March 2026 – Business Law Section

Barrister Banter: Ambyr O’Donnell

The purpose of the series is to bridge the gap between junior and senior business lawyers in Oregon, fostering understanding and camaraderie. For this quarter’s installment, we interviewed Ambyr O’Donnell, M&A and IPO advisor and the winner of the 2025 James B. Castles Leadership Award. Read on to learn how what’s important to Ambyr—tech, ethics, and ringing the bell on Wall Street—has informed her successful career.

Tell me about your path to being a lawyer. What inspired you to pursue this career?
I started my undergraduate degree as a computer science major and quickly realized I didn’t love living in a computer lab. An advisor pointed out that law fit my interests in policy, history, and international relations. I took the LSAT, applied to law schools, and never looked back. My interest in tech never went away.
What is your practice area?

I work with technology companies going through transformational phases: IPOs, M&A, international expansion, and other major growth moments. I’m a general business lawyer focused on corporate law, M&A, IP, and employment law. I work closely with board members, CEOs, founders, and executive teams to structure and drive strategic outcomes for their business.
How long have you been in your current role?
I’ve spent about fifteen years as a general counsel or chief legal officer after starting in-house right out of law school. Over time, my work has evolved into broader business advisory roles, which I absolutely love.
How have you seen the practice change since you started practicing?
Lawyers used to do legal research in physical libraries with books and send faxes or letters for written notice. Now so much of what we do is digital and far more efficient, but also less personal. In the last couple years, AI has also changed how I work. I use AI to get smarter faster, synthesize lots of data, create presentations, and simplify complex communications. I learn new things I can do with AI agents every week. I never outsource judgment and I always carefully vet any AI output before it goes to anyone.
What do you wish you had known before you started working as a new lawyer?
Your career path might not look like everyone else’s. You may not look like the other lawyers in the room. What is important is what you have to contribute. Listen more than you speak, and speak when something needs to be said.
What are your career highlights?
I’ve always wanted to stand on the platform to ring the bell on Wall Street. In 2021, I had the privilege of doing that at the New York Stock Exchange with my team at our company’s IPO. What made it even better was being able to bring my son, who was in high school at the time, onto the NYSE trading floor.

Every deal we close for the purchase or sale of a company feels like an important career milestone. None of my career highlights were achieved alone. Business law is a team sport.
What is your favorite part of the job?
Solving hard problems with smart people and helping companies turn bold ideas into reality. At the end of the day, it’s all about people working toward something meaningful.
What parts of the job do you wish you could outsource to AI?
Scheduling and expense reports! Oh, and resolving meritless claims. Those can be so distracting and wasteful.
What advice would you give a new business lawyer?

There are many ways to create a successful career using your law degree. Seek out projects and people doing interesting things early on and put in the time. Many very successful business people started out in law.

When I was in law school, I read a quote by former Oregon Supreme Court Chief Justice William M. O’Connell, who said: “Without ethics ours is a crass calling.” This is especially true for business law. Choose to work for good people and businesses doing good things. It matters.
What advice would you give a senior lawyer who is charged with mentoring a new lawyer?
Move past the day-to-day work. Work with the new lawyer to create a vision for what they might want to do (or at least what they could be qualified to do) in a few years. Identify specific skills and experiences they should pursue to advance their career toward their vision.

Remind new lawyers that it is okay to take risks and support the businesses they advise in taking smart, calculated risks, so long as everything is legal and ethical.

I had the benefit of working with an incredible mentor early on and it had a very positive impact on my career. ♦

Self-Compassion for Lawyers: Interrupting Stress and Choosing our Path Forward

Bridget Donegan, Oregon Attorney Assistance Program

There is a specific sense of relief that comes when a friend, after hearing us confide an uncomfortable truth about our inner lives, responds with ease: “Well, of course!” “Of course you’re having a hard time sleeping with all that pressure on you!” “Of course you’ve lost your confidence after what they said to you!” “Of course you’re overwhelmed!” When our distress is met with total, untroubled acceptance, a layer of our own trouble melts away. Our friend’s connection and compassion interrupt our inner turmoil and get us back on track, grounded in reality. Yes, the uncomfortable truth is still true and still uncomfortable. But a compassionate, connected perspective gives us a toehold from which we can choose our next step. We can move forward responsibly.

Compassion is a wonderful way we support each other. Directed inward, it is a powerful way we can support ourselves. In a flood of studies over the last twenty years, researchers are confirming what ancient wisdom traditions have long taught: self-compassion does not weaken our resolve or dim our ambitions. Instead, practicing self-compassion helps build resilience, reduce our distress, and increase our motivation. Amid the many demands of our professional lives, self-compassion is a way to relieve some of the internal pressures we may not even realize we add on top of all the stressors we cannot control.

