Greg Siskind is a founder of Siskind Susser, a national immigration law firm based in Memphis, Tennessee....
Victor Li is the legal affairs writer for the ABA Journal. Previously he was a reporter for...
Published: | April 16, 2025 |
Podcast: | ABA Journal: Legal Rebels |
Category: | Legal Technology |
“May you live in interesting times.” For immigration lawyers, that old proverb is now a reality. Ever since the start of the second Trump administration, immigration lawyers have been busier than ever, and they have plenty on their plates.
Special thanks to our sponsors Verbit AI and ABA Journal.
Announcer:
Welcome to the ABA Journal Legal Rebels podcast, where we talk to men and women who are remaking the legal profession, changing the way the law is practiced, and setting standards that will guide us into the future.
Victor Li:
May you live in interesting times for immigration lawyers. That old proverb is now a reality. Ever since the start of the second Trump administration, immigration lawyers have been busier than ever, whether it’s dealing with ice raid deportations, executive orders, slowing down the visa process, limiting the birthright, citizenship and rec receiving Obama and Biden era immigration policies, as well as nervous clients worried about what the new regime might mean for them. Immigration lawyers have plenty on their plates. Technology, particularly generative AI, can help with some of that increased workload. My name is Victor Li and I’m assistant managing editor for the ABA Journal. My guest today is Greg Siskind an immigration lawyer and tech enthusiast. Greg is the founding partner at the law firm, Siskin Susser and co-founder of Visa law.ai, a tech company that creates AI powered software for immigration lawyers. He’s here today to talk about how tech can help immigration lawyers work more efficiently, as well as how much has changed in the immigration landscapes since January. Welcome back to the show, Greg. Nice
Greg Siskind:
To be back.
Victor Li:
Yeah. So for those people who may have missed our last conversation a couple years ago, can you tell me a little bit about yourself and your background?
Greg Siskind:
Sure. So I’m an immigration lawyer. I have been practicing immigration law for most of my career, which started in 1990. I started out in big law, but left and started up my immigration law firm in 1994. And I’ve been doing a real mix of immigration work in the years since. And my solo practices that has grown to, there’s about 60 people now at our firm, so we’re a different kind of operation. And I also have been involved in legal tech since the early part of my career. In fact, when I left Big Law in 1994, it was because I was launching a website for my New Solo practice. So that sites turned 30 last year. And over the years there have been a variety of technology changes that we’ve embraced, whether it was social media or in 2015 starting to work on AI apps. And then in a couple of years ago, getting into generative ai, which I know we’re going to be talking about today.
Victor Li:
So I don’t know if I asked you this last time, but how do you balance both of those hats? You have your immigration hat and then you have your tech hat, and how do you balance those two and how do you decide, okay, well, I need to work on this and maybe not that at this time, or I need to kind of balance them both or figure out how to work on one not the other. How do you manage that time?
Greg Siskind:
Yeah. Well, it’s often not easy, but that’s one of the benefits of being in a larger operation than we used to. And right now I mentioned there were about 60 people, the law firm side, and we have about, I think eight or nine people right now on the software side. So I can, in a lot of respects, delegate tasks that in the past I would have to have done myself. But also the law firm itself has become the lab for the work that we’re doing on the technology side. So in a lot of cases, the work that I’m doing on the software side is directly benefiting the lawyers and the paralegals and other staff on the tech side. So it helps actually to have a foot in both worlds because it’s a lot easier from a design perspective to be working on what I’m working on when I’m working directly with the lawyers and I have an understanding of what they need because I practice in the area as well.
Victor Li:
And you also, you provide products for other immigration lawyers in the field? I mean, visa law creates things for other lawyers. Right
Greg Siskind:
Now there’s about 500 law firms that are using the AI suite that we created.
Victor Li:
Okay. And you alluded to this during your earlier answer, but yeah, the last time we spoke about immigration technology, that was before generative AI had become available to the general public. So since those, in that last two and a half years or so, how has this technology changed things for immigration lawyers?
