Ten years ago, an employment case ran on paper, phone calls, and in-person depositions. Today it runs on texts, Slack and Teams messages, call logs, calendars, metadata, social posts, and surveillance footage, most of it filed and argued electronically.
The tools changed.
What decides a case mostly didn't.
Our Founder and Managing Partner, William K. Phillips, recently discussed that change with Pioneerly in an article he penned with three other contributing attorneys, titled Everything About Practicing Law in New York Changed. Except What Actually Matters. In the article, they looked back on a decade of changes in the legal profession, with a focus on how technology, artificial intelligence, digital evidence, client expectations, law firm economics, and the practice of law have changed, while many of the fundamentals of successful litigation remain the same.
Key Takeaways
- Digital evidence and AI have changed how New York employment cases are investigated, evaluated, and litigated.
- Technology can make evidence easier to collect and review without necessarily making employment litigation substantially faster.
- AI can misvalue employment cases because confidential settlements, dismissed cases, reduced verdicts, and unsuccessful claims are often missing from public data.
- Employees increasingly research employment lawyers, case results, reviews, and potential case values before contacting a law firm.
- AI can improve legal research, document review, and drafting, but experienced legal judgment remains critical in evaluating evidence, damages, litigation risk, settlement strategy, and case value.
- Employment cases still depend heavily on evidence, credibility, preparation, litigation experience, and judgment.
Digital Evidence Has Changed Employment Litigation
One of the biggest changes in employment law is the sheer amount of evidence that now exists in a typical case. Texts, emails, Slack and Teams messages, call logs, calendars, metadata, social media posts, and surveillance footage can all become important evidence in sexual harassment, discrimination, retaliation, hostile work environment, whistleblower, and wrongful termination cases because technology has made it far easier for lawyers to collect, organize, search, and review large quantities of evidence. What that technology hasn't done is guarantee that a case will move any faster.
As Phillips told Pioneerly: "Technology makes it easier to collect and review that evidence, but it does not necessarily make the case move faster."
Discovery, depositions, summary judgment, trials, and appeals all still take time. Moving documents electronically does not eliminate contested facts, credibility disputes, overloaded court calendars, extensive discovery, or the strategic decisions that arise during litigation, either, so more time can be added to a case at any one of those points, no matter the technology involved.
Clients Research Employment Cases Differently Today
Technology has also changed what happens before someone ever contacts an employment lawyer.
A potential client may now research several law firms, compare attorney biographies, read reviews, examine settlements and verdicts, research similar cases, and ask an AI platform whether they have a claim or what their case may be worth. That access to information can be useful, but it can also create unrealistic expectations. The problem is that the information available online does not represent every employment case, but an AI-assisted search result might not make that clear.
On one hand, public verdicts and large settlements receive attention, and on the other, confidential settlements usually do not. Dismissed cases and those lost at summary judgment receive far less attention still. A defense verdict might be likely to disappear from public discussion altogether, and an initial jury verdict may later be reduced by the trial court or on appeal.
The disparities in how much traffic a case result gets based on its type of result creates a significant problem when AI attempts to value an employment case based primarily on publicly available information.
Can AI Accurately Value an Employment Case?
Typically, AI and AI-powered search results cannot value an employment case reliably on its own. AI can help employees understand the factors that may affect the value of a sexual harassment, discrimination, retaliation, or other employment case, but public data can present a distorted picture of actual employment-case outcomes. Large public verdicts are relatively easy for AI systems to identify, but confidential settlements, dismissed cases, defense verdicts, unsuccessful claims, negotiated resolutions, and awards later reduced by courts may be much harder to identify or may never become public at all.
Pioneerly highlighted one of our own cases as an example: In Sooroojballie v. Port Authority of New York and New Jersey, a jury returned a verdict of approximately $2.31 million. The damages award was later substantially reduced through the post-trial and appellate process, although liability and punitive damages were upheld. An AI system that finds only the original headline verdict without understanding what happened afterward could reach a very different conclusion about the outcome of the case.
That is one reason case valuation requires more than searching for comparable verdicts, but there are many others.
When valuating a case, employment lawyers may consider numerous factors, including:
- Strength of liability
- Quality of the evidence
- Credibility of the witnesses
- Whether documents corroborate the employee's account
- Whether the employer knew about the misconduct
- Prior complaints involving the same person
- Retaliation
- Lost wages and benefits
- Bonus and compensation losses
- Emotional distress damages
- Mitigation and the employee's job search
- The employer and available insurance
- Venue
- Applicable law
- Potential defenses
- Litigation risk
- Motion practice
- Trial risk
- Appellate risk
Two cases involving similar allegations can have dramatically different values because the evidence, damages, witnesses, employer, venue, and litigation risks are different.
AI's role in employment law isn't limited to case valuation. It's also creating new discrimination claims of its own, as hiring algorithms increasingly come under legal scrutiny in New York.
AI Can Make Lawyers Faster. It Cannot Replace Judgment.
Artificial intelligence is already changing legal research, document review, drafting, case organization, and other parts of legal practice, and it is safe to assume that those tools will continue to improve. But making a first draft faster is not the same as knowing whether the first draft is right.
A lawyer still must determine which facts matter, which documents change the case, which witnesses are credible, whether an employer's explanation makes sense, whether damages can be proven, when additional discovery is worth pursuing, and whether a settlement should be accepted or rejected.
As Attorney Phillips told Pioneerly: "The best lawyers will use AI as a tool, but they will not outsource their judgment to it."
