like they're just type, type, type, type, type, no headings, hardly any paragraph carriage returns.

Cherise Bacalski 
It's hardly any paragraphs. It's daunting. So you see, you're able to show them the way that space works for them and is their friend, the way that headings work for them and are their friend, the way that, you know, focus paragraphs work within an opinion, roadmaps, all of these things that make it easy for the attorneys and parties reading their work so that they understand what the judge...

was doing, right? So that you're not just throwing your work at them, like making it visually, making the structure explicit. And this is a Tim Terrell principle, making the structure explicit is really important in opinions, legal opinions. anyway, and then I also gave them my writing checklist for their clerks so that their clerks did a lot of the heavy lifting.

as far as style and making it easy to read and making sure that things were consistent throughout before it got to them so that they weren't editing for minor little errors, they were editing for larger big principle concepts.

Tim Kowal 
Okay, and then based on the feedback you're getting from judges and what you're teaching judges, have you derived any principles that are changing or affecting the way that you are approaching advocacy, brief writing?

Cherise Bacalski 
I'm

I think, I think going back to what I said before about how these judges are busy and they want to get it right. ⁓ when I gave them my checklist, a lot of them were, you could see the relief just kind of like, they just were visibly relieved. ⁓ some of them came up and talked to me afterward and they thanked me. Like, thank you so much. This is going to make working with my clerks so much easier. Like the work product I get back is going to be so much better.

It just confirmed to me that they really are so busy and they really do have so much work to do. If you as an advocate can get them a document that is simple and easy to read, you're going to...

I think have the case in the bag a little bit more than a very convoluted confusing document.

Tim Kowal 
Could you give us an example or two of the items that are on that checklist just to give us an idea of what they value, what they think is going to enhance their efficiency and effectiveness in working with their clerks and drafting opinions?

Cherise Bacalski 
Yeah. Yeah.

Yeah, some of the items on the, so I have a brief writing checklist and I made an opinion editing checklist just for them. Some of the items on the opinion editing checklist were, so we go from the macro to the micro. We're looking at an entire issue. We're looking at paragraphs and we're looking at sentences and the way that the sentences.

work together. One of the things that is the most useful writing principle that applies across genres and across the board is leading with old information. Leading with old information helps you to steer clear of just constantly trying to explain things to people, right? So, you know, there's that litigation mantra, if you're explaining, you're losing. Well, how do you get away from that?

in legal writing, you are literally explaining the entire time. But if you lead with old information, not only are you increasing flow, you're helping propel your reader forward at the speed of thought, but you're also doing far less explaining because you're leading with familiar concepts, familiar language and terms so that your reader's not going back.

and saying, what does this reference? yeah, that's what it references. That's poetry. You're veering into poetry for making your reader go back in time and space. You want to propel your reader through. So just having your clerks track old information first and teaching them what that means is really important.

Tim Kowal 
So it's kind of, tell me if you agree with this analogy. It's like leading them up a flight of stairs. They don't want to take any one of the steps, but if you at least hold your hand out to them and you're a familiar hand, they'll take the hand and then you can lead them up the next step and then the next step and then the next step. And as long as each step starts with information that they're already familiar with, they're willing to take the next step.

Cherise Bacalski 
Yeah, yeah.

would even flip that analogy. would say if you have a poorly written legal document, it is like climbing a flight of stairs and you pulling them up, right? But if you have a really well written legal document, it's just a joy to read. It's like, it really is. It's a joy to read. It's beautiful. And it's like being on a scooter and with the wind at your back and you're just being pushed and you've got, it's exhilarating.

Tim Kowal 
Thank

Cherise Bacalski 
And I think that putting old information first really helps to get rid of any roadblocks on your path.

Tim Kowal 
If you've written a successful brief under that standard and it's in the hands of your hostile reader, when does your hostile reader become a joyful reader? Is it after the introduction or is it just by the conclusion? it somewhere in the middle?

Cherise Bacalski
Mm-hmm.

Yeah, I'm.

I will say, yeah, it's gotta be the introduction. An expertly done introduction tell you why you're reading this, right? It answers the why. Why am I reading this? It identifies the area of law. It identifies the question that the judge has to answer. And it gives a little bit of factual background. It orients the judge. So the judge understands this is the job I have been hired to do by this brief, right? I know exactly what it is.

And a good introduction will also preview the issues that the judge is going to encounter. So, and maybe even we'll do it structurally and visually.

Tim Kowal
Visually, how important do you think it is to include visuals in your brief? You try to include them in every brief or only selective briefs. What if it's like a contract case, for example? Do you think it's important to include screenshots of the most important contract provisions?

Cherise Bacalski 

Yeah, yes, yes. And I've heard of very

successful legal briefs, including graphs of data as well. So instead of asking the court to kind of track the timeline, the successful legal brief will show the court the timeline.

So I think that visuals are well received and they can help if they're well done.

Tim Kowal 
Okay, I could go on and on with questions about brief writing, but we're running a little long. But I wanted to ask you one question, because I got outvoted on a previous discussion that Jeff and I were having with...

Oh, with Patrick Hagan about drafting the chronology of facts or the statement of facts. I like to include lots of headings that take my reader through the chronology. So I always start with, you know, in January, 2020, this happened. And then in March, you know, 2021, this happened. You know, I don't get granular, like with the days, but or if the month doesn't even matter, just in 2020, the, you know, the employer hired the employee.

Cherise Bacalski
Yeah.

Mm-hmm.

Yeah.

Tim Kowal 
whatever it is, just to give the broad strokes of the chronology. So I'm obviously asking a leading question for you to answer in the affirmative that you agree with my approach, but I actually do want your honest answer. Do you think that it's important to put the chronology in the headings or do you leave them out in your own writing?

