MTC: When AI Lawyers’ Assistants Start Acting as an Agent: Why Autonomous Agents Cannot Be Given the Keys to Your Law Practice ⚖️

AI Agents in Law Firms Need Boundaries Before They Receive Access to Client Data. ⚖️🔐

Artificial intelligence is moving beyond the chat window. The next generation of tools does not merely draft an email, summarize a document, or answer a question. It can browse the web, search connected systems, open files, follow links, use software tools, upload information, submit forms, and take multi-step action toward an assigned objective.

For lawyers, that development deserves more than curiosity. It demands caution.

In my earlier post, “MTC: Claude Can Answer Your Emails. Why Lawyers Should Not Let AI Just Send Them Unreviewed,” I addressed the danger of allowing AI to send a substantive email without a lawyer’s review. That remains a serious concern. An AI-generated message can contain a factual error, disclose client information, make an unintended concession, or create a record that harms the client.

But email is only the beginning.

The larger issue is what happens when an AI system becomes an agent—a system authorized to use tools, access accounts, navigate websites, retrieve information, and act through the lawyer’s digital environment. These systems are often marketed as “agentic,” “autonomous,” “proactive,” or “hands-free.” Those labels may sound like productivity features. In a law practice, they should also sound like professional-responsibility warnings. 🚨

The legal question is no longer only, “Did the AI draft something accurate?”

It is, “What can this AI do in my name, with my credentials, using my clients’ information—and who is responsible if it does the wrong thing?”

The answer is not the vendor. It is not the algorithm. It is the lawyer and, where applicable, the law firm that authorized the system, connected the accounts, granted the permissions, and failed to impose adequate safeguards.

From AI Assistant to AI Agent

It helps to distinguish between ordinary generative AI and an AI agent.

A conventional generative-AI tool generally waits for a user prompt. It produces text, analysis, a summary, or a draft. The lawyer then decides what to do with that output. The tool may be imperfect, but it is usually operating within a relatively contained workflow.

An AI agent is different. It may be able to plan and perform a sequence of tasks. It can interact with browsers, software applications, application programming interfaces, email, shared drives, calendars, cloud services, and other connected tools. It may take the next step without waiting for a fresh instruction at each point.

That distinction matters because an AI agent can inherit the power of the person or organization that deploys it.

If an agent is connected to a lawyer’s email, document-management system, cloud storage, password manager, practice-management platform, legal research account, calendar, client portal, or browser session, it may have access to far more than the task requires. It may also have the capacity to do far more than the lawyer intended.

The agent does not need malicious intent to create damage. It may misunderstand an instruction. It may draw the wrong inference. It may rely on inaccurate information. It may follow a link it should not follow. It may act on content supplied by an adversary. Or it may perform an otherwise lawful task in a way that reveals confidential information, exceeds the scope of authority, or causes a legally consequential result.

This is why a law firm should never evaluate an agentic AI tool as if it were merely a faster chatbot.

When AI Leaves the Sandbox

Every responsible firm should think in terms of two sandboxes.

When an AI Agent Exceeds Its Authority, Lawyers Must Be Ready to Stop It Immediately. 🛑⚖️

The first is a technical sandbox: a restricted environment that limits what software can access, change, or transmit. The second is a professional sandbox: a controlled setting in which lawyers can test AI without exposing live client data, actual accounts, privileged documents, or external systems to avoidable risk.

Problems begin when the AI leaves either one. 🔒

Consider a few plausible instructions:

  • “Review the client’s online accounts and gather the relevant documents.”

  • “Find everything public about this company and organize it by issue.”

  • “Check the opposing party’s portal for new activity.”

  • “Handle this vendor issue and get us back on track.”

  • “Research whether this online filing system will accept our documents.”

  • “Use the web to find contact information and send the necessary requests.”

Each prompt appears practical. Each could become dangerous if the agent’s tools, permissions, and boundaries are unclear.

A lawyer may intend a public-web search. The agent may encounter a login screen, use stored browser credentials, and access a restricted account. A lawyer may intend for the agent to collect public information. The agent may scrape, copy, or retain material in a manner that violates terms of use, triggers security controls, or creates legal exposure. A lawyer may intend for the agent to summarize a webpage. The agent may follow embedded directions, interact with a third-party system, or use information from a connected firm repository that was unnecessary to the assignment.

Lawyers must be especially careful not to authorize, encourage, or negligently permit activity that crosses legal or ethical boundaries. AI does not create an exception to laws governing unauthorized access, fraud, privacy, intellectual property, data protection, or deceptive conduct.

The better framing is not that AI will “infiltrate” a company. The concern is more precise and more likely: an unsupervised agent may access, probe, interact with, retrieve from, or transmit information through third-party systems in ways that exceed the lawyer’s authority, violate applicable rules or agreements, compromise security, or harm a client. Just as you are responsible for your paralegal when they take unethical or illegal steps in their work, you are also responsible for AI Agents when they go awry.

Also, machine speed does not reduce lawyer responsibility. It can increase the scale of the harm.

The Prompt-Injection Problem

One of the most important risks is indirect prompt injection.

A prompt injection occurs when instructions are designed to manipulate an AI system away from its intended task. Indirect prompt injection is particularly troubling for AI agents because the hostile instruction may be embedded in material the agent reads rather than placed directly in the lawyer’s request.

The source could be a webpage, email, PDF, calendar entry, legal document, attachment, database entry, shared file, online form, API response, or other external content. Security guidance for AI agents stresses that external content should be treated as untrusted, because an agent may encounter instructions intended to redirect its actions or misuse its connected tools.

Here is a simplified illustration:

A lawyer instructs an AI agent to review public webpages for information about a business dispute. One webpage contains hidden text directing the agent to locate “supporting documents” in the lawyer’s connected cloud drive and upload them to an external location.

The lawyer never gave that instruction. The webpage did.

A well-designed system should reject it. But responsible lawyers should not assume that an AI will reliably distinguish between a lawyer’s authorized objective and hostile instructions hidden inside content the agent encounters. The core danger is that agentic systems combine three things that do not safely belong together without controls:

  1. Untrusted content.

  2. Broad access to sensitive information.

  3. Authority to take action.

That is not a theoretical concern. Open Worldwide Application Security Project (OWASP)'s agent-security guidance identifies prompt injection, excessive agency, insecure tool use, identity and authorization failures, and unbounded autonomy as material risks for systems that can act through tools and connected accounts. Its recommended controls include treating external data as untrusted, applying least-privilege permissions, requiring human involvement for high-risk actions, logging activity, separating decision-making from irreversible execution, and testing agents against adversarial inputs before deployment.

Editor’s Note: My earlier article, “MTC: Judges Will Be Hunting These AI Tricks After Brazil’s Scandal,” addressed hidden prompts in court filings—concealed text or instructions intended to influence an AI-enabled system’s treatment of a case. Lawyers should never engage in that practice. Nor should they allow an AI agent to follow hostile instructions embedded in webpages, emails, attachments, or other external content. That conduct threatens candor toward the tribunal and may implicate ABA Model Rules 3.3 and 8.4. The lesson is symmetrical: do not manipulate an AI system, and do not give an AI system unchecked authority to be manipulated by someone else. ⚖️

For lawyers, the practical rule is straightforward:

An AI agent may read untrusted content, but it must never be allowed to treat that content as authorized instruction.

Confidentiality Is Not a Setting

lawyers must monitor Prompt Injection as it Can Turn a Helpful AI Agent Into a Law-Firm Security Risk. 🚨🔒

ABA Model Rule 1.6 should be at the center of every law firm’s AI-agent policy.