Greg Siskind:
Well, I mean, I think it’s really sort of making over the entire way that we practice our product. We started out focusing on legal research and we were working with the open AI language models and basically trying to build out what was and what is now the largest immigration library in the world to power a research app. And we were noticing that the products that were already coming out in that space were more general and not really focused on that niche area. So we collaborated with the American Immigration Lawyers Association to build that library and set our app up so that the answers are coming just from there. But that was the place that we started when we were working on the generative AI software. And it wasn’t just sort of the answer legal research questions, but to do a lot of everyday tasks like create a checklist of what I need for this particular kind of matter, or if I’m going to, after you query the AI for a legal research question, you may say, okay, I want to build out a questionnaire form for clients, or I want to build out a letter to a government agency citing the laws.
It was stated in the legal memo that came out from it. So it’s sort of a variety of tasks that we were working on on that end with that chatbot interface that looks similar to chat GPT. But the big thing was that the answers were a lot more reliable because they were only coming from the library. And also we had a very highly detailed system prompt to build out what we were working on. And then also we lowered the temperature, which I know a lot of people probably aren’t familiar with that temperature when it comes to generative ai, but it is a technique that legal research companies use to make the product essentially more conservative in terms of the algorithms and how it’s answering questions and not just guessing and answering anything, even if it doesn’t really have it in the data set. A good answer for the question.
So we did a lot of those things initially and then later started working on other tools. The big one where we’re putting a lot of energy in right now is our drafting product. And this is probably in terms of time savings. And the reason why I think it’s really going to change the profession even more so than legal research is because of, I mean, most of the reasons why there’s an access to justice gap in immigration laws, it just takes so much time to work on an immigration matter, particularly when it comes to making the legal brief and ought to be other parts of that case that require a lot of drafting work. So we’ve been building tools that essentially automate with the generative ai, a lot of the drafting part of the process where we can sometimes reduce the time potentially as much as 90% that it takes to produce a document that should make it possible for immigration lawyers to be able to take on a lot more work.
And then probably, and inevitably prices will go down just because it doesn’t take nearly as much time to do that kind of work. So those are a couple of the things that we’re working on. And I think the immigration bar has always been a very innovative bar. This was a bar that 40 years ago moved away from Arrowy billing to flat billing, and probably 90% of immigration lawyers flat bill their work. This was the immigration bar were the first, and I was the first with a website, but it wasn’t for very long. There were a lot of immigration lawyers starting in the mid nineties jumped into that. A lot of ’em were very early on social media, and there has been an embrace of AI in immigration law. I know there’s been that embrace broadly in the legal profession, but I think there’s a more positive attitude about it in immigration law just because of the culture of the profession and the history.
Victor Li:
Gotcha. So you talked about the access to justice gap. It seems like despite everyone’s best efforts, and this is probably also connected to what’s going on right now, there’s still a lot of people in the system who end up having to go pro se. How big a problem is it just in your experience?
Greg Siskind:
It’s a really big problem, and I know that there’s been some data that’s come out of the immigration courts, for example, that shows that I think only about 30% of people in immigration court have representation.
I think that that number was only a few years ago, more like 50 50. So it’s actually gotten worse, not better in the last few years, but it also comes up to sort of just in routine immigration work that a lot of people can’t afford it or they can’t find lawyers available to help them with the work depending on where they are. That’s another way that I think tech has helped over the years with immigration laws. A lot of lawyers, we’re in a federal practice area, we can practice across state lines, and that’s helped as more lawyers have gotten over the years, have gotten online and offered their services nationally. So in that regard, it’s a little bit easier probably if you’re in a place like a rural area or a place without a lot of immigration lawyers to get access to that help. But there’s basically, I think 17,000 immigration lawyers in the US at least that are members of the A LR our association, and probably most immigration lawyers are members of the association. And when we’re talking about, I don’t know what the figure is, something like 1.2 million lawyers, generally, we’re not a very big bar and there’s not nearly probably as many immigration lawyers as there need to be
Victor Li:
One appeal for generative AI tools that is very intuitive. It’s very easy to use. I mean, for people that are pro se and they just don’t have access to a lawyer, I mean, how effective can these tools be if they’re forced to navigate the system on their own?
