📢 Tech-Savvy Saturday Postponement: We're Getting It Perfect for You! 🛠️✨

I must apologize for a second postponement of our highly anticipated Tech-Savvy Saturday event, “Preparing Your Old Office Technology for Your Kids’ Back-to-School Success,” originally moved to today. The slidedeck isn’t quite ready, and you deserve engaging, practical, and properly vetted content crafted especially for our legal audience.

Thank you for your continued patience and enthusiasm. This session matters—and making sure it delivers the best possible value is my top priority. Mark your calendars for next Saturday, August 30, 2025. Expect a session packed with actionable advice, clear step-by-step instructions, and the latest insights on repurposing office tech for your family.

Stay tuned for updates and get ready for an enriched, expertly presented seminar next week. Your support means everything, and I can’t wait to see you there! 🚀

How to Ask AI "Are You Sure?" for Better Legal Research Accuracy!

Lawyers need to be “sure” their AI use is accurate

Legal professionals increasingly rely on AI tools like ChatGPT, Claude, and Google Gemini for research and document preparation. However, these powerful tools can produce inaccurate information or "hallucinations" — fabricated facts, citations, or legal precedents that appear credible but don't exist. A simple yet effective technique is asking AI systems "Are you sure?" or requesting verification of their responses.

The "Are You Sure?" Technique:

When you ask ChatGPT, Claude, or similar AI tools "Are you sure about this information?" they often engage in a second review process. This prompt triggers the AI to:

  • Re-examine the original question more carefully

  • Cross-reference information internally

  • Flag potential uncertainties in their responses

  • Provide additional context about confidence levels

For example, after receiving an AI response about case law, follow up with: "Are you sure this case citation is accurate? Please double-check the details." This often reveals when the AI is uncertain or has potentially fabricated information.

Other AI Verification Features

Google Gemini offers a built-in "double-check" feature that uses Google Search to verify responses against web sources. However, this feature can make mistakes and may show contradictory information.

Claude AI focuses on thorough reasoning and can be prompted to verify complex legal analysis through step-by-step breakdowns.

ChatGPT can be instructed to provide sources and verify information when specifically requested, though it requires explicit prompting for verification.

Essential Legal Practice Reminders 

While AI verification techniques help identify potential inaccuracies, they never replace the fundamental duty of legal professionals to verify all citations, case law, and factual claims. Recent court cases have imposed sanctions on attorneys who submitted AI-generated content without proper verification. If you don’t, you run the risk of running afoul of the ABA Model Rules of Professional Conduct — including Rule 1.1 (Competence), which requires the legal knowledge, skill, and thoroughness reasonably necessary for representation; Rule 1.1, Comment 8, which stresses that competent representation includes keeping abreast of the benefits and risks associated with relevant technology; Rule 1.3 (Diligence), which obligates attorneys to act with commitment and promptness; and Rule 3.3 (Candor Toward the Tribunal), which prohibits attorneys from knowingly making false statements or failing to correct false material before the court.

Best practices for legal AI use include:

  • Always verify AI-generated citations against primary sources

  • Never submit AI content without human review

  • Maintain clear policies about AI use in your practice

  • Understand that professional responsibility remains with the attorney, not the AI tool

The "Are you sure?" technique serves as a helpful first-line check when you notice something seems off in AI responses, but thorough legal research and verification remain your professional responsibility. Your reputation and bar license could depend on it.

ILTACON 2025 Attendance Forces Postponement of Exciting TSS - Preparing Old Office Tech for Your Kids' Back-to-School Success 📚💻

Dear Tech-Savvy Saturday Community,

Due to my attendance at ILTACON 2025 (August 10-14, 2025) at the Gaylord National Harbor Convention Center this week, this month's Tech-Savvy Saturday session originally scheduled for August 16 has been postponed until Saturday, August 23, 2025 at 12 PM EST 🕐.

This postponement presents the perfect opportunity to dive deeper into our upcoming topic: "Preparing Your Old Office Technology for Your Kids' Back-to-School Success." As legal professionals, we often have reliable office equipment that could serve our children well as they return to school. This session will explore practical strategies for repurposing scanners, laptops, printers, and other office technology to create productive learning environments at home.

Our session will cover device preparation techniques, security considerations for family use, and creative ways to transform professional equipment into educational tools. We'll discuss how to properly clean and configure devices, implement age-appropriate restrictions, and ensure data security when transitioning office equipment to personal.

Stay tuned and mark your calendars for Saturday, August 23, 2025 as we explore this practical intersection of legal technology and family needs 📅✨.

Have a Great Weekend and Stay Tech-Savvy!