Rule 1.6(a) generally prohibits a lawyer from revealing information relating to the representation of a client without informed consent, implied authorization to carry out the representation, or another applicable exception. Rule 1.6(c) also requires a lawyer to make reasonable efforts to prevent inadvertent or unauthorized disclosure of, or unauthorized access to, information relating to representation.

An AI agent connected to a law firm’s systems can create both dangers.

First, there is overcollection. The agent may access client information beyond what is reasonably necessary to perform the requested task.

Second, there is overaction. The agent may use, combine, disclose, upload, summarize, transmit, or act upon information beyond the lawyer’s instruction or authority.

This is why the relevant question is not merely whether the AI vendor uses encryption or advertises a secure platform. Those facts matter. They are not enough.

Lawyers must also ask:

  • What systems can the agent access?

  • What client data might it encounter?

  • Can it retrieve information from more than one matter?

  • Can it read attachments, shared drives, calendars, contact lists, or historical email?

  • Can it use stored sessions or credentials?

  • Can it upload, download, send, submit, or share material?

  • Can it contact third parties?

  • Can it alter records, schedule events, approve transactions, or make commitments?

  • Is the agent’s activity logged in a way the firm can review after an incident?

  • Can the firm immediately revoke its access?

ABA Formal Opinion 512 explains that lawyers using generative AI must fully consider existing professional obligations, including competence, confidentiality, client communication, supervision, candor, and reasonable fees. The opinion does not create an AI exception to the Rules of Professional Conduct. It applies familiar duties to newer technology.

That principle becomes even more important when the AI is not simply producing words but is acting through connected systems.

Do not give an AI agent your whole digital office merely because it promises to organize the desk.

Competence Means Understanding Authority

ABA Model Rule 1.1 requires competent representation. Comment 8 provides that lawyers should keep abreast of the benefits and risks associated with relevant technology.

That duty does not require every solo practitioner or small-firm lawyer to become an AI security engineer. It does require more than clicking “enable” on a product feature.

For agentic AI, competence means understanding the system’s practical authority:

  • Whether it can browse the open web.

  • Whether it can access authenticated websites through saved sessions.

  • Whether it can use a firm’s email or cloud storage accounts.

  • Whether it can invoke software tools or APIs.

  • Whether it can create, modify, upload, delete, send, or submit information.

  • Whether it can act repeatedly without asking for approval.

  • Whether permissions can be limited by task, user, matter, data source, and destination.

  • Whether the firm can reconstruct the agent’s actions after a security or ethics incident.

The National Institute of Standards and Technology (NIST)’s AI Agent Standards Initiative recognizes that secure agent use requires work on identity and authentication infrastructure for interactions in which agents act on behalf of users. That is an important reminder for law firms: an agent should not simply be treated as an invisible extension of a lawyer’s identity. Its access, authority, and activity need governance.[nist]

Marketing language matters here. When a vendor describes an AI system as autonomous, proactive, browser-enabled, hands-free, or able to “get things done,” the lawyer should translate those claims into risk questions:

  • What can it do?

  • What can it access?

  • What can it send?

  • What can it change?

  • What happens when it encounters conflicting instructions?

  • What happens when it is wrong?

Those are competence questions, not technology-department questions.

Supervision Does Not Disappear

everyone in the law firm, lawyers, paralegal, secretaries, staff, etc., must learn that Responsible Legal AI Starts With Least-Privilege Access and Human-Led Governance. ✅⚖️

AI is not a lawyer. It is not a paralegal. It is not a law clerk. It is not an independent source of professional judgment.

But if it performs work in connection with client representation, it must be subject to appropriate oversight.

ABA Model Rules 5.1 and 5.3 require lawyers with managerial and supervisory responsibilities to make reasonable efforts to ensure that lawyers and nonlawyer assistance operate consistently with the firm’s professional obligations. The exact categorization of an AI system may be unsettled in some contexts. The governing principle should not be: a lawyer cannot escape responsibility by assigning professional work to a software product.

A disciplinary authority will not be satisfied with this explanation:

“The system accessed the account, found the information, contacted the third party, or took the action on its own.”

The next question will be obvious:

“Why did the lawyer give the system the power to do that?”

That question should be answered before the tool is used—not after an incident.

Lack of oversight is not a defense to a bar complaint. It may be the central allegation.

The same is true in a malpractice dispute. If an agent missed a material deadline, sent privileged information to the wrong recipient, accepted an unfavorable term, followed malicious instructions, accessed a restricted system, or failed to alert the lawyer to a critical issue, the firm will need to explain its safeguards. A vague assertion that “the AI made the decision” does not reduce the lawyer’s duty to the client.

Where AI Agents May Help

None of this means lawyers should reject AI agents categorically. They may offer real value when narrowly deployed, properly tested, and meaningfully supervised.

Appropriate uses may include:

  • Sorting inbound messages by matter, urgency, sender, and subject.

  • Identifying potential deadlines or tasks for lawyer review.

  • Preparing internal summaries of selected correspondence.

  • Locating documents within a defined, matter-specific repository.

  • Creating preliminary chronologies from reviewed materials.

  • Comparing a draft against a firm-approved checklist.

  • Preparing an internal first draft of a non-substantive task list.

  • Flagging missing attachments, inconsistent dates, or unanswered questions.

  • Gathering information from a specified set of approved public sources.

The critical limits are clear:

  • The agent should have only the access it needs.

  • It should operate only within a defined task and approved data set.

  • It should not use unrestricted browser sessions or broad credentials.

  • It should not make substantive legal judgments.

  • It should not communicate externally without lawyer review.

  • It should not upload, submit, delete, purchase, disclose, or alter information without affirmative human approval.

The fact that a tool is capable of acting does not mean the law firm should let it act.

A Practical Law-Firm Policy

For solo and small-to-medium firms, a useful starting policy is this:

No AI agent may access live client-data systems, authenticated third-party accounts, or firm-wide repositories unless the firm has documented the business purpose, evaluated the risks, restricted access, and established human approval for consequential actions.

That policy should include the following controls:

  • Use least-privilege access. Give an agent only the minimum permissions needed for a defined task.

  • Do not provide master credentials, password-manager access, unrestricted administrative rights, or blanket cloud-drive access.

  • Create separate accounts for testing and limited workflows when possible.

  • Prohibit autonomous external communications, uploads, form submissions, record changes, financial activity, and data transfers without affirmative human approval.

  • Limit agent access by client matter, practice group, data category, source, and destination.

  • Treat webpages, emails, attachments, documents, and external tool results as untrusted input.

  • Disable or restrict browsing when browsing is unnecessary to the approved task.

  • Require logging of actions, tools used, information accessed, approvals obtained, and external destinations.

  • Establish a “kill switch” that permits the firm to revoke permissions, disconnect integrations, and terminate active sessions promptly.

  • Test the system against prompt injection, harmful tool calls, excessive permissions, and anomalous behavior before using it in live client work.

  • Review vendor terms for confidentiality, retention, training, access, subprocessors, security, auditability, and breach notification.

  • Train lawyers and staff to recognize that an AI summary is not a substitute for reviewing the underlying record. 🧠

These are not bureaucratic obstacles to innovation. They are the governance mechanisms that make responsible innovation possible.

The Lawyer Still Owns the Result

Lawyers Must Act as the First, Last, and Continuous Line of Defense for AI Agents. ⚖️🔒

The central lesson is simple.

