March 24, 2023

#108: Donald Sherman - Government Ethics & Oversight Lawyer

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In today’s episode I speak with Donald Sherman who is a government ethics and oversight lawyer who is currently the Senior Vice President & Chief Counsel at Citizens for Responsibility and Ethics in Washington, CREW (where, full disclosure, he works with my wife). In addition to his non-profit litigation experience at CREW, Donald has worked in all three branches of government. He served for a number of years as Senior Counsel to Ranking Member Senator Claire McCaskill on the Senate Homeland Security and Governmental Affairs Committee. Before that he was Chief of Staff and Senior Counsel for Oversight and Investigations in the Office of General Counsel at the U.S. Department of Housing and Urban Development (HUD). And before that he worked for Rep. Elijah Cummings, then-Ranking Member of the House Committee on Oversight and Government Reform including as Chief Oversight Counsel. He started his legal career as a law clerk Honorable Neil E. Kravitz of the District of Columbia Superior Court and worked in private practice at Crowell & Morning. Donald is a proud graduate of both Georgetown University and Georgetown Law (Go Hoyas).

In our conversation we discuss his decision to become a lawyer in elementary school, how crashing a wedding helped him get his first job in government oversight, the nuts and bolts of being an oversight and ethics lawyer on Capitol Hill and in the non-profit space, how the Hill and advocacy organizations interact when it comes to government oversight work, developing the skills of factual development and investigations, what constitutes success when advocating for major political change, the ways to transition from the private to the public sector, the superpower of being an effective generalist, and the role that people/kindness/relationships play in the life and career of a lawyer.


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Jonah Perlin [00:00:00]:

Welcome to How I Lawyer, a podcast where I talk to attorneys from throughout the profession about what they do, why they do it, and how they do it. Well, I'm your host, Jonah Perlin, a law professor in Washington, DC. This episode is sponsored, edited, and engineered by my friends at Law Pods. Law Pods is a professional podcast production company focused solely on attorney podcasting. I absolutely love working with them, and if you're considering becoming a legal podcaster or just want to learn more, check them And now let's get started.

Jonah Perlin [00:00:35]:

Hello and welcome back. In today's episode, I'm excited to speak with Donald Sherman. Donald is a government ethics and oversight lawyer who's currently the Senior Vice President and Chief Counsel at Citizens for Responsibility and Ethics in Washington, often known by its acronym Crew, where, full disclosure, he works closely with my wife, Deborah, and it's just so great to have him on the show. In addition to his nonprofit litigation experience at Crew, donald has worked in all three branches of government. He served for a number of years as senior counsel to ranking member Senator Claire McCaskill on the Senate Homeland Security and Governmental Affairs Committee. Before that, he was Chief of Staff and Senior Counsel for Oversight and Investigations in the Office of General Counsel at the US. Department of Housing and Urban Development. And before that, he worked for representative Elijah Cummings, then the ranking member of the house committee on oversight and government reform. He started his legal career as a law clerk to Honorable Neil E. Kravitz of the District of Columbia Superior Court and worked in private practice. Of interest to me, he also wrote a blog called Somebody Does that, where he interviewed people about cool jobs. So I think Donald's going to fit right in here at how I lawyer. So he's a proud graduate of both Georgetown University and Georgetown Law.

Jonah Perlin [00:01:43]:

Go Hoyas.

Jonah Perlin [00:01:44]:

Welcome to the podcast, Donald. Thanks for being here.

Donald Sherman [00:01:47]:

Oh, thanks so much for having me on. Really excited to be here.

Jonah Perlin [00:01:51]:

Sweet. Well, look, let's start from the beginning. I want to hear about what made you decide to become a lawyer and hear a little bit about if what you decided or the reasons you decided still stand today in the law that you practice.

Donald Sherman [00:02:03]:

Yeah, so a lawyer is the only thing I ever wanted to be, but I don't know that I sort of was a particularly ambitious kid. It was just the thing that seemed most interesting to me. My mom I've had asthma since I was nine months old, and so my mom always said, oh, you're going to be a doctor and find a cure for asthma, which, god, sounds awful, though finding a cure for asthma would be great. But in the fifth grade, I had this teacher. Her name was Stacey Divak. She was relatively new. I don't know if it was her first or second year out of school, but obviously we tortured her for it because that's what nine and ten year old morons do. But she was always having us do these new and sort of unconventional things. She brought in filthafish and matza and had us try that, and she took us on all these interesting field trips. And one of the things that she did was she had us participate in this program called Constitution Works, and we got to be mock Supreme Court justices and have a mock war argument. I got to be one of the Justices.

