"Chronicle is a backbone of my firm these days": How Hawaii Disability Legal Services serves 500 Pacific Island cases with a team of five

Diane Haar built Hawaii Disability Legal Services around a conviction that might seem obvious: disability claimants going through the hardest thing they've ever faced deserve to feel seen and heard. Her firm doesn't just file paperwork. It goes to hospitals when asked. It shows up at homeless shelters. It sends someone to meet with a client on a Neighbor Island or flies to American Samoa.

"We're talking to people when they're going through something that they've never gone through before, and it is often the hardest thing they've ever gone through."

She launched HDLS in 2012, and a practical reality shaped the firm from day one: Diane needed to be able to pick up a laptop and see everything, from anywhere. She was paperless from the start, an early necessity for a practice that required island-hopping. She even coded her own case management software before she had capital for commercial tools. What she called "the duct tape that got me through."

But the physical infrastructure of SSD practice kept finding ways to slow her down.

The ERE was a persistent problem. Before Chronicle, working it meant managing a single login with two-factor authentication: if a staff member needed access, Diane had to physically hand off her cell phone. Files weren't OCR scanned on download. Uploads were slow. The connection required to stay logged in was unreliable.

"It was slow, was clunky, it was difficult, and it took a really strong connection to get in and out of when it worked."

Then there was the mail. Hawaii's Neighbor Island offices added a layer of uncertainty that mainland firms don't think about. Mail simply didn't always arrive: returned to sender, delayed between islands, lost without explanation. Social Security itself has a "good cause" regulation that acknowledges the problem exists, but a regulation is cold comfort when a deadline is running. All of this pulled staff away from the work Diane had built the firm to do. Scanning mail. Managing ERE logins. Chasing documents. Hours that should have gone toward calling clients, taking hospital visits, making the connection that HDLS existed to provide.

Diane had been coding her own workarounds for years, filling gaps until something better came along. She knew the duct tape couldn't last.

"I'm a lawyer. Foremost, I'm a lawyer. So I actually want other people to create these things."

She was looking for commercial providers who would make the software their full-time job: keeping pace with SSA updates, building what disability firms actually needed. When she first encountered Chronicle, she was impressed. It was far ahead of the other platforms available at the time. But the fuller picture came at a NOSSCR conference, where she met Nikhil.

Most tools in legal tech are built by people who understand software. What Diane found was someone who understood the SSA side as well. That combination of technical depth and domain knowledge answered the questions she had about whether this was actually built for how disability firms work.

The change Diane felt first was geographic. Hawaii operates five to six hours behind the East Coast. The SSA runs on Eastern Standard Time: documents post, statuses update, and the workday closes while HDLS is still open. Before Chronicle, that meant either checking in early to catch Eastern-time updates or working with yesterday's data through the evening.

"Chronicle is ready to go when I'm ready to go. And that's a big deal too because everything is controlled by Eastern Standard Time and I am not in Eastern Standard Time."

By the time Hawaii's workday begins, Chronicle has already done the pulling. "It's already got everything up to date without me having to press a button," she said, "so that when I'm ready to work in the evening, when everything is closed down on Social Security side but we're still working here, it's completely ready to go."

The mail problem became a solved problem. Chronicle catches documents that never physically arrive. The team moved from scanning whatever showed up in the mailbox to trusting a source that was simply more reliable.

"Frankly, I hate to say we trust Chronicle more than we trust the US Mail."

When a client calls about something they received, the team no longer says "let us download that and call you back." They click into Chronicle and the document is already there, ready before the client finishes explaining.

Diane also built integrations that watch for document events in Chronicle and fire automatically. When a decision posts, it triggers a Clio stage change. That stage change creates tasks for her staff before anyone has even opened the document.

"People have tasks before they ever even see the document. The stage change hits, nobody actually has to click it themselves."

"It's touchless."

What Diane engineered herself, other Chronicle firms can now get out of the box. Chronicle's native Clio and Lex Med integrations bring the same automatic document-to-workflow pipeline to practices that don't want to build it from scratch.

Diane's team is smaller now than it was earlier in the firm's history. That's not a coincidence. As each layer of manual work got replaced (mail scanning, ERE logins, document routing), fewer people were needed to do it. That reduction in headcount didn't reduce capacity. It redirected it. The people who remain spend their time on what HDLS was built to do: calling clients, visiting hospitals, meeting families at shelters, making the connection that the firm's philosophy demands.

For hearing preparation and post-hearing wrap-ups, the combination of Chronicle's hearing transcriptions and LLM-assisted brief drafting has produced a shift in quality. Transcriptions from hearings are ready quickly; Diane feeds them into prompts she built, alongside case law and SSA rulings for her circuit, and gets a pre or post-hearing working brief draft that surfaces arguments she might not have found on her own.

"What I am doing is submitting an astronomically better product than I used to do because it cuts down on the time to do this. It finds the little nuggets that you may not see otherwise and it puts it all together."

"I know I'm getting more compliments from the ALJs these days."

She's precise about what that means. Her win rates were already high. What changed is the quality and completeness of her filings. Fourteen years into a practice she built with her own code and her own infrastructure philosophy, Chronicle is now central to how it runs.

At conferences, Diane's message to other disability attorneys is direct. The tools are there. The math isn't complicated.

"I started investing heavily in generative AI when I did a cost-benefit analysis and I realized that what was going to come back to me in financial benefit was so much more than what the cost was of taking it on. And that's Chronicle as well."

For anyone still scanning mail manually, still handling the ERE with two-factor handoffs, her position is unambiguous.

"Anyone who's still manually opening the mail, anyone who is still manually checking the ERE, what I would tell them is, it doesn't have to be that way."