🎙️ Ep. 117: Legal Tech Revolution,  How Dorna Moini Built Gavel.ai to Transform the Practice of Law with AI and Automation.

Dorna Moini, CEO and Founder of Gavel, discusses how generative AI is transforming the way legal professionals work. She explains how Gavel helps lawyers automate their work, save time, and reach more clients without needing to know how to code. In the conversation, she shares the top three ways AI has improved Gavel's tools and operations. She also highlights the most significant security risks that lawyers should be aware of when using AI tools. Lastly, she provides simple tips to ensure AI-generated results are accurate and reliable, as well as how to avoid false or misleading information.

Join Dorna and me as we discuss the following three questions and more!

  1. What are the top three ways generative AI has transferred Gavel's offerings and operations?

  2. What are the top three most critical security concerns legal professionals should be aware of when using AI-integrated products like Gavel?

  3. What are the top three ways to ensure the accuracy and reliability of AI-generated results, including measures to prevent false or misleading information or hallucinations?

In our conversation, we cover the following:

[01:16] Dorna's Tech Setup and Upgrades

[03:56] Discussion on Computer and Smartphone Upgrades

[08:31] Exploring Additional Tech and Sleeping Technology

[09:32] Generative AI's Impact on Gavel's Operations

[13:13] Critical Security Concerns in AI-Integrated Products

[16:44] Playbooks and Redline Capabilities in Gavel Exec

[20:45] Contact Information

Resources

Connect with Dorna:

Websites & SaaS Products:

  • Apple Podcasts — Podcast platform (for reviews)

  • Apple Podcasts — Podcast platform (for reviews)

  • ChatGPT — AI conversational assistant by OpenAI

  • ChatGPT — AI conversational assistant by OpenAI

  • Gavel — AI-powered legal automation platform (formerly Documate)

  • Gavel Exec — AI assistant for legal document review and redlining (part of Gavel)

  • MacRumors — Apple news and product cycle information

  • MacRumors — Apple news and product cycle information

  • Notion — Workspace for notes, databases, and project management

  • Notion — Workspace for notes, databases, and project management

  • Slack — Team communication and collaboration platform 

Hardware:

Other:

🎙️ Bonus Episode: TSL Lab’s Notebook.AI Commentary on June 23, 2025, TSL Editorial!

Hey everyone, welcome to this bonus episode!

As you know, in this podcast we explore the future of law through engaging interviews with lawyers, judges, and legal tech professionals on the cutting edge of legal innovation. As part of our Labs initiative, I am experimenting with AI-generated discussions—this episode features two Google Notebook.AI hosts who dive deep into our latest Editorial: "Lawyers, Generative AI, and the Right to Privacy: Navigating Ethics, Client Confidentiality, and Public Data in the Digital Age." If you’re a busy legal professional, join us for an insightful, AI-powered conversation that unpacks the editorial’s key themes, ethical challenges, and practical strategies for safeguarding privacy in the digital era.

Enjoy!

In our conversation, the "Bots" covered the following:

00:00 Introduction to the Bonus Episode

01:01 Exploring Generative AI in Law

01:24 Ethical Challenges and Client Confidentiality

01:42 Deep Dive into the Editorial

09:31 Practical Strategies for Lawyers

13:03 Conclusion and Final Thoughts

Resources:

Google Notebook.AI - https://notebooklm.google/

MTC: Florida Bar's Proposed Listserv Rule: A Digital Wake-Up Call for Legal Professionals.

not just Florida Lawyers should be reacting to New Listserv Ethics Rules!

The Florida Bar's proposed Advisory Opinion 25-1 regarding lawyers' use of listservs represents a crucial moment for legal professionals navigating the digital landscape. This proposed guidance should serve as a comprehensive reminder about the critical importance of maintaining client confidentiality in our increasingly connected professional world.

The Heart of the Matter: Confidentiality in Digital Spaces 💻

The Florida Bar's Professional Ethics Committee has recognized that online legal discussion groups and peer-to-peer listservs provide invaluable resources for practitioners. These platforms facilitate contact with experienced professionals and offer quick feedback on legal developments. However, the proposed opinion emphasizes that lawyers participating in listservs must comply with Rule 4-1.6 of the Rules Regulating The Florida Bar.

The proposed guidance builds upon the American Bar Association's Formal Opinion 511, issued in 2024, which prohibits lawyers from posting questions or comments relating to client representations without informed consent if there's a reasonable likelihood that client identity could be inferred. This nationwide trend reflects growing awareness of digital confidentiality challenges facing modern legal practitioners.

National Landscape of Ethics Opinions 📋

🚨 BOLO: florida is not the only state that has rules related to lawyers discussing cases online!