Jonah Perlin [00:03:19]:


Donald Sherman [00:03:20]:

And I just remember, I think it was Denver Dispatch versus the United States. It was like a first amendment case. I can't remember the details, but I just remember being so interested and excited about the role and really intrigued at this idea of precedent and how lawyers, through their arguments and justices through their decisions, got to be a part of history. And that was really exciting and compelling to me. And so that became the thing that I wanted to do. I don't know that I had Supreme Court aspirations, and my sort of specific aspirations within the profession were quite a moving target. But that's what got me excited about the law, and it's still the thing that has gotten me excited about the work that I have done, especially in government and government adjacent roles like the one I have at Crew.

Jonah Perlin [00:04:21]:

I love that. And it's so funny because after I've done a bunch of these interviews, the number of times I hear the name of fourth, fifth, and 6th grade teachers is shockingly high. The names are always different. Obviously, for me it was, and I say this in the trailer to the podcast that I recorded two years ago, tina Yalen's 6th grade class, where I got to represent Mr. Scott Free in a mock trial. And it changed my life. And it's amazing how those little moments have such an impact on who we are and what we become. Even though you sort of torture her, I'm so glad that she gets the props she deserves in your story. So let's fast forward a little bit. So you go to Georgetown, you go to Georgetown Law and you start your career as a judicial law clerk and in private practice, but pretty quickly thereafter move to Capitol Hill and start working in sort of this government oversight space. Talk to me a little bit about sort of how those jobs came about and also what interested you early on in that kind of work.

Donald Sherman [00:05:16]:

Sure. So I was at a firm, I think, like a lot of law students, I was vaguely interested in litigation or what I thought was litigation, and someone who didn't come from a lot of money. My mom was a teacher. My dad was a truck driver. It seemed like the kind of thing that was at least too much money to turn down without trying at first. And so I went to a firm. And I think at the time, I realized that that particular experience wasn't a good fit for me. And I had some vague notion that I was interested in policy. And so that sent me on a path of basically talking to everybody that I could think of about wanting to work on Capitol Hill. And I do what people do. I did the coffees and the whatnot, but it was really when I sort of quasi crashed a law school classmate's wedding that sort of set me down an entire career path that I just didn't know existed before. So one of my good friends, Ron Hahn, who actually is in the career services office at USC Law School now, he was in town for a fellow classmate's wedding. I hadn't been invited to the wedding, but I hadn't seen him since school. So I came to the cocktail hour, and I was talking to him and another classmate who was there who had summered with me, I was just telling everybody that I was interested in working on the Hill. This guy, Yan, he knew one person who worked on the Hill at the time. He lived in Oklahoma, and it was somebody that he married to his coworker in Oklahoma who had recently moved back to DC. And so at this random event, talking to someone that I never could have anticipated would be there, he put me in touch with the one person that helped me get my first job on The Hill. And it was working for the House Ethics Committee, which also happens to be one of the few committees on the Hill where not having prior Hill experience is an asset as opposed to a liability.

Jonah Perlin [00:07:34]:

Okay, so I want to break that down. There's a couple of follow ups. First of all, it's amazing that pseudo crashing a wedding is part of your professional story and professional path. It sounds like one of those stories where it's like, my dentist's friends, barber shop operator helped me get a job. It's something I tell students all the time. Right. It's all about maximizing the number of interactions because that's the only number you have control over. You don't know which one is going to be the one that changes your life, but you have control over talking to other people. But you said that you were going into that conversation with sort of a vague interest in policy. And I think I have students and people who listen who say that, but when you sort of dig a level deeper, they don't know what policy means as a lawyer. So talk to me about what you thought policy was and maybe how you frame policy. Work as a lawyer now.

