ALEXANDER POWELL: 0:00

Welcome to Cited Authorities. I'm honored to have today's guest with me, Melissa Wiley. Melissa is a partner at Kostelanetz and one of the most respected voices in tax controversy and someone I've been looking forward to having on the show. Melissa, thank you for being here.

MELISSA WILEY: 0:19

Thank you so much for the kind introduction.

ALEXANDER POWELL: 0:22

Melissa, you started your career in actuarial science. How did you end up practicing tax law?

MELISSA WILEY: 0:28

Great question. So when I was in school, when I was growing up, there were a handful of things I always really loved when it came to school. One of them was math. I love solving problems. I love getting to the end of a problem and that satisfaction of having worked through it and gotten to the answer. And I really loved writing. I really loved expressing myself in words. And that was also true of music. I really loved music. And so while I feel like most of my classmates kind of either were English and history buffs or they were math and science buffs, I was kind of this weird mixture of math and writing and speaking and music. And so when I thought about what I wanted to do and what was most likely to make me a successful adult, I thought, well, there are a lot of people who are really good at math. And so I thought, well, there are a lot of people who are really good at music. And there are a lot of people who are really good at writing. But there are a lot of people who really don't like math and a lot of people who are really intimidated by it. And at the time, the actuarial field, the profession of being an actuary was showing up at the top of all of these lists as like best job, you know, in terms of stability and pay and challenge. And I thought, well, I really like math. And so I ended up deciding that that is what I should pursue. I think it's funny that we have kids, and I mean kids, when they're 16, 17 years old, trying to decide what they want to do for their lives. But that is what I decided at that age. And so I sought out actuarial science programs. I ended up going to the now defunct, it's part of St. John's University now, College of Insurance, where I majored in actuarial science. And I ended up going to the now defunct, it's part of St. John's University now, College of Insurance, where I majored in actuarial science. And I ended up going to the now defunct, it's part of St. John's University now, College of Insurance, where I majored in actuarial science. Had a really great time there. You know, really enjoyed my classes. Same things that appealed to me about math appealed to me about my actuarial classes. And I got a lot of work experience, too. I was part of my college's co-op program, and so I got to experience what it would be like to work in the insurance industry. And what I realized pretty quickly was that while I really loved the work, like the personality of the job wasn't quite fitting in as much as I would like. And so I tried a little bit to move around the industry when and I worked for a reinsurance brokerage firm for a while where I had a little more of an ability to, I guess, persuade and enjoyed that aspect of it, but then sort of ended up losing some of the technical rigor. And the more and more I thought about it, I was like, you know, I'm still young and I still have the ability to pivot. And given that I have a very specific undergraduate degree, if I want to do something else, I should go back to school and hopefully go back to school in something that will give me more options than working in the insurance industry. So I settled on law school. I thought long and hard about law school, about a master's in teaching, about studying psychology, and ended up going to law school. I attended Georgetown, made some really lucky choices because I had never been to the law school until the first day of orientation, just kind of showed up having never visited the campus. I had been to D.C. and I knew the school was a great school. And I was so lucky, that I really enjoyed it. And what I found in law school, and I think what ultimately led me to tax law, was that you could still be technical. You could find an area of the law that still had that rigor of difficult problem solving, while at the same time having it be important that you can express yourself well and that you can advocate for clients. And I took a tax class with Marty Ginsburg, Justice Ginsburg's late husband. And I was like, I'm going to do this. I'm going to do this. husband, who was a brilliant tax lawyer and just a really amazing human being. Just funny, really dry sense of humor, truly cared about his students, remembered his students like the ones who actually cared about tax, and encouraged his students to, you know, continue to learn more. And so I took a part-time job my third year of law school in tax controversy and sort of never looked back. You know, it's

ALEXANDER POWELL: 5:21

a common theme in the show, and it seems like every other guest, the law is not their first career.

MELISSA WILEY: 5:28

Yeah, and I think to some extent the law sort of encourages that, right? I mean, when you look at the breadth of things that people with a law degree do, even those who practice law, there are so many different ways that you can choose to be a lawyer. You can be a lawyer to large numbers, you can be a lawyer to a large number of people, you can be a lawyer to large corporations and help them on massive deals, you can be a lawyer to children and custody disputes, you can be a criminal lawyer, you can be a family lawyer, you can be a lawyer who only does appellate work, you can be a lawyer who stands up in court. There are so many ways for people who just appreciate a challenge to be able to find their place in law. And so I think that that might be part of the reason that so many people get to a point where they're in their life where they feel like they want to solve some sort of problem in the law. The law might be the place that they can do it.

