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November 5, 2025 9 mins

I spoke with Howard Ankin, the Founder of Ankin Law, a personal injury and workers’ compensation law firm based in Chicago. We discussed the best practices for building a strong team of lawyers and legal professionals to enhance law firm growth, how technology can enhance client service, and how trial work will change in an AI-centric future.

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(00:01):
Welcome to Reinventing Professionals,a podcast hosted by industry analyst
Ari Kaplan, which shares ideas,guidance, and perspectives from market
leaders shaping the next generationof legal and professional services.
This is Ari Kaplan, and I'm speakingtoday with Howard Ankin, the founder of

(00:21):
Ankin Law, a personal injury and workers'compensation law firm based in Chicago.
Hi Howard.
How are you,
Ari?
It's great to be here with you today.
It's my privilege.
I'm looking forward to the conversation.
So tell us about your backgroundand the genesis of Ankin Law.
I'm the oldest grandson on bothsides of my family, and I'm also

(00:43):
the oldest child for my parents.
My dad is a lawyer and on my mom's side ofthe family, my grandfather was a lawyer.
So coming out of the womb inmy mom's world, both her father
and her husband were lawyers.
So her firstborn son is a lawyer.
So I'm doing today.
I guess what was expected of me.

(01:05):
What I like most about beinga lawyer is helping people.
What's great about being alawyer is everybody could
practice law in their own way.
In the personal injury field, it'sbased on a contingency fee or a
percentage of what the lawyer'sable to recover for their client.
The interaction that they have withclients in terms of that attorney-client

(01:28):
relationship that makes personalinjury lawyers have a lot of personal
satisfaction in their career.
How has trial, practice andlitigation changed since you
founded the firm in 1997?
We never had the technologythat we have today.
Some of that technology is great.

(01:48):
Some is very distracting.
I used to, for example, have to take.
Doctor's depositions, and you used to geta lot of interaction with the physician.
So a lot of doctors ended up liking me.
I got referrals.
I got to have a little bit moreinteraction with the doctor to talk
to about my client and the case.
Now, you gotta make an appointment anddo a Zoom call to talk about the case.

(02:11):
So technology has changed both for thegood it saves a lot of time and for
the bad you don't get that interaction.
There are a lot of things that arehappening now at the courthouse
where they're done by Zoom.
It's a time saver and I could justget done what I need to get done.
However, on the flip side, I've beendoing this for over 30 years and

(02:35):
remember looking at lawyers that wereof my stature 30 years ago when I got
started, and they got to see my style.
They got to see how I argued the case.
They got to see how it unfolded.
The younger lawyers are not getting that.
I have a, team here of a hundred people.
I have 26 lawyers with me.
My younger lawyers get me.

(02:57):
So that's good for ourpractice here at Inkin Law.
But overall for the practice of law,younger lawyers are not seeing me and
even my own lawyers are not seeingdiversity amongst more established,
prominent lawyers to be able tounderstand how to argue a case
properly and how to be a good advocate.

(03:19):
I'm not at the courthouse, I'm online.
If I was at the courthouse, I wouldalso be seeing younger lawyers
and how they argue and advocate.
We don't get as much interaction anymore.
We've cut out a lot of wasted time.
But some of that wasted time when yousitting in the lobby of the courthouse
, you got a lot of interaction and therewas really something about that I

(03:41):
really enjoyed about being a lawyer.
I like that comradery and it's greatfor the legal system overall role.
What best practices have you employed tobuild a strong team of lawyers and legal
professionals that helps grow the firm?
We have an in law guidebook.
These are non compromising deliverablesthat are the expectations, of

(04:06):
lawyers and of people here thatwe're asking to be delivered.
We want people to be individuals andto have a lot of flexibility, but
ultimately to deliver the advocacythat we need for our clients, and
we're constantly building on that.
Then the other thing today,ai, it's taken over the world.
So the amount of technology, theamount of money that goes in techno

(04:30):
to technology is never ending.
I have a separate IT company.
I have two people in house that runit for my office internally here.
The amount of resources that goes intorunning a law firm these days in terms
of computer technology, software, noneof this was around, over 30 years ago.