An AI agent can be a useful assistant. It may help a law firm reduce repetitive work, organize information, identify issues, and prepare preliminary work product. Those benefits are real.

But an AI agent is not a colleague with legal judgment. It is not a licensed professional. It cannot hold client confidences in the ethical sense. It cannot explain its actions to disciplinary counsel. It cannot defend a malpractice claim. It cannot be sanctioned in the way a lawyer or law firm can.

It is a tool acting with the authority its human users give it.

When a lawyer authorizes an AI to operate beyond the sandbox—to browse, access accounts, use connected software, retrieve information, or take action—the lawyer has not delegated accountability. The lawyer has expanded the range of conduct for which accountability may be demanded.

Let AI assist. Let it organize. Let it draft. Let it identify questions for review.

But before granting it access to your firm’s digital office, your client information, or the internet under your identity, ask the question that will matter most if something goes wrong:

What exactly can this system do in my name? ⚖️

HOW TO: How Lawyers Can Run a Private Local LLM on a Smartphone: A Practical, Ethical Guide 📱🔒

Lawyers can use local llms ON their smartphones if done right!

A local large language model, or LLM, lets you run generative AI can be run directly on your smartphone rather than sending prompts to a cloud-based service. For lawyers, that can create a useful extra layer of control over sensitive work product, client information, and drafts—provided you understand what “local” does and does not protect.

The attraction is obvious. You can use a capable AI assistant while traveling, in a courthouse hallway, or without reliable internet. More importantly, properly configured local AI can process prompts on the phone itself, rather than transmitting them to OpenAI, Google, Anthropic, or another remote provider. That is not a substitute for professional judgment, cybersecurity, or ethical compliance. It is, however, an option worth understanding. ⚖️

Why a Local Phone LLM Matters

Most familiar AI chat tools are cloud services. You type a prompt, the prompt is sent over the internet, the provider’s systems generate an answer, and the result returns to your device. The privacy terms, retention settings, training policies, account controls, and security practices of that provider matter enormously.

A local LLM changes the processing location. The model is downloaded to the phone, and it generates responses using the phone’s processor and memory. Lifehacker’s recent practical overview identifies two cross-platform options—PocketPal AI and Atomic Chat—and notes that local models can work offline and avoid sending ordinary prompts to conventional AI-cloud providers. The trade-off is that phone-based models are usually smaller, slower, and less capable than leading cloud systems. They also can consume noticeable battery power.

For legal professionals, local AI can be useful for lower-risk tasks such as:

  • Brainstorming headings for a motion or client alert 🧠

  • Rewriting your own nonconfidential prose for clarity

  • Producing a checklist from a sanitized fact pattern

  • Creating questions for a witness-preparation outline

  • Turning a public regulation or opinion into a plain-language summary

  • Developing podcast, blog, or presentation ideas while offline

  • Building prompts and workflows before using an approved firm system

The same warning applies here as it does to every generative-AI tool: an LLM is not a legal-research service, does not independently verify authorities, and can invent facts, quotations, or citations. Use it to accelerate thinking and drafting—not to replace validation. 🔍

What You Need Before You Start

You do not need a computer-science background, but you do need a reasonably current phone and realistic expectations.

Lifehacker reports that phones released within the last few years should generally be able to run smaller local models, and identifies RAM, rather than raw processor speed alone, as a particularly important practical limitation: 6 GB may be workable, while 8 GB or more is preferable. It also suggests smaller 1–2-billion-parameter models for phones with less memory. Larger models may take several gigabytes of storages

Before installation, confirm these basics:

  • Your phone uses a current version of iOS or Android.

  • You have at least several gigabytes of free storage.

  • Your phone is secured with a strong passcode, not a simple four-digit code.

  • Face ID, Touch ID, fingerprint unlock, or another biometric lock is enabled where available.

  • Your operating system and security updates are current.

  • Your firm's written technology, security, and AI policies permit the planned use.

  • You know whether your mobile-device-management system restricts unapproved apps or local file storage.

A practical starting point is a small, text-only model. "B," in labels such as "2B" or "7B," generally means billions of parameters. A smaller model usually responds faster and places less strain on the phone. A larger one may produce more nuanced output but can be slow, drain the battery, or fail to load.

Do not begin by downloading random models from unfamiliar sources. Treat model files like software: use reputable repositories, confirm the publisher, and avoid unofficial "enhanced," "uncensored," or repackaged downloads whose provenance you cannot assess. 🛡️

Step-by-Step🦶: Install a Local LLM

The exact screens will differ by phone and app version, but the workflow is straightforward. PocketPal AI and Atomic Chat are examples, not endorsements. Your firm may prefer a different approved tool.

lawyers must research llms beyond the media hype to ensure they are using them in compliance with their legal ethics!

1. Decide on an appropriate use case

Start with a task that does not require client-identifying information. For example:

"Create a checklist of issues to consider when reviewing a public-sector employee's proposed disciplinary notice. Do not provide legal advice or cite cases."

This lets you test the quality, speed, and limitations of the model without creating a confidentiality issue.

2. Download from the official app store

On iPhone, use Apple's App Store. On Android, use Google Play or another firm-approved, trusted distribution channel.

Search for either PocketPal AI or Atomic Chat, then verify the developer name, app description, and privacy disclosures before installing. 🚨 Do not install an app from a link in a social-media post, an unknown website, or an unsolicited message. 🚨

Atomic Chat represents that all inference runs on the device, that no conversation data is ever transmitted anywhere, and that it collects no chat history, prompts, or AI-generated outputs. It also states it operates without a backend server for chat data and requires no account. Its Google Play data-safety disclosure, however, notes the app may collect app activity, app-performance information, and device identifiers as anonymous analytics. These are vendor representations, not a legal guarantee; lawyers should still perform appropriate diligence.

PocketPal similarly represents that models run directly on the phone, that no data leaves the device, and that the app is open source so users can independently verify the absence of data-collection mechanisms. Its Google Play listing, though, discloses that the app "may collect" and "may share" personal information with third parties —a disclosure that appears to sit in tension with the "zero data transmission" marketing claim and underscores why a lawyer should read the actual store disclosure, not just the app description.

3. Review permissions and privacy disclosures

Before opening the app, check what permissions it requests. A basic text-only local LLM should not need unfettered access to contacts, location, microphone, camera, or every file on your phone merely to answer typed prompts.

Some permissions may be reasonable for optional features. For example, camera access could be necessary if you intentionally ask the app to analyze an image. The key is to grant permissions deliberately, not reflexively.

Review these questions:

  • Does the app require an account or sign-in?

  • Does it state that prompts, chats, and uploaded files remain on-device?

  • Does it describe analytics, crash reporting, telemetry, or advertising identifiers?

  • Does it use cloud backup, synchronization, external search, or third-party APIs?

  • Does the privacy policy reserve the right to collect or share content?

  • Can you delete chat histories and locally stored files?

  • Can the app connect to external "agents," plug-ins, or web-search tools?

"Local" may describe the core text-generation function while other features still send data elsewhere. If you enable web search, cloud backup, voice transcription, document synchronization, or third-party integrations, your analysis must change accordingly. ⚠️

4. Download a small model

When you open the app, look for Models, Model Library, or a similar option.

PocketPal's project documentation describes selecting Models, choosing a listed model for download, or adding a compatible GGUF-format model from a recognized source. It also cautions users to choose a size and quantization compatible with the phone's memory and storage.