ALEXANDER POWELL: 6:27

Melissa, what does your practice focus on day to day?

MELISSA WILEY: 6:30

Sure. So my practice over 20 something years now has been pretty much exclusively in tax controversy. And my cocktail party response when people want to know what I do is I fight the man. The more, the more detailed version of that is that I represent taxpayers and all sorts of interactions with both the IRS as well as the state and local taxing authorities. So it may be somebody is under audit. I represent clients at administrative appeals within the IRS. I represent them in litigation with the government. I also represent clients who are looking to come into compliance with their tax obligations who maybe have not been as much in compliance as they should have been. And I also represent clients who are looking to come into compliance with their taxes as they would have liked. So really, anytime somebody is doing something, I like to say sort of reactive to the tax. Those are my clients. And I say that to contrast it to the folks who do kind of planning or deal work in the area of tax, people I have enormous respect for and could never do their job. I've always been really lucky to work at places where I've had those people with those brains and that expertise available because I think it makes me better at representing my clients to have, to have those kinds of voices and that expertise available.

ALEXANDER POWELL: 8:02

You also teach at Georgetown, your alma mater.

MELISSA WILEY: 8:05

Yeah, it's all, it was really very, very surreal. The first time that I got my letter from Georgetown, extending the offer to, to serve as an adjunct professor. I guess it should go without saying I loved my time in law school. I really enjoyed Georgetown. I often joke our office is right across the street from the law school. And so I'll often joke now that like, I really didn't get very far in 23 years. But I, I love teaching. I love the questions that students come up with. I, I taught and, and will be teaching again this fall, a class in tax research and writing, which it, it cannot be overstated how much when you have to teach something, even if it's something you already know, you learn so much. A big part of what we talk about in the class is sort of legislative history and how you use different pieces of legislative history to be an advocate for your clients or to understand the tax law. And, you know, I really, I really understood the context of all those little pieces. And I, I describe it to them as, you know, you have to know what the path is and what, what is generated, what evidence is generated at each point in the path and what crumbs it leaves to put things into context. And all of that in, in, in the process of coming up with the class and, and what I was going to teach my students, I realized that I was organizing that in my head in a way that now made it, you know, much more useful to me. So I, I have loved teaching. Yeah, just, just for the experience of, of working with students and helping them understand things. And, and a part of our class too is writing. So it's giving them feedback on their writing and then sort of giving them advice on, on how to be more persuasive without overdoing it. And, you know, part of what I love about the law too, and particularly in what I do is, is the importance of, of those kind of softer skills of judgment, of writing, of, of how you present your arguments. And it's, it's just been a wonderful opportunity to revisit those.

ALEXANDER POWELL: 10:29

I think that is common for newer attorneys and law students who are newer to advocacy. Generally, there's a tendency to, to overdo it. Like you said, to, to, you know, not lean in. So, okay, what are the facts? What's the law? And then really hammer that home as far as clean quality, plain English writing. And there's, there's a tendency for newer attorneys and law students to be more ornate, try to get too fancy, which can backfire.

MELISSA WILEY: 10:56

Yeah, absolutely. And it's, you know, it's funny. I, I just earlier today had a meeting. We have these sort of mentoring teams within our firm with folks at all level of, of the organization come together once every quarter or so for, for a mentoring meeting. And one of our paralegals asked something to the effect of, you know, how, do you learn trial skills in law school? She's planning on going to law school about a year from now. And, and all the lawyers just kind of laughed. And we were like, I guess in theory, I mean, you learn, you learn some of it, but there's a part of it that you just can't, can't learn at all until you show up. And, and so much of it, and I have always said this to young lawyers and, and those who want to be in the law, that you really just, you have to sit and watch. I cannot commend enough just going into a courtroom and sitting and watching. And what you realize is every lawyer has their own approach. Every lawyer has their own personality. And you start to see like what lands well with witnesses, with juries, with judges, with different judges, right? We know they all have their own preferences. I find that to be kind of the, the like anthropological interest of the law. I love learning about the preferences of different judges and adjusting your technique to, to whoever you're talking to. And, and so you're right. I think there, there are people who think like, oh, I have to go out tougher. Oh, I have to, you know, one, one partner I worked with early in my career in editing, one of my briefs was like, you never in a brief, and he was a former judge. So his, his weight, the weight of his words was significant. He said, you never in your briefs want to say that something is clear or clearly answered. Because if it was clear, you wouldn't be in front of me in my courtroom. I was like, all right, I will never forget that. 15, more than 15 years later, I still remember that in my writing.