Greg Siskind:
Well, I do think that they can give you pretty good answers on there, and you can learn a lot. I think about the, and I’ve always felt like individuals who educated themselves about the process are better clients. I think that it’s gotten better with generative AI as far as having access to that, especially since the models have gotten better. The usual cautions would be there regarding generative AI and give us cautions lawyers as well, which is to check where the information’s coming from. So to the extent that the tools in 2025 are giving citations and giving links to those documents that they are coming from, they’re better than what they were in late 2022 where you got an answer and you had in a lot of cases hallucinations, and the answer was not accurate. And you can still definitely get that today,
But at least now there’s the ability to do a lot more verification than before. And so I think pro se folks who are trying to use those tools, that same caution applies, which is that go look and see where this came from. It might be out of date, it might just be misstating what was actually said in the original materials. It may be coming from a source that’s not a reliable source like a website from some lay person who is not an expert somewhere on Reddit giving immigration advice on a Reddit or a place like that. So those cautions apply. But I do think that actually people can find quality information through generative AI models if they look, and they may find that at that point, once they’re doing that, it’s like, oh, this isn’t as simple as I thought. Maybe I do need to use an immigration lawyer for this, and I’d rather have people going into, and there are processes that are, I think are simpler, that you don’t always need to have an immigration lawyer.
I’m not one of these people who, there are some immigration lawyers who would say, any process, you need an immigration lawyer, no matter how simple it seems. I think that that doesn’t have to be the case. I think if you have a very straightforward naturalization application, you can do that on your own. And the government put some quality materials out for that that can help you do that process. And you don’t need to have a lawyer necessarily doing that. It’s more convenience than a necessity unless there are issues with your background. And that may be why somebody at least might want to talk to a lawyer, even if they’re not going to be preparing the case just to see if there are any red flags that are not jumping out that they might want to be looking at. So that’s one group of SE folks who are doing matters that can, I think that can be done without a lawyer or without a great deal of risk.
And then there are just people who, unfortunately there’s no pro bono services available and there’s no affordable legal services that are available and they’re on their own. And in that case, I’d say that this is better than nothing. Being able to use the generative AI tools that are out there. In a lot of cases, they can also be really good at translating documents to help you understand the process better than if those tools weren’t available. So I wouldn’t discourage people from using generative AI for even complicated pro se representation because it’s still better than not having those tools available.
Victor Li:
Before we continue, let’s take a quick break for a word from our sponsor, and we’re back. So we’ve established that you’re bored out of your mind. Immigration law is slow, nothing’s going on right now. You’re sitting back drinking pina coladas on a beach. No, seriously though, were you surprised at the speed with which the administration acted on
Greg Siskind:
Immigration A little, but this is not our first rodeo when it comes to an administration that is not friendly to immigration. So this is our second go around with Trump and some of the things that, it does seem that some of the things that they are focused on this time in immigration are not the same things that they were focused on last time. And maybe that’s because of all the litigation that happened last time and stopped a number of measures. Or maybe it’s because their priorities have just changed and they’re interested in some issues and not others. So we have, and also I think we’re a little bit better prepared in some respects. For example, the last go around, most immigration lawyers prior to President Trump’s first term were not particularly skilled when it came to federal court litigation.
There were a lot of lawyers that went to immigration court, which is an administrative court, but not a lot of lawyers. You would usually just send that work out to another, I mean, there were some firms that specialized in federal court litigation, particularly on mandamus cases when you had delays that you were trying to resolve, that really changed a lot from the 2017 to 2021 period where it was organically because of the environment that grew. But also there were a lot of efforts to try and educate immigration lawyers in federal court litigation to give them that capability and that didn’t go away. So a lot of lawyers have that skillset now and our filing cases again, the other thing that sort of took a little while in the last administration was these national organizations to get going. Yes, there were suits right away when the big one was, we forget how shocking this was when Trump came in, when he announced right off the bat that he was imposing a ban on people from various countries coming into the United States.