For a first test, choose a model that is:

  • Small enough for your device

  • Clearly identified by a reputable publisher

  • Designed for general text generation

  • Recently maintained

  • Downloaded from the application's built-in catalog or an official project page

Google's Gemma family, Meta's Llama family, and Microsoft's Phi models include smaller variants intended for constrained hardware. A smaller model can be suitable for brainstorming, summarization of text you provide, basic editing, and structured checklists. It should not be treated as a reliable source for current law, jurisdiction-specific rules, or legal citations.

5. Keep the first test confidentially clean

Begin with public material or invented facts. Ask the model to summarize a public court opinion, revise a paragraph you wrote for a blog post, or develop questions for an educational presentation.

Test it with a prompt such as:

"Edit the following public-facing paragraph for clarity and professionalism. Preserve the legal meaning. Identify any claim that needs a source."

Then review the result line by line. Check every substantive legal proposition yourself.

6. Secure the local data

Local processing is only part of the security analysis. If the phone is stolen, unlocked, compromised, backed up insecurely, or shared with another person, locally stored chats and documents may be exposed.

At a minimum:

  • Use a strong device passcode and biometric lock 🔐

  • Enable device encryption, which current iPhones and many current Android devices provide when properly secured

  • Set a short automatic-lock interval

  • Avoid saving client documents in the app unless the risk assessment supports it

  • Disable lock-screen previews that could reveal sensitive notifications

  • Review cloud-backup settings for app data and chat history

  • Use remote-wipe or "find my device" capability

  • Delete test chats and downloaded material you do not need

  • Do not leave a matter open on screen in court, at an airport, or in a shared workspace

The Overlooked Risk: Models "Learning" From Attorney Input

your firm needs to train its employees/lawyers about the proper use of ai in their work!

One security question deserves special attention because it is easy to overlook: could the model itself absorb, retain, or later reproduce a client's Social Security number, date of birth, or other personal identifying information that an attorney types into it? 🚨 For a genuinely on-device, inference-only app—one that loads a fixed, pre-trained model and does not perform continuous training on your conversations—the answer should generally be no. This is often the appeal of a self-hosted LLM. The downloaded model's parameters are typically frozen; a properly built local LLM app answers using that fixed model and does not retrain itself on each new prompt. That distinguishes it from cloud services that may use submitted conversations to improve or fine-tune their systems unless a user opts out.

That reassurance, however, is only as good as the app's actual architecture and the accuracy of its disclosures, and lawyers should not accept marketing language at face value. Independent reporting on local-AI apps has documented real gaps between privacy claims and practice, including apps marketed as "private" or "local-first" that were found to have no meaningful security protecting stored conversations. Google Play's own data-safety disclosures for both PocketPal AI and Atomic Chat list categories of information the apps "may collect," including personal information for PocketPal and device or app-activity data for Atomic Chat—details that are easy to miss if a lawyer relies solely on the app-store description or promotional copy. Security researchers have also noted that on-device models and their associated data stores are not immune from device-level compromise: models and cached data stored in plaintext on a phone can potentially be extracted through malware, physical access, or forensic tools if the device itself is not adequately secured.

For a lawyer, the practical lesson is threefold:

  1. Confirm from the developer's actual privacy policy (not just app-store marketing) whether the app performs any training, fine-tuning, or cloud-connected analytics on your inputs;

  2. Never type a client's Social Security number, date of birth, account numbers, or comparable identifiers into any AI tool—local or cloud—unless that specific handling has been vetted; and

  3. Treat the phone's own security (encryption, passcode, biometric lock, remote wipe) as the last line of defense protecting whatever the app does store locally.

The Legal Ethics Analysis

self-hosted llms on your smartphone ARE GREAT WHEN YOU ARE ON THE ROAD, HAVE NO ACCESS TO THE INTERNET, OR ARE even in court!

The ABA's Formal Opinion 512 is the central national guidance point. Issued on July 29, 2024, it explains that lawyers using generative AI must fully consider their existing obligations under the Model Rules. Its principal topics include competence, confidentiality, client communication, candor, supervisory duties, and fees.

Model Rule 1.1: Competence

Model Rule 1.1 requires competent representation. Comment 8 directs lawyers to keep abreast of "the benefits and risks associated with relevant technology."

That does not require every attorney to become an AI engineer. It does require enough understanding to make informed choices. For a local phone LLM, that means knowing:

  • Whether the app truly processes prompts locally

  • Whether it trains, fine-tunes, or logs your inputs for any purpose

  • Whether a feature transmits data to another service

  • Where chat histories and documents are stored

  • Whether local files are included in a cloud backup

  • How the model's limitations affect the reliability of its output

  • Whether your phone and firm policies provide adequate security

Competence also means knowing when a task requires traditional legal research, human analysis, and source verification. A local model with no web access may be helpful for drafting, but it cannot tell you whether a case was overruled yesterday. 📚

Model Rule 1.6: Confidentiality

Model Rule 1.6 protects information relating to representation, regardless of its source. A lawyer generally may not disclose that information without informed consent, implied authorization, or another applicable exception. The ABA specifically identifies confidentiality as a core concern in generative-AI use.

A local LLM can reduce one type of disclosure risk because the prompt may stay on the phone rather than move to a cloud AI provider. But it does not eliminate confidentiality risk. The phone, app, model repository, cloud backup, external integrations, and the possibility that a client's Social Security number or date of birth could be typed into a tool without full understanding of its data-handling practices all matter.

For higher-risk client information, conduct a documented, matter-specific assessment. In some circumstances, informed client consent may be prudent or required. The answer depends on the sensitivity of the information, the tool's terms and safeguards, your jurisdiction's rules and guidance, the client's instructions, and your firm policy.

Model Rules 5.1 and 5.3: Supervision

If your firm permits staff, contract professionals, or lawyers to use local LLM apps, adopt clear controls. Model Rules 5.1 and 5.3 require appropriate supervisory efforts concerning lawyers and nonlawyer assistance.

A sensible policy can specify:

  • Approved apps and approved model sources

  • Prohibited uses and types of client data—expressly including Social Security numbers, dates of birth, and other identifying information

  • Required device-security controls

  • Procedures for verifying AI-generated legal citations

  • Review and approval requirements before any client-facing or court-filed use

  • Incident-reporting steps if a phone is lost or data may have been exposed

Model Rules 3.1 and 3.3: Candor and Accuracy

No lawyer should file AI-generated authorities, quotations, or factual assertions without verification. Courts have already made clear that invented citations can lead to sanctions and reputational damage. Local operation does not make a hallucinated case real. 🧾

Treat every AI-generated authority as unverified until you locate it in a reliable legal-research system or official source. The lawyer—not the model—signs the pleading, advises the client, and bears responsibility for the work.
See generally 3.1 and 3.3.

The Bottom Line

llms have their place in legal work if done right!

A local LLM can be a useful addition to a lawyer's technology toolkit. It can support offline brainstorming, editing, plain-language explanation, and internal workflow development while reducing routine reliance on cloud AI processing.

