In May 2026, Chronicle hosted the first two sessions of Disability Peers in Practice, a monthly roundtable that Chronicle runs as part of building the virtual community the SSD bar has been missing: no slides or vendor pitches, just practitioners talking through what’s actually working in their practices right now.
The topic for the inaugural small-firm cohort: what software are you actually using to run your practice? Over the course of two sessions, a group of solo and small-firm practitioners from Ohio, Pennsylvania, New York, Texas, Washington, Massachusetts, Florida, and New Jersey walked through their case management setups, their AI experiments, and the specific frustrations they’re trying to solve. Here’s what came out of it.
About This Cohort
The small-firm cohort included solo practitioners and firms with up to four attorneys handling Social Security disability cases, generally running between 100 and 300 active cases at a time. Some were long-tenured disability attorneys with 20+ years of experience; others had launched their disability practices in the last year or two. Most had pieced together their current tech stacks over time rather than building them from scratch, and several were actively evaluating changes.
The complete Session 1 cohort for Disability Peers in Practice
The complete Session 2 cohort for Disability Peers in Practice
Case Management Is Sticky: Everyone Feels the Switching Cost
- No single platform dominated; anxiety about switching was universal regardless of current system
- Integration with ERE monitoring has become the primary evaluation criterion, outweighing any individual feature
- Succession planning is reshaping software decisions for practitioners thinking about exit or sale
No single case management system dominated the room, but the anxiety about switching was universal. Prevail, Clio, MyCase, DibCase, and Crocodile DS Wings all came up, and each had both advocates and critics.
Kelly put the migration calculus plainly: “Anytime you switch case management systems, it’s going to be a huge headache and hassle. Trying to make things line up perfectly isn’t always going to be possible.”
The CMS conversation in Session 2 surfaced a useful frame: practitioners aren’t choosing between features so much as they’re choosing between trade-offs. Ned described his current system this way: “MyCase is, like, a Toyota Camry, it kind of gets you from A to B, but doesn’t have all the bells and whistles.” He added that the lack of a Chronicle integration was a meaningful gap, given how much of the ERE-monitoring work flows through Chronicle now.
Beverly, who had just switched to Clio earlier that week, pushed the evaluation criteria further: “I have less time right now. I prefer to pay a little extra and have more time.” She had built out 15 workflow stages in Clio in her first week, tracking intake through case close.
Her view on MyCase vs. Clio for a practitioner like Dave, who was exploring his first real case management system:
If it’s only two licenses, I would go with Clio, probably the difference is about $50 per month total. If you’re considering selling in the future, I think it could be more attractive for someone to buy a Clio practice. — Beverly
Dave (practicing since 1992, running 100 to 125 cases out of Miami) was candid about where he stood: “I’ve got to modernize everything I’m doing here for the last 34 years. There’s a lot of paper and pen still.” The succession angle was explicit: nobody would want to take over a practice built on spreadsheets and institutional memory, even if the caseload itself was strong.
What’s driving CMS decisions more than any individual feature: integration with other tools, especially with ERE monitoring. See also: Case Management Tools That Integrate with ERE and ERE Monitoring vs Case Management Software: What’s the Difference?.
AI for Briefs and VE Questions: Useful, But Verify Everything
- Practitioners are splitting tools by task: ChatGPT for VE questions, Claude for brief drafts
- Accuracy anxiety is near-universal; everyone still reads the record independently, regardless of tool
- The most-valued AI tools are built for disability-specific problems, not generic legal AI wrappers
Nearly everyone in both sessions had experimented with at least one AI writing tool. The uses ranged from VE question generation to brief drafts to hearing prep summaries, but every practitioner paired their AI use with a strong caveat about accuracy.
Karen had developed a clear tool-by-tool workflow: “ChatGPT is better for me when it comes to what kind of questions do I want to ask the vocational expert. Claude is better for me when it comes to brief writing.” She was also using Perplexity and LexMed as part of her preparation routine, and using Claude via direct prompting as an alternative to more expensive subscription tools.
One practitioner described where the trust breaks down: the AI “gave my client a whole bunch of cardiac conditions, and my client had no asthma or cardiac conditions.” She still reads every page herself. “As long as I know the record well, I can then work with it and kind of adjust.”
The sharpest framing came from Ned:
Don’t get upcharged on a fancy wrapper. A lot of the AI tools do similar things at the same sort of level, broadly speaking. — Ned
He’d tried several AI tools and found the most value in ones built for disability-specific problems rather than general legal use, a point that also applied to his appreciation for Chronicle as an ERE-specific tool.
For brief writing specifically, the group converged on a view that AI is most useful as a starting point for structure and an accuracy check, not a substitute for knowing the record. Joseph walked through how he uses LexMed post-hearing: downloading the audio, running it through LexMed, and using verbatim transcript excerpts to challenge VE testimony in post-hearing briefs.
More on hearing prep tools: Hearing Prep Complete Guide for Disability Attorneys, Pre-Hearing Brief Software for Disability Attorneys, and Hearing Prep Without the Manual Work: Chronicle + LexMed.
Medical Chronology Tools: The Price-vs-Accuracy Tradeoff
- Three Chronicle-integrated options in the room: Dodo ($50/case flat), Superinsight (credit-based), LexMed (per-product)
- Per-case cost sensitivity is real at small-firm scale; the pricing model matters as much as the output
- Accuracy remains the unmet need: practitioners want a tool they can rely on without page-by-page verification
Medical chronology tools were a center of gravity across both sessions. Three tools that integrate with Chronicle came up: Dodo (basic level, $50/case flat rate with refreshes included), Superinsight (deeper analysis, credit-based pricing), and LexMed (disability-specific training, per-product pricing). The conversation was candid about where each fits.