(04:52):
Where have you found technology to be mostvaluable in supporting your clients, and
where do you typically avoid using it?
I don't know that you could avoid usingtechnology in any regard these days.
When you're talking about doing ajury trial these days, it used to
be the oral advocacy, famous trialsof yesteryear and would talk about,

(05:14):
the oratory skills of the lawyer andthey might do a closing argument that
would go, historic eight, 10 hours.
Nobody would put up with that these days.
We're doing a lot of things where we havejury focus groups both live or on Zoom.
Where we're pre-hearing the case.
When we're talking about the advocacy,these days, finding the right word is

(05:39):
not is important is finding the rightexhibit and how is that gonna convey what
we're trying to advocate on behalf ofthe client , that picture that's gonna
go up in that courtroom, how is thatgoing to convey what we're trying to
advocate more than me over talking someonefor 20 minutes to convey that ideal.

(06:02):
The use of that technology now in thecourtroom you just cannot be without it.
That drives into when we're doingdepositions that are recorded.
And how we exchange and mark exhibits.
Even how we obtain the documentationthat we need from police reports or
medical records or, people's lost time.

(06:23):
Like how that's all put togetherand how that's packaged and how
that, is put together for demand.
We're constantly trying to be on theforefront of that because the smaller
firms that don't have these resources,the advocacy that they're providing to
their client, it's really such a greatdivide today because other firms can't

(06:44):
afford those resources to do it that way.
The difference in advocacy now.
Between people that are using technologyand people that aren't at the level
of technology and over the next 10years there's gonna be the haves
and the have nots . The consumer isgoing to figure out which are the
firms that are on the cutting edgeof technology and using it and which

(07:07):
firms are not, and the firms thatdon't have it I don't know, if they're
gonna be around in 10 years from now.
And when I say 10, I can mean five.
The world is really changing quickly.
What skills do you look for whenadding a team member at the firm?
I look for different things.
For me, I represent people, I representhuman beings, and I need to know that

(07:32):
people care about the advocacy andalso really care about being the best.
My clients wanna work with the best.
I wanna work with the best.
I wanna be the best.
I want people to be the best.
Ultimately, do they have the coreability to get the work done?
How do you see trial workevolving in an AI centric future?

(07:54):
Who knows.
Ultimately, with AI it could be the twocomputers are arguing with each other
and they hash out your result . A lotof things are going to mediation , but
I think the mediations were working alot more effectively a few years ago.
I'm now seeing that the insurancecarriers and defendants are really
not using mediation to come toa common ground on a dispute.

(08:20):
The defendants are using mediationto advocate their position and to
make, an unreasonable plaintiffunderstand, what their position is
and to try to get them to understandtheir position from reasonableness.
Cases are settling by mediation morenow because maybe the plaintiff,
they are looking at things fromthe point of view where the defense

(08:41):
or the insurance companies andthose cases are getting settled.
But in my office two weeks ago ourfinal offer in a case was $38,000.
I stood on my head trying to movethat 38,000 offer, but the jury came
back 1.26 million and I still don'tunderstand what the defendant's
evaluation of that case was.

(09:03):
I think my office did an unbelievablejob with it but that's just the disparity
that's happening now in the legal world.
People need the right lawyer thatknows how to evaluate these cases,
and they need lawyers and law firmsthat are willing to take the cases
that need to be taken to the mat.
At the same time, people need to be ableto have somebody that has the knowledge

(09:24):
like my firm does, to be able to say thisis a good offer , you need to accept this.
This is Ari Kaplan speaking withHoward Akin, the founder of Akin Law of
Personal Injury and Workers' CompensationLaw firm based in Chicago, Howard.
It's really been a privilege.
Thank you so much,
Ari, it's always great talkingto you and I appreciate you

(09:44):
letting me be on your show.
Thank you for listening to theReinventing Professionals Podcast.
Visit reinventing professionals.com orari kaplan advisors.com to learn more.
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