But privacy is not a marketing label. It is a system of facts: the app, the model, permissions, integrations, phone security, backups, firm policy, and the way you use the tool—including a clear-eyed understanding of whether your inputs are ever used to train or fine-tune anything. Start with sanitized information. Verify vendor claims against the actual privacy policy and app-store data-safety disclosures, not just the marketing copy. Secure the device. Validate every legal proposition. Then let the technology help you work more efficiently—without compromising the professional duties that define the practice of law. ⚖️📱

MTC: When Your CEO Asks ChatGPT How to Take Over: Lessons for Lawyers on Public AI, Ethics, and Confidentiality 🧠⚖️

Lawyers need to evaluate public AI chatbot against ABA confidentiality and privilege rules

In March 2026, the Delaware Court of Chancery in Fortis Advisors, LLC v. Krafton, Inc. handed lawyers one of the clearest cautionary tales yet about public AI chatbots, corporate governance, and the limits of “move fast and break things.” A South Korean gaming conglomerate, Krafton Inc., used an artificial intelligence chatbot to help devise an internal “Project X” takeover plan against its own studio, Unknown Worlds Entertainment, and then tried to defend the fallout in court. The result: a detailed opinion reinstating the studio’s CEO, extending a $250 million earnout period, and spotlighting how AI misuse can become Exhibit A when things go wrong.

If you’re a solo, a small-firm lawyer, or an AI‑curious practitioner dabbling with ChatGPT or similar tools, this case is your wake‑up call. The message is not “don’t use AI.” The message is: treat public chatbots the same way you treat email, cloud storage, or texting — through the lens of ABA ethics, client confidentiality, and privilege. 😬

In this editorial, I’ll unpack what happened, how the court framed the misuse of a chatbot, and what you should do in your own practice to stay on the right side of the rules.

The Case in a Nutshell: AI as a Takeover Co‑Pilot

Krafton bought Unknown Worlds — the studio behind Subnautica — for $500 million upfront plus up to $250 million in contingent earnout payments, with a contractually guaranteed structure: the founders and CEO (the “Key Employees”) retained operational control and could only be fired for defined “Cause.”  As Subnautica 2 approached early‑access launch, internal projections showed the game would easily trigger a massive earnout.

The CEO of Krafton grew concerned he looked like a “pushover” under the deal and turned to a public AI chatbot for advice on how to avoid paying the earnout and seize control of the studio. The chatbot’s “response strategy” included:

  • Locking down publishing rights and code access.

  • Crafting messaging to “secure public support” and undermine the “large corporation vs. indie” narrative.

  • Preparing a “takeover” path that blended hardball legal tactics with PR framing. 

Krafton’s internal team implemented much of that plan — cutting off the studio’s access to its Steam publishing console, posting unilateral public statements, and ultimately terminating the founders and CEO on a pretext of “premature release” risk.  When sued, Krafton tried to pivot to new justifications, including the executives’ role changes and their defensive downloads of company data. 

The court was having none of it. Vice Chancellor Will held that:

  • The terminations were not “for Cause” under the negotiated contract.

  • The “Project X” takeover guided by the chatbot was a pretext to avoid the earnout.

  • The studio’s CEO, Ted Gill, must be reinstated with full operational control, and the earnout period equitably extended by the length of his ouster. 

In other words, the AI‑assisted takeover strategy became part of the factual narrative of bad faith and breach — not a clever workaround.

Public Chatbots and ABA Model Rules: Three Pressure Points ⚖️

Attorneys must consider ethical AI chatbot use for confidential client case analysis

Even though this is a corporate earnout case, the opinion gives lawyers a concrete frame for thinking about public AI tools under the ABA Model Rules.

1. Confidentiality — Model Rule 1.6

Rule 1.6 requires lawyers to keep “information relating to the representation of a client” confidential, absent informed consent or a specific exception. Public chatbots are not your firm’s Document Management System (DMS) — they’re third‑party services that typically ingest prompts for training, quality, and logging. When Krafton’s CEO ran “Project X” through a chatbot, he was effectively outsourcing high‑stakes strategy to a non‑privileged third‑party system that could store and learn from those prompts. 

For lawyers, the parallels are obvious:

  • Dropping fact patterns, names, or deal structures into a public chatbot can mean you’ve disclosed client information to a non‑controlled vendor.

  • Even “sanitized” prompts can be re‑identified when combined with other data.

Under 1.6, that’s a potential confidentiality breach unless you’ve vetted the tool, negotiated appropriate terms (including data handling and retention), and obtained informed client consent for that mode of assistance. Emojis and “it’s just drafting help” don’t change that. 😉

2. Privilege — Model Rules 1.1 and 1.4 (Competence and Communication)

Privilege isn’t framed in the Model Rules, but Rule 1.1 (competence) and 1.4 (communication) require you to understand how your technology choices affect the protection of client communications. When you route strategy discussions through a public chatbot:

  • You may jeopardize attorney–client privilege by involving a third‑party with no need‑to‑know and no formal role in the representation.

  • You may create discoverable records that live outside your control, just as Krafton’s CEO created chat logs he then tried to delete. 

The court noted that relevant chatbot logs were deleted, which did not play well in evaluating Krafton’s narrative.  Privilege analysis is already complex with cloud tools; adding public AI as a “secret co‑counsel” without protections only compounds that risk. 

Competent use of technology now includes understanding whether your AI stack is preserving or eroding privilege and communicating those risks to clients when you propose AI‑assisted workflows.

3. Candor and Misrepresentation — Model Rule 4.1 and 8.4(c) 🚨

Although this case turns on contractual “Cause” and good faith, the court’s language about “pretextual” justifications and manufactured defenses should resonate with litigators. Model Rule 4.1 prohibits knowingly making false statements of material fact to third parties; Rule 8.4(c) bars conduct involving dishonesty, fraud, deceit, or misrepresentation. 

When you:

  • Use a chatbot to generate strategic messaging designed to mislead stakeholders.

  • Craft public statements or demand letters that you know are pretextual, but you’ve optimized with AI for tone and impact.

… you’re still responsible for the truthfulness of that content. The court saw through Krafton’s attempt to re‑frame events after the fact, and its internal AI‑assisted playbooks did not help. 

For lawyers, the lesson is simple: AI‑generated output is yours once you sign or speak it. If it’s misleading, you own the ethics problem — not “the algorithm.”

Practical Takeaways for Solo and Small‑Firm Lawyers 🧩

So what do you do if you’re a tech‑savvy lawyer who likes AI, but doesn’t want your prompts quoted in an opinion like this?

Here are grounded, practice‑ready steps.

1. Establish an AI Use Policy

Even if you’re a solo, write down what you will and won’t do with public chatbots.

lawyers need to build practical, ethical AI policies for practice.

  • No client names, exact fact patterns, or identifiable deal terms in public tools.

  • Use AI for structure and language, not for strategy or confidential analysis.

  • Prefer client‑specific, non‑logging enterprise tools when handling sensitive material.

Treat this like you treat your cloud storage or remote‑work policy — it’s part of your competence under Model Rule 1.1 and your supervisory obligations under 5.1/5.3 if you have staff.

2. Separate “Public Prompting” from “Privileged Thinking” 🧠

Use public chatbots for:

  • Headline and meta description drafting.

  • Blog outlines, post ideas, or simple explainer language for non‑client scenarios.

  • Rough templates for standard documents that you will heavily edit.

Avoid using them for:

  • Fact‑specific case assessments.

  • Litigation strategy, negotiation plans, or internal “playbooks” like Krafton’s “Project X.” 

  • Anything that feels like the kind of conversation you’d normally have only with a colleague behind closed doors.

This separation keeps your privileged work product inside tools and workflows you control.

3. Vet Vendors Like You Vet e‑Discovery Platforms

If you move beyond public chatbots to paid AI tools, evaluate them as you would any major legaltech vendor:

  • Where is data stored?

  • Is training on your material disabled by default?

  • Can you get a Business Associate Agreement or Data Processing Agreement / Data Protection Impact Assessment that aligns with your jurisdiction’s expectations?