Donald Sherman [00:08:26]:

Sure, yeah. I didn't really know what policy was then. I thought, oh, I thought policy meant I'll just go work for a congressperson and, I don't know, get an issue and write some laws, I guess. The funny thing is, I never got an interview for a policy job on The Hill, so I never had to fake my way through an interview at the time. So I don't know what I actually thought because the first interview I got was for an investigative role, which is exactly what I was looking for, but didn't know it. I think now policy development is pretty complex, but it still derives from a lot of the oversight and investigation work that I have done and that we do at Crew. And so whether it's filing somewhere upwards of two dozen hatchet complaints and then having conversations with people on Capitol Hill about how they can strengthen the law to prevent those kinds of abuses from happening long term, or it's having conversation with partners on the Hill and committees about gaps in the Freedom of Information Act that we've identified through litigation. I think now my policy expertise, such that it is, is informed by experience, and maybe that's the big difference. Right. 15 years ago, when I was looking for a policy job, I didn't know anything and hadn't done anything that would have informed or helped create any sort of passable expertise on policy issues. I was just all, I guess, book learning and lived experience. But there was no job experience to speak of that would inform policy like my approach to policy as it does now.

Jonah Perlin [00:10:25]:

And I guess the other follow up I have is you mentioned that you thought sort of the big firm litigation route didn't necessarily fit your skill set, but the area that you ended up, which was in Investigations and Oversight, was something that both did fit your skill set. And I don't want to misstate your words, but I think you basically said it was the one area on the Hill where a lack of experience on The Hill is actually beneficial. Like say more about what investigations work on the Hill is and sort of why that is the case, that less Hill experience may be beneficial.

Donald Sherman [00:11:01]:

I think the challenge for me going into law firm was I didn't know what I wanted to do. And so I think law firms are very good at putting work on your plate because you are a person that's graduated from law school and they have lots of work to be done. But I think it's always better to go into a firm with some direction or some sense of your interest. And I just didn't have that in the law yet. But one of the things that was helpful to me when I was applying for jobs when I applied for the job on the Ethics Committee was I hadn't had a partisan job. And the Ethics Committee is one of the only nonpartisan staffs on the Hill. So because I hadn't had a Hill job before, I wasn't in a partisan box. And so that made me an attractive candidate for both the Chair and the ranking member, a Democrat and Republican who would then hire me. But also coming from private practice, the one thing that I did have experience with was doing lots of doc review, which is a not insignificant part of being a congressional investigator, whether that's on the ethics side or on the oversight side.

Jonah Perlin [00:12:12]:

Yeah, it's funny when I think about sort of law firm hiring sometimes, and I know you're a sports fan, so I think this reference may make sense, but tell me if I'm wrong. Sometimes law firms are sort of looking for the best available lawyer, even if they don't have a specific role, because they're like, look, if you can sit in a chair and research long enough and you're smart enough and you've taken enough classes, we can teach you all the details. But those intangibles we can't teach. So we're going to find the best available mathlete instead of athlete and get them in the door. Does that sound right to you? Is that how law firms I'll put.

Donald Sherman [00:12:47]:

It this way, that is a very positive and complimentary assessment of at least how I ended up at a firm. And so I will take it.

Jonah Perlin [00:12:58]:

I love it. And in terms of that, investigations work. I think people have seen law and order in suits or they think they know what lawyering looks like. I try to sort of dispel those myths week by week on the show, but talk to me about a day in the life of an ethics investigator on the Hill, because I think that's something that we don't see from the outside, like, what are you doing? Who are you communicating with? What's the work product? Like, what's that all about?

Donald Sherman [00:13:27]:

Sure. So on the ethics committee, for a good period of time, it was sort of a mix of both advice and investigations. So you're fielding calls from staffers about questions about the code of conduct for members and staff, which being an ethics lawyer, especially giving advice as an ethics lawyer, lawyer is always an adventure. You're having conversations with, for example, we'll say a young staffer who has been on a couple of dates with a person and is now looking to looking for a gift exception to accept travel, international travel from this person that they would like you to agree is a friend so that they can accept the travel. But on the investigation side, it starts with reviewing the underlying facts. A lot of cases that come in, they either come by referral from the Office of Congressional Ethics, which is an independent body that investigates allegations of misconduct by members and staff, or it's something that where there's an ethics scandal that kicks up enough dust in the media that the committee will take it up on its own. In either case, you're doing some background research to identify what the underlying allegations are, what the potential violations of law and the code of conduct might be, and then developing a plan for whether you need more information to make a recommendation to the members of the Committee to open a formal investigation or you're identifying a plan to do that investigation and proposing subpoenas and document requests to the member to outside entities for information in furtherance of an investigation. So it's interesting work. It is challenging work because the rules aren't the congressional rules exist unto themselves. It's not like you're reviewing a lot of precedent or necessarily reviewing a lot of case law. But it certainly was I felt like it was important work, protect the integrity of the institution and it was fun work.