Of course you are stressed!

Some stress is unavoidable, and the varied stressors of law practice are often outside of our control and can sometimes continue day after day without much relief. Depending on the lawyer, work stressors can include short deadlines, unpredictable client needs, high-stakes projects, billable hours pressure, uncertain outcomes, financial or job insecurity, competition for work or clients, office bullying or conflict, and more. We all experience potential stressors differently—you may enjoy being energized by a tight deadline, while your colleagues will find it distressing, and on another day your roles may switch. Given our high expectations for ourselves, the prevalence of potential stressors, and the fact we can always identify someone in a similar role who seems to be thriving, when we experience distress, we tend to believe that we are the problem. In other words, we think we ought to feel fine. We may think, “This is what lawyering is, so I need to be able to handle it without letting it get to me.”

I want to highlight two of the problems with that very common line of thinking. First, once we are feeling the irritability, exhaustion, overwhelm, tension, lack of motivation, etc., the stress response is already happening. We can wish that it was not, but it is irrational to believe we “should” feel differently than we do. We can aspire not to think about work when it is time to sleep, for example, but that is altogether different from thinking it is wrong that the thoughts keep coming.

Second, and relatedly, our intolerance of our stress response is self-defeating. Telling ourselves that we should not feel the way we do only puts more pressure on us: it is stressful to keep thinking that the way we are is wrong.

The upside here, though, is that our stress about our stress is something we can control. The amount of external pressure lawyers are under is real, even if someone else feels it differently than you. Your experience of that pressure is legitimate; it is the way your body knows how to muster ongoing attention and energy for things in your life that matter. Remembering that is a way to interrupt the cycle of feeling unhappy about the way things make us feel. We can offer ourselves a moment of kind acceptance that our stress response (that is, our frustration, tension, worrying, etc.) is an indication not of our weakness, but of our liveliness amid the dynamic pressures of our lives.

The elements of self-compassion

Self-compassion can feel threatening, especially for high performing individuals, because it calls on us, in the words of researcher Dr. Kristin Neff, to “stop judging and evaluating ourselves altogether.” That does not mean lowering our standards. It means accepting ourselves as we are. And studies consistently show that self-compassion improves our resilience through a variety of life challenges.

In her research, Dr. Neff has identified three elements of self-compassion: mindfulness, a balanced awareness of our difficulties, rather than over-identifying with problems; self-kindness, rather than criticism or judgment; and common humanity, understanding our predicament as part of being human, rather than feeling isolated or alienated by our pain. Any time we notice some distress, practicing a bit of compassion toward ourselves can be a helpful relief and reality check.

Mindful attention to your predicament

Compassion is, by definition, responsive. It is a discerning, motivated way of interacting with another upon noticing their suffering. Self-compassion similarly is responsive, but to our own suffering—we must be willing to turn toward our suffering, and not be absorbed into it, to practice self-compassion. Mindfully acknowledging our own suffering means holding a kind of balanced awareness without avoiding or exaggerating our present-moment discomfort. With practice, compassion allows us to see that we can choose the meaning we make of our experience, rather than being carried along or defined by the emotional force of the situation.

As we trend away from balanced awareness, we trend more toward being swept up in our distressful thoughts and feelings. Instead of saying, “I dread going to work,” we say, “I’m an anxious person” or “I can’t hack this.” When a client meeting goes terribly, we start to think, “I’m terrible.” Rather than experiencing our distress from a broader contextual perspective, our discomfort takes on outsized authority, and we begin to believe it indicates a truth about who we are. Sometimes our habit of letting our failings define us prevents us from looking truthfully at our shortcomings; the internal consequences are hard to bear. A more mindful approach notices how terrible we feel, and maybe also notices that we think “I’m terrible,” while also keeping some awareness that those feelings and thoughts will change in time.

Balanced awareness, according to Dr. Neff, “is the pillar on which self-compassion rests,” because it provides the perspective needed to bring caring responsiveness to ourselves when things are not going well. When you notice some stress without grabbing on to it or shoving it down—just seeing it, even for a moment—you are practicing this core component of self-compassion.

Kindness: Being emotionally available when life becomes difficult

Treating ourselves kindly is probably what most immediately comes to mind when we think of self-compassion. If self-criticism and shaming are at one end of a continuum, kindness is on the other. Self-kindness can sound like a simple acknowledgement with a kind tone: “This is hard right now.” “I want this so badly.” “I do not know what to do.” “This hurts.” And also, “What do I need?” “What is there I can do for myself right now?”

