Prepared for Litner + Deganian, P.C. Chief Information Officer Thursday, 20 August 2026

Nobody calls you
on a good day.

That is the part of this work I understand best, and it is most of why I want the job.

What follows is not a plan. I have not watched your team work yet, and a plan built without that would only be a guess delivered confidently. It is how I think about a firm like yours, and the handful of things I would want to understand before suggesting you change anything at all.

One The person on the other end

There is a person on the other end of every file.

Nobody who calls a personal injury firm is having a good year. They are hurt, they are behind on things, and they are being asked to explain the worst day of their life to somebody they have never met.

I learned the same lesson from a different seat. I was the chief operating officer at ChartRequest, which retrieves medical records for law firms and insurers. Millions of requests moved through that system, and it would have been very easy to treat them as volume. But nobody requests their medical records because life is going well. Every one of them was a person in the middle of something hard, waiting on paper that somebody else controlled.

That is most of what I believe about operations, and I do not mean it sentimentally. When a case sits for three weeks waiting on a records custodian, what has actually happened is that somebody does not know what is going on with their own life, and when they call to ask, the best answer anyone can give them is that we are checking on it. Fixing that is worth real money to a firm. That is the second reason to do it.

"We recognize that being a lawyer isn't just about paperwork and negotiating with people in court. It's about stories, and each story that comes to our door matters to us."Steve Litner & Arman Deganian

I would like the version of this job where the work is measured by how many of your team's hours go back to the people whose stories they are.

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Two The stack you named

Your stack, and where I have stood on it.

SmartAdvocateCase management. The system of record. At ChartRequest I owned the roadmap for native case-management integrations. Clio shipped. SmartAdvocate was next in the queue when I left, so I never pushed that code, but I have built a records platform into a case system and scoped that exact one.
Microsoft 365Mail, documents, identity. Administered, including identity and access. Worth saying early: a sanctioned, retention-policied place for files is something you are already paying for, which makes the Dropbox workaround a configuration conversation rather than a purchase.
RingCentralPhone and video across five offices. I have administered cloud VoIP on 3CX, Google Voice and Ooma. The phone system is also where your intake data lives, so routing, after-hours coverage and call recording are the same conversation as conversion.
CaseStatusProactive client updates. Its whole job is keeping a client from having to call and ask. I ran the records side, where that question was the support load, and I built an AI-native support and ticketing system end to end.
Co-CounselAI assistant, already in the building. I have deployed AI agents against real P&L work and rolled AI tooling out to non-technical staff. The part that needs an owner is what client data is allowed to go where, in writing, before somebody decides it case by case.

That is the stack from your posting. I have administered or built against every category on it, in a HIPAA-regulated business serving law firms. What I do not know is how you have it configured, and that is what the rest of this is about.

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Three Where a case waits

Most of a case is spent waiting on somebody else.

YoursThe first call
YoursIntake and sign‑up
TheirsTreatment
TheirsRecords and bills
YoursBuilding the demand
TheirsAdjuster review
TheirsNegotiation
YoursLiens and disbursement
Four stretches the firm can actually push on. A body healing, a records department, an adjuster with no reason to hurry.

Technology pointed at the four you control gives your team hours back and gets your client an answer sooner. Pointed anywhere else it becomes a monthly bill with a nice login page. Before recommending anything I would want to know how many days actually live in each of those stretches here, by case type, going back a couple of years.

"Steve is the 'energizer bunny' who drives cases forward efficiently until he gets the result that you deserve."litnerlaw.com

Most of what I am describing is turning that instinct into something the whole firm runs on, so a case moving quickly does not depend on which partner is watching it.

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Four What I would want to understand

Four things I would want to understand.

Four questions I would expect a firm to be able to answer about itself. I do not know any of the answers here yet, and I would rather be handed them than guess.

Where the good cases come from
What it costs to sign a case, broken out by where it came from. Answering that honestly takes call tracking and attribution wired into the case system. Without it, the sources worth more money and the ones worth less look about the same on a statement. L+D
How long a case waits
Sign-up to demand, and demand to resolution. Two people pay for a slow case. The firm carries the costs in the meantime, and the client waits on money they usually needed a while ago. L+D
How many systems hold one case
Count the systems holding a piece of a single matter, then count how many times a day a person moves something between two of them by hand. That second number, sorted high to low, is the integration backlog already in priority order. L+D
What the stack costs, and what goes unused
Cost per user per month across every subscription, with seats that nobody has opened in ninety days marked. Renewal dates on one calendar. This is usually the fastest money a new CIO finds, and it buys the budget for the things worth doing. L+D

I would expect at least one of these to be uncomfortable to look at. That has been true at every company I have worked in, including the ones that were doing well.

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Five The question I would ask first

"When a document comes back signed, who puts it in the case file, and how?"

I would ask a case manager rather than a partner, because the case manager is the one who knows. If the answer involves downloading a file from one place and uploading it somewhere else, I would not want to talk about software yet. I would want to know how many times a day that happens and how long it takes each time.

a day  ×  minutes  =  hours a week

Whatever that adds up to is somebody's week. It never appears in a budget, because it shows up as a paralegal staying late rather than as a line item, which is how it can go on for years without anyone ever deciding to allow it.

Where else the hours go

  • The status call. You own CaseStatus, which exists precisely so a client does not have to ring and ask. What share of clients actually activate it, and did the calls measurably drop when it went on?
  • The records chase. Someone called that custodian last week. Does the next person to pick up the file know what was said, or do they start again?
  • The second entry. Anything a person types into one system after already typing it into another.
  • The private spreadsheet. The file somebody keeps on their own desktop because the system will not hold what they need. There is always one, and it usually turns out to be doing something important.

