Free · The Disability Firm Playbook

How to evaluate legal software
before you sign

The buyer's framework from our NOSSCR workshop: a scorecard you can bring to any demo, the five questions to ask before you sign, and the red flags that mean walk away.

The framework

Four things that actually matter

Score each criterion 1 to 5 during the demo. Weight them by what your firm needs most. That is the whole system. Cost is deliberately not a fifth box: price only means something relative to these four, which is why the money questions live in the question bank below.

1

Built for this work

Generic legal software can be configured into disability work. Purpose-built software starts there. Configuration is a real cost: in dollars, in time, and in the workflows your staff invents to bridge the gaps.

What to look for

  • Does the workflow speak SSD natively (hearing levels, CE exams, OTR requests), or do you rename "matters" and build it yourself?
  • Who else in disability law uses it? Ask for names you recognize.
  • Configuration depth cuts both ways: power for firms with someone to wield it, a tax for everyone else.
2

Plays well with your stack

Integration is no longer a feature checkbox. It has become the lead criterion. A tool that does not talk to your stack creates a part-time data-entry job you never budgeted for.

What to look for

  • Direct integration vs. middleware (Zapier) vs. nothing, in that order.
  • Open API vs. closed: can you get your data out, and can other tools get in?
  • "Integration" on the roadmap is not integration. Score what exists today.
3

Your staff will actually use it

Implementation is where good purchases die. The buyer evaluates features; the staff lives with friction. Training burden is scoreable in the demo, if you know to ask.

What to look for

  • Time-to-first-value: what can a paralegal do after one hour? After one phone call?
  • Who does the training, the vendor or you? Is onboarding a product or a PDF?
  • Will it survive your actual team, including remote and overseas staff?
4

The vendor will still be around

Once a tool becomes load-bearing, vendor health is your firm's risk. You cannot read their books, but you can read the proxies.

What to look for

  • Shipping velocity: when did they last release something? Did customer feedback visibly shape it?
  • Trajectory of the customer base: growing in your practice area, or harvesting it?
  • Roadmap honesty: do they ever say "no" or "not yet"? A vendor with no "no" is selling, not building.
  • Security posture as a durability proxy: certifications cost real money and discipline. A vendor who invested in them is planning to stay.

The scorecard

Four rows, one demo

Score 1 to 5 per criterion, in or right after the demo, while it is fresh. Set your weights before you shop, not after: a solo and a 600-case firm should weight these differently.

Download the scorecard (PDF)
Criterion Weight (High / Med / Low) Score (1–5) Notes from the demo

1. Built for this work

____ __ / 5

2. Plays well with your stack

____ __ / 5

3. Your staff will actually use it

____ __ / 5

4. The vendor will still be around

____ __ / 5

Tie-breaker: two tools tied on total? The one with the higher staff adoption score wins. Every time.

Ask these in any demo

Five questions that make you the smart buyer in the room

A vague question ("Do you integrate with my CMS?") invites a vague yes. A precise question gets the real answer, because the vendor knows you will check.

  1. 1

    "Is that live today, or on the roadmap?"

    Ask it about every feature that matters to you. If it is not live, it does not exist yet.

  2. 2

    "Show me this working on a disability case."

    Hearing levels, CE exams, SSA deadlines. Your workflow, not a generic matter.

  3. 3

    "What is my total first-year cost, in writing?"

    Implementation, training, add-ons, and what the price becomes at renewal.

  4. 4

    "What can my paralegal do after one hour?"

    Then ask who runs the training: them, or you.

  5. 5

    "What does your SSD forms library look like, and can I take it with me?"

    Purpose-built software ships CE exam, OTR, and hearing templates. A generic tool does not, and may not let you export your own either.

Go deeper

The extended question bank

Per-criterion versions of the five questions, for when a purchase is big enough to deserve a second demo.

Built for this work
  • · Show me a disability case in your system. Are hearing levels, CE exams, and OTR requests native, or do I configure them myself?
  • · Which SSD firms use this today? Give me names I would recognize.
  • · How much configuration does a firm my size typically need before this is useful, and who does that work?
Plays well with your stack
  • · Which of your integrations with my current tools are live today, direct, and not through Zapier?
  • · Is your API open? Can I export my data, and can other tools connect to it?
  • · Can I talk to a firm that uses this exact integration right now?
Your staff will actually use it
  • · What can my paralegal do after one hour in the product?
  • · Who runs training, you or me? Is onboarding a product or a PDF?
  • · How does this work for remote or overseas staff?
  • · For references: "If this tool disappeared tomorrow, how would your staff react?"
The vendor will still be around
  • · What did you release in the last 90 days, and what customer feedback shaped it?
  • · Is your customer base in disability law growing?
  • · What have you said "no" or "not yet" to on the roadmap?
  • · Which security certifications do you hold, and can I see the report?
If the product says "AI" on the label
  • · Point to the click: where exactly in my workflow does the AI do something? Show me the moment.
  • · What happens when it is wrong? Real AI products build in a verification workflow, because their builders know the failure modes.
  • · What would I lose if you turned the AI off? If the honest answer is "nothing," you are paying AI prices for the label.