The Florida Bar's approach aligns with a broader national movement addressing lawyer ethics in digital communications. Multiple jurisdictions have issued similar guidance over the past two decades. Maryland's Ethics Opinion 2015-03 established that hypotheticals are permissible only when there's no likelihood of client identification. Illinois Ethics Opinion 12-15 permits listserv guidance without client consent only when inquiries won't reveal client identity.

Technology Competence and Professional Responsibility 🎯

I regularly addresses these evolving challenges for legal professionals. As noted in many of The Tech-Savvy Lawyer.Page Podcast's discussions, lawyers must now understand both the benefits and risks of relevant technology under ABA Model Rule 1.1 Comment 8. Twenty-seven states have adopted revised versions of this comment, making technological competence an ethical obligation.

The proposed Florida rule reflects this broader trend toward requiring lawyers to understand their digital tools. Comment 8 to Rule 1.1 advises lawyers to "keep abreast of changes in the law and its practice," including technological developments. This requirement extends beyond simple familiarity to encompass understanding how technology impacts client confidentiality.

Practical Implications for Legal Practice 🔧

The proposed advisory opinion provides practical guidance for lawyers who regularly participate in professional listservs. Prior informed consent is recommended when there's reasonable possibility that clients could be identified through posted content or the posting lawyer's identit1. Without such consent, posts should remain general and abstract to avoid exposing unnecessary information.

The guidance particularly affects in-house counsel and government lawyers who represent single clients, as their client identities would be obvious in any posted questions. These practitioners face heightened scrutiny when participating in online professional discussions.

Final Thoughts: Best Practices for Digital Ethics

Florida lawyers need to know their state rules before discussing cases online!

Legal professionals should view the Florida Bar's proposed guidance as an opportunity to enhance their digital practice management. The rule encourages lawyers to obtain informed consent at representation's outset when they anticipate using listservs for client benefit. This proactive approach can be memorialized in engagement agreements.

The proposed opinion also reinforces the fundamental principle that uncertainty should be resolved in favor of nondisclosure. This conservative approach protects both client interests and lawyer professional standing in our digitally connected legal ecosystem.

The Florida Bar's proposed Advisory Opinion 25-1 represents more than regulatory housekeeping. It provides essential guidance for legal professionals navigating increasingly complex digital communication landscapes while maintaining the highest ethical standards our profession demands.

MTC

Word of the Week: “Phishing” 🎣 in the Legal Profession - What Every Lawyer Needs to Know in 2025 🛡️

Lawyers Battle phishing on a daily basis.

Phishing is one of the most persistent and dangerous cyber threats facing law firms today. Phishing is a form of computer and internet fraud in which criminals use fake emails, websites, or messages to trick recipients into revealing sensitive information such as passwords, bank details, or client data. For lawyers and legal professionals, the stakes are especially high: law firms hold vast amounts of confidential client information, making them prime targets for cybercriminals. The American Bar Association (ABA) Model Rules for Professional Conduct, particularly Rule 1.6 (Confidentiality of Information) and Rule 1.1 (Competence), require lawyers to protect client data and maintain competence in technology relevant to their practice.

How Phishing Targets Law Firms

Phishing attacks against law firms have become more sophisticated in 2025. Criminals now use generative AI to craft emails that closely mimic real communications from clients, colleagues, or even senior partners. These messages often create a sense of urgency, pressuring recipients to act quickly—such as transferring funds, sharing login credentials, or downloading malicious attachments. Business Email Compromise (BEC) scams are particularly damaging, as attackers impersonate managing partners or clients to divert wire transfers or request sensitive documents.

Impersonation: The Hidden Dangers in Your Inbox

Attackers often use email spoofing to manipulate the display name and email address, making a message appear to come from someone you trust. The display name (the name that appears in your inbox) can be set to any familiar contact, but the actual email address may be subtly altered or completely fake. For example, a scammer might use “john.smith@lawfirm.com”or “John Smith of ….” as the display name, but the underlying address could be “jjohn.smith@lawf1rm.com” or “john..john.smith@lawfirm.co@lawfirm.co.” These changes are often just a single character off, designed to trick you into replying or clicking a malicious link.

Lawyers should always examine the full email address, not just the display name, before responding or acting on any request. On many smartphones and email clients, only the display name is shown by default, so you may need to click or tap to reveal the actual sender’s email address. If the message requests sensitive information, money transfers, or urgent action, verify the request through a separate communication channel, such as a phone call using a known number—not one provided in the suspicious email. This vigilance aligns with ABA Model Rule 1.1, which requires lawyers to maintain competence, including understanding risks associated with technology.