Jonah Perlin [00:15:57]:

Is it hard being the sort of the office that checks on you when you do something bad? Like did people avoid you in the lunchroom?

Donald Sherman [00:16:08]:

That is exactly what they did. You hear about this Hill experience and it's like, oh, it's a very social place. There are all of these young staffers, there's receptions and you see these members of Congress. That was not my experience. I had a handful of friends who worked in Hill offices and they talked to me. But mostly it was like my handful of colleagues on the ethics committee. We would get lunch together and we would never be invited. Nor could we attend the kinds of receptions and parties that you would typically think of and you typically hear about and often fairly get a bad rap on the Hill. That was not my Hill experience and so we kept to ourselves. I account many of those colleagues as good friends to this day. But yeah, we were not the Happy fun bunch, or at least we weren't invited to the Happy Fun Bunch party, fun as we might.

Jonah Perlin [00:17:13]:

It makes sense. You got to be the person who's able to do the investigation and ask the questions. So you have to kind of be above reproach. It makes a ton of sense. After you worked on the House side, you had opportunities to work first in the executive branch and then on the Senate side, but still doing a lot of this same sort of oversight and ethics work. Talk to me a little bit about just the differences to somebody who's unfamiliar of practicing in this practice area but in different either branches of government or parts of government.

Donald Sherman [00:17:44]:

Sure there are specific differences in the rules between the House and the Senate, but I think fundamentally the House is just a bit of a circus, right? It's a bit of a jungle. It's rough and tumble. Committee chairs have unilateral subpoena authority, so a lot of them see no interest in being cooperative or judicious when they issue subpoenas. And so you're just sort of running in the thick of it. The Senate, just by general practice moves more slowly. The investigations move more slowly and subpoenas. Most subpoenas have to be issued by a vote and it has to be usually a bipartisan vote or at least there's a lot more process involved. And so the investigations just tend to be a bit more methodical. Also, because the Senate confirms high level appointees, they also have slightly different tools in their toolkit to get information from the targets of investigations. Like in the House, I did, I don't know, probably 100 transcribe interviews of senior government officials, either as a first chair or a second chair in the Senate. I didn't do any, but I did interviews of nominees seeking to get confirmed, including Christian Nielsen when she before his gag for her nomination to become DHS secretary. So I think there are different levers and a different temperament of the institutions. I think on the administrator, when you're in the administration and you're sort of preparing to be on the receiving end of oversight, I always look back at that experience fondly. I don't know that I would describe that aspect of it as fun. Right. You're always waiting for some shoe to drop, if I recall. You're always thinking about there's the things that are happening in your agency that the Hill is already engaged on and you know about. There's the things that the Hill is doing and could come at any time that you don't know about, and then there's the stuff happening at your agency that you don't know about that could invite a congressional investigation. And those last two categories of shoes can drop at any time, and you just sort of have to drop everything to deal with them.

Jonah Perlin [00:20:25]:

Sure. One of the things it sounds like is common to all of these jobs is the ability to both sort of go through written information and also to get information by interviewing people in various formats just as a sort of brass tax. Like, how do you think about that fact development work? What are some of the tools and techniques that are important to you, having done this for as long as you have?

Donald Sherman [00:20:50]:

Yeah, you obviously have to know your facts, or you have to know what you know, and you have to know what you don't. Right. And that takes careful study, and you have to know enough to know what you don't know. And that's hard too, especially because I worked on committees of pretty broad jurisdiction. So on oversight, oversight can investigate any matter at any time. I worked on investigations related to allegations of political targeting at the IRS, a botched gun introduction operation on our border with Mexico. I worked with the NFL and the NFLPA on their substance abuse policy. And then I was asked to work on sort of bigger policy, more policy focused investigations like college affordability and things like that. And so it sort of runs the gamut. But in terms of approaching fact gathering, you have to do as much homework as you can do. That includes scouring government websites, talking to outside experts, reading lots and lots of news and other things in the public record. Sometimes it includes talking to whistleblowers. One of my first investigation on oversight was this investigation on the southern border and the Republican majority. They had already been in touch with the whistleblowers, and so we were a little bit at a disadvantage. But funny as it is, the key whistleblower in that investigation wrote a book about his experience, which included a description of when he first met me, which is always a little bit weird. Oh, wow. It seems like this high drama thing. He wrote about the interview that we did and the questions that I asked, which were through some fault of my own but some not, were not well informed. So that's memorialized in a book somewhere. But he also talks about me walking into a bar and seeing him sitting with the Republican staffers and me just sort of walking up to the table and like, hey guys, what's everybody doing here? And getting myself a beer and parking down with them. So there's a lot of fact gathering work that needs to be done. There's a lot of work to figure out how to develop rapport with witness, if you can. And sometimes you just need to be prepared to go into these situations with no idea of what you're walking into because especially in the minority, you're not the one setting the interviews, you're not the one driving the agenda. So you try and prepare as much as you can, but sometimes you just have to fly blind.