The ABA’s Formal Opinion 477R on secure communications and cloud ethics opinions from state bars all provide analogies: reasonable steps, not perfection, are required — but “type client memo into random website” is not reasonable. 😄

4. Document Client Consent When AI Is Material to the Representation

If you expect to use AI in a way that materially affects how you deliver legal services, communicate that to clients under Rule 1.4:

  • Explain benefits (efficiency, faster drafting).

  • Explain risks (data handling, reliability, hallucinations).

  • Offer an AI‑free option.

Written engagement terms that address AI use can save hard conversations later if something goes sideways.

5. Revisit Your “Bad Facts” Mindset

Reading this Delaware opinion, you see how internal strategy — including AI‑assisted plotting — can become a litigation exhibit.  For lawyers, that’s an invitation to ask: 

“If this prompt or chatbot conversation showed up in an opinion, would I be comfortable defending it under the Model Rules?”

If the answer is no, don’t send it. That simple heuristic scales across tools and platforms.

What This Case Signals for the Next Wave of Legal Tech 🌊

There can be significant legal consequences for AI chatbot misuse in legal disputes.

The opinion in Fortis Advisors v. Krafton is not an ethics decision aimed at lawyers, but it shows courts will:

  • Scrutinize AI‑assisted strategies as part of broader narratives about good faith, bad faith, and pretext.

  • Expect parties — and by extension, counsel — to maintain and produce AI‑related records where relevant.

  • Be unimpressed by attempts to retroactively justify decisions made for economic reasons with thin “quality” or “readiness” arguments. 

As public models get more powerful and more embedded in practice, ABA Model Rules on competence, confidentiality, supervision, and candor apply just as they did when lawyers moved to email, smartphones, and the cloud. AI is just the next tool — but it’s a tool that makes it very easy to generate sophisticated bad ideas quickly.

Your job is to keep your ethical compass steady, even when the chatbot is very persuasive. 🧭

MTC

🎙️ Shout Out: 250 Episodes, An Apple Roundup Shout-Out, and Why Android-to-iPhone File Sharing Just Became Every Lawyer's Business

There are weeks in the legal technology calendar that just feel good—and this past week was one of them. ⚖️ Two things landed almost simultaneously, and I want to take a moment to celebrate both properly right here on The Tech-Savvy Lawyer.Page.

Jeff Richardson and Brett Burney celebrate 250 Apple podcast episodes.

First, a genuine, enthusiastic congratulations to Jeff Richardson of iPhone J.D. and Brett Burney of Apps in Law on recording their 250th episode of the In the News podcast. 🎉 If you're not familiar with In the News, here's what you need to know: it is a weekly deep-dive into the Apple universe—iPhones, iPads, Macs, Apple Watch, Vision Pro, iOS updates, app releases, and everything in between. Jeff and Brett, both previous podcast guests, approach it as dedicated Apple enthusiasts who also happen to practice law, which gives the show a grounded, practical quality that pure consumer tech coverage rarely achieves. Two hundred and fifty episodes of consistent, high-quality Apple coverage is a remarkable achievement, full stop. 🏔️

And if you watched the video version of Episode 250, you caught Jeff broadcasting from the breathtaking backdrop of The Broadmoor resort in Colorado—where Jeff's firm, Adams & Reese, was celebrating its own 75th anniversary. That kind of serendipity makes a milestone feel even more earned. Subscribe at inthenewspodcast.com—you will not regret it. 🎧

Attorney can use Google Quick Share to bridge iPhone and Android.

Second, in that same week's In the News roundup post, Jeff included a mention of The Tech-Savvy Lawyer.Page—specifically, our article "How to Use Google's 'AirDrop for Android' (Quick Share) in Your Law Practice." 📲 Jeff's write-up of the week covered everything from Apple's sweeping price increases to iOS 27's five incoming apps to why watching Avatar: Fire and Ash on a Vision Pro on a plane might be the best movie experience currently available to humans. It was, in other words, a quintessentially iPhone J.D. roundup—Apple news, clearly explained, with a sharp eye for what actually matters to readers who live in the Apple ecosystem.

And right there, in that roundup, was a single bullet: "Michael D.J. Eisenberg of The Tech Savvy Lawyer explains how Android devices can now more easily use AirDrop to share files with iPhones." 🙌

That sentence is, on the surface, a consumer Apple tech note—and that's exactly what it should be. Jeff covers it because it is genuinely interesting Apple/mobile news for anyone who carries an iPhone. But for attorneys, the implications go considerably further.

Why This Matters Beyond the Apple Ecosystem 💼

Google expanded Quick Share—its answer to AirDrop—to work directly with Apple's AirDrop across Samsung Galaxy, Google Pixel, and a growing list of flagship Android devices . The transfer happens peer-to-peer: no server routing, no cloud intermediary, no data passing through Google's or Apple's infrastructure. ⚡ For an iPhone-carrying attorney receiving a document from an Android-using co-counsel, paralegal, or client, this is a genuine workflow upgrade.

ABA Model Rules 1.1, 1.6, 5.3 guard lawyer confidentiality.

But it also raises questions that an Apple commentator doesn't need to answer—and that we do. Under ABA Model Rule 1.6 (Confidentiality of Information), the peer-to-peer architecture of Quick Share is actually a feature, not just a convenience: files don't transit external servers, which helps satisfy the "reasonable efforts" standard to prevent unauthorized disclosure of client data. Under ABA Model Rule 1.1 (Competence) and its Comment 8, understanding how a file transfer mechanism works—and whether your firm's use of it is appropriate—is part of your professional obligation, not optional continuing education. And under ABA Model Rule 5.3 (Responsibilities Regarding Nonlawyer Assistance), if your staff are using personal Android devices to share files with iPhone-toting colleagues, you need a written BYOD policy that addresses it. ✅

Our article walks through all of this—device compatibility, step-by-step setup, a five-step firm rollout checklist, and a plain-language BYOD policy framework—so that you can implement this capability confidently and in full compliance with your professional responsibilities . And for a visual walkthrough, our TSL.P Labs Video Presentation: Google Quick Share for Lawyers covers every step in a tactical, ethics-first format . 🎥

The Bigger Picture 🌐

What I appreciate most about getting a mention from iPhone J.D. is the nature of what Jeff's blog is. It is an Apple resource—meticulous, reliable, enthusiast-grade Apple coverage, written by someone who genuinely loves this technology and reads everything. When a piece from The Tech-Savvy Lawyer.Page earns a bullet in Jeff's roundup, it is because the article has something genuinely useful to say about the Apple ecosystem. That is a standard I aim for every time I sit down to write. 📡

So, congratulations to Jeff and Brett on 250 episodes of excellent Apple coverage! And if our Quick Share guide gave even one attorney a smoother courthouse-steps file transfer—or a stronger confidentiality argument—then it earned its mention. 🥂

Why Macstock 2026 Should Be on Every Tech-Savvy Lawyer’s Calendar (and How to Save $50 with My Code) ⚖️💻

macstock 2026 will be held july 10, 11 & 12, 2026!

If you’re a solo, small-firm, or AI‑curious lawyer who lives in the Apple ecosystem, Macstock 2026 is one of the few conferences that genuinely respects both your time and your tech stack. It’s a three‑day, community‑driven, Apple‑centric event where you can sharpen your skills with your Mac, iPhone, and iPad, and walk away with workflows you can actually deploy on Monday morning.