ALEXANDER POWELL: 12:59

That is important advice. As far as client counseling, that is very difficult to teach. Also aligning with judgment. There are a lot of difficult conversations that you must have where you're, you're not able to offer the news that you would prefer to offer despite best efforts and then offering the options to the client in terms of, okay, there, here's option A, here's option B. What should newer attorneys, law students know about client counseling?

MELISSA WILEY: 13:28

This is another great one that I learned from one of my very first jobs. It was actually my like law clerk job from my third year of law school. The, the attorney I worked for told me this story about this client that he had, who he had worked all this time for it. In audit thought was treated very unfairly in the audit. Objectively was treated very unfairly in the audit, went to appeals, got a great appeal settlement, went to the client and said, look, I've got this excellent, you know, we, we've won essentially. And the guy said, I don't care about the money. I want an apology. I was treated really unfairly. And he said, I will never forget that client because he taught me to always understand and always ask what it is you're a client. And he said, I will never forget that client because goals are. And oftentimes you get a client who comes to you and the first, the, the first conversation, right? They're telling you all about the facts. That's what they want you to know. The facts, the facts, the facts. And I try to always remember my version of what a successful resolution of those facts are may not be my clients. And so the answer, the question that I always need to ask before the end of that very first call is what do you want out of this? And that can be every thing from, I just want the government off my back. I never want to see another letter from the government in my mailbox again. It could be, I want this other person to pay something. It could be, I just want to fix this so that I can sleep well at night again. And I've had clients say, look, my, if I have an individual client, look, my wife is, is so nervous about this. Like I, what do I do? How do I, and, and it's really listening. We bring the text, technical skills, but what we need to listen to our clients about is, is what results, what services can we provide that will get them to that goal? And so if I have a client who says, my wife is so angry at me right now, I will always offer like, do you want me to talk to, I'm happy to talk to your wife and explain what is going on. I'm happy to answer whatever questions about the process you need. Oftentimes your clients will want things that you can't get them, right? That wanted an apology from the IRS. We all know that was not coming. And, and so you want to make sure that your clients have reasonable expectations too, so that if you get them, what you think is the perfect solution, they don't come back and say, well, I'm not happy. That's not actually what I wanted. I wanted something different and explaining to them what the limitations of what we can do for them are. I think it's also super, super helpful. I can't tell you the number of times that I've been in a voluntary disclosure space that I work with where those are the ones who will call and say, I cannot sleep at night. This is keeping me up at night. I need to fix this. I just, I, I need to fix this. Um, and one of the first things I tell them is about how the IRS has programs to fix these things because there are so many other people in your situation. You're not an outlier. Like there are other people who find themselves in the same situation. And the reason the IRS has those programs is they want you to be able to fix it and really listening to what is going on beneath the client's ask of you as a tax lawyer, um, and trying to get them at a better headspace, trying to give them that counseling, right? Not like the legal advice, but that counseling that they really need. And I think it's, it's really easy to, to forget about that part. And in, in some practices it's more important than others. But for me, that's, that's a big part of it. That's such an important part of how I represent clients because I think it's important, but also because it's the part that's most meaningful to me. Um, I, I will always feel better about letting a client feel like a weight is off their shoulders than I will about getting the client, you know, a concession in terms of cash. Um, that, that quality of life difference. Um, I'm, I'm really proud of the cases where I can give a client that.

ALEXANDER POWELL: 17:47

You have the right demeanor where if I were the client and you know, my wife were upset about what was going on and you offered to speak to her, I'd be like, yes, of course. That'd be great. You know, I could think of other attorneys where, you know, they're more cold or more terse or like, no, thanks. Um, I'm good. I'm good on that. Melissa, there's been a lot of news this year,

CITED AUTHORITIES: 18:08

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