The kindness of self-compassion is not self-indulgence; it does not mean “anything goes.” It means moving away from self-condemnation. A lot of us have been conditioned to feel a certain amount of self-protection in being harsh with ourselves, like there is some morality there, or we are proving to ourselves that we know how one ought to behave. Experimenting with kindness toward ourselves reveals, however, that accepting the simple reality of our immediate condition is different from encouraging it in the future. Like the power in naming something, when we kindly acknowledge our distress with a willingness to help, we gain some leverage for dealing with it.

Understanding your common humanity

Finally, when we practice self-compassion, we shift away from our tendency to see our pains and hassles as unique flaws that set us apart from others. That isolating tendency might sound something like, “Everyone else is handling this fine.” “Nobody else is struggling like I am.” “I am too broken to belong here.” “I should be fine.” That feeling of being abnormal leads to feeling disconnected and lonely, exacerbating our suffering. When we practice self-compassion, we remember that life’s challenges, big and small, are inherent to being human, as are our physiological, emotional, and cognitive stress responses.

My experience is that most of us intellectually grasp that nobody is perfect. Everybody fails. But that abstract understanding often feels irrelevant when we are in our own struggles, which are decidedly not “everybody’s”; my struggles are mine and nobody else’s. When I fail, it feels highly specific and textured; it hurts in a particular way, seems to hold a truth personal to me, and is not a tidy, static thing. How could something that specific to me be universal?

The way I understand this component of self-compassion is on two levels. Although there is truth to the deep specificity of our individual experiences, the more we share with and listen to other people, the more we can directly experience our essential similarities; we do relate to each other’s pain. For many of us, that is a lesson we learn over and over again, every time we dare to confide in a trusted, caring person. We are simply more similar, and more deeply so, than we tend to remember.

At the same time, the specific details, histories, and contours of our personal experiences are unique. We cannot know another person’s inner life. But that precisely is the universality of our predicament. That experience of being not perfectly the same is shared by us all. The specificities of my struggle, those edges of my experience that do not quite line up with yours, do not mean that I am alone; those are the essence of our common humanity.

Choosing a path forward

I spent many months as a practicing lawyer living with a hum of vigilance. It felt absolutely essential to maintain a constant background level of tension so I did not miss something important, or so I could catch and fix anything that was missed. To do otherwise felt dangerous.

In my experience in law practice and at the OAAP, such periods of vigilance are not uncommon for lawyers. A small experiment in self-compassion might be worth a try for those of us feeling that anxious hum now. We can notice the hum and the tension. And then notice whatever comes next. Perhaps consider what help you might offer yourself, including talking to someone else or asking for help.

One of the greatest benefits of practicing self-compassion is more ready access to mental freedom and flexibility. Constricted thought and rigidness, on the other hand, are some of the risks of holding tight to our vigilance. When we stop straining against our own experiences, we tend to find that the pressure releases. Dropping that struggle, seeing our natural responses as the ongoing unfolding of life that they are, opens up a significant amount of space for choice. How do you want to approach your day? ♦

Winter 2026 CFIUS Update

Kassim Ferris, Miller Nash LLP

The Committee on Foreign Investment in the United States (CFIUS) has expanded its reach and impact over the past few years through jurisdictional expansion, increased penalties, stable funding, and dedicated enforcement and monitoring teams, while weathering staff turnover and growing pains. A more detailed summary of CFIUS’s powers and procedures was previously published in the September 2023 issue of Oregon Business Lawyer. In light of CFIUS’s expanded reach and heightened scrutiny, it is increasingly essential for attorneys who handle M&A, financing, and real estate transactions to know how to spot potential national security risk issues for a proposed transaction and when to call in a CFIUS specialist.

CFIUS is an inter-agency committee led by the U.S. Department of the Treasury and is empowered to investigate national security implications of foreign investments in U.S. businesses and acquisitions of certain U.S. real estate. CFIUS can impose mitigation measures and make recommendations to the President of the United States to prohibit transactions. Presidential action is not reviewable by the courts, and recent administrations have increasingly exercised these powers against perceived threats, especially those involving Chinese investors and buyers. Consequently, many prospective foreign investors in U.S. businesses have become acutely concerned about CFIUS issues. CFIUS diligence and clearance are gating issues in many transactions and require technical expertise and knowledge of complex CFIUS regulations and committee practices.

A filing with CFIUS is mandatory for certain non-passive foreign investments in “TID U.S. Businesses”: those that deal with critical technologies, critical infrastructure, or sensitive personal data. CFIUS has the power to impose penalties of up to the value of the transaction against each party that fails to file when mandatory. For all other transactions, filing with CFIUS is voluntary, but if CFIUS is not formally notified, it retains jurisdiction to investigate foreign investment transactions at any time, including after a transaction has been completed. Foreign buyers who have failed to notify CFIUS have later found themselves forced to divest U.S. operations and real estate when foreign ownership was deemed to present national security issues.