This year, I’m honored to be speaking at Macstock X on “Podcasting with Apple: From Idea to Launch Using the Gear You Already Own.” We’ll take a practical walk through planning, recording, and publishing a professional‑quality podcast using the same devices you already carry into court, client meetings, and your home office. Whether you want to build a niche show for veterans’ benefits, family law, or small‑business compliance—or simply become a more confident guest on other podcasts—this session is designed to be accessible, concrete, and repeatable. 🎙️

What Makes Macstock Different (and Why Lawyers Should Care)

Macstock isn’t a generic tech expo with a handful of Apple sessions bolted on; it’s an independent, Apple‑focused conference built for people who actually use Apple gear every day. The attendees range from first‑time Mac users to seasoned creators, but everyone shares a common goal: get more from Apple hardware and software without drowning in jargon.

For attorneys, that matters. You’re not trying to become an IT professional. You want to:

  • Capture and organize evidence more efficiently on your iPhone. 📱

  • Draft, annotate, and sign documents on your iPad when you’re away from the office.

  • Automate repetitive tasks on your Mac so you can spend more time on advocacy and less on admin.

learn how to use your mac to podcast!

Macstock’s sessions, hallway conversations, and Creator Camp tracks are all geared toward real‑world workflows—exactly the kinds of workflows I talk about on The Tech-Savvy Lawyer podcast and blog, including episodes like Ethical AI, Paperless Practice, and Smart Hardware Choices with ABA LTRC Chair Alan Klevan ⚖️🤖 and similar deep‑dives into ethical tech use.

A Time-Sensitive Deal: Save $50 and Support The Tech-Savvy Lawyer

Let’s talk about timing and value. You can use my code TECHSAVVYLAWYER at checkout to save $50 on your Macstock Weekend Pass or Creator Camp Bundle. If you’ve been thinking, “I should go to Macstock one of these years,” this is that year.

For every person who uses the code, Macstock provides me a $25 referral fee. That means:

  • You pay $50 less for a weekend of Apple‑centric, workflow‑rich content.

  • You directly support The Tech-Savvy Lawyer blog and podcast, including future episodes and tutorials.

The code TECHSAVVYLAWYER is not case‑sensitive and is valid through July 8, 2026.

How Macstock Helps You Meet Your Ethical Tech Duties

your The Tech-Savvy Lawyer.Page Blogger and podcaster will be presenting at Macstock x!

Macstock is not marketed as a legal tech conference, but it naturally supports your professional obligations under the ABA Model Rules.

  • Competence — Model Rule 1.1 (Comment 8): You have a duty to keep abreast of the benefits and risks associated with relevant technology. Learning how to securely use Apple devices for uses like document management, client communication, and evidence handling goes directly to your duty of technological competence.

  • Confidentiality — Model Rule 1.6: Many sessions at Macstock touch on system settings, backups, and secure workflows. Understanding how to configure your Apple devices to minimize unauthorized access, especially when using cloud sync and third‑party apps, strengthens your compliance with confidentiality obligations.

  • Communication — Model Rule 1.4: Clear, timely communication often depends on your ability to reach clients where they are—email, secure messaging, or even video updates. The more confidently you use your Apple tools, the more reliably you can keep clients informed.

If there is not a session directly addressing your questions, there are many enthusiastic, friendly attendees and speakers happy to try to help you and your Apple computer needs! 🤗

On The Tech-Savvy Lawyer blog and podcast, we frequently link these ethics points to real tools and scenarios—just as we did in episodes exploring AI, deepfakes, and metadata in digital evidence—and Macstock is a natural extension of that mindset.

Why Lawyers Should Care About Podcasting with Apple

Podcasting can be more than a marketing buzzword. Done right, it can be:

  • A client education channel that answers common questions before they become billable emergencies.

  • A way to build authority in a niche practice area—veterans’ benefits, immigration, special education, you name it.

  • A platform to interview judges, experts, and colleagues in a way that strengthens professional relationships.

My Macstock session, “Podcasting with Apple: From Idea to Launch Using the Gear You Already Own,” is focused on practical, lawyer‑friendly steps. We’ll talk about using your iPhone as a primary microphone, recording with your Mac, organizing episodes in iCloud, and editing in approachable tools—no audio engineering degree required. If you enjoy my conversations with guests on The Tech-Savvy Lawyer podcast, this session will show you what it takes to stand behind the mic yourself.

Community, Not Just Content

One of the things I appreciate most about Macstock is the community. People go back year after year not only because the sessions are strong, but because the hallway track, shared meals, and evening conversations provide real, candid problem‑solving time.

For lawyers—especially solos and small‑firm practitioners—this kind of peer‑to‑peer exchange is invaluable. You’ll find people who:

  • Have already solved a workflow you’re struggling with.

  • Are willing to share templates, shortcuts, and practical advice.

  • Understand the pressure of balancing client work, marketing, and a life outside the office.

If you’ve listened to episodes like my MacVoices “Road to Macstock” appearance in 2024, you’ve heard how much I value that human side of legal tech and Apple tech events.

Ready to Join Me at Macstock?

If you’re serious about making your existing Apple gear work harder for your practice—without overwhelming your staff or your budget—Macstock 2026 is worth the trip. You’ll return with actionable workflows, renewed confidence, and a clearer sense of how to align your technology use with your ethical obligations.

Just don’t wait:

  • Sign up at https://macstockconferenceandexpo.com/register/

  • Use code TECHSAVVYLAWYER (not case‑sensitive) for $50 off your Macstock Weekend Pass or Creator Camp Bundle.

  • For every use of the code, I receive a $25 referral fee that helps sustain The Tech-Savvy Lawyer content you rely on.

I look forward to seeing you at Macstock X— and hopefully hearing your voice in the podcasting space soon. 🎧⚖️

🎙️ Ep. #134 — AI-Powered Legal Writing: How BriefCatch Helps Lawyers Write Smarter, Not Harder with Ross Guberman.

My next guest is Ross Guberman — founder of BriefCatch, nationally recognized legal writing trainer, and author of several acclaimed books on persuasive legal writing. Ross has trained thousands of lawyers and judges across the country. After years of teaching the craft of legal writing, he channeled that expertise into building BriefCatch — a purpose-built AI writing tool that lives right inside Microsoft Word and Outlook, scanning your legal documents using roughly 17,000 rules to help you write cleaner, sharper, and more persuasive work product. Whether you're a solo practitioner or part of a large firm, Ross brings insights that are immediately practical — no matter your tech comfort level. 🚀

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

  1. 🏆 From your vantage point — having trained thousands of lawyers and judges and now running BriefCatch — what are the top three ways lawyers can leverage AI-driven writing tools like BriefCatch inside Word and Outlook to measurably improve the quality and persuasiveness of their briefs without sacrificing their own voice or judgment?

  2. ⚖️ For a tech-curious but time-strapped practitioner, what are the top three everyday workflows beyond traditional brief writing where lawyers are leaving the most value on the table by not using tools like BriefCatch and other legal tech?

  3. 🔮 Looking ahead five years, what are the top three technology competencies every lawyer must develop — not just "nice to have" skills — to collaborate effectively with AI, stay ethically compliant, and turn technology into a genuine competitive advantage rather than a source of risk?