Recent Phishing Incidents Involving Lawyers

Phishing Email Threatens Law Firm Cybersecurity Defense

What Lawyers Should Watch For

  • Impersonation: Always check the sender’s full email address, not just the display name. Watch for addresses that are off by one or more characters.

  • Urgency and Pressure: Be cautious of emails that demand immediate action, especially those involving money or confidential data.

  • Suspicious Links or Attachments: Hover over links to check their true destination, and never open unexpected attachments.

  • Unusual Requests: Be wary of requests outside normal procedures, such as buying gift cards or changing payment instructions.

Prevention and Best Practices

  • Employee Training: Regular cybersecurity awareness training is crucial. Staff should be able to recognize phishing attempts and know how to report them. This supports ABA Model Rule 5.3 (Responsibilities Regarding Nonlawyer Assistance).

  • Multi-Factor Authentication (MFA): MFA adds an extra layer of security, making it harder for attackers to access accounts even if credentials are compromised.

  • Incident Response Plan: Every law firm should have a clear plan for responding to phishing incidents, including communication protocols and legal obligations for breach notification.

  • Client Education: Educate clients about phishing risks and encourage them to verify any unusual requests that appear to come from your firm.

Professional Responsibility and Phishing

lawyers need to be proactive Against Cybersecurity Threats in 2025!

The ABA Model Rules make clear that lawyers must take reasonable steps to prevent unauthorized access to client information (Rule 1.6(c)). Lawyers must also keep abreast of changes in technology and its associated risks (Rule 1.1, Comment 8). Failing to implement basic cybersecurity measures, such as phishing awareness and email verification, may expose lawyers to disciplinary action and civil liability.

Final Thoughts

Phishing is not just an IT problem—it’s a business risk that can compromise client trust, cause financial loss, and result in legal liability. By staying vigilant, investing in training, and adopting robust security measures, lawyers can protect themselves, their clients, and their reputations in an increasingly digital world. Compliance with the ABA Model Rules is not optional—it's essential for ethical and effective law practice.

📖 Word(s) of the Week (Wow): "Service as a Service" (SaaS) & "Hardware as a Service" (HaaS)!

SaaS vs. HaaS: What Law Firms Need to Know About Service as a Service and Hardware as a Service in 2025 ⚖️💻

Exploring SaaS vs. HaaS in Legal Tech!

Legal practices are rapidly embracing cloud-based solutions, and two models stand out: Software as a Service (SaaS) and Hardware as a Service (HaaS). Understanding these models is essential for law firms seeking efficiency, security, and cost-effectiveness in 2025.

What is SaaS?
SaaS is a cloud-based software delivery model. Instead of buying software outright and installing it on each device, law firms subscribe to web-hosted applications. This means no more managing physical servers or complex installations. Leading SaaS providers handle updates, security, and maintenance, freeing attorneys to focus on clients and cases.

Benefits of SaaS for Law Firms:

  • Centralized, secure document management—enabling paperless workflows and real-time collaboration.

  • Cost savings by eliminating expensive hardware and IT support. Firms pay only for what they use and can scale up or down as needed.

  • Remote access to case files, calendars, and billing from anywhere, supporting hybrid and remote work environments.

  • Automatic updates and improved security, with providers responsible for compliance and data protection.

  • Specialized legal features, such as document automation, calendaring, and legal billing, tailored for law practices.

Legal Considerations for SaaS:
SaaS agreements replace traditional software licenses. They must clearly define service levels, data privacy, and compliance with regulations. SaaS lawyers play a crucial role in drafting contracts, protecting intellectual property, and ensuring regulatory compliance across jurisdictions.

What is HaaS?
HaaS provides physical hardware—like computers, servers, or networking equipment—on a subscription basis. Law firms avoid large upfront purchases and instead pay a monthly fee for access, support, and maintenance. HaaS often includes installation, configuration, troubleshooting, and ongoing monitoring.

Benefits of HaaS for Law Firms:

Knowing your SAAS and Haas agreement terms is essential to maintaining client confidentiality and security

  • Predictable budgeting with no surprise hardware expenses.

  • Up-to-date equipment and proactive maintenance, reducing downtime.

  • Comprehensive support agreements, including warranties and rapid response times.

  • Enhanced security and compliance, as providers manage device updates and data protection.

Legal Considerations for HaaS:
HaaS contracts should specify the scope of services, pricing, service-level agreements (SLAs), liability, data privacy, and dispute resolution. Clear terms protect both the law firm and the provider, ensuring accountability and compliance with industry standards.