The paperwork that matters

"Are you SOC 2 compliant?" Here is what you are actually asking.

SOC 2

An independent auditor checked the vendor's security controls. Type I means the controls existed on audit day. Type II means they actually operated over months. Ask for Type II, and ask to see the report.

The honest decoder

Certifications do not mean the product is good. They mean the company submitted to outside scrutiny and invested in staying around. No certification plus vague security answers on medical data is a walk-away, not a discount.

One line to ask: "Can you share your SOC 2 Type II report and your data-handling summary?" Then watch whether the answer is a document or a story.

Walk away

The red flags that should end the conversation

1

"It's basically ready."

Roadmap answers to current-state questions. If it is not live, it does not exist.

2

Pricing you can't get in writing.

If the price needs a phone call, the price is negotiable. Which means someone else paid less.

3

No references in disability law.

"Law firms love us" is not "SSD firms use us."

4

Your data, their hostage.

No export path, closed API, or vague answers about leaving.

5

The demo never touches your workflow.

If they will not demo your use case, the polish is the product.

Free · 20 minutes · No pitch required

Want a second set of eyes? Book a free software strategy session.

Bring your current stack, a decision you are weighing, or a filled-out scorecard, and we will walk through the framework as it applies to your firm. Often the biggest finding is a tool you can stop paying for.

  • Audit what you already own against the four criteria
  • Pressure-test a purchase you are considering, any vendor
  • And if you want to see how Chronicle scores, bring the scorecard to that too

Also from the Playbook series

AI tools for your ERE status reports

Four copy-paste prompts that turn a raw ERE CSV export into clean, actionable spreadsheets. Works in ChatGPT, Claude, or Gemini. No account or login needed.

How to use these tools
01

Open an AI assistant

ChatGPT, Claude, or Gemini — any of them work.

02

Use a prompt below

Click "Open in Claude" or "Open in ChatGPT," or copy and paste manually.

03

Attach your CSV export

Drag your ERE status-report CSV in and send. SSNs are masked to the last 4 digits.

The four tools

Click to open directly in Claude or ChatGPT, or copy and paste manually.

Share: LinkedIn

Events

Hearings & CE Appointments

Pulls every scheduled date out of a status report and lines them up in one spreadsheet — hearings from a hearing report, or consultative-exam (CE) appointments from an Initial/Recon report. Use it when you want a single calendar-style list of everything coming up.

Attach: One hearing report OR one Initial/Recon report

View full prompt

Outstanding Questionnaires

Track Overdue Paperwork

Scans an Initial/Recon report for questionnaires SSA sent to your claimant that haven't come back yet, sorted by how long they've been outstanding — so the most overdue are at the top. Use it when you need to chase missing paperwork.

Attach: One Initial/Recon report

View full prompt

What Changed

Compare Two Reports

Compares two reports of the same level and tells you exactly what moved for each claimant — decisions, status changes, ALJ swaps, fee changes, and more — plus who's new and who dropped off. Use it when you pull reports regularly and want just the "what's new since last time."

Attach: Two reports of the same level (older + newer)

View full prompt

Active Caseload by Status

Snapshot Dashboard

Counts up your cases and groups them by lifecycle stage for that level — Not Scheduled, Scheduled, Hearing Complete, Closed by outcome — for a quick at-a-glance dashboard. Use it when you want to know how many cases are sitting in each stage right now.

Attach: One report (any level) — or attach several at once

View full prompt

ERE exports already mask Social Security numbers to the last 4 digits — safe to paste into any AI assistant.

Missed an earlier session?

The Disability Firm Playbook is an ongoing series. Watch the replay below.

Session 1 replay

Session 1

Spotting At-Risk Cases Before They Escalate

Read recap →
Session 2 replay

Session 2

What You're Missing Every Time You Log Into ERE, AARPS, and AROS

Read recap →

Get future Playbook sessions

The Disability Firm Playbook covers what proactive firms are doing differently. Get the next session and new tools directly in your inbox.

No spam. Unsubscribe any time.

Want this without the manual step?

Chronicle runs this across your entire caseload — automatically, every night.

These prompts work great. But they still require pulling a CSV, opening an AI assistant, and running the analysis each time. Chronicle connects directly to ERE and surfaces changes, hearings, questionnaires, and caseload snapshots automatically — so your team opens Chronicle instead of logging into the portal.

Chronicle platform dashboard view

See How Chronicle Works for Your Firm

Compare for yourself how daily monitoring changes your workflow.

Book a Demo

Join disability practices across the country

Free training invites, workflow guides, and industry reports.