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Articles by Craig Hersch
The Associate in the Server Closet: On-Premises AI
Sometime this week, an estate-planning attorney will paste a client’s trust instrument into a free artificial intelligence chatbot and request a summary. The summary will be good: It will arrive in seconds, be mostly accurate and save an hour of reading. The question of where that trust instrument just went, whose servers now hold it and what those servers will do with it may not occur to anyone until much later. That small moment captures the bind our profession is in.
Michael B. Hill
Homechevron_rightchevron_left Author Teamchevron_right Michael B. Hill Partner, Sheppard Law Firm As a partner of Sheppard Law Firm and a board-certified specialist in Wills, Trusts, and Estates, Michael is committed to redefining estate planning for families in southwest Florida. With over two decades of legal expertise, he, along with his partners, have distinguished their practice through a blend of exceptional legal acumen and deep personal empathy.
Using AI to Draft Post-Estate-Planning Meeting Letters: Part II
In Part I of this column, which appeared in the March 2026 issue, I addressed how artificial intelligence can be responsibly integrated into the post-estate-planning workflow by using AI-enabled meeting recording and transcription tools, as well as ethical considerations and common attorney concerns. I’ll now provide a series of real world, detailed AI prompts that estate-planning attorneys can use to draft high quality follow up letters across a range of planning scenarios.
Community Property Opt-In Trusts
For sophisticated married clients, basis planning often represents the largest remaining opportunity for permanent tax savings. Estate and gift tax exposure can frequently be managed through portability, exemption planning and valuation techniques. Capital gains tax, by contrast, is generally unavoidable once an appreciated asset is sold. That reality keeps the community property basis rule, Internal Revenue Code Section 1014(b)(6), highly relevant for advanced estate planners.
Using AI to Draft Post-Estate-Planning Meeting Letters: Part I
Trusts and estates attorneys’ work doesn’t end when the client meeting concludes. In many ways, the most consequential work begins afterward: documenting advice; confirming decisions; outlining next steps; and clearly allocating responsibility between lawyer and client. The post–estate-planning meeting letter, whether styled as a follow‑up letter, memorandum or planning summary, is one of the most underused risk management and client service tools in the profession.
Ten Lessons Learned From 35 Years in an Estate-Planning Practice
I didn’t set out to prove that a small, focused law firm could compete with large national ones. But over the past 35 years, that’s exactly what happened. Along the way, I’ve gathered lessons that go beyond technology, marketing or even law. They’re about people, mindset and the evolution of a profession that’s changed more in one generation than in the previous three combined. I’ve condensed that 35 years of experience into 10 lessons of wisdom I hope resonate with you.
Using AI to Draft Client Follow-Up Letters
Craig R. Hersch provides instructions on how to use artificial intelligence-powered tools to generate professional, accurate follow-up letters. After a productive meeting with a client, most attorneys move on to the next matter. There’s little time to pause, summarize and communicate everything discussed, let alone assign tasks or outline next steps. That’s a mistake. When there’s no follow-up letter, the client forgets what you advised. The paralegal forgets what you promised.
Ethical Obligations for Attorneys Using AI
Craig R. Hersch explains how to navigate attorneys’ ethical duties to protect clients’ interests while harnessing the benefits of artificial intelligence. Integrating artificial intelligence (AI) into estate and trust law offers numerous advantages, but it also places significant ethical responsibilities on attorneys.
AI Ethics For Estate-Planning Attorneys
Craig R. Hersch explores the risks artificial intelligence poses to confidentiality and outlines the ethical obligations attorneys must uphold. Artificial intelligence (AI) transforms estate and trust law, providing tools that streamline drafting, research and dispute resolution. Attorneys can use AI to analyze complex trust provisions, draft wills or evaluate fiduciary performance. However, these technologies introduce ethical challenges, particularly concerning client confidentiality.
Craig R. Hersch | WealthManagement.com
https://estateprograms.com/ Craig R. Hersch is the creator of The Freedom Practice™, The Family Estate & Legacy Program™ estate planning practice system and The Estate Settlement Program™ probate and trust administration practice system. He developed these practice systems in response to the quickly changing and challenging legal marketplace.
Avi Z. Kestenbaum | WealthManagement.com
Avi co-chairs our Trust & Estates Practice Group, nationally ranked Tier 1 by U.S. News and World Report, and chairs our Tax Exempt Organizations Practice Group. He is also a partner in the firm’s Business & Real Estate Taxation, Trust & Estate Litigation and Private Wealth & Taxation groups.