Jonah Perlin [00:23:43]:

Yeah, I think that makes so much sense from my limited interaction with doing things like depositions. Right. The more you know, the better footing you are. But you don't always have that benefit. And that first answer can go totally different place than you thought. And if you're not listening and you're not ready to play it by ear a little bit and let the witness go where the witness is going to go, it's impossible. And it's good to hear that someone with as much experience as you have thinks the same thing, that it's really about knowing what you don't know, which is really hard. So I want to talk about your move out of government now. So we've spent some time talking about your time in government and of late, minus a brief stint, which maybe we'll talk about in the administration, you've moved to the other side. And so I'm just curious about what brought you to crew into sort of the nonprofit external organization more generally, and then we can talk a little bit about how that's different and how that's the same than the work you were doing.

Donald Sherman [00:24:39]:

Sure. So I very much consider myself a government guy. I love being in government, and not only did I love the work, but I take great pride in it. But one of the things that happened when Trump was elected was I was concerned about what seemed quite clearly to be a crisis of ethics in the executive branch. I went to the Senate in part because I thought that the Senate could be a force for promoting accountability. That's always hard when you're in the minority, which we were at that time. But also, quite frankly, the Senate is not built to do the kind of oversight that I thought that was needed in that moment. And so I was working for Senator McCaskill, which was a fantastic experience. She's a great boss, was a great senator. But I started thinking about if I might want to make a move back to the House or do something else. And through my network, someone pinged me about a job at Crew. And I had known Crew from my time in the Ethics Committee when they didn't have such great things to say about our work. But I also knew that unlike some of the other organizations that sort of sprung up because Trump was elected president, crew had been in government ethics for 15 years prior, and that they had a proven track record and credibility on government ethics issues. And that was compelling to me because I wanted to be someplace where I felt like I could use the particular set of skills that I had developed, such as they were to meet the moment. And I think Crew, through its litigation and through its policy work and its research, really was doing that. And I felt like I had something to contribute. I pursued and was fortunate enough to get an opportunity to come here.

Jonah Perlin [00:26:50]:

And what's that relationship like between sort of private litigation or private research or private policy work like the work Crew does versus sort of that internal congressional oversight? You sort of I think we're hinting at I don't want to put words in your mouth, but hinting at there's a tension there of internal ethics work and ethics work from the outside. How do you see those as sort of are they overlapping? Are they different tools? Do they have the same purposes? How do you think about that spectrum?

Donald Sherman [00:27:20]:

They're not the same tools, but they certainly can complement each other. And I think in an ideal world, they complement each other when it's appropriate and may sort of be at odds when it's appropriate. So I think just a couple of examples. One, you look at the emoluments cases against Donald Trump in 2017. Crew was the first organization to sue Donald Trump for violating the emoluments clauses of the Constitution, and also the second organization to sue Donald Trump for violations of the foreign and domestic monuments clauses of the Constitution. There was a third lawsuit. It was from Congress. It was filed after those first two ones. And I think the reality was that crew, because it's not a giant bureaucracy with lots of different members and lots of different opinions in a position to actualize things pretty quickly, was able to move and take that action before Congress could check all the boxes and corral all, hurt all the cats, if you will, to bring a lawsuit. And so that's an example of where someone on the outside and folks on the inside are sort of trained on the same issue, but someone on the outside can pursue it in a different way and possibly a more effective or certainly a speedier way than can be done on the Hill. By contrast, there are things like impeachment where the best that you can hope for on the outside is that you can provide some influence and insight and advocacy so that the members with the actual authority to take action are doing something. Another example is with FOIA right. Crew sued and successfully got the memo from Attorney General Barr. That was the sympathetic explanation and potentially erroneous explanation of the Mueller report. Congress, for a number of institutional reasons, which may be good or not good, doesn't use the FOIA right. They obviously have independent authority to get documents and information. But while those cases can often end up tied into court and have some success and some frustration, crew was able to sue under the Freedom of Information Act and after a couple of years get that memo and make it publicly available in a way that Congress either could not or would not. And so there are different tools in the toolkit, but also, I think sometimes the process, despite not having political power, an organization on the outside can be freer to move more quickly and use different tools to promote accountability. Another good example of this is our work on the 14th amendment. Obviously, the January 6 committee did an exhaustive investigation of the attack on the Capitol and made recommendations that government officials involved who took an oath be disqualified from office. While they were doing that, Crew went out to New Mexico and brought a case directly on behalf of through New Mexico residents to remove a government official from office under section three of the 14th amendment. Again, our ability to take action isn't defined by which party is in power in Congress. So that is not insignificant data point that allows us to move and take action on issues where congress may be hamstrung, right? January 6 committee doesn't exist anymore. And so there's a question of, well, who's going to take that baton, right? And I think folks in the government community like Crew have to be ready, willing and able to take the baton to help bring about the accountability that the January 6 committee identified as being necessary.

