SHRM26 Debrief · AI, Data & Tech · #1949

Investigations and Separations: Smarter Compliance for HR's Riskiest Moments

with Jim Link

& Katie Sammarco

& Jacqueline Schafer

▶ Watch on the SHRM portal ~73 min, distilled

workplace investigationsoff-boarding and separationsAI in HR compliance

"Compliance is compassion, and you really just need to have both."

What it was about

Two Workplace Tech Accelerator startups, Clearbrief (investigation drafting) and Onwards HR (off-boarding/separations), show how purpose-built, evidence-grounded AI tools can bring compliance and speed to HR's highest-risk moments without sacrificing the human empathy those moments require.

By the numbers

10,000+ hours

Time spent by HR, finance, and legal teams collectively on separations before adopting Onwards HR

16 states and counting

Number of U.S. states with 'mini-WARN' regulations more protective than the federal WARN Act

six-minute increments

Standard legal billing increment referenced by Natasha Baker to illustrate lawyer time costs

Key notes

Use tools that link every sentence of an investigation report or separation notice back to underlying evidence (emails, notes, interview transcripts) so findings are defensible and neutral rather than opinion-laden.
Treat 'little i' investigations (routine employee relations complaints) with the same documentation discipline as formal investigations, since they carry similar legal risk.
Avoid drafting investigation findings directly in generic generative AI tools like ChatGPT because they tend to be sycophantic and will jump to biased conclusions (e.g., assuming guilt) rather than neutral fact patterns.

The contrarian takeThe most surprising takeaway: when the audience was polled on whether they conduct investigations under legal privilege, the largest group said they only invoke it when they fear litigation is coming. The moderator flagged this as strategically unwise, since privilege should be established proactively (and can always be waived later) rather than retrofitted after a problem is anticipated.

Take this back Monday

Do this for your team

Ask whoever handles separations: are we still using spreadsheets, mail-merge, and one person's memory for severance paperwork?

Say this in your next leadership meeting

Compliance is compassion: skipping documentation to move fast on a separation actually puts both the employee and the company at risk.

Watch out for

Relying on a single, irreplaceable employee who manually manages severance/separation processes via spreadsheets, Excel mail-merge, and memory, creating a single point of failure and burnout risk.
Using generic generative AI (ChatGPT, Copilot, etc.) to draft investigation reports or separation materials without security/privacy protections or citation checking, risking hallucinated facts and loss of legal privilege.
Assuming a template written to comply with California's strict employment law will automatically be compliant everywhere else — one customer had California-specific language mistakenly included in every state's separation agreement templates.

Fun fact · Jacqueline Schafer

Jacqueline Schafer teaches law at Columbia while running Clearbrief, named 2025 ABA Legal Rebel for AI that catches legal hallucinations.

If this landed, see these

↳ Go deeperBeyond the Gut Feel: How AI-Powered Structured Interviews Are Transforming Hiring OutcomesSame evidence-grounded AI approach, applied earlier: structured interviews instead of separations.⇄ The counterpointRight Hire, Right Growth: A Practitioner's Unfiltered Look at AI Across Hiring and RetentionAI already broke old hiring signals here; the real fix is human coaching.✦ The unexpected oneState of the Workforce 2026: What to Keep, What to Change, and What AI Is Actually Doing to Your EmployeesWhile investigation AI evolves fast, this 10-million-respondent study shows the human core barely moves.