So we had that shock and awe technique used the last time as well. The difference this time is I think a lot more organizations are in a position to litigate on a lot of this stuff. So very few things are being left unchallenged. In fact, some of the groups that are doing high impact litigation, the question is, it’s like not whether they should sue, but it’s like, is anybody already who’s working on this already? Should we be focusing on an issue that hasn’t been dealt with? Should we be kind of reserving ourselves for that next thing that’s going to come along? But that’s as far as the, yeah, I mean, we knew what was going to be happening after the last election because we have gone through it before. But yeah, even then, I mean, there are some things that are just a, I mean, think last time there was a little bit less concern about whether due process was going to be adhered to. They were going to go after immigrants hard, and they did go after them and that first administration, but not in a way that now where they’re trying to bypass a lot of due process,
And that’s scary. The other thing is also a lot of clients in the last time, it was basically people that were either out of status immigrants, illegal immigrants is the co term, but you call ’em undocumented out of status or whatever. And there was also some effort to go after work visas like H one Bs the last time the dynamics changed a little bit this time where it seems like the yes, everything, a lot of aiming at undocumented folks, but this time much more of an effort at going after students, less so on skilled workers. And that might be because of the Elon Musk role in the administration where he has made it very clear that he is going to oppose changes that would affect skilled workers, probably because his company is a very heavy user of highly skilled workers. So that’s something that we haven’t seen that we did see the last time where there was a lot of people that were having visas denied that were coming in to work in software occupations and other areas.
So less of that this time. But I mean, my goodness, the students have, it started with student protestors, but really they’re going after students who have any irregularities in their backgrounds and doing things that we really had not seen the last time. Like revoking visas at the consulates ice, going into the student and exchange visitor information system, the system that students that was put in place after nine 11, the system that ICE manages where schools have to track their students and ICE has been revoking deleting records for students that instantly put them out of status and then going in and detaining them on there. And initially there was just sort of anecdotally, you would hear about a case in this state or a case in that state one at a time. But definitely in the last two weeks
It has seems like there must be a ton of them happening just based on comparing notes with a lot of other firms and the number of calls that they’re getting from people that have had their CVA status revoked. So yes, immigration lawyers are stressed out right now, but I don’t think any of us are surprised that in general there’s an attack. I think I’m on some of the things that they are pursuing this time are very different than what they were doing last time, and we’re trying to get up to speed and get ready to start defending on a lot of those issues.
Victor Li:
And plus, Trump is different now. I mean, he’s got that first time out of the way. He understands a little bit more about what he can get away with, what he might not be able to get away with maybe different possibilities to different, different priorities. Yeah. You mentioned that Muslim ban, that seems like a lifetime ago.
Greg Siskind:
Oh, it’s coming back on there. He did these day one executive orders,
Many, many on immigration. The last time there were one or two I think that were immigration related on the first day, but he sort of planted a lot of little ticking time bombs of things that were going to go off after a certain, so I think because of the Supreme Court cases from the last time, there’s a process that he has to go through if they’re going to survive litigation, and that takes a couple of months to be able to basically build the case that he’s going to need for the litigation. So that’s going to be coming in the next couple of weeks, or certainly probably by summer where we’re going to see bands and the New York Times today a good job breaking the news that it’s going to be as many as 43 countries affected this time versus the six countries that we dealt with the last time.
Victor Li:
So this might be a little bit of an off the wall question, but you talked about federal court litigation and just my very elementary understanding when it comes to technology and the way it can be used there is that probably the best use of it is to do free discovery purposes to help come through documents, transcripts, videos, and things like that. Is that within the capabilities of your software, or is that not really within your purview?
Greg Siskind:
Yes, on there. And it’s not really that different than doing an analysis of a foia, freedom of Information Act requests, which actually is more in the day-to-day, one of the day-to-day things that immigration lawyers do where we have to get files on clients and see what’s the government actually has in their systems. But we have a section of our website. We may rename it. Right now it’s just called document Q and A, but essentially you can create custom prompts and upload an unlimited number of documents and be able to do different kinds of document analysis. So one of them we have is for foia. I had been experimenting with both a due diligence and a e-discovery prompt that’s sort of geared more toward immigration lawyers, where it’s essentially doing that needle in a haystack kind of analysis. But yes, it’s something that we have those capabilities and probably, and I think more and more lawyers will probably use tools like ours for that task more in the immigration space.