Artificial Intelligence-Friend or Foe?
https://www.wealthmanagement.com/sites/wealthmanagement.com/files/logos/WealthManagement_com_white.png Skip navigation Recent Recent Featured As estate-planning attorneys, CPAs, trust officers and financial planners, we stand at the crossroads of technological advancement. Artificial intelligence (AI) is increasingly reshaping our professional landscape, bringing opportunities, challenges and ethical questions. Will AI replace us? How can we use AI to enhance client value?
Creating an AI Bot: A Productivity Tool for Legal, Tax and Financial Professionals
https://www.wealthmanagement.com/sites/wealthmanagement.com/files/logos/WealthManagement_com_white.png Skip navigation Recent Recent Featured Artificial intelligence (AI) is transforming professional practices by improving productivity, enhancing document management and streamlining administrative tasks. In high stakes fields like law, tax and finance, AI bots are being tailored as powerful internal tools for professionals, but they can also be created as direct client-facing applications.
AI: Embracing the New Frontier in Your Practice
https://www.wealthmanagement.com/sites/wealthmanagement.com/files/logos/WealthManagement_com_white.png Skip navigation Recent Recent Featured As I sit down to write this inaugural column for Trusts & Estates, it’s important to introduce myself. I’m Craig Hersch, a 60-year-old senior shareholder of the Sheppard Law Firm, a 100-year-old boutique office in Fort Myers, Fla. We specialize in wills, trusts and estates, serving a wealthy and quite demanding clientele.
The Dreaded Drive-By Delegator
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What I Wish I Knew Before Engaging a Social Media Marketing Agency
As a senior partner in a boutique estate-planning law firm, I search for ways our 98-year-old firm can remain relevant and keep up with the times. New residents to Southwest Florida, where we’re located, don’t really care about our firm’s longstanding history of service. Like many, they ask their friends and neighbors whom to visit to update their estate plans. Others choose to go online to research law firms.
What We Learned, and How COVID-19 Changed Our Practice
One attorney’s experiences during the pandemic Craig R. Hersch | Dec 17, 2021 I could see their faces on my screen, but when their mouths moved, I couldn’t hear anything. “Mr. Smith, do you see the icon that looks like a microphone at the bottom of your screen?” I found myself yelling into my microphone, a souped-up version that looks like the prop Larry King used on CNN.
Florida Throws its Hat Into the Lucrative Trust Situs Ring
On June 29,2021, Governor Ron DeSantis signed legislation to create the Florida Uniform Directed Trust Act (FUDTA) and the Community Property Trust Act (CPTA). The legislation was effective July 1, 2021.
Selling Advanced Estate-Planning Services
Overcoming your client’s perception of a commoditized document Craig R. Hersch | Jan 27, 2021 With a new administration in Washington, many clients worry about tax increases (particularly with gift, estate and income taxes). Your clients consume information from webinars, on websites and, of course, the ubiquitous Google. Consequently, they arrive at your conference room (or appear in your videoconference) believing they already know the strategy that’s best for them.
Is My Heart Up For It? Literally!
Finding solutions in the midst of a pandemic. Craig R. Hersch | May 21, 2020 Last September, during swim practice with my triathlon team, I suddenly felt my chest tighten and experienced difficulty breathing. My wife took me to the ER, where a cardiologist performed a heart catheterization, resulting in the discovery that I had advanced heart disease.
The Successful Sale of Your Estate-Planning Law Practice
https://www.wealthmanagement.com/sites/all/themes/penton_subtheme_wealthmanagement/images/logos/footer.png Proactive steps to maximize your firm’s value to a prospective buyer. Craig R. Hersch | Jan 23, 2020 There comes a time in nearly everyone’s career when the thought of a permanent vacation from the practice of law outweighs a consistent draw from revenues. “Let someone else trudge into my office to slay the dragon every day,” you say aloud to your spouse.
Bridging the Experience Gap
Many estate-planning attorneys quote fixed fees for services. Therefore, I commonly ask my colleagues, "Do you ever quote a fee that's below the true value of the services you're about to render?"
Patrick Carlson | WealthManagement.com
Patrick Carlson, JD, LLM, is the Director of Practice Development at Wealth Counsel, which is a membership-based organization that provides estate and business planning attorneys with legal document drafting software, as well as educational services and nationwide networking opportunities in a community of over 4,000 professionals.
Do You Take Enough Time Off?
Growing and maintaining a successful practice takes constant vigilance. Many advisors feel that they can never afford to take a day off. This is the wrong attitude, as there's little point in taking care of your business if you aren't also properly taking care of yourself. In this episode, Craig and Patrick discuss whether planners take enough time off and when the best time it is to do so. Browse more episodes in this podcast series ...
Is the New Tax Law a Death Knell or Jobs Act for Estate Planners?