One practitioner was direct about small-firm cost sensitivity: “The cost is outrageous for some of them. $50 is a lot of money per case.” She’d experimented with Superinsight but found the pricing model a barrier, defaulting instead to running her own prompts through Claude for cases where the cost didn’t justify the tool.
Ned had downgraded his Superinsight plan from a monthly prepay to credit-by-credit: “My practice isn’t big enough yet to really justify that.” He’d used it primarily for intake triage (analyzing a case to determine whether to take on a client) rather than full hearing prep.
One practitioner described what they wanted from any chronology tool: accuracy they could rely on without page-by-page verification. “I’m still looking for a better product for chronology, one that can be more accurate. I need it to be right so that I can rely on it without having to go back and double-check everything.” The AI tools they were using would get the broad shape right but misread specific dates and document context in ways that mattered.
Beverly’s take on Dodo: she’d done a demo at NOSSCR the prior year and was impressed, and liked the clear per-product pricing over a credit system. “I like to support the small businesses.” She was planning to start with Dodo for her new practice.
For more on the chronology tool landscape: Best Medical Chronology Software for Attorneys, One-Click Medical Chronologies: Chronicle and Superinsight, and Choosing the Right AI Medical Record Platform.
Pre-Hearing Briefs: A Generational Debate With Shared Logic
- Practitioners split on whether to always write them; unanimous on the underlying purpose (give the ALJ a roadmap)
- In overwhelmed hearing offices (Seattle was cited with only 2 active judges), briefs are practical strategy, not courtesy
- AI accelerates brief structure; knowing the record cold is still non-negotiable
The group had an unexpectedly animated conversation about whether to always write pre-hearing briefs. The through-line: the purpose of the brief (giving the ALJ a roadmap) was universal, but the calculus on effort versus return varied by geography and experience.
Joseph made the case for briefs from a capacity standpoint: “In Seattle, we’re down to 2 living, breathing judges. Poor, two overworked judges don’t know what to do. So give them a pre-hearing brief, give them a roadmap, give them an easy way to resolve the case.”
Karen agreed: “I do do a brief, because I want the judge to have a roadmap. And it helps me prepare for my case when I do a brief, always.” Dan took a more situational view: not opposed to briefs, but questioning whether they’re always read in a context where judges are processing enormous dockets.
The point both sides agreed on: knowing the record cold is non-negotiable. AI can accelerate preparation, but the practitioner’s independent judgment about what matters in a case remains the foundation.
Integration Is the New Feature Race
- “Does it connect with other tools?” has overtaken feature sets as the primary CMS evaluation question
- Direct integrations are beating Zapier; practitioners specifically cited wanting Chronicle-Clio to work without middleware
- DibCase’s lack of integrations was cited as the main reason practitioners switched away
In both sessions, “does it connect with other software” surfaced as the primary evaluation criterion when practitioners were choosing or switching tools, sometimes outweighing the tool’s native features.
Beverly switched from Lawcus to Clio specifically because of integration possibilities: “I really like the integration that you guys have with Clio, which is more straightforward than going through Zapier. I don’t love Zapier.” She was planning to connect Clio with Claude for admin tasks (call notes, data entry, client updates) as her next configuration step.
Ned pointed to the integration gap with his current system as the primary reason he was seriously evaluating a switch to Clio: “MyCase is really solid from managing your documents, but it kind of lacks a Chronicle integration, whereas Clio now does.”
Karen cited DibCase’s lack of integrations as a longstanding frustration: “There were no integrations, and that’s one of the things I really wanted.” The arrival of the Chronicle-Clio integration came up as a meaningful recent development in both sessions, particularly for practitioners who wanted ERE updates to push directly into their CMS rather than living in a separate system. See Keep Every Clio Matter Current: Chronicle’s Native ERE Integration.
Succession and Practice Modernization Are Intertwined
- Multiple practitioners explicitly tied modernization decisions to succession planning or future sale
- A practice built on spreadsheets and institutional memory isn’t attractive to a buyer or a successor associate
- Clio was specifically mentioned as making a practice more sellable than alternatives
Also in This Series
The May 2026 cohort also included a separate session for larger practices. That conversation covered COO hiring, custom AI automation, Filevine vs. Clio trade-offs at scale, and the field-office association problem that doesn’t improve with volume.
About This Series
The SSD community has been missing a regular virtual space where practitioners in similar situations talk through real operational problems together. Chronicle built Disability Peers in Practice to be that space.
Sessions run monthly, segmented by firm size, free and capped to keep them small. No slides, no pitches. Just practitioners comparing notes on what’s actually working.
Register for the next session →
About Chronicle
Chronicle is an SSD ERE monitoring and analysis platform built for Social Security disability practices. It automatically checks the ERE and e-file for changes across your firm’s cases, surfacing status updates, new documents, and upcoming deadlines so your team stays ahead of what the SSA is doing. Chronicle integrates with Clio, Filevine, and other case management systems, and connects with medical chronology tools including Dodo, Superinsight, and LexMed. Disability Peers in Practice is one of the ways Chronicle brings the SSD community together outside of conference season.