Jonah Perlin [00:31:48]:

It's a really interesting and thoughtful answer about a really sort of hard question about thinking that if somebody is a lifelong resident of Washington DC. I've seen live with friends and family members, the sort of the feeling of what government can do and what everyone else who's working in this town outside the halls of government can do differently and powerfully. And I think that's a really interesting and thoughtful way of thinking about it. The next question I have. Is about sort of what is success in your work like? So much of what you do is long term. So much of what you do is reviving old doctrines or creating brand new legal theories that either are untested or haven't been tested in quite some time. What is success in your work, whether that's sort of small s success or the longer term capital success? And maybe how is that different than sort of what it looks like? For a government committee to find success.

Donald Sherman [00:32:47]:

In both, you have to take the long view and celebrate the short term wins. Right. I supervise our legal team, and I work with a number of dynamic and creative lawyers, one of whom who has been here for, I think, seven or eight years, working to try and get Citizens United overturned. Right. That's not something that's going to happen in a day. And with the current makeup of the Supreme Court, I don't know that he or I would feel confident putting a wagering a guess on when that might happen. But I think we view success as incremental progress, trying to bring about as much accountability and as much transparency under existing law as we can. And trying to bring about as much accountability for bad actors as we can. In the current legal regime, all the while keeping our eyes trained on hopefully overturning what we believe is a wrongly decided decision that is incredibly bad for democracy. But I think you don't go into this work unless you are optimistic about government and resilient in your approach to work. And I think those are similar qualities as I think most people that go into public service. Right. You take, for example, just this week, president Biden fired the architect of the Capitol after pretty scathing. IG report identifying financial mismanagement of government funds and weird and highly problematic conduct like impersonating a law enforcement officer and giving quote unquote patriots tours of the Capitol while the facilities were closed in the fall of 2020. And so that's not a position in government that anybody cares about. But in the fall, we kicked up enough dust. After this, IG report happened that some folks on the Hill started to take notice. There was a hearing about it last week, and based on the news and fallout there, there was accountability for Blanton. Now, that's not going to be the case in every situation, certainly there's accountability that is hopefully coming for Donald Trump and others involved in the attack on the Capitol, but you sort of take it as it comes. The other thing that I would say is, especially around January 6, is I am someone who spent a good deal of time reading legal precedent from what happened after the Civil War, what state legislators did, what Congress did, to hold people accountable for being Confederates and for being engaged in rebellion against the United States. One of the things that weighs on me on a daily basis is the words of my former boss, Elijah Cummings, who a couple of years ago, before he passed, obviously said, people will ask us when we're dancing with the angels, what do we do to keep our democracy intact? And I think about what the historical record is going to look like, what legal precedent is going to look like in the aftermath of the insurrection on January 6, and will there be a sufficient body of case law? Will there be a historical record demonstrating that there was accountability for the assault on our democracy? Those are the things that I think about. That is what I would consider success. It doesn't mean that there isn't going to be failure along the way or setbacks along the way. But I think being generally optimistic, taking your victories, small as they are, as they come, and remaining trained on the larger goals, is something that I've seen as being consistent within my work, both in the nonprofit sector and in government.