It is a common misconception that CFIUS is only an issue for large transactions. In fact, there is no size or value threshold, and CFIUS has blocked many small transactions and forced the divestiture of several small businesses (such as Emcore and MineOne) to address national security threats or vulnerabilities, including vulnerabilities that may not have been apparent or present at the time of the transaction.

Another pitfall is to assume that a particular buyer or investor is not a foreign person. U.S. domiciled entities that are directly or indirectly controlled by foreign nationals, companies, and/or governmental bodies are considered foreign persons subject to CFIUS scrutiny. And the regulatory definition of control for the purpose of CFIUS jurisdiction is broader than conventional notions of control in the corporate context. When a seller of a TID business is unable to verify the ultimate buyer’s or investor’s ownership or nationality, including for significant minority investors, then care is warranted to mitigate the unresolved risk of violating mandatory CFIUS filing requirements. In many cases this may mean demanding that the buyer or investor either join in making a filing with CFIUS or give fundamental CFIUS representations and warranties and accept strong indemnity obligations with an extended survival period.

In reviewing a transaction, CFIUS assesses evidence of the vulnerabilities of the target U.S. business in terms of susceptibility to impairment of national security, the threat posed by the foreign acquirer or related foreign persons, and the potential consequences to national security that could reasonably result from exploitation of the vulnerabilities by the threat actor. Accordingly, assessing the activities of the U.S. business and identifying the investor/buyer and its direct and indirect owners are important first steps in CFIUS diligence.

Several recent developments and CFIUS actions summarized below illustrate these principles.

Expanded jurisdiction over real estate transactions

In 2018, Congress expanded CFIUS’s jurisdiction to include the acquisition or lease by, or concession to, a foreign person of covered real estate near certain military sites and within significant ports and airports. Since then, CFIUS has continued to extend its reach through regulatory changes. The most recent changes occurred in late 2024, when CFIUS added sixty military sites to the list. The scope of covered real estate now includes 227 military sites, including sixty-four for which real estate within an extended range of one hundred miles is subject to review. Covered real estate also includes offshore training complexes (including the entire coast of Oregon and Washington) and missile fields in Colorado, Montana, Nebraska, North Dakota, and Wyoming. Nearly 30 percent of the American West is now considered covered real estate, as illustrated in the map below.

A CFIUS filing is not mandatory for a real estate transaction not involving a U.S. business. However, in at least one instance, a real estate acquisition provided the only jurisdictional hook for CFIUS action that resulted in a presidential prohibition and forced divestiture:

In May 2024, President Biden issued an order retroactively prohibiting the purchase of real estate near Cheyenne, Wyoming, by MineOne, a cryptocurrency mining company allegedly majority-owned by Chinese nationals with ties to the Chinese Communist Party or state-owned entities. By the time CFIUS was tipped off, MineOne had built a cryptocurrency mining facility on the property. The property was located within one mile of Warren Air Force Base, the home of the strategic command for all U.S. Air Force intercontinental ballistic missiles. It was also located across the street from a Microsoft data center handling some defense work and near a National Science Foundation supercomputing center. The order included a requirement to remove all improvements and equipment from the property. Some observers noted that the cryptocurrency mining equipment, which was made in China, not only raised concerns about surveillance but allegedly included back doors that could allow a threat actor to remotely and suddenly shut down the equipment and destabilize the power grid—potentially affecting critical national defense capabilities. Notably, if this greenfield project had been built in the adjacent vacant lot just one thousand feet further from Warren AFB, then CFIUS might not have had jurisdiction.

Enhanced penalties for noncompliance

Penalties for noncompliance with CFIUS laws and regulations also increased in late 2024. In particular, penalties for material misstatements and omissions in a submission to CFIUS were increased to a maximum of $5 million per occurrence, up from $250,000. CFIUS also established penalties for violations of a mitigation agreement—of up to the greater of $5 million, the transaction value, or the current value of the interest in the U.S. business or real estate.

The tenor of these changes is reflected in CFIUS’s announcement of several significant penalty actions over the past few years, including a $60 million fine against T-Mobile for violation of a national security agreement relating to a proposed merger with Sprint. T-Mobile allegedly failed to prevent access to sensitive data or to promptly report the unauthorized access to CFIUS.

In less egregious cases, and in cases involving first-time offenses or other mitigating factors, instead of pursuing monetary penalties CFIUS may issue a Determination of Noncompliance Transmittal (DON’T) Letter pursuant to a relatively new practice of the committee. While these letters do not result in penalties or enforcement action, CFIUS’s enforcement policy states that a DON’T Letter can be an aggravating factor in future enforcement action.