Challenges Law Firms Face in Using SaaS and HaaS

Law firms adopting SaaS and HaaS face several notable challenges:

  • Security Vulnerabilities: SaaS platforms can be susceptible to misconfigured access controls, inadequate monitoring, and insufficient threat detection. These weaknesses make law firms prime targets for cyberattacks, such as unauthorized access and data breaches, as seen in high-profile incidents involving major firms.

  • Data Breaches and Compliance Risks: Sensitive client data stored in SaaS environments is at risk if proper security measures are not in place. Breaches can expose confidential information, leading to regulatory penalties, reputational damage, and class action lawsuits if firms fail to notify affected parties promptly.

  • Integration Challenges: As law firms rely on multiple SaaS vendors, integrating various software platforms can become complex. Poor integration may disrupt workflows and reduce efficiency, especially if systems do not communicate seamlessly.

  • Shared Responsibility Confusion: SaaS providers typically secure the platform, but law firms are responsible for data security and access controls. Many firms mistakenly believe vendor security alone is sufficient, which can leave critical data exposed.

  • Reliable and consistent internet access: Reliable and consistent internet access is essential for law firms using SaaS and HaaS, as these cloud-based solutions require an active connection to access software, documents, and case management tools; any internet outage or slow connectivity can disrupt workflows, limit access to critical information, and impact client service. (What if you are on travel and the airplane, hotel, or location does have (reliable) internet connection - how do you get your work done?)

  • Business Email Compromise (BEC): SaaS ecosystems increase the risk of BEC attacks. Compromised email accounts can be exploited for fraud, impersonation, and data theft, often going undetected for extended periods.

  • Data Classification and Visibility Issues: Rapid adoption of SaaS can lead to scattered data across multiple platforms. Without a formal data classification strategy, firms may lose track of where sensitive information resides, complicating compliance and incident response.

  • Legal and Contractual Complexities: SaaS contracts involve nuanced licensing agreements, third-party vendor relationships, and service level commitments. Discrepancies between vendor terms and client expectations can result in disputes and legal challenges.

  • Dependency on Providers: Both SaaS and HaaS models make firms dependent on external vendors for uptime, support, and updates. Service disruptions or vendor instability can directly impact firm operations.

  • Hardware Lifecycle Management: With HaaS, firms avoid upfront hardware costs but must rely on the provider for timely upgrades, maintenance, and support. Poor vendor performance can lead to outdated equipment, downtime, or security gaps.

  • Cost Over Time: While SaaS and HaaS reduce initial capital expenditures, ongoing subscription fees may add up, potentially exceeding the cost of traditional ownership in the long term if not carefully managed.

Lawyers need to know the pros and cons in using saas and haas products!

While SaaS and HaaS offer significant advantages, law firms must address these risks through robust security practices, careful contract negotiation, and ongoing vendor management to protect sensitive data and maintain operational integrity. This may be easier for large law firms but difficult if not nearly impossible for mid- to small- to solo-size law practices.

Why Law Firms Should Care
Both SaaS and HaaS offer flexibility, scalability, and security that traditional IT models cannot match. By leveraging these services, law firms can modernize operations, improve client service, and reduce risk. The right contracts and due diligence are critical to ensure business continuity and compliance in a rapidly evolving legal tech landscape.

🎙️ Ep. 112: How Judges and Lawyers Can Use AI Wisely: Judge Scott Schlegel on Best Practices, Pitfalls, and The Future of Legal Tech.

My next guest is the Honorable Judge Scott Schlegel, a nationally recognized judicial innovation and technology leader.

With extensive courtroom and technological experience, Judge Schlegel offers valuable insights into how attorneys can effectively leverage artificial intelligence and legal technology to enhance their workflows. He emphasizes the importance of avoiding common pitfalls while maintaining the highest standards of professional responsibility. Judge Schlegel also underscores the critical need to keep the human in the loop, advocating for a balanced approach that upholds efficiency and legal expertise.

Join Judge Schlegel and me as we discuss the following three questions and more!

  1. What are the top three ways lawyers should use AI for their work, and what are the top three ways lawyers do not use AI correctly today?

  2. What are the top three things lawyers still get wrong with using technology in the courtroom?

  3. AI is the current advancement in technology in the workplace. What are the top three technological advances lawyers should be keeping an eye on soon?

In our conversation, we cover the following:

[00:59] Top Three Ways Lawyers Should Use AI

[04:01] Security and Privacy Concerns with AI

[06:49] Common Mistakes Lawyers Make with AI

[11:52] What Lawyers Are Still Getting Wrong in Court

[18:30] Future Technological Advances for Lawyers

[22:18] Keeping the Human Element in AI Use

Resources:

Connect with Judge Schlegel:

Software & Cloud Services mentioned in the conversation: