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Divorce Dialogues helps people navigate divorce with dignity, clarity, and perspective. Through thoughtful conversations with experts and practitioners, the show explores the emotional, financial, legal, and relational realities of divorce, so listeners can make better decisions, communicate more effectively, and move forward with greater confidence.
Because divorce is more than a legal transaction, it’s a deeply human transition.
Jamie Lima (00:00):
I hear it day in and day out like, oh, my husband's a narcissist or my wife, or she's crazy. All these things. And if that's really the case and you're dealing with somebody who is very, very challenging and communication is a struggle and so on, being able to leverage AI and simply say, okay, take this lengthy email that this person sent me and help me respond appropriately, but also do so in three sentences, because we never want to do more than three sentences, send that back to them and then you can be on with your day.
Katherine Miller (00:29):
Welcome to Divorce Dialogues. I'm Katherine Miller. This is where we have honest, thoughtful conversations about divorce, the emotional, financial, legal, and family questions no one prepares you for. From deciding whether to separate to navigating the process with dignity to rebuilding what comes next, Divorce Dialogues is here to help you find clarity, perspective, and a better way forward. One of the first things that people do when they're thinking about divorce is to start looking for answers. What are my rights? What will happen to the children? Can I afford this? What should I do next? And traditionally, people have turned to friends, families, books, therapists, financial advisors, or lawyers to help answer those questions. And of course in recent years they've turned to what I call professor Google to Google it, but increasingly they're turning somewhere else first. They're turning to AI, ChatGPT, Claude, or whatever their AI agent of choice is.
(01:38):
And it's really a fascinating thing because it raises a bigger question. What are people actually looking for in those moments? Are they looking for information, reassurance, a sounding board, a sense of certainty when everything else might feel uncertain and without judgment anyway? And because AI can provide answers, divorce isn't just an information problem. It's also an emotional problem, a financial problem, a decision-making problem, an identity problem. So what this conversation is really about is understanding where AI can be genuinely helpful, where it falls short and how people can use it in a way that supports better decisions rather than creating new risks. My guest today, Jamie Lima, is uniquely positioned to explore that question. Jamie is a former Morgan Stanley infidelity executive, a divorce financial specialist, and the co-founder of Secure Split. Through both professional work and his own personal experience with divorce, he's seen firsthand how technology is reshaping the way people seek support, information and guidance during one of the most challenging transitions of their life.
(02:46):
Today we're talking about why people are turning to AI during divorce and before divorce and what needs its meeting, where it can help and where it can lead people astray and into dangerous territory. Welcome, Jamie. It's such a pleasure to have you on the show.
Jamie Lima (03:01):
Thank you for having me.
Katherine Miller (03:03):
So I know from your bio that you have experienced divorce personally, as have I, and you now work in both the divorce finance and also on legal technology. And I'm really curious about how your own experience has shaped the way that you think about AI as a support tool.
Jamie Lima (03:21):
Well, I wish AI was in existence when I was going through my own divorce almost nine years ago now. I maybe would've went differently in a couple different ways. I feel like leveraging AI then would've helped take some of the emotion out of the equation. It would've helped me make some better decisions overall. Maybe I would've been more of an advocate for my situation and so on, but it didn't quite exist at that time. So definitely struggled along the way going through my own divorce in a few different areas. But had I had AI at the time and been able to leverage that as a knowledge base and a resource for me, I think things would've went a little bit differently.
Katherine Miller (03:55):
Well, I'm curious to hear you say that it would've taken some, and I think I'm quoting you, saying it's taken some of the emotion out of it. How do you think that would've helped or hurt?
Jamie Lima (04:05):
So we see this happen all the time, especially in a lot of the divorce cases that I work, and you've probably seen this on your side as well. There's a lot of emotion that's involved in divorce. Very few cases that we come across are simply two people who want to uncouple because they fall in love of love and they just want to go their separate ways and they want to be very friendly about the process. In my particular case, it was not amicable. It was a very stressful, it was very challenging. And we hear the narcissist word being thrown around a lot to whether they're actually diagnosed as a narcissist or we just think these people are narcissists. I hear it day in and day out like, oh, my husband's a narcissist or my wife, she's crazy. All these things. And if that's really the case and you're dealing with somebody who is very, very challenging and communication is a struggle and so on, being able to leverage AI and simply say, okay, take this lengthy email that this person sent me and help me respond appropriately, but also do so in three sentences, because we never want to do more than three sentences, send that back to them and then you can be on with your day.
(05:07):
What I fell into the trap of is I get a long diatribe email on all these things going through the divorce and the first instinct is I want to go reply back at the same level and go tit for tat. That's not the way to handle things. And looking back, I see that, but when you're in the moment and you're feeling the heat, it's tough to take a pause, take a beat and respond appropriately. Natural instinct is to fire back, but using AI to be able to respond and help you in your responses could be super, super helpful.
Katherine Miller (05:37):
Yeah, I think that's really, really a wise use of AI because it's not like when you first said take the emotions out of it, of course you're emotional. This is an emotional thing. I mean, obviously it's an emotional thing as well as a legal thing, a financial thing, a parenting. There's a lot of feeling here. And I don't know that you can take that away or that you should because of course marriage and partnership is emotional among other things. But this way of processing it without just diving into the conflict, like what I call the conflict trap where you're each trying to show the other person how right you are as if that's possible, right Jamie? As if you're ever, no matter any email you could ever send or get, is ever going to convince the other person, "Oh, you know what? I just didn't see it that way."
Jamie Lima (06:19):
And they're just going to keep sucking you in and roping you in. They enjoy that. They enjoy that experience.
Katherine Miller (06:26):
It's really familiar. And so it feels comfortably uncomfortable or something like that. It's very familiar. We do this sometimes here in the firm, but I think so much better use of somebody's money to have chat or Claude or something or an app that does this for you to help you bring it down to need to know, not responding. Obviously I see this differently than you, but it's pick up at two or three on Saturday. Make it simpler. So obviously more people are turning to AI and they're doing that during the divorce process, but also way before they ever contact a divorce professional. And so what do you think that they're really looking for in those first conversations with whichever agent they're choosing?
Jamie Lima (07:10):
It's different depending on the situation. I mean, some people are leveraging AI to organize their thoughts and get some information on how should I approach this? We have other people that have come to us that they've done some research on AI. They kind of get an understanding of what might be at risk in the divorce from a financial perspective. I think it kind of runs the gamut. But one thing I want to hit on that you mentioned in the lead up to this conversation is people start with Google. People like, find a divorce lawyer. How do I divorce my narcissist, husband or whatever? The problem with leveraging AI in the same way that you leverage Google as a research is it's not designed that way. So AI is not designed to be just another search engine. And I think that's a huge mistake that a lot of people make is not prompting it correctly.
(07:59):
So if you're in the early stages of a divorce, it's not necessarily like how do I get a divorce in Cleveland, Ohio? It's like, help me find the best divorce attorneys in the state of Ohio, specifically in Cleveland, Ohio, who have a five-star rating on Yelp reviews and who have experience dealing in this space or maybe with small business owners. You have to prompt it and give it much more information so the responses back are much more valuable to you and much more accurate to your situation. And we can dive into this a little deeper if we want to, but the biggest mistake I make, especially people that are coming to me in the very early stages of the divorce, is the information they've received is not always accurate because they're not prompting AI in the way that they're supposed to and they're just using it as another Google and it's not how it's designed.
Katherine Miller (08:50):
It's obviously a very wise comment about the use of AI in general, but with regard to divorce and something that's so, for some people, shameful or emotional and scary to be able to say, I'm thinking about divorce and this is particularly what my concern is, or this is particularly the kind of question that I have, the kind of professional that I'm looking for to be as detailed as possible. Even if you don't necessarily know how to frame the question, the more you tell it about you and what it is that's important to you, the more curated and bespoke results you're going to get. And I think that's what you're saying. Is that right, Jamie?
Jamie Lima (09:28):
Absolutely. And the more information you provide, the better the results are, but also it'll learn more about you. It'll learn your preferences. It'll learn your voice. My wife and I are in the process right now on the personal side of things. We're actually full-time RV and we're going to be traveling the country for the next few years. And one of the things we're working through right now is relocating to South Dakota for a variety of reasons. And I can literally now tell Claude, who I use basically every day, I can say, "Hey Claude, I need you to send me an email to this campground to find out if there's availability between these particular dates." And it will literally draft the email. It already knows all our preferences, the size of our RV, the type of amperage we need, all the stuff. And that's how over time it's learned me, my preferences and everything else.
(10:15):
It's the same thing with any other concept, divorce or whatever it is. It will start to learn your voice and learn what you're looking for. And that's part of the learning language model that is embedded in these tools. So over time, it will continue to get better and better for you. It'd be a better resource and a tool for you.
Katherine Miller (10:30):
Which is both thrilling and terrifying. Obviously divorce creates a lot of uncertainty and fear for a lot of people. What emotional need do you think that AI can fill that they might not be getting somewhere else?
Jamie Lima (10:43):
The first thing I though about when we were asking that question is it can help you be a little more pragmatic and practical because again, there's a lot of emotion that's involved. And if you're asking questions, it can help you stem some of that emotional, that turmoil that you're going through and really just keep it down to brass tacks effectively. But at the same time, the one thing that I would caution everybody about and want to make sure that everybody is aware of is because it's learning your voice and learning your responses to different things, it will also placate. So instead of it saying, "You know what, Jamie, listen, your ex - wife said this, this is part of her MO, this is exactly how you should respond." And just giving it to you straight, over time you'll start to see that it'll shift and it'll say, "Jamie, you're absolutely right.
(11:31):
She's crazy and she's this and she's that. " And it's going to start to placate to your feelings. You have to be aware of that and help try to redirect it. Listen, I appreciate that Claude, but listen, I need you to just give me straight and redirect. And that's where, to your point about it being a little bit scary, it starts to learn your personality and we'll start... It happens all the time. Sometimes I'm just say something in Claude and I'm like, something is frustrating or I can't figure this thing out or whatever it is. And it'll want to try to soothe me through it when that's not necessarily what you need either. So you've got to be aware of it.
Katherine Miller (12:05):
This is how I think of it. It's trying to make you happy and that isn't always the best thing for you.
Jamie Lima (12:11):
Correct. And if it catches a mistake, so this actually happened to me yesterday, but I said that doesn't really make any sense. I'm not really sure why you responded that way. Oh, you're absolutely right. I'm sorry, that was my mistake. And it wasn't a small mistake.
Katherine Miller (12:27):
So
Jamie Lima (12:27):
It's always trying to make you happy and rectify the situation.
Katherine Miller (12:30):
Yeah. And in the law, you see this in the legal journals all the time where it's made up a case or it's made up some evidence. It's gone through somebody's inbox and made up emails that weren't there. Stuff like that that is really, really careful. And I think that people also consult with AI when they're considering or starting the divorce process and even in the middle of it on more factual things. So where do you think that AI can really help them safely feel more informed or prepared?
Jamie Lima (13:03):
The thing that we need to remember with AI is that you always want to ask for citations, specifically when it comes to things like the law. Brief example, and you may have heard of this, that there was a case here in California where an attorney was actually disbarred because the entire case brief that was presented to the courts was drafted by AI with a bunch of hallucinations and false citations. So you've got to prompt it the right way, ask for the references and so on. And by doing that, you can leverage it as a resource. So I would always ask that every morning I have Claude send me an update on any of the tax code changes, family law court form updates, you name it in all 50 states across the country because we need this information for secure split. But we also asked for the corresponding citation and whether it's a particular statute or wherever it is so we can cross-reference this information.
(13:57):
We can use it as a weapon. We can use it as a support system, but trust but verify. Anytime you use it in your case, it can be advantageous, but you still have to trust the information, but you want to verify it as well.
Katherine Miller (14:10):
Divorce Dialogues is brought to you by Miller Law Group. We believe divorce isn't just a legal process, it's a human transition. At Miller Law Group, we help people navigate divorce with dignity, clarity, and respect, focusing on conversations that lead to better outcomes for families. Learn more at miller-law.com. I've found that sometimes the tone is really off. Obviously our clients and my colleagues' clients are going to Claude or chat and checking what the right answer is all the time. And sometimes it'll come back super adversarial when really that's not the right approach to take. And sometimes it comes back maybe a little more soothing than is the right approach. So there's some things about the tone and the timing and the strategy that it doesn't quite get right. But what are some examples of advice or guidance that you've seen AI claude or whatever get actually right when it comes to divorce-related questions from a client's perspective or somebody considering or going through a divorce?
Jamie Lima (15:18):
I use AI a lot in some of the valuation calculations that we do. We do a lot of work, for example, in the state of Alaska, believe it or not, and we do a lot of pension valuations. We work with some of the government plans that are there. And they're very complicated. And if you try to go through the supplemental plan description, the SPD book that all these plans have, you're talking about 60, 70, 80 pages worth of legalese and it's very tough to disseminate sometimes does this client actually qualify for the pension? How long have they been a part of the pension plan? Is this a different version of the pension plan than the one that exists now? And so on. And being able to get information on those types of things with the citations and references and so on, it makes the work a lot easier.
(16:03):
But in many ways it's a lot more accurate than having a human go through the documents. Unless you're an HR specialist and you've had a hand in drafting these documents, forget about it. It's very, very tough to understand. So a lot of times when we have these particular cases, I'll feed it whatever information I have. Obviously not any personally identifiable information for the client, but I'll give it the information like, "Hey, here's the plan and here's the payment amount. Here's the years of service. Tell me more about the plan." And sometimes it crosses different types of plans, so it'll give me that information. And that's just one example. I mean, there's a thousand different examples, but in the more complicated, time-consuming stuff, it can really, really be beneficial. And if you're a divorce professional, parenting, mediator, financial analyst like myself, you can leverage it without giving, again, personally identifiable information to AI.
(16:54):
It can make your time much more efficient and keep down the billable hours for the client as well.
Katherine Miller (17:00):
Where do you think that from a client's perspective, it's risky because AI creates a false sense of certainty that actually ultimately makes it harder for them?
Jamie Lima (17:10):
Well, this is where it goes back to the trust, but verify. It starts placate as the emotions that are involved and so on. It's like, okay, hey Susie, don't worry. Everything's going to be okay. You're going to get $3,000 a month in alimony. You're going to get $3,000 a month in child support. Your expenses are this and everything's going to be copacetic. Then you get into the courtroom and you run these numbers and it's $1,000 a month and $800 in spousal support.You're like, wait, what? What happened? I thought I was going to get $6,000 a month. Sometimes it overinflates the information. So again, just comes back to the trust but verify. I would not be using it to run calculations and give you estimates of what you're going to walk away from the divorce with and so on. Leave that to the professionals. Where it could really be a leverage point for you is helping with the emotional piece, managing, communicating with your attorney.
(17:55):
You can use it as a way to say, okay, I just had a meeting with my attorney. Here are the five things they asked me for. Help me draft the nice succinct email back to the attorney outlining the other questions that he or she had, whatever it is. But I think there are some areas of this that are still left to the professionals.
Katherine Miller (18:11):
Yeah. So one thing that I have found is that clients sometimes will take something we've drafted, and I think they should be looking at everything that we draft because they're the ones who have to live with it and running it through Claude and then coming back with all of these comments. If you were talking directly to a client here, the listener is a client working with an attorney, what do you think is the best way to use Claude or a similar something in that process of reviewing your lawyer's work to get the best result?
Jamie Lima (18:44):
I would not be using it to poke holes in anybody's work because there's always going to be something. I mean, we see this happen a lot where people are like, well, I provide them with an analysis of their whatever it is. And they're like, well, I'm going to go take this to somebody else and I'm going to ask them for a second opinion on it. Sure enough, that other person's going to have a second opinion and they're going to poke holes in it. And you can get a third, fourth, fifth opinion, and all you're going to do is just get more opinions and you're never going to be able to make any decisions and then just makes things more complicated. How I would be using it if I had to do it all over again is simply like, help me understand what this actually means.
(19:20):
I mean, you're drafting these documents all day long and it can be complicated. Especially for those of us that don't have a legal background. Even myself, I had a financial background and going into my own divorce, look back and I'm like, why did I agree to some of these things? Because it made sense in the moment, but now that I look back on it five or six years later, it didn't really make sense that we agreed to that particular thing. So being able to send it through to say, okay, help me understand what I'm signing here. Help me understand where my blind spots may be. Are there any additional questions that I need to ask Katherine? Just for clarifying. I don't want to come back and say, Hey Katherine, guess what? There's a statute over here that you missed and you missed this period over here and there's a T not crossed and an I not dotted over here.
(20:01):
That doesn't do anything, doesn't help anybody. But I could come back and say, Hey Catherine, in paragraph 20, you mentioned this particular thing. What does that really mean? It would help you with some clarifying questions and just to make sure that you, at the end of the day, you understand what you're signing because these are permanent decisions.
Katherine Miller (20:19):
Yeah. It's an incredible tool and can be incredibly time-saving as you mentioned earlier, Jamie. But if you're having this on going back and forth, back and forth, let's move this comma over here and let's do this and that, it's like perfection becomes the enemy of the good enough.
Jamie Lima (20:36):
Yeah. Paralysis by analysis. You're never going to make a decision. You're never going to sign the document. There's always going to be a problem with it. And we'll be here forever doing this and all you're going to do is burn billable hours, make any adjustments anyway.
Katherine Miller (20:47):
Yeah. You mentioned the example of Susie who relies on Claude to say she's going to get this level of support and then in the courtroom finds out it's that level. One thing that I think is really important for people, this has nothing to do with AI, but when a person feels like I have a legal right to something, I should get this amount of child support or I should get that. Whether or not Claude told you that, your last lawyer told you that, your mother told you that, it doesn't really matter. It's not like that right is a little chit that you just walk down to the courthouse, slide it through the clerk's window, and then you get that money. The legal process and the negotiation process is a lot more complicated than that. And I think overly relying on AI or anyone else besides your lawyer telling you what the range of likely outcome is probably at this point in time a risky business.