Increased funding, staffing, and enforcement capabilities

CFIUS’s mission is supported by stabilized funding, including through government appropriations and collection of filing fees of up to $300,000, imposed on a sliding scale based on the size of the transaction. Program budgets increased from $42.2 million in FY 2024 to $45.2 million in FY 2025, with about $21 million expected to come from filing fees annually. CFIUS has seen several changes in leadership and senior staff over the last three years while also growing its bench. According to program budget summaries, CFIUS now has about 110 full-time equivalent (FTE) employees. At the same time, filings have decreased, from a high of 440 filings in FY 2022 to 325 filings in FY 2024 (the last period for which data is available as of the writing of this article). Despite an increase in resources and decrease in filings, the challenges posed by staff turnover and the change in administration in early 2025 have led to delays in processing and occasional inconsistencies in mitigation and enforcement actions.

CFIUS has also sharpened its enforcement capabilities by establishing a dedicated non‑notified team that scrutinizes transactions for which the parties did not notify the committee. CFIUS now has the power to require parties to provide information needed to determine whether a transaction is covered, whether it raises national security concerns, and whether it triggers a mandatory filing requirement. This has enabled CFIUS to proactively identify and investigate more transactions that might otherwise escape review, particularly those involving foreign investors from countries of concern.

A good example of enforcement action by CFIUS on a non-notified transaction is the January 2, 2026, presidential order requiring HieFo Corporation to divest its indium-phosphide wafer fabrication business. Indium-phosphide semiconductors are critical technology that provides high-speed, high-frequency capabilities for applications such as fiber optic communications, 5G/6G transmitters, and satellite communications. HieFo acquired the business in 2024 from its former parent, EMCORE Corporation, for only $2.9 million. In the order, President Trump claimed that HieFo was controlled by a Chinese citizen and that there was credible evidence the acquisition could threaten U.S. national security. A CFIUS press release cited a risk of diversion of the supply of indium-phosphide chips. HieFo’s founders included its CEO, Dr. Genzao Zhang, who received his PhD from the University of Ottawa, Canada in 1991 and had previously worked at EMCORE in Alhambra, California for twenty years, most recently as its vice president of engineering.

The order against HieFo highlights the U.S. government’s suspicion of Chinese owners and its continued suppression of exports to China of advanced semiconductor technology and other sensitive technologies, such as supercomputers, AI chips, 6G technology, and quantum computing technologies. Enforcement actions like this can be expected to continue, resulting in ongoing fragmentation of global supply chains.

America First investment policy directive

On February 21, 2025, President Trump issued a memo regarding his America First Investment Policy. The memo largely reiterated existing policies and practices of CFIUS and other agencies but did focus on framing economic security as national security. Much of the memo is devoted to emphasizing the importance of protecting U.S. technology, businesses, and resources from the People’s Republic of China (PRC) and restricting outbound U.S. investment in Chinese companies involved in sensitive technology sectors or areas implicated by the PRC’s military-civil fusion strategy—topics already addressed by CFIUS and various other regulatory powers. Among other things, the memo included directives to:

ease restrictions on foreign investors “in proportion to their verifiable distance and independence from the predatory investment and technology-acquisition practices of the PRC and other foreign adversaries . . .,” and
create a “fast-track” process to facilitate foreign investment in the U.S. from allies, subject to requirements to avoid partnering with foreign adversaries.

In response, CFIUS announced in May 2025 that it is developing a Known Investor Program (KIP) seeking to increase efficiencies by collecting information from eligible foreign investors in advance of a CFIUS filing. Think of it as a sort of TSA PreCheck program for foreign investment. Frequent flyers will still need to walk through the metal detector, but at least they may get through security a bit faster. A pilot of the KIP was slated to run in late 2025 with a small number of selected investors. CFIUS recently solicited input from the public via a Request for Information (RFI) in anticipation of a broader rollout. The RFI suggests the KIP is likely to have strict eligibility criteria and will only be available to foreign investors that have made at least three CFIUS filings within the preceding three years.