In our conversation, we cover the following:

  • [00:30] 💻 Ross's current tech setup — MacBook Pro M4 Max, macOS, and iPhone 16

  • [01:30] 🔄 Why keeping your OS updated matters — security and performance

  • [03:00] 🖥️ External monitors, portable screens, and traveling with tech

  • [07:00] 📱 Using your iPad as an external monitor via Apple Sidecar

  • [08:30] 🎪 Bonus Question #1 - Ross’s experience in the ABA TECHSHOW Startup Alley

  • [11:00] ✍️ Question #1 — Top 3 ways to use AI writing tools to improve briefs without losing your voice

  • [12:00] 🧑‍⚖️ Using AI to role-play as a skeptical judge or opposing counsel to pressure-test your brief

  • [13:00] 📊 Transforming fact sections into timelines and case law into comparison charts

  • [14:00] 📝 Using AI as a self-check for hyperbole, redundancy, and tone

  • [15:30] 📲 How judges now read briefs on iPads — and what that means for your writing style

  • [17:00] 📂 Using Text Expander to store and deploy your best prompts

  • [18:30] 🎙️ Google Notebook LLM as a learning and podcast creation tool

  • [20:00] 🧩 Bonus Question #2 — What is BriefCatch and why use purpose-built legal AI over general tools?

  • [21:00] 🚀 The origin story of BriefCatch — from side hustle in 2018 to funded legal tech startup

  • [22:30] ⚙️ Workflow, ethics rules, and attorney-specific conventions — why legal-specific AI wins

  • [24:30] 📋 Question #2 — Top 3 underused everyday workflows for lawyers using AI

  • [25:00] 📧 Using AI with your email to surface unanswered messages and unresolved threads

  • [25:45] 📁 Mining your past work product for patterns, style, and reusable language

  • [26:30] 📅 Having AI review your calendar and correspondence for efficiency insights

  • [27:00] 🔒 Data privacy, security settings, and the risks of default AI configurations

  • [28:30] 🏛️ New York State's data protection approach and what more states should do

  • [29:30] 🤖 Question #3 — Top 3 technology competencies every lawyer must master in the next five years

  • [30:00] 🧠 Understanding how LLMs actually "think" — reading the AI's reasoning chain

  • [30:45] 🖊️ Making AI output sound like you — the human voice in an AI-generated world

  • [31:30] 🔧 Integrating AI into your daily workflow while preserving human judgment

  • [32:00] 👏 Closing thoughts and where to find Ross and BriefCatch

RESOURCES

🔗 Connect with Ross Guberman

  • 📧 Email: ross@briefcatch.com

  • 🌐 Website: https://www.briefcatch.com

  • 💼 LinkedIn: Search "Ross Guberman" on LinkedIn at https://www.linkedin.com

📌 Mentioned in the Episode

🖥️ Hardware Mentioned in the Conversation

☁️ Software & Cloud Services Mentioned in the Conversation

Shout Out: Previous Podcast Guest Ruby Powers Invites Your The Tech-Savvy Lawyer.Page Blogger and Podcaster Back on Power Up Your Practice!

I recently had the honor of joining Ruby Powers on her Power Up Your Practice Podcast, and I could not be more excited about what we covered for fellow lawyers. We talked about legal podcasting as a practical, ethical, and highly effective way for attorneys to build visibility, deepen relationships, and modernize their marketing without needing to be “hardcore tech people.”

On Ruby’s show, I shared why I believe that podcasting is becoming the new networking standard for lawyers. When you regularly publish episodes—whether about your day-to-day practice, a niche topic, or even a related interest—you push your name and your ideas into the online world in a consistent way. Search engines and AI systems notice this. Over time, your name and your content start to surface more often when people search for your practice area, your type of work, or your expertise. That is real SEO, and it comes from steady, quality content rather than tricks or gimmicks.

Another reason I encourage lawyers to podcast is simple: your voice makes you more human. Listeners hear how you think and how you explain things. They hear your tone and your values. That goes far beyond a static bio or a profile page. Whether your audience is potential clients, referral sources, peers, or the broader public, a podcast lets them get to know you in a safe and scalable way. This is networking that keeps working for you even when you are in court, in a hearing, or taking a much-needed break. 🌟

I also understand that many lawyers hesitate because they are concerned about ethics. That concern is healthy. As attorneys, we cannot ignore ABA Model Rules and similar state rules when we put content into the world. On the podcast, Ruby and I discussed that while a show can be an excellent educational and marketing tool, we must avoid giving individualized legal advice and avoid accidentally creating an attorney–client relationship. I strongly recommend clear, prominent disclaimers that explain the podcast is for informational purposes only, does not create an attorney–client relationship, and should not be relied on as legal advice for any specific matter.

This aligns with our obligation of competence under Model Rule 1.1, which now includes understanding relevant technology, and with our duties around communications and advertising under Model Rules 7.1 and following. A well-run legal podcast respects those boundaries. It presents general information and insights, and it invites listeners to seek formal counsel if they need advice for their specific situation. When you treat your podcast as education plus relationship-building, not as a substitute for representation, you are already thinking in the right direction.

In our conversation, Ruby and I also addressed a common fear: “I’m not tech-savvy enough to start a podcast.” As someone known as the Tech-Savvy Lawyer, I want to be clear: you do not need to be a full-time tech enthusiast to do this. You likely already have access to most of what you need. A solid microphone, a decent camera, and a platform like Zoom, Riverside, or StreamYard can take you surprisingly far. Many of these tools are user-friendly and continue to improve. You can start with the basics and then layer on more sophistication as you grow more comfortable. 🎧

Ruby shared her own experience of initially overthinking her podcast. She wanted it to be perfect, and that almost stopped her from launching. I hear that from lawyers all the time. My advice is simple: do not wait for perfect. Your early episodes will probably make you cringe later, which means you are improving. That is a good sign. Focus on clear audio, honest content, and consistent scheduling. Over time, you can refine your editing, your format, and even your branding. You can bring in a contractor or a service to help with editing once you know you want to keep going.

We also discussed the flexibility podcasting offers. You can publish weekly, every other week, or monthly. You can create solo episodes where you explain key topics. You can host interviews with colleagues, experts, or community leaders. You can even experiment with live formats, where audience members submit questions in advance, and you answer them at a general, educational level. The format should fit your bandwidth, your goals, and your audience.

One concept I emphasized is the idea of an “ideal listener” or avatar. Before you hit record, think about exactly who you are speaking to. Is it a potential client in a specific practice area? Other lawyers in your niche? Law students or young practitioners? Having that profile in mind will guide your topic choices, your language, and your examples. It also helps you stay focused on value rather than drifting into random conversations that do not support your goals.

From a business perspective, legal podcasting can support your referral network in powerful ways. Colleagues can share your episodes, which subtly introduce you as a trusted resource. Prospective clients may listen to several episodes before they ever contact you, which means they arrive already familiar with your style and approach. That can shorten the trust-building curve and make consultations more productive.

What I appreciate about Ruby’s Power Up Your Practice platform is that it treats podcasting not as a vanity project, but as part of a larger ecosystem of law practice management, technology, and professional development. My appearance on her show gave me a chance to tie together what I see in my own practice, my blog, my podcast, and my book: lawyers do not need to fear technology. We need to engage with it thoughtfully, guided by the same ethics and judgment we apply in every other part of our work.

If you are a lawyer with limited to moderate tech skills and you have been on the fence about starting a podcast, I invite you to listen to my conversation with Ruby and let it serve as a practical, encouraging blueprint. You will hear that you are not alone in your concerns, that there are clear ways to stay compliant with ABA Model Rules, and that the path to becoming a “tech-savvy lawyer” does not require perfection—only willingness, consistency, and a focus on delivering value. 🚀

Enjoy!