Many observers harbor the belief that the Tax Cuts and Jobs Act will toll the death knell for estate planning as we know it. It's easy to see where they're coming from, since the tax act effectively eliminates the estate tax, largely eliminating the need for many Americans to plan for it. However, is that really such a sweeping change?
Funding Trusts 101
A lot of planners make the promise of trust-based estate planning- faster administration, lower costs, etc. That only works though, when the trust is fully funded. Someone has to take the time to ensure that all of the required assets are put into the trust. Craig and Patrick discuss the importance of funding trusts and some pitfalls to be aware of. Browse all the episodes in this podcast series. ...
How to Deal With Client Complaints
Not all client interactions can be happy ones, but that doesn't mean the relationship has to suffer. While some clients have reason to be disgruntled, many others are simply venting about something that may not have much to do with you at all. Listening and deciphering what they're actually upset about is a key skill for planners. In this episode, Craig Hersch and Patrick Carlson discuss what planners can do when their clients complain. Browse more episodes in this podcast series. ...
The Golden Age of Multimedia for Planners
Do you ever have clients asking the same questions over and over again? Do they want their information directly from and immediately rather than waiting or having a team member assist them? Perhaps they just don’t have time to make a call or want to ask a question in the middle of the night and need easy to digest information on their own time. Media (think podcasts and videos) offers a variety of options for how to leverage your time and that of your staff while fulfilling client needs.
What Is a Sales Funnel and Why Is it Important to Estate Planning
Craig and Patrick discuss what processes you should develop to find prospective clients and educate them prior to their first consultation, as well as how to engage a completely willing new client without having them make big leaps to the full commitment when they're not ready. Browse more episodes in this podcast series.
What Makes an A+ Client
Finding your perfect client can be challenging. Push-back and resistance almost seem like part of the job when you’re accepting business that walks in your door. In this episode, Craig Hersch and Patrick Carlson discuss their take on how to deal with difficult clients by transforming them into A+ clients, and how to get those clients that are more than pleased with your services into your conference rooms. Browse all episodes in this podcast series. ...
Hiring an Advertising and Public Relations Firm
Estate planners, CPAs and financial planners in solo and small-to-medium size firms grapple with how to advertise or otherwise get the word out to the general public. Do you hire an advertising and public relations firm? If so, how do you select one?
Finding the Right Team Members for Your Firm
Wealth planning is an increasingly complex endeavor, and no advisor is an island. Assembling the right team of professionals and support staff to best serve the oft-disparate needs of your clients is essential to success. In this week's episode, Craig and Patrick discuss how to identify and secure team members that are right for your firm. Browse all of the episodes in this podcast series.
Wealth Planner Misconceptions About Advertising
Today's ever-changing legal marketplace can seem daunting to those in the estate planning realm. How does one distinguish oneself from the competition? How do you get A+ clients through the door? How do you hire a new team member that's sure to be the right fit? These topics and many more face estate planning attorneys on the rise on a daily basis. Nevertheless, solutions exist. Advertising is a sticky subject for all attorneys.
Kickstarting Your Client Base
Estate planners face unique challenges when looking for prospective clients in that not only must they tackle all of the new client obstacles that other advisors do, but they must also reckon with issues of motivation. There's no escaping the fact that estate planners force clients to deal with death and family issues head on, and those scary realities can create uncomfortable situations and doubt in even the steeliest individuals.
The Biggest Challenges for Small Estate Planners
Most lawyers didn’t go to law school to learn how to run a business. Yet, that’s exactly what solo practitioners are doing. Today’s small and solo estate planning practices face the challenges of commoditization, automated online document preparation and how to distinguish themselves in an increasingly competitive marketplace. Practice development experts Craig R. Hersch and Patrick Carlson provide valuable insight into these issues and the mindsets necessary to overcome them.
An Advisor’s Guide to Podcasting
Podcasting is a cost-effective and valuable method for educating your existing client base, attracting prospective clients and strengthening your brand with referral sources. It’s important to distinguish your practice in an age of competition and commoditization. Clients are bombarded from all angles with options for selecting legal, tax and financial professionals.
How to Create Your Own Podcast Series
While growing up in Indianapolis, I used to fall asleep listening to WIBC radio sportscaster Bob Lamey1 broadcasting the then-ABA Indiana Pacer’s basketball games. I lived and died with those early 1970s championship teams that included Billy Keller, Freddie Lewis, Don Buse, George McGinnis, Mel Daniels, Roger Brown and “Dr. Dunk” Darnell Hillman. Whenever a Pacer got hacked by an opposing player, but the officials didn’t call a foul, Lamey hollered into his
Difference Between Reactive and Responsive
“I get a pit in my stomach before I enter my office each day,” Steve, a colleague of mine confided, “wondering what emergencies are going to hit me before I even sit down at my desk.” Sound familiar? Every professional in the legal, tax and financial world experiences similar feelings. On my drive to work, I mentally review the litany of tasks I intend to conquer that day, only to be derailed within minutes (if not seconds) of entering the back door to my office.