Cherise Bacalski
I've never put chronology in the headings. It's never happened. So I guess, I guess never, never. I'll tell you what I do try to put into the headings. I try to tell the story in the headings, in the fact headings. So you've got in Utah, statement of the case, you've got the factual background and the procedural background. And the procedural background is the point at which the law enters.

Tim Kowal 
Never happened.

Cherise Bacalski 
Right? You know, the wheels of justice start turning. So everything before that is my client's perspective, the story from my client's perspective. And I try to highlight those facts that work for my client so that when the judge reads the table of contents for the first time, they have a favorable story to my client.

And I also of course have to deal with bad facts, but I definitely don't highlight those bad facts. And so what I try to do is just humanize my client and tell the story. And I'm not sure unless chronology is really important. I have seen some briefs where chronology is actually very important. And I have seen some legal writing coaches say, why do you need that data in there?

Well, sometimes you need it for statute of limitations purposes, right? So it's very helpful for a judicial opinion to actually communicate the year or date that an event occurred, even if it's not important to the narrative or to any of the legal questions. It helps to answer some of those kind of procedural questions. But as far as putting dates,

in the headings. I have never done that just because I haven't encountered a case where that would be important. Now, one of the cases that I recently read, United States Supreme Court case authored by Justice Barrett, her and her entire, every single topic sentence was a different month and year.

and a different actor. And it was important to the story because we were dealing with COVID, we were dealing with government actors, many different government actors. And it was just important to see the chronology of when certain tech companies were doing certain things on a month by month basis. She didn't have headings for those, but it was the topic sentence of every paragraph led with.

the date and the month. So I don't think it's a bad practice. I think it just kind of depends on what is called for by the content brief. Okay.

Tim Kowal 
Yeah, I'll take that as vindication of my practice. Okay, so just

so that we don't end on a granular question of writing style, we talked a little bit about chat GPT and AI. So I'd like to get your sense more generally, and we'll make this the last question. Do you have any predictions for how AI will change the practice of law or maybe even just the brief writing practice?

Cherise Bacalski
Yeah.

Well...

I hope that the law continues to be done by humans. I hope that we don't ever outsource our judicial, you know, jurist positions to AI. I think there is a, you know, it's the reason that we have a jury, you know, a

group of people who design outcomes, they decide facts. There are things that that AI can do, like comb through important information, you know, a huge amount of information and kind of extract some important things. But I mean, it leaves some things, some really important things out. I have had AI where I've gone through a thousand page record that council sent me and it took me like a day to get through it. And then

And then I drop it into AI and I say, hey, where's all the bad evidence of this? Or where's the evidence that this guy is a bad guy? And it misses the...

the gun and this is the smoking gun. And then I asked it like, why did you ignore the smoking gun? you're right. I did ignore the smoking gun. I'm sorry. I won't do that again. So I don't think we're there yet. I think you've got to have human eyes on everything. And I really hope that in the future, we don't get to a place where we're outsourcing attorneys or the judicial branch of the government to AI.

Tim Kowal 
You

Cherise Bacalski 
I think that there might be some, judges are overwhelmed. They've got a big job to do. And I hope that we don't start outsourcing judges.

Tim Kowal
Yeah, certainly for the decisions, the application, but maybe parts of it like, you know, draft me the legal standard. ⁓ And you can have it do research on what the legal standard is and I could.

Cherise Bacalski 
Mm-hmm.

Yeah, it just depends

on how many years of awesome legal standards AI is drafting before you completely hand it over, right? So right now we're in the beginning phases of AI. I think in 20 years, we might be a lot more comfortable with just handing over entire areas of the legal sector to AI, if that makes sense.

Tim Kowal 
Yeah.

Well, 20 years,

the Terminators will be roaming the Earth. We won't be having it, Yeah, I think it's, yeah, well, and it's still advancing at an exponential rate. And you're right, we don't know where it's gonna go. But to your point about the law being human, ⁓

Cherise Bacalski 
All right, well, we wouldn't even be having this conversation.

Mm-hmm.

Yeah.

Tim Kowal 
Obviously AI is not human. And the only way you can mimic a human response is by looking at past decisions. It's data set that lives on the internet of past judicial decisions and other types of decisions. Here's how a human likely would respond to this situation that you've given me based on my review of past human situations. But what if our data set

Cherise Bacalski 
Mm-hmm.

Yeah.

Mm-hmm.

Tim Kowal 
2025 going forward is, imagine you waved a magic AI wand and all of the judicial decisions were derived from AI. Now you don't have a human data set anymore. You only have an AI data set. Here's how AI has been interpreting past, pre-2025 human decisions. And you won't have a human data set anymore.

Cherise Bacalski 
Yeah, yeah, yeah.

Mm-hmm.

Yeah, yeah, that's a conundrum. Hopefully we humans stick around for a while.

Tim Kowal 
Yeah, it is. 

Yeah, well, here's to that, to humans sticking around for a while. Well, thank you, Cherise Bacalski, for joining me today. This has been a fascinating conversation. I hope to carry it forward. And like I said, I got more questions for you talking shop. And I'm interested in your take, more of your take on AI and applications, how we can use it safely and responsibly.

because it does pose just a huge tremendous advantage to clients if we can, you know, rest the efficiencies out of it without taking the humanity out of what we're doing.

Cherise Bacalski 
Yeah, absolutely.

Absolutely. I agree.

Tim Kowal 
Okay, well that'll wrap us up this time. If you have suggestions for future episodes, please email us at info at calpodcast.com. In our upcoming episodes, look for tips on how to lay the groundwork for an appeal when preparing for trial. We'll see you next time. Thanks, Charisse.

Cherise Bacalski
Alright, thanks Tim.