New outbound investment security program

One other development tangentially related to CFIUS is the U.S. Treasury Department’s issuance of final rules, effective January 2, 2025, implementing the Outbound Investment Security Program (OISP) pursuant to Executive Order 14105. Under the OISP regulations, U.S. persons are prohibited from engaging in certain investments and joint venture transactions involving persons of “countries of concern” (currently, only China, including Hong Kong and Macau) that operate in certain technology sectors. Targeted sectors currently include semiconductor technologies, microelectronics, quantum information technologies, and artificial intelligence. The regulations include specific technical thresholds for prohibited transactions. For certain other outbound investments in the targeted sectors, a notification is required under the OISP regulations. Unlike the CFIUS regime, the OISP regulations do not require the Treasury Department to review or respond to a mandatory notification. And the Treasury Department has so far declined to provide advisory opinions or guidance on the scope of prohibited transactions, so U.S. persons investing in China and in businesses operated by persons with ties to China would be wise to take a conservative approach when interpreting the scope of the OISP’s prohibitions and notification requirements.

Applicable penalties are established in the OISP regulations pursuant to the International Emergency Economic Powers Act (IEEPA) and include civil penalties of $377,700 or up to twice the amount of the transaction. Willful violations are subject to criminal fines of up to $1 million and up to twenty years in prison upon conviction.

A statutory framework for the OISP was recently included in the National Defense Authorization Act for Fiscal Year 2026 (Pub. L. 199-60 at Sec. 8521). It expands the scope of targeted sectors to include high-performance computing and hypersonic systems, while defining certain limited exceptions to the scope of covered transactions. It also authorizes, but does not require, the Secretary of the Treasury to prohibit U.S. persons from knowingly engaging in covered transactions in prohibited technologies. The Secretary of the Treasury has until March 15, 2027, to issue implementing regulations.

Conclusion

Foreign investments can raise U.S. national security issues deserving of careful attention. Failure to submit a CFIUS filing, when mandatory, can subject all transaction parties to harsh penalties. Regardless of whether a filing is mandatory, when a filing is not made, CFIUS retains the power to force the divestiture of a U.S. business or real estate even after a foreign investment or acquisition has concluded. Assessing the activities of the target business to determine whether it qualifies as a TID U.S. Business, and identifying the investor/buyer and its direct and indirect ownership, are important first steps in evaluating whether a CFIUS filing is mandatory or warranted for a proposed transaction.

Several other countries have CFIUS-like regimes. Also, new outbound investment security regulations prohibit covered investments by U.S. persons in certain sensitive high-tech businesses in the semiconductor, microelectronics, quantum computing, and AI sectors operating in China or controlled by persons with ties to China. Certain other covered outbound investment transactions in these same sectors that are not outright prohibited now require a notification to the U.S. Department of the Treasury.

As the U.S. government continues to sharpen its scrutiny of foreign investments, it is increasingly essential for deal parties and their counsel to begin their diligence on potential national security issues early to avoid big problems and hefty penalties. ♦

Beyond the Hype: What We Know So Far About the Value of AI Tools for Lawyers

Jennifer Ballard, Good Journey Consulting

In November 2025, Stephen Embry of Above the Law issued a wake-up call to outside counsel: in-house lawyers are increasingly using AI tools and experiencing efficiency gains, and it is only a matter of time before they require the same from their outside lawyers.

However, identifying one or more AI tools that will be the best fit for law practice is a daunting task. There are hundreds of AI tools for lawyers crowding the market, and there is significant hype surrounding the AI industry in general. Fortunately, there are a growing number of independent efforts to evaluate the real-world utility of AI tools for lawyers. These studies offer some data about AI tools at fixed points in time that can be used to make better informed decisions about AI tool selection.

Independent evaluations of AI tools for lawyers

Below are summaries of seven such independent studies, which individually and collectively reveal helpful insights into where it may (or may not) currently be worthwhile to integrate AI tools with your practice.

Contract drafting study

A September 2025 contract drafting study from Legalbenchmarks.ai, a collaboration between legal professionals, AI experts, and researchers, evaluated 13 AI tools (seven legal industry AI tools and six general-purpose AI tools) against a human baseline that consisted of in-house commercial lawyers with an average of 10 years of working experience. The legal industry AI tools included in the study were August, Brackets, GC AI, InstaSpace, SimpleDocs, Wordsmith, and an anonymous tool, while the general-purpose tools were ChatGPT, Claude, Copilot, Gemini, Le Chat, and Qwen. The study found that some AI tools outperformed the human baseline in producing reliable first drafts of contracts. The study did not find a meaningful difference in the output reliability or output usefulness between the general-purpose and legal industry AI tools. The top performing tools for output were Gemini, ChatGPT, GC AI, Brackets, August, and SimpleDocs. The study concluded that while the legal industry AI tools were not outperforming general-purpose AI tools on output, they were beginning to differentiate themselves with workflow and support functionalities for lawyers, such as integrating with Microsoft Word, and offering clause libraries and templates. The most meaningful differentiator the study found among the legal industry AI tools was whether the tool integrated with existing workflow and technology. For workflow integration or support, the top performers were Brackets, GC AI, and SimpleDocs. You can read this study here.