Jamie Lima (21:39):
100%. I couldn't agree more.
Katherine Miller (21:42):
So do you have any guidance for the listener who's already using AI to help them navigate the divorce process? You've already said that check your citations. Are there any other best practices for using it wisely without, I don't know, maybe becoming addicted to it?
Jamie Lima (22:01):
I think it really just starts with the prompt. And we talked about this in the early part of our conversation. The prompt is where everything starts where you set the tone for the conversation. You set the tone for what it's going to deliver for you. A proper prompt is you're my family law attorney or you're my certified public accountant or you're my financial analyst telling you your role to play. What is it I'm asking you to do by playing that role? What are my specific outcomes that I'm asking for? Citations, references, whatever it is. You make sure you have to feed it. You have to feed it. It's not just, I find a divorce attorney in Cleveland, Ohio. It's in Google. It's much more complicated than that. But once you get the hang of it, and there are times when I'm sitting here, I have my phone right here, I'm like, I'll just sit here and just prompt it and it'll recognize your voice and you do the voice prompt.
(22:55):
And sometimes it's a two-minute, three-minute prompt. And then I hit send and let it dig through its thing. I would encourage everybody to do that. The more information you can give it, the more questions you have and the more stuff that you're asking it to do at the outset, the better.
Katherine Miller (23:08):
Great. We're nearing the end of our time today and I have just a couple more questions. And one is a question that I like to ask my guests that I call the reframe. A question I have for you about that is what's one shift in thinking that you'd like people to make about the role AI should play during divorce?
Jamie Lima (23:24):
AI should not replace human professional advice. I say that not just because I'm in this space and I'm biased, but I've seen technology evolve over the years, especially in the investing world. There was a point where we were constantly talking about free trades and digital trading and cryptocurrency and all these things that have come out over the years and how that's going to replace advisors that are out there. You no longer need a financial advisor because we have an AI version of that. That's the newest thing. But AI is never going to replace the human element simply because that human interaction that we need to have as humans, being able to sit here face-to-face and have this conversation with you is certainly much more fruitful and beneficial for me, not only from an emotional perspective, but the information that I'm gleaning and the way that I'm learning, that all happens because of that human interaction.
(24:15):
AI is not going to replace that human interaction. Even though we all have an AI avatar these days and all the training that you see that's out there, all these videos on TikTok and whatnot, half the time my wife will scroll through social media every once in a while and I'm like, it's AI. It's not real. They look so real. But I truly believe there's a human element here of being able to go walk into your office, sit down face-to-face with you across the desk and really just have you shepherd me through the divorce process. That is invaluable. You cannot do that with AI.
Katherine Miller (24:47):
Yeah, the human energy.
Jamie Lima (24:48):
Yeah, exactly. I'm envisioning myself going into your office and just talking about my case. You can't do that with the technology that's out there.
Katherine Miller (24:55):
So what's one thing that you wish that everyone knew or you wish I'd ask you about before just turning to AI for answers about their divorce?
Jamie Lima (25:04):
One thing I will leave listeners with is, and this is all due respect to folks like you and other attorneys that are out there, but relying on your attorney solely to get you through this experience and using just AI or using AI in combination with your attorney, you're also missing the mark. I firmly believe in surrounding yourself with team you as you're going through this experience and having a financial person like myself to help you through it. Having a good therapist, having your religious leaders walk, be there to support you, friends and family, you name it, surrounding yourself with these people because this is an experience. It takes a long time. It's very emotional, it's stressful. Like all the things, one of the mistakes that I made in my own divorce was trying to keep those people away so they didn't have to get themselves involved in it.
(25:53):
And it turned out to be one of the bigger mistakes that I made in my own divorce. So not necessarily AI related, but in general, that's something that I think that listeners need to hear.
Katherine Miller (26:02):
100% agree with that. Divorce affects you in every area of your life. It can't not. And so you should have an advisor, even if you don't talk to them every day or you talk to them once or twice. It doesn't matter. You have someone in your corner who can guide you and give you their perspective on their area of expertise. Jamie, thank you so much for being my guest on Divorce Dialogues. It's been truly a pleasure to have you.
Jamie Lima (26:24):
Thanks for having me.
Katherine Miller (26:28):
If this conversation was helpful, share it with someone who might need it. And if you're navigating divorce yourself, you'll find more resources and episodes at miller-law.com. Make sure to subscribe wherever you get your podcasts.