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June 1, 2021 19 mins

If Kitty Hailey didn't exist, some enterprising author would have conjured her up. A well put-together woman of a certain age, she resembles a hip kindergarten teacher - a fact which has served her well in her actual occupation; she's a private investigator. Using the skills she's honed over decades of investigative work, Kitty has risen to a position of prominence in her field, evolving from the typical "cheating spouse" assignments to doing trial work that has had positive, life-changing impact for the folks she's worked with.

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:06):
This is on the Job, a podcast about finding your
life's work. On the job, is brought to you by
Express Employment Professionals. This season, we're bringing you stories of
folks following their passion to carve their own career path.
For this episode, we look at a pretty non traditional
career path, being a private investigator. It's a complicated line

(00:28):
of work that comes with a lot of assumptions being
made about it and maybe something a lot of people
don't feel like they're cut out foreign paper. But sometimes
doing a job is less about your hard qualifications and
more about the bigger ideas that drive you. Now that

(00:49):
you know that we're talking to a real PI today,
you probably have some idea in your head of what
that means. So let's get that out of the way. Okay,
so what do people say to you when they hear
you're a PI. The first thing is that everyone goes, wow,
that must be exciting. Well, I've been doing this for
almost a half a century, and I don't think exciting

(01:12):
is the word that I would use anymore. Maybe at
one time, but not anymore. This is Kitty Kitty Hailey.
I am a professional investigator, sometimes called a PI or
a private investigator, and I am old enough to know better.
Kitty works and lives in Philadelphia. She got fiery red hair,
she's put together, kind of looks like she might be

(01:33):
a kindergarten teacher. You wouldn't look at her and think
she's a PI, which is also what people say to
her when they find out what she does. And then
they start to tell me how they would be a
good investigator. And they tell me either how they located
their long lost second cousin or they found their husband cheating,

(01:53):
and they watch all the cop shows on TV. The
thing is, Kitty is pretty much the opposite of what
you'd see on a cop show. She's been an investigator
in many forms, but currently most of what she does
is investigate the police in cases where someone is wrongfully
convicted or an officer abuses their authority. So no, I'm
not a police investigator. All right. So you've done a

(02:16):
lot of different things in your career, but boiled down,
what is it that you do. I gather information, period,
That's what I do. I don't censor it, I don't
editorialize it. I am a fact finder. However, the facts

(02:37):
that are find are about some very interesting and unusual situations.
Right now, Kitty is a criminal investigator, but for a
while she was what was called a full service investigator,
which means she did a little bit of everything, domestic people, cheating,
locating missing people. Now she does civil rights work, investigating

(03:00):
cases similar to George Floyd's where there's been an incident
with the police. My other clients are incarcerated and they
may not be guilty, So it's an interesting mixture of work,
but primarily I do civil rights and post conviction work.
While I was asking Kitty questions, I was surprised by
how much goes into being a PI that you'd never

(03:23):
know without talking to one. But some of the time,
just like on TV, Katy ends up in a courtroom
in front of a jury, presenting the facts and making
her case. Do you like being in a courtroom? I
love it. It's the best time because I think we're
all different people at different times. I'm not pretending, but
I am performing. I'm performing the Kitty Hailey who is

(03:44):
the investigator. I mean sometimes I'm a grandmom, and you know,
I sit on the floor with a couple of grandkids
and I play games and I make them cookies and
do all the things that grandmas do, but when I'm
in a courtroom, have control. Long before she was dominating

(04:06):
courtrooms and swaying juries, young Kitty Haley grew up a
pretty straight laced, brainy kid. I was a young geek.
I read a lot of books. I mean, Nancy Drew
was my best friend for the longest time, so maybe
that was part of it. I don't know. She had
a brother and a sister. They were a tight family unit,
had dinner every night with mom and dad. We're Jewish,
so we went to synagogue every Friday night together. I

(04:29):
don't think any of us ever got in trouble once
in our entire lives. Even so, growing up in a
non Jewish neighborhood, she saw a lot of prejudice against
her family. There were places she couldn't go, things she
couldn't do. So I knew what it was like to
be an outcast. I knew what it was like to
have in equity. And I think if I had not
been an investigator, I probably would have ended up in

(04:51):
some sort of social work at some point in time.
Because the inequities of the world are so great and
I can't stand a look at them. I need to
be a part of the solution, not accorded the problem.
In high school, she was great at art, so she
went to school for it, and afterwards she got a
job teaching art at a high school in Camden, New Jersey.
It was a predominantly black school during the Civil Rights movement,

(05:13):
and Kitty was asked to leave the school system after
being blamed for causing an uprising against the school system.
I didn't I didn't stop it. Apparently, she just helped
the students with their manifesto. Yeah. I think that was
my problem, help them to put their manifesto together. And
the problem was that I did during school time, during
school copy machines, So yeah, I shouldn't have done that maybe. Unsurprisingly,

(05:38):
this is when she had encountered with a police captain
who ended up becoming her husband. He was branching off
from the force to start his own PI firm, and
she started to help out while she got another teaching
job at Rutgers. And I worked as a teacher counselor
for a couple of years, doing investigative work part time,
and then eventually just transitioned over because it's what I
really wanted to do. So twenty four years old. Kitty