Information extraction study

The second study from Legalbenchmarks.ai, released in April 2025, focused on information extraction tasks for in-house lawyers. This study evaluated six AI tools, including two legal industry AI tools: GC AI and Vecflow’s Oliver, as well as two general-purpose AI assistant tools: Google’s Notebook LM and Microsoft Copilot, and two general-purpose LLM chatbots: DeepSeek and ChatGPT. All of the AI tools were scored on both accuracy and usefulness. The study found that the two legal-industry AI tools, GC AI and Oliver, received the highest combined scores, concluding that while general-purpose AI tools could match legal industry AI tools in accuracy, the legal industry AI tools delivered more value in usability and workflow integration. You can read this study here.

Vals Legal AI Report

In February 2025, Vals AI, a platform that seeks to advance generative AI with independent and scalable evaluation infrastructure, released the Vals Legal AI Report (VLAIR), which evaluated four legal industry AI tools (CoCounsel, Harvey Assistant, Oliver, and Vincent AI) and compared the results to a lawyer control group. The tools were evaluated across up to seven tasks commonly performed by lawyers (each company could opt into as many of the task evaluations as desired). One or more AI tools beat the lawyer control group on four tasks (document extraction, document question-answering, document summarization, and transcript analysis), while the lawyer control group surpassed the AI tools on two tasks (redlining and EDGAR research) and matched the highest performing tool on one task (chronology generation). Harvey Assistant, which participated in six of the seven tasks, had the strongest performance, receiving the top score on five tasks and the second-place score on one task, and beating or matching the lawyer control group in five tasks. This study can be accessed here.

VLAIR—Legal Research

In October 2025, Vals AI released an extension of VLAIR focusing on legal research. VLAIR—Legal Research evaluated three legal industry AI tools (Alexi, Counsel Stack, and Midpage), as well as ChatGPT and a human baseline of lawyers from one law firm who were all experienced in conducting legal research. The study involved 200 legal research questions. The AI tools and the lawyer baseline were each given a weighted score, with 50% of the score given to accuracy, while 40% was given to authoritativeness, meaning whether the response was supported by citations to proper sources, and 10% of the score was given to appropriateness, meaning whether the response was easily understood and could be shared as-is with others. The study found that the legal industry AI tools received the highest weighted scores, ranging from 76% to 78%, followed by ChatGPT at 74%, with the lawyer baseline scoring the lowest at 69%. Counsel Stack had the highest score of the legal industry AI tools.

Notably, the study found that when the AI tools outperformed the lawyer baseline, they did so by a large margin. Of the 200 questions included in the study, AI tools outperformed the lawyer baseline on 150 of the questions, and the average point margin was 31%. In contrast, when the lawyer baseline outperformed the AI tools, it was by an average point margin of 9%, and typically involved questions concerning complex multi-jurisdictional analysis, judgment-based synthesis, or when a deeper understanding of context was necessary. You can read this study in its entirety here.

Vals AI LegalBench contributions

In 2023, researchers created a benchmark called LegalBench, which included 162 legal reasoning tasks evaluated across 20 large language models (LLMs). Benchmarks are datasets and tasks that have been standardized to measure the capabilities of an AI model across an industry. Vals AI contributed to the LegalBench benchmark with a December 2025 update, which evaluated 92 AI models on legal tasks, finding that the top performing AI models were: (1) Gemini 3 Pro (87.04% accuracy), (2) Gemini 3 Flash (86.86% accuracy), and (3) GPT 5 (86.02% accuracy). You can read more about Vals AI’s contribution to LegalBench here.

Law student study

The University of Minnesota published a study in March 2025 called AI-Powered Lawyering: AI Reasoning Models, Retrieval Augmented Generation, and the Future of Legal Practice. In this study, law students tested Vincent AI, a legal industry AI tool that was refined using retrieval augmented generation (RAG) and OpenAI’s o1-preview, an AI reasoning model, on six legal tasks, finding that one or both AI tools significantly enhanced the quality of the legal work compared to the legal work performed without AI in five out of six tasks: (1) drafting an email for a client, (2) drafting a legal memo for a partner, (3) analyzing a complaint and drafting a written analysis, (4) drafting a motion to consolidate, and (5) drafting a persuasive letter. Additionally, the study found that both AI tools significantly boosted productivity in the same five out of six legal tasks, with particular strength in tasks like analyzing complaints and drafting persuasive letters. Neither tool demonstrated improvement in quality or efficiency for the sixth task, drafting a non-disclosure agreement. The study noted that it was the only task where participants were provided a general template to use in their response, which may have reduced the potential for AI-driven quality improvement. You can read this study in its entirety here.