Jonah Perlin [00:36:52]:

And when you talk about sort of this important work, how do you think about the balance between litigation and legislation? Right? I mean, one of the big changes historically, right, is Congress goes through new phases and approaches and the courts certainly have gone through many different sort of versions over the last 100, 200 years. How do you think about that balance, at least today, about how to bring ethics work and do this work? Well, using litigation as one tool and legislation as another, I think you got.

Donald Sherman [00:37:28]:

To use all the tools in the toolkit, right? This is going to sound cynical, but I don't mean it this way. You got to take advantage of scandals, right? That is the only time that Congress actually implements reform is when there is a big enough scandal, that kicks up enough dust that the public is animated and the media are animated about it. And so being ready for that moment, whether it's with having your facts lined up so that you can advocate for changes in the law or being ready to sue, to bring about accountability in the court, you have to be prepared for those moments and you don't necessarily know when they're going to come. But I think we try to use every tool in the toolkit. And so, as you all know, we have a really dynamic policy team and we work pretty closely with the legal team so that our advocacy is informed by the accountability work that we do, right? Like, if there are gaps in the law being exploited, then it's time to talk to Congress about changing the law. And if there are lessons to be learned from scandals that we expose, then we want to make sure that that is included in our testimony and statements for the record and our advocacy. Up on the Hill, we've heard a.

Jonah Perlin [00:39:03]:

Lot about sort of how you got here and what you do. The third leg of the three legged stool of how I lawyer is about how to do it well. And so I just would be curious to hear about you run a team now and you've been doing this work for some time. What do you think that someone should sort of look in the mirror and see in themselves if they think this sounds interesting to me and I want to do this work, what should they look in the mirror? What skills might they have, what interests might they have, what temperaments might they have that suit them well to getting into sort of government oversight and ethics type work.

Donald Sherman [00:39:41]:

Doing oversight on the Hill, especially on committees of general jurisdiction and even the Ethics committee, right? Like you're moving from substantive issues that are really divergent, right? Like this isn't like being an energy lawyer or a policy expert on taxes. For one ethics investigation, one member alone, I had to learn about tax policy. I had to learn how rent control and rent stabilize housing worked in New York and I'm from New York, but I never had to deal with that before. I had to understand how financial disclosures work and then I had to learn some things about the real estate market. Right, that's one investigation. And then going to oversight, you not only have to learn things quickly enough to understand an investigation and be able to distill it for members and for the public, but then you have to leave it. And so if you're someone that prefers to work in one lane and prefers to work with in a regimented way, then this is probably not the space, which is fine. I tend to be a generalist, which when you get to my point in my career, is always a little bit uncomfortable because I feel like there's a tension where people want you to be expert in something. But I think that there is a great deal of expertise in being a generalist, right? Like it is a particular skill set to be able to drop somebody into an operation and have them get quickly up to speed and be able to navigate it without years and years of experience doing that substantive thing. Now, obviously I'm biased because I'm talking about my own skills, such as they are, but I think that's certainly something that has served me well and I think I have seen it in a lot of my colleagues who have thrived in this space as well.

Jonah Perlin [00:41:51]:

Yeah, it's a surprisingly common answer on how I lawyer, that people, the best lawyers are the ones who are curious and that being able to sort of be curious about something that you've never heard about, learn it, learn it really well and then move on to the next thing. I think that's a very valuable skill for all lawyers. But it sounds like for your work it's sort of essential in a profession that's gotten so siloed, your silo is more skills based than topic based. Although given everything else you said, I think you may be underselling the level of expertise on substantive areas as well. The other question that I get pretty frequently from law students, and this goes back to where we started, is they come to law school wanting to work in government or work in the nonprofit space or use their law degree to make the world a better place. Like that is the North Star of many students who come to law school. And then the practical realities set in, the hierarchies set in. People go to law firms, they try it out, and people are often a little bit concerned about being able to transition sort of a couple of years into their career into the kinds of spaces that you were able to transition to. What kinds of recommendations do you have for those folks who may have started their path in private practice and are considering moving to government or non governmental spaces? Is it networking? Is it pro bono cases? Is it law school classes, skills? What are the things you'd recommend for those folks?