How Much Should You Budget Towards Marketing?
As an estate planning national practice development expert, I’m frequently asked “How much should I spend on marketing?” It’s a very good question.
Florida Electronic Wills Act
It doesn’t seem all that long ago when my firm transformed its estate-planning practice from renting thousands of dollars worth of storage space for paper files into electronic storage of scanned-in, signed documents.
Bittersweet realization as children grow up
Several years ago, whether strolling through a shopping mall or dining out at a restaurant, our toddlers attracted much attention from retirees who missed their own grandchildren. “Appreciate them now — they grow up fast,” we were often counseled. Neither Patti nor I felt like the time was slipping away too quickly while enduring the constant needs of small children. Midnight feedings. Toddler tummy aches. Tooth fairy dollars under the pillow. Dance recitals. Taekwondo belt tests. Braces.
Effectively Using Media to Market Your Practice
Traditional marketing methods alone don’t work anymore. Today’s experience economy, which shapes the delivery of our services, reveals how to identify your target clients and employ specific strategies to attract them. With increased client mobility, it no longer matters whether you’ve had years of practice experience or that your firm has been in the community for almost 100 years. Sure, those attributes help, but that alone won’t bring business to your doorstep.
Marketing the Modern Estate-Planning Practice
In 1989, I graduated from law school and soon after landed at my present firm. Founded in 1924, it’s a stalwart in Fort Myers, Fla. and the surrounding area. At the time, Southwest Florida had a small but fast growing population; the local bar was collegial, and the clients were abundant. To get my name around town and build my professional reputation, I published an article or two in journals like Trusts & Estates magazine, among others, using them as a sprin
Have I Answered All of Your Questions?
It’s often the little things that matter. A few years ago, I lost a client who, on the way out, gave me valuable information through a complaint she registered with one of my team members. “He wasn’t listening to me,” she said, “and always seemed so rushed. I know that I’m not his wealthiest client, but I didn’t feel valued.” Running a successful estate planning practice requires one to juggle a mind-numbing number of tasks. Dozens of client files need attention, direction and delegation.
Pushing that Boulder Up the Mountain
It can be deflating confronting internal opposition when committing to making transformational changes inside of your practice. It’s like trying to push the proverbial boulder up the mountain. “That’s not the way we always do things.” “I’m too old to learn new tricks.” “If it ain’t broke don’t fix it.” Believe me, I’ve heard it all. It’s not that your partners and staff don’t want to improve the way that your firm operates. Everyone enjoys the benefits of higher productivity, revenue and profits.
Turning Your ‘No’ Into a ‘Yes’
Remember when your kids were little and one of the first words they learned to say after “Mama” or “Dada” was an emphatic “NO!” As a toddler, my daughter Gabrielle would march around our home pointing at her baby doll yelling “No! You can’t do that!” It’s obvious that children feel the need to voice their frustrations at being told “No” all the time, so they do this to the family pet or to inanimate objects they feel a sense of control over.
Hourly or Fixed Fee?
How do you charge for estate planning services? I’ve known lawyers who for many years haven’t budged from charging for their services by the hour. They don’t believe that any other way is practical or appropriate. “How do I pull a number out of the air?” they might ask. Or, “what if the file takes many more hours to complete than we originally anticipated?” Both are good questions. Let me address each separately. Problems with Hourly Billing As to the first, I counter with another question.
Income and Wealth Inequality
The income and wealth inequality political movement has been growing for quite some time, coming to a head in this year’s presidential race. Whether you agree inequality is bad or good is beside the point. The issue I’d like to address here is how it affects your clients, and therefore your practice.
Getting the Word Out
Most small to medium size estate planning law firms don’t have the budget to create, produce, edit and run a large-scale media advertising campaign. Newspaper advertising rates in many markets are very expensive, even as readership declines. Television advertising, likewise, is both expensive and fragmented. Yet, in today’s experience economy, content is king. In past columns, I’ve harped on the necessity of creating a valuable educational experience to promote your practice.
Packaging Your Wisdom
As an estate-planning professional, how do you package your services so that your clients can identify the uniquely valuable client experience that you and your firm offer? I wrote in an earlier column that since the development of the microchip and with it the Internet, our clients view the wills, trusts and legal documents we prepare as a commodity. They can’t tell the difference between our wills and trusts against what might be downloaded off a legal document preparation website.
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