Victor Li:
Okay. All right. Let’s take another quick break for a word from our sponsor. And we’re back. So we’ve talked about technology, we’ve talked about immigration law. So looking forward, what can lawyers do in the meantime to most effectively represent the clients in all of this change and all of this constant updating and new things happening every day and curve balls being thrown your way. Do you just play for the worst and go from there? Or are there other ways that you can approach these issues?
Greg Siskind:
Well, there are a number of things, and it depends to some extent on the kind of clients that you represent. So a lot of lawyers that represent people that are undocumented or educating them on, for example, on knowing their rights and making sure that they have an understanding of what they have to, what they face in an nice encounter, what they do and what their options are. So that’s part of it. Part of it’s also educating clients on having plans. What if you do get picked up and you’re put in detention? What does that mean for your kids? What does that mean for the rest of your family? So some of that, and we did those things the last go around. So with Trump. So we’re somewhat prepared for that. And in a lot of cases it’s sort of we’re trying to play out scenarios.
So I do a lot of work with Ukrainian parolees, for example. And we know that the administration will probably, in fact, a couple of days ago, it leaked an email that, I mean, accidentally, they sent an email out to a number of Ukrainian parolees telling them that their status was revoked, which we know is probably was an early draft of something that wasn’t supposed to go out yet. So it was a pretty good hint of what’s going to be happening. But in a lot of cases, we’re working on trying to prepare for things that we don’t know for sure what’s going to happen. We don’t know what’s going to be happening in the courts. And so we’re trying to play out different scenarios. We’ve come up with different strategies that will protect our clients for things that may be happening down the road. And it’s definitely harder to navigate right now, for example, with Venezuelans that are here, they have a status called temporary protected status, and the Trump administration announced that they were ending that status in 30 days, which is going to be coming up.
We were scrambling and trying to figure out for those folks what strategies might work, but now it’s tied up in the courts and we don’t know how that’s going to turn out, but we’re preparing for, well, maybe we’ll get a good result. And this whole thing we’re working on is not necessary, but we’re sort of planning it out, playing it out in best case and worst case scenario. So in a lot of instances with immigration lawyers, we may be looking at multiple strategies for dealing with things because we just don’t know. This mix of the courts with the administration is really hard in a lot of cases for us to come up with the perfect strategy. So sometimes we’re having to have plan A, plan B, and sometimes we’re working on more than one thing at a time just in case it goes in one direction or another. So it’s definitely, it’s is hard to advise clients right now. This is one of the things that we face. We like to have certainty in giving clients a strategy that this is going to be a winner, and we don’t like uncertainty where we don’t know and at least what the client’s chances are. And that’s been tough for immigration lawyers.
Victor Li:
Yeah, I mean, we’ve talked about this between the two of us. I mean, just what are some things that anybody can do if they’re worried about getting even just caught in the net erroneously or just being picked up without any cause, should have their passport on them at all times, should they have a lawyer on standby? I mean, not everyone think is going to be able to be able to afford that, but what are some things that people can do? Is there a program they can use to more effectively bring up what their rights are and what they’re allowed to do and what they’re not allowed to do?
Greg Siskind:
Yeah. Well, I mean, a lot of folks, for example, we advise people to do things that will minimize the chances of a negative encounter. So a lot of the issues have come up with people that are leaving the country and coming back into the country. And we’ve generally advised, at least for the next couple of months, that you might want to travel domestically and not internationally, because it seems like a lot of the worst examples that we’re seeing are people that are encountering problems at ports of entry with CBP officers. And a lot of it involves phones. So we’ve been having these discussions with them, with folks about what the rules are regarding taking a phone in from out of the country and the rights that you think you have that you don’t have when you show up at a port of entry. Some of it’s about what documents to carry.
So one of the things that the administration is doing right now is they are using this process called expedited removal, where if somebody enters the country without inspection, in other words, illegally at a border, if they’ve been in the US less than two years, they don’t get due process. They can be picked up and immediately put on an airplane and sent out of the country. If you have been here more than two years, though, the burden is on you to be able to show the government officer that you have been here for more than two years. We actually counsel clients like you should be carrying with you your kids’ school transcripts and your electric bills and other things like that to show that you’ve been here more than two years. Because if you do and you get picked up, you at least will be put into removal proceedings, which you are entitled to due process.