Legal research hallucination study

Stanford RegLab published a preprint study in May 2024 called, Hallucination-Free? Assessing the Reliability of Leading AI Legal Research Tools. This study tested OpenAI’s GPT-4 along with three legal industry AI tools refined with RAG: Westlaw’s AI-Assisted Research, Ask Practical Law AI (both Thomson Reuters products), and Lexis+ AI, concluding that all four tools hallucinate. The hallucination rates of the RAG-tuned AI tools tested in the study were reduced compared to GPT-4 (which it found hallucinated 43% of the time) yet remained substantial. The study found that Westlaw’s AI-Assisted Research hallucinated one-third of the time, while Ask Practical Law AI and Lexis+ AI produced hallucinations in more than one of every six responses. LexisNexis and Thomson Reuters both responded that their internal testing and customer feedback demonstrated higher rates of accuracy than the study results, with Thomson Reuters asserting an accuracy rate of approximately 90% for their AI-Assisted Research tool. While the results of this study are already dated given the recent swift progression of AI developments, the Stanford study identified that the most important takeaway of its results was that the legal industry needs thorough and transparent benchmarks and evaluations of AI tools. This study can be accessed here.

What insights do these studies collectively provide?

When these studies are considered collectively, it becomes evident that lawyers should not summarily dismiss AI tools. Several independent studies have now concluded that using an AI tool to perform certain tasks may elevate a lawyer’s work through improved quality and/or efficiency. Tasks that were found by the studies to benefit from the use of an AI tool included contract drafting, document extraction, document question-answering, document summarization, transcript analysis, drafting emails and letters, drafting complaints, analyzing complaints, drafting motions, and some legal research tasks.

In contrast, tasks where AI tools did not add value within the parameters of the studies included redlining, EDGAR research, and chronology generation. While the Minnesota law student study did not find added value in using AI tools to draft a non-disclosure agreement when the students were provided a general template to use in their response, lawyers can compare this finding to the more recent Legalbenchmarks.ai contract drafting study finding that some AI tools outperformed the human baseline of commercial lawyers with 10 years of experience in producing reliable first drafts of contracts. Additionally, lawyers can consider testing one or more AI tools for contract drafting to draw their own conclusions.

Over time, the findings from these studies can also be used to evaluate how AI tools are evolving. For example, when the findings of Vals AI’s LegalBench contributions are compared to the Stanford hallucination study, it appears that the accuracy of OpenAI’s GPT AI models has improved significantly since May 2024 (December 2025: 86.02% accuracy, May 2024: 57% accuracy). This is notable in part because many legal industry AI tools use OpenAI’s models and their competitors’ models as their underlying infrastructure.

Some of the studies concluded that it is a toss-up whether you can presently get better output from a general-purpose AI tool or a legal industry AI tool. Further, some of the studies note that legal industry AI tools are distinguishing themselves from the general-purpose AI models by offering better workflow integration and support. Additionally, lawyers should know that some legal industry AI tools may offer more data privacy and security advantages than consumer-grade general-purpose AI tools.

What else should lawyers consider when evaluating AI tool options?

Lawyers should be prepared to distinguish between independent studies, such as the ones discussed above, and in-house evaluations by the companies making AI tools for lawyers. Some AI tool studies are conducted by AI companies themselves and publicized for marketing purposes. While an AI tool company’s evaluations of its own product may provide useful data, it’s important to be mindful of the source of any data utilized for decision-making purposes.

Additionally, while the studies highlighted above have yielded helpful insights, the evaluations conducted to date have only assessed the tip of the iceberg. There are many uses for AI in legal practice and hundreds of AI tools for lawyers that have not been independently evaluated. This means that lawyers who will evaluate AI tool solutions beyond the tools and tasks included in the studies covered in this article should be prepared to do their own testing to determine if an AI tool is a good match for their organization.

Finally, AI tool selection should not begin and end with considering the AI tool options available. Instead, lawyers should start the AI tool selection process by gaining an understanding of the many possible uses that AI tools currently offer and prioritizing the technology issues experienced by their organizations. AI tools for legal research command significant attention in the legal industry, yet many lawyers have not taken time to consider whether legal research is really the highest priority technology issue that their organization needs to address with an AI tool.

Once a lawyer has clarity about where improved technology solutions are most needed in their unique practice, the information in this article becomes most useful, and better-informed decisions can be made about which AI tools deserve further consideration. Further evaluation of an AI tool prior to final selection may include testing the AI tool to assess its real-world performance and should always include a risk assessment of the AI tool’s data privacy and security policies to confirm alignment with a lawyer’s professional responsibilities. ♦

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