(06:01):
Haley was a PI, but it definitely wasn't glamorous. You know,
we have a small agency initially, and it was really
it was really difficult because it was just my husband enough.
They took whatever work they could get, which was mostly
domestic work. People cheating, abuse cases, custody issues, families stealing

(06:21):
from each other, messy stuff. My kids went to college
because I did domestic work. I mean, God, bless cheating people.
It was wonderful. Infidelity pays the bills. Yeah, absolutely, the
stereotypical stuff people think of when you're a PI, sneaking around,
following people, looking in their windows to see when the
light goes on or off. Yeah, I've done all that stuff.
I sat on surveillance for days and nights and weeks,

(06:44):
and I used to bring my kids on surveillance when
they were little. Sometimes they'd be so busy that her
husband would be working right through bedtime when Kitty had
to go do her surveillance work. So she'd throw the
kids in the back of the car with a blanket
and I'd go out. We'd all stood on surveillance together.
I read them books, I tell them stories as we
were driving. You hook them in with seatbelts and give

(07:07):
them things to play with, and every once in a
while I go, Okay, guys, hang on, mama's gotta go.
You did what we had to do. We'll get back
to our story in a second. First, a word from
Express Employment Professionals. A strong work ethic takes pride in

(07:27):
a job well done. This is you. But to get
an honest day's work, you need a callback. You need
a job. Express Employment Professionals can help. We'll connect you
to the right company. We're committed to your success and
never charge a fee to find you a job. Express
Nose Jobs. Get to know Express find your location at

(07:50):
expresspros dot com or on the Express Jobs app. Now
back to on the job. Despite the life of starting
a PI firm, Kitty was hooked. I loved the excitement,
the adventure and it was creative in its own way. Also,
having a background in art made me capable of observing

(08:12):
things that other people didn't see. She picked up on details.
She could recreate rooms that she was invited into during
theft investigations, and a client might be able to point
out the thing that they said was stolen from them.
This is one of the many skills that's helped Kitty
stay in the game as long as she has. What
makes someone good at what you do? Wow, I always

(08:33):
tell people who are interested in my field, they have
to be able to do several things really well. They
have to be able to think. You have to be
able to think and analyze. You have to be able
to observe and put your own personal prejudices out of
the way while you're observing what happened or what the
evidence is. She says. You also have to know a

(08:53):
lot about the law and how the court system works,
so that you know what constitutes evidence. Evidence is really
important because everything you do has to be admissible in
a court of law or you can't do it. One
of the most overlook skills, she says, writing You've got
to be able to put together a good report. If
you can't write what you did to explain it to

(09:16):
an attorney, then you might as well never have done
the work. Basically, you might do seventy hours worth of
surveillance and finding information, computer research and interviewing people, and
all you can give to an attorney is a five
page report. So it's like a master class in essay writing.
Sounds like there's a lot of skills they don't tell

(09:36):
you about on Law and Order SVU. Yes, so you
have to be able to deal with people, communicate well,
and know how to build so that you can keep
your job. That's the whole thing. It's a business. People
forget that. They think this is oh, this is great.
But if you're working for yourself, you've got to do
all of that or good work for somebody else, which

(09:57):
you can do. Katie says. There are so many respects
of the work. You can always try it all out
and figure out what you'd like to specialize in. Especially
in the age of social media. You could be a techie,
you could work online investigations. There's a ton of different
ways to go about it. That's not what I like
to do. It's not my comfort zone. Put me in
front of somebody and I will interview them until I

(10:19):
get every lest bit of information out of them, and
that I do well. Kitty says, in the beginning, she
was saying yes to any job that came her way.
She had to. That can get you in trouble. There
was a nice couple who came to see us. They

(10:39):
had just come from a funeral actually, and so they
were well dressed, and she wanted us to find her
missing children. The woman's ex husband had taken the kids.
It's not uncommon in these cases, so Kittie got involved,
only to later find out that without their nice clothing,
they were members of the Hell's Angels who were involved

(10:59):
in a dispute with a rival gang. We were right
in the middle of it, and I was stupid. I
didn't know anything about this. It was my first introduction
to anything criminal. I only learned about it when I
left their house and four big black SUVs pulled me
off to the side of the road and four people
identify themselves as the FBI and wanted to know what

(11:20):
I was doing in the house. That was not something
that a twenty four year old should have to go through.
It was scary. Do they make you second guess? Oh
my god, like, what am I doing? No? It maybe
learned to be more careful about who my clients are,
at least to know what was really expected of me,
Because my clients right now, some of them are guilty

(11:42):
as hell. You know some of them are innocent, but
you don't know until you investigate it. So I need
to I've learned to investigate my clients as well as
to investigate what they want me to investigate. Do you
ever do jobs for people that you kind of don't
feel comfortable doing. Yeah, but I'm not them. I'm still

(12:06):
doing my job. So take any case where there's a
prosecutor and a defendant. Whether she's hired by the defense
or the prosecution, her job doesn't change. So if there
was a bullet, we're going to find a bullet. If
you have a witness who says she saw X Y
and Z, bolt investigator is going to find x Y
and Z. The prosecution investigator and the defense investigator are