And by the way, this was a problem that started before the first Trump administration, but right now there’s 4 million cases that, and probably before Trump came in, right beforehand, there were 4 million people that were already in immigration proceedings in the immigration courts, and those cases were taking eight to 10 years to work their way through before you actually get your day in court. And that’s going to be a lot worse. And that’s one of the reasons why the administration doesn’t want people to be put in immigration proceedings because they know that that problem is going to mean for a lot of people that they’re going to be here for a while while they’re waiting for a judge to finally hear their case. So that’s one of the things we’re counseling, and it really kind of depends on the situation. We talk to high skilled immigrants about just making sure when you are going to consulates and making sure that you are being hypersensitive about complying with immigration rules and making sure that you are being very consistent and having all your documentation and not having even the minor violations.
And students, for example, some of the ones that have been denied entry or had their visas revoked, or people who’ve had really minor violations where they’ve said something that in an application that they thought was not a big deal and it turned out to be a big deal. So it really depends on the person. But in general, the theme is that you should be very diligent about documenting what you need to be documenting at the time, not going out of your way to get in high risk encounters and making sure that you yes, have an immigration lawyer that you have a relationship with that you can reach out to in a hurry so that you don’t have some of the problems that I’ve been talking about.
Victor Li:
Gotcha. And just talking about generative AI and just technology in general, where do you see that technology heading? Do you think it’s going to get much better over the next few years, and do you think it will help with some of these problems, particularly with the access to justice gap and immigration?
Greg Siskind:
I do. They’re still both in terms of people that are able to do more on their own or more, and where immigration lawyers are focused more on the more complex matters as opposed to the ones that can be automated and generative AI make them more affordable and more reliable. The tools that are coming out, and I, I’m excited about some of the, not necessarily medium or long-term, but even things that are going to be coming at in the next few months with voice and with the ability of these tools to sort of be the extra lawyer in the room that can listen in on conversations with your clients and give you real time advice about making sure that you’re spotting all the issues or that you’re not missing any red flags. I think on the drafting side of things, we’re really only at the very, very beginning of that, and probably not just drafting these longer documents, but a lot of the aspects of, especially with AI agents where you can go from an initial consultation and AI is basically helping you through the entire process of putting the case together so that you can file something much more quickly, much less expensively, and hopefully much more accurately.
So I do think that these tools are going to be much more prominent in lawyers’ practices in the coming years, and that should reap benefits. I’m also worried about how the government’s using generative ai, and that’s a different discussion, but we know that it’s being used right now, for example, to comb through social media records for folks and that that’s causing visa revocations In other countries. They’re using generative AI and other AI tools for things like detecting accents for people that are applying for things to see if they are really from the area that they’re claiming for asylum cases. And I’ve heard from Germany does that, and I’ve heard from lawyers there that they’re inaccurate in a lot of cases, leading to really bad results for people that had perfectly legitimate claims because the technology wasn’t great. So I’m concerned about that side and the black box problem where we have decisions coming from government agencies where we have no idea how it’s making decisions, and even the examiners that are the ones signing off on the decisions may not really understand how the AI is making the decisions. So there are challenges in that regard as well that we’re going to be having to think about as a society with generative AI and along with the good parts, which is hopefully making services better and more affordable.
Victor Li:
Yeah. Well, that’s the thing with technology, right? There’s always good and bad with it.
Greg Siskind:
Yep.
Victor Li:
Well, to wrap up, if our listeners wish to get in touch with you for any reason, what’s the best way to do that?
Greg Siskind:
They can find me on my website for the law firm at visalaw.com or for the software company, visa law.ai, and then I’m easily findable buying my name on LinkedIn or other social media platforms.
Victor Li:
Great. Thanks again for joining us, Greg. I appreciate it.
Greg Siskind:
Thank you, Victor.
Victor Li:
If you enjoyed this podcast and would like to hear more, please go to your favorite app and check out some other titles from Legal Talk Network. In the meantime, I’m Victor Li, and I’ll see you next time on the ABA Journal Legal Rebels Podcast.
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