That applies to lawyers and to employees using AI to evaluate what happened to them at work. AI can be a useful starting point for understanding sexual harassment, discrimination, retaliation, workplace relationships involving power imbalance, severance agreements, accommodations, or other employment issues, but it should not be treated as a substitute for analyzing the facts, evidence, law, damages, and risks of a particular case.
Technology Has Not Eliminated the Risk of Litigation
Another thing technology has not changed is the basic reality that litigation involves risk. A strong employment case can still be dismissed. A plaintiff can survive a motion to dismiss and later lose at summary judgment, survive summary judgment and lose at trial, win at trial and have the damages award reduced, win only to see a favorable decision appealed, and so on.
At Phillips & Associates, PLLC, that’s why we do not evaluate cases based only on the best possible outcome. We evaluate liability, evidence, damages, witnesses, employer knowledge, mitigation, venue, defenses, litigation costs, timing, settlement possibilities, and the risks associated with continuing the case.
The question is not simply, “What is the largest possible verdict?”
The better question is, “What outcome makes sense after considering potential recovery, litigation risk, timing, and the client's goals?” In other words, what are the risks of filing the claim, and do the potential outcomes justify taking those risks?
Technology Has Changed How Law Firms Operate
Technology has made it easier to open and operate a law practice. Cloud software, electronic filing, video conferencing, AI, digital research tools, remote document access, and other technology allow lawyers to work differently than they did a decade ago.
But access to technology does not create litigation experience. Employment litigation still requires lawyers to develop evidence, prepare clients and witnesses, take and defend depositions, analyze damages, brief motions, negotiate with defense counsel, prepare cases for trial, and make judgment calls when the answer is not obvious. It also requires the financial ability and infrastructure to continue litigating when a case does not resolve quickly.
Employers and their defense lawyers understand as much. They evaluate not only the allegations but also the law firm representing the employee and whether that firm is prepared to continue through discovery, depositions, summary judgment, trial, and appeal. For example, if the law firm has a dedicated employment litigation team, the employer might hesitate to push the case to trial.
Collaboration Still Matters in the Digital Age
Technology has also made remote legal work easier, but Phillips & Associates, PLLC has taken a different approach. Our attorneys work together in the office, where lawyers and litigation teams can discuss evidence, case valuation, depositions, motions, settlement strategy, and litigation issues as they arise.
Employment cases frequently involve judgment calls that benefit from more than one perspective. One lawyer may recognize an evidentiary issue, another may see a damages problem, and another may identify an inconsistency in the employer's explanation or recognize how a particular defense firm is likely to approach the case.
Technology, no matter how easy it has made communication, does not eliminate the value of experienced lawyers collaborating on difficult cases.
What Hasn't Changed About Employment Litigation?
Technology can help lawyers find evidence faster, AI can help organize information, electronic filing can make court submissions more efficient, and digital research can find cases in seconds that once required hours in a library.
But technology cannot decide which witness a jury will believe. It cannot automatically determine whether an employer's explanation is credible, know whether one document fundamentally changes the value of a case, or decide whether accepting a particular settlement is better for a particular client than continuing to litigate for another year or two. Those decisions require judgment from an attorney who has been there to see similar decisions and contests before.
As Phillips told Pioneerly: “That may be the biggest lesson from the last decade. The technology surrounding employment litigation has changed dramatically. The importance of evidence, credibility, preparation, experience, and judgment has not.”
(To learn more, click here to read the full Pioneerly article by William K. Phillips and other contributing attorneys: Everything About Practicing Law In New York Changed. Except What Actually Matters.)
William K. Phillips and Phillips & Associates, PLLC's Experience in New York Employment Law
Attorney William K. Phillips is the Founder and Managing Partner of Phillips & Associates, PLLC, an employment law firm that represents employees exclusively. Before practicing law, he served as a Vice President at Fieldstone Private Capital Group, a New York investment bank, where he worked on international mergers, acquisitions, and restructurings. That business background continues to influence how he approaches employment-case valuation, litigation risk, settlement strategy, negotiation, and the financial considerations involved in resolving employment disputes. Phillips also founded the National Plaintiffs' Summit on Sexual Harassment and Employment Discrimination, a national conference for plaintiff-side employment attorneys focused on litigation strategy, best practices, and advocacy in sexual harassment, discrimination, retaliation, and related employment cases. He also writes about workplace conduct, employment litigation, management, and litigation strategy for Forbes Business Council.
Together, our legal team at Phillips & Associates, PLLC has handled more than 9,500 employment matters, litigated approximately 2,000 employment cases, and recovered more than $360 million for employees. Our attorneys have also appeared before more than 110 United States District Judges and more than 70 United States Magistrate Judges. Our litigation record includes federal jury verdicts, appellate decisions, and published employment-law decisions, including the Second Circuit's decision in Vasquez v. Empress Ambulance Service, which addressed cat's paw retaliation liability.
Questions About an Employment Case? Talk to Us Today.
AI and online research can provide useful general information, but employment cases are highly fact-specific. If you want to know more about your legal options, you should start by talking with an attorney from Phillips & Associates, PLLC. We represent employees in sexual harassment, discrimination, retaliation, whistleblower, and other career-impacting employment matters.
Keep in mind that speaking with a lawyer does not mean you have to file a lawsuit. A consultation can help you understand the evidence, potential claims, risks, possible damages, and options before deciding what to do.
Consultations are free and confidential. There are no attorney fees unless we recover for you. Call (866) 229-9441 or contact us online to begin.