Donald Sherman [00:43:18]:

Get your money, right, whatever the situation is, whatever that means for you, right? I was fortunate enough to have a scholarship for law school, which is the number one reason why I was able to leave a firm within two years of graduating. So make sure that you do whatever you need to do, financial, planner, whatever, so that you can make that move. You can make less money and afford whatever lifestyle you want before moving to the nonprofit or government sector. In terms of skills, honestly, I think getting real practical legal skills, right, whether that's at a firm, whether that's at a public defender's office or prosecutor's office, whether that's clerking that is always going to serve you well. Law school is a lot about checking boxes, right? There's still quite a bit of that as you move along in your profession. And being able to demonstrate that you have real lawyering skills is never going to hurt you, even if you don't want a lawyer or don't want to litigate afterwards. So I would say that as well. I think from the networking perspective, I have a couple of pieces of advice. One, tell everybody that you know what you want to do. You don't need to be pushy about it. But again, my entire career exists because I had a conversation with someone about my aspirations that I did not expect to see, did not have any idea could help me. And we weren't even that close when we were having that conversation. We are now close friends, but at that point in time, he was a friend of a friend, an acquaintance from law school and from the summer. So you should be very intentional about that. I think the other thing that you should do is make sure that you network with your network, right. The people that are your closest friends. The people that are in your family are the people that will help you regardless of who you are and what you do. Right. I remember distinctly I was trying to meet the White House Council because White House Counsel's office helps identify people for oversight jobs at agencies. And so I was talking to Deborah's employer, ACS, and went to their holiday party, and somebody was going to introduce me to somebody who was going to introduce me to the White House Counsel. So I get to this party and my contact at ACS says, oh, hey, I'm going to introduce you to someone who used to work here. They work very closely with the House Counsel's office and she can put you in touch. Then she said the person's name. This person, Christine, is someone who I have known since I was ten years old. Like, we are close friends. We call each other siblings. The only reason that this had not happened before is because we are such close friends that we never talked about work, we never talked about our career aspirations, we talked about relationships, we talked about Casa from school, we talked about missing New York. Right. But this is someone who unquestionably, would do whatever she could to help advance my career. I just never asked her because it never crossed my mind. Right. You have to start with the people that care about you the most before you go trying to recruit some strangers to do something for you. Right. Start with your network and your inner circle, your kitchen cabinet, and be intentional with them before going to ask strangers to do something that you haven't asked your best friend.

Jonah Perlin [00:47:06]:

Wow. Well, normally I always end by asking for a piece of advice or something you wish you knew, but I think we already covered that, so I'm so grateful for it. I think that's so right. Is building your network and relying on your network's. Network is such a powerful tool that I've seen time and again in my own career. And you've shared your story and how it helped you. Well, look, Donald, it's been great to spend the last sort of better part of an hour together, and I just wish you the best of luck on all the big cases you have going on and all the big work you're doing. We're lucky to have you beating the drum for democracy over at Crew. So thanks for doing this, thanks for taking a break for it, and obviously we'll be in touch.

Donald Sherman [00:47:48]:

Thank you. I do have one other thing to add, if that's okay.

Jonah Perlin [00:47:51]:

Please, go for it. If you got advice, go for it.

Donald Sherman [00:47:54]:

No, honestly, the number one piece of advice I give whenever I'm asked is be nice. Law school is a place where that I think is wrongly characterized as being fairly cutthroat and competitive. But one, being nice is good for the world, but two, if you're the most cynical person in the world. Being nice means that there are people that want to be nice to you. And if you do favors for people easily, it makes it easier for you to ask favors of people. Right? It is a skill, just like anything else. And so if you are nice, people will remember that just as much as they remember if you are a jerk in law school and your career is long. But it could be pretty short if everybody that you went to law school with thinks you're a jerk. So, yeah, that's the other piece of advice that I give.

Jonah Perlin [00:48:50]:

Absolutely. Well, we're definitely in agreement on that one. And, yeah, thanks so much for taking the time, Donald. And yeah, best of luck. Thank you again.

Jonah Perlin [00:49:00]:

I am Jonah Perlin, and this is the How I Lawyer podcast. Thanks to podcast sponsor Law Pods for their expert editing. If you're a lawyer considering starting your own podcast, definitely check them And thanks to you for listening. If you enjoyed the episode, I hope you'll consider sharing it with friends and colleagues or on social media. And of course, if you haven't already done so, please sign up for the email list  at or subscribe to the show wherever you listen to podcasts. As always, if you have comments, suggestions, or ideas for the show, please reach out to me at or at Jonah Perlin on on Twitter. Thanks again for listening and have a great week.