(12:29):
both going to find the same information because the facts
don't change. I'm not supporting a person, I'm finding out facts. Still,
she knows that what she does has a huge impact
on people's lives. When I ask if she's okay with that,
she tells me about a case where a guy called

(12:50):
Kitty saying he suspected his wife was cheating on him
every day when he went to work. He wanted her
to find out. Turns out his wife was with a
neighbor next door. Kitty had the evidence and testified in
their court hearing the following morning. I'm in my office
and I get a phone call and it's the woman
who I testified against, and she says to me, how

(13:12):
can you sleep with yourself doing the ugly work that
you do, spying on people, peering in windows? How do
you sleep with yourself? And I remember saying to her,
I don't. I don't sleep with myself. I speak with
my husband. You out her hand, sleep with somebody else
who says this. So no, I'm not the people I'm

(13:37):
working for or against. I'm still me with my own
ethics and my own morals. But if in the process
I help somebody make a life decision that will change
the course of their life, or allow them to make
an informed decision, then I've done a good job. Kitty

(13:58):
has a deep respect for the impact her work has,
good or bad, which is why over the last many
years she's become a nationally recognized investigative ethicist. She literally
wrote the book on ethical standards for being an investigator,
and she tours the country giving lectures on how to
do this job in a responsible way. Recently, she was

(14:18):
doing a session with a pretty elite group of investigators
and somebody asked me the question, how do you show
empathy and it just blew me for a loop. And
I said, I don't I feel it being a PI
sounds like a cool job, and Kitty says it is.
But on the flip side, there are times when you

(14:41):
are talking to a person on the worst day of
their life, people who have lost a loved one or
were a victim of a crime, people scared for their life.
And if you don't appreciate that, then maybe you shouldn't
be doing this job. You've got to understand that everyone
has been traumatized in some way, and I'm a to
their horror and I need to record it. I need

(15:04):
to be able to elicit the information from them so
that I can take their statements so that when I
present it in court it has meaning and gravatas, and
that comes from respect. Talking with Kitty reminded me of

(15:25):
something pretty amazing I heard the famous therapist and author
Esther Perel say on a podcast once when she was
talking about our relationship to our jobs. She said, next
time you're at dinner with new friends or at a
party and you're about to ask the routine question what
do you do for a living? Instead ask what would
you do if you weren't doing the job you do now.

(15:48):
That's always stuck with me because I feel like so
many of us write off what we can do for
work because we don't have the education for it, or
we didn't grow up around it, or we don't look there.
But sometimes what qualifies you for a job is your
deepest beliefs, the thing that gets you up in the morning.
Kitty still looks like a high school art teacher, but

(16:10):
her desire led her to being one of the most
respected investigators in her industry. That desire she had as
a young nerdy outcast to be part of the solution
rather than the problem. I asked her if she still
felt that way about her work. Oh, my, every day.
You know, we work so hard on a case and

(16:32):
don't always see the end of it. Sometimes all the
information goes to an attorney and you never know what happened. Wow,
I didn't even think of that. That's some very delayed satisfaction,
if any at all. Yeah. Okay, So I worked with
a gentleman from Philadelphia. I could say his name because

(16:56):
he is now free. It's jim Dennis. He was wrongfully
incarcerated almost twenty years ago. Jimmie Dennis is an R
and B musician in Philadelphia, and when he was twenty one,
he was wrongfully convicted of our murder. No physical evidence,
no weapon, no DNA, and he was put on death row.
Kitty worked on his case, and eighteen years later I

(17:18):
was sitting in a coffee shop and I got a
telephone call and a voice said, missus Kitty, I just
want to thank you, and I said, who is this?
He said, this is Jimmy Dennis. I'm on my way
home from prison. And I said in that coffee shop
and cried like a baby. It was so wonderful to

(17:45):
know that work I had done for eighteen years had
finally resulted in someone going home to a family a
baby he had never held, a child he had not seen.
You know, it was somebody whose life was able to
be not put hole again, but at least she was
able to live a life outside of the four walls

(18:05):
of an eight by ten seven, which he was in
for eighteen years. You know, that was That's humbling. So yeah,
I love what I do. It's not easy, it's hard work,
it's long hours, and it's so free and satisfying. It's great.

(18:26):
And I'm going to do it until I can't stand
up anymore. For On the Job, I'm Otus Gray. To
learn more about Kitty and her work, go to Kitty
Hailey dot com. Thanks for listening to On the Job,

(18:53):
brought to you by Express Employment Professionals. The season of
On the Job is produced by Audiation. The episodes written
and produced by me Otis Gray. Our executive producer is
Sandy Smallens. The show is mixed by Matt Noble for
Audiation Studios at the Loft in Bronxville, New York. Music
by Blue Dot Sessions. Find us on iHeartRadio and Apple Podcasts.

(19:16):
If you liked what you heard, please consider rating and
reviewing the show on Apple Podcasts or wherever you listen.
We'll see you next time. For more inspiring stories about
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