Why I would start with records

Medical records are the longest stretch in most personal injury cases, and it is the part of this I would not be learning at your expense. I spent years on the other end of the request your paralegals send several times a day. I know why they come back late, what actually moves a custodian, where the authorization friction really sits, and what the alternatives cost.

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Six The unglamorous half

What happens when it breaks, and who you are paying.

Questions I would want answered in month one

  • When was a restore last actually tested? Backups running and backups restoring are two different facts, and most firms find out which one they have on the worst possible day.
  • If SmartAdvocate is unavailable for three days, what do we do? Court deadlines do not pause for an outage, and law firms sit near the top of the ransomware target list.
  • Who can see what, and what leaves with somebody? Access review and clean offboarding are most of practical security at thirty users.
  • Is any of it written down? Your posting asks for documentation for knowledge transfer and continuity, which usually means somebody once left with all of it in their head.

I carried the HIPAA program and SOC 2 Type II at ChartRequest. A Type II is an observation period rather than a certificate, so it is evidence the controls actually ran month after month. That is the same muscle your posting calls implement and maintain, and it is why I would rather test a restore than write a policy.

What I would inventory first

  • What you own against what you use. Every subscription, seat count, cost per user, renewal date. At thirty-plus users, shelfware hides well.
  • What the managed-services vendor is on the hook for. Read the agreement, find the service levels, then find out whether they are being met or merely invoiced.
  • Who owns each relationship. Renewals negotiated by whoever happens to answer the phone get priced accordingly.
  • What the last three purchases were meant to fix. Whether they did is a question the people using them can answer in about a minute.

I have negotiated vendor contracts, run managed-services relationships and enforced service levels. None of this is glamorous and all of it is the job.

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Seven Restraint

What I would not do.

I have been on the receiving end of the new person who arrives with a plan. It is not much fun, and it rarely works.

The fastest way to lose a firm's trust is to show up already holding the answer, and once you have lost it you do not get to fix anything at all. So the first quarter is mostly restraint, and I would rather say that out loud now than have you find out later whether I meant it.

  • I would not replace SmartAdvocate. You chose it and you have paid for it, and at most firms the gap between what a system can do and what it has been set up to do is far wider than the gap between one system and another.
  • I would not buy anything in the first quarter. Anything I recommended before understanding how you actually work would be a guess with a purchase order attached.
  • I would not reorganize anybody. The people doing the work are not the problem, and suggesting otherwise on day thirty is a good way to never hear the truth from them again.
  • I would not fire your managed-services vendor in month one. I would read the agreement, find out what they are actually on the hook for, and work the relationship before deciding it is the problem.
  • I would not hire consultants to explain your firm to you. Your staff already knows where it breaks. Asking them is cheaper, faster, and considerably more accurate.
  • I would not put a roadmap in front of your partners before I had sat with intake, a paralegal and a case manager, and watched a real case move.
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Eight The first ninety days

Listen, then count, then fix one thing properly.

Month oneListen
Sit with intake and take live calls. Walk one case end to end with a paralegal and a case manager. Listen to recordings, including the calls that did not sign, because those are the expensive ones. Get to all five offices and find out what is genuinely different about Columbus and Rincon. Read every vendor agreement and the managed-services contract, because that is a weekend of reading that pays for itself.
Month twoCount
Put real numbers against the four questions, and count the small repeated things nobody has ever had reason to count. At the end of it, one written page for you and Justin: what I found, what it is costing, and what I would do first.
Month threeFix one thing
Take the smallest change with the clearest payoff, finish it properly, and let the firm watch it work before I ask for anything larger. In a firm this size trust gets built one completed thing at a time, and I would rather earn it than assume it came with the title.

One thing I would ask you for, and it is inexpensive

A seat in your SmartAdvocate instance on day one, the vendor's advanced training, and a ticket to their user conference in the fall. There is no certification to go earn, I checked. The way anybody gets genuinely good at the system a firm runs on is to live inside it, and I would rather do that myself than manage it from a distance through somebody else.

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Nine The real roadmap

Questions I would ask your team.

What do you end up doing twice?
Which of our systems do you not trust, and why?
What do you keep in your own spreadsheet because the system will not hold it?
What did you have to work out yourself because nobody had written it down?
What do clients still ring to ask that CaseStatus was meant to answer?
What did you stop asking for because nothing ever came of it?
Which provider takes the longest, and what have you already tried?
If you did not need anyone's permission, what would you fix on Monday?

The answers to these are the actual roadmap, and I would rather earn them from your people over a month than guess at them in an interview. In my experience the two about trust and about nothing being written down tell you the most, and they are the ones nobody thinks to ask.

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Ten Why this one

Why this one.

For the last three years I have been inside the plaintiff's bar technology stack. At ChartRequest, a HIPAA-regulated medical records platform where roughly eighty percent of revenue came from law firms, I owned IT, information security and product at the same time, and carried the HIPAA program and our SOC 2 Type II certification. Before that Kanga, which we sold to GEODIS.

The company went from a two million to a sixteen million run rate, and forty people to a hundred and eighty, while I was there. I have been the person who has to keep the systems standing while the business doubles.

Your posting says you want someone to help the firm get more out of the technology it already has, for the client base and the employees both. That is the work I am genuinely good at, and I find it more interesting than building something new from nothing.

I also want to be somewhere the work is close enough to touch. Five offices, ten years of history, a good system that is probably doing half of what it could, and a partner group that decided to hire somebody to own this rather than patch it for another year. I would take that over a larger title somewhere the results are hard to find.

And the last thing is really the first thing. A paralegal who is not chasing a custodian is a paralegal who can return a client's call. The person on the other end of that file is having the worst year of their life, and most of what good operations does is hand your team back the hours to treat them like a person rather than a file number.

Everett Steele 678.899.3971
Atlanta, Georgiaeverett.steele@gmail.com
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