Difficult Conversations in Leadership

James Orsini (1s):
Delegation really comes from something that you should be doing, that you bestow on somebody else to get
done for you. And facilitation is really looking at a much broader landscape and taking the time to really
understand what it is that people do well. And then how connecting the dots between two folks whose paths
normally wouldn’t cross and how they bring value when united together on a particular project.

Announcer (27s):
Welcome to Difficult Conversations: Lessons I Learned as an ICU Physician with Dr. Anthony Orsini. Dr
Orsini is a practicing physician and the President and CEO of the Orsini Way. As a frequent keynote speaker
and author, Dr. Orsini has been training healthcare professionals and business leaders, how to navigate
through the most difficult dialogues. Each week, you will hear inspiring interviews with experts in their field
who tell their story and provide practical advice on how to effectively communicate.

Announcer (1m 3s):
Whether you are a doctor faced with giving a patient bad news, a business leader who wants to get the most
out of his or her team members, or someone who just wants to learn to communicate better this is the
podcast for you.

Dr. Anthony Orsini (1m 12s):
Welcome to another episode of Difficult Conversations Lessons I learned as an ICU Physician. This is Dr.
Anthony Orsini I’ll be your host today and every Tuesday moving forward. Today I’m especially excited
because I have my cousin as a guest James Orsini. James Is the President of The Sasha Group, which is a
VaynerX Company. Working alongside Gary Vaynerchuk it’s CEO in a serial entrepreneur, james leads The
Sasha Group to help small businesses reach explosive growth, potential.

Dr. Anthony Orsini (1m 43s):
The Sasha group provides educational consulting and marketing services for companies from 1 million to
200 million in revenue, James previously held key high level positions, four VaynerMedia, including Chief
Operating Officer and Chief Integration Officer. Before coming to VaynerMedia, James held prior positions
as chief executive officer and member of the board of directors of site to Mobile. He has more than 35 years
of experience and operations experience across a broad range of marketing and communication disciplines.
James was the executive vice president and director of finance and operations for Saatchi and Saatchi in
New York, where he worked closely with the CEO to provide strategic and day to day direction for all
financial and operational functions.

Dr. Anthony Orsini (2m 21s):
His impressive resume continues prior to joining Saatchi and Saatchi, James held the key leadership
positions that they had brand North America, KPMG and Goldman Sachs. James graduated, Magna c*m
laude from Seton Hall University in New Jersey with a bachelor of science in business administration. He
received at universities, presidential academic scholarship is still served the university today. He is a

licensed New York state certified public accountant. On a personal level, James is a board member of
renovation house in New Jersey, New York a residential substance abuse rehabilitation program.

Dr. Anthony Orsini (2m 53s):
He served as a member of the board of regions for Seton hall university, but perhaps his best
accomplishment was winning that third and fourth grade little league championship with his cousin. Yours
truly wouldn’t you agree that’s your highest accomplishment of life?

James Orsini (3m 8s):
Absolutely. I take every occasion to mention it to where they allow me to do so,

Dr. Anthony Orsini (3m 13s):
You know, I think you and I were the two worst player’s on the team. You played center field, I was a second
base man, but somehow I think both of us or the championship went three for three.

James Orsini (3m 23s):
Yeah. Yeah. And I gave birth to an athlete. So I make it All level off now

Dr. Anthony Orsini (3m 28s):
That’s right after you’re a stellar career in third grade, you’re son went off to play college baseball. It must’ve
been Joanne’s genes, I guess,

James Orsini (3m 35s):
Absolutely Joann who we met when she tripped and I picked her up. So we do not have any kind of finesse
when it comes to sports.

Dr. Anthony Orsini (3m 44s):
All kidding aside, your career has been an incredible story of one success after another. And I really enjoyed
watching your accomplishments pile up. As I read your bio in the position that you’ve had I thought anybody
would be it happy just to have one of those positions, but each career defining step that you made, you just
took on more and more and had more and more success. I think that’s incredible. I just want to say, I’ve
personally enjoyed watching your career just give better and better. .

James Orsini (4m 11s):
It was unplanned, but the, but it unfolded really in a, in a nice way.

Dr. Anthony Orsini (4m 16s):
So the topic of this podcast that has always difficult conversations and particularly we are going to talk about
Difficult Conversations in Leadership, you’ve held so many positions in leadership, but before we get into

that, I just want the audience to know that James Orsini that I know. So tell us about James Orsini. How
would you describe yourself? What drives you and what is your leadership philosophy?

James Orsini (4m 37s):
Well, I’m a family man. I love every aspect of my family and look to spending as much time as I can with
them. I actually see business as my hobby, which most people find strange and unusual. So it wouldn’t be
crazy for me to be on a vacation, still reading the wall street journal where a, a, a business book and hand.
So that’s why it, my passion has actually become my profession. And I don’t feel like I really work. I just
show up and do what it is that I like to do.

James Orsini (5m 7s):
So, you know, my leadership style is one a servant leadership. You know, I actually serve out of this to get
the best out of them. I am a facilitator rather than the delegator. So a that means you gotta do to really take
the time to understand what it is that people do well, and then how your needs plug into their talents. You
know,

Dr. Anthony Orsini (5m 26s):
It’s interesting. You bring that up. I read a piece that you actually wrote, I think in 2017, right? Don’t Delegate,
Facilitate, So just expand upon that. Could you just mentioned that a little bit? What did you mean by that?

James Orsini (5m 37s):
Yeah. You know, delegation really comes from something that you should be doing that you bestow on
somebody else to get done for you. And facilitation is really looking at a much broader landscape and taking
the time to really understand what it is that people do well. And then how connecting the dots between two
folks whose paths normally wouldn’t cross and how they bring value when united together on a particular
project. I kinda see things from 30,000 feet.

James Orsini (6m 6s):
So things look small to me, but as a result of that, if you think about it, right, when you’re up in an airplane
and you see these little puddles that you realize there’s, somebody’s swimming pool, but you were at 30,000
feet. So they don’t look grand in any way, shape or form. And that’s the way I see problems. I just don’t see
them big. I have a different vantage point and I help people navigate through them.

Dr. Anthony Orsini (6m 27s):
That’s great. So you had some great positions and then tell us the story, because you know, you can get
through an interview without somebody asking you about GaryV right? So he’s just bigger than life. And you
work with him, and I have a couple of questions about Gary V how did you end up at VaynerMedia? If you
could tell us the story and then tell is how the soccer group started it and why you started that.

James Orsini (6m 47s):
So it wasn’t interesting that I went to Seton Hall, University basketball game. I was invited by another board
member at the time, and he brought his son and his son brought a friend and their friend was AJ Vaynerchuk
Gary’s younger brother. At that time, I was Chief Operating, Officer it Saatchi and Saatchi. And, you know,
we’ve got to talking and I just invited him down to Saatchi to see what it was like when he gets big. And it
took me up in the offer, but most importantly, he knew enough to stay in touch with me and use me as a
mentor, you know, oftentimes ask, have you ever done this?

James Orsini (7m 19s):
You know, somebody who does that, how would you handle this? So we kind of stay in touch over the years.
And I left Saatchi. I went out to become the CEO of Sito Mobile and then I stood, there are three and a half
years. I had a three year employment contract. I spent three and a half years, and now I was leaving to
come back into big advertising. So I just called AJ to just say, Hey, man, I’m going to see you again. You
know, I’m going to be back in big advertising. And he’s like, you know, did you ever meet my brother Gary.?

James Orsini (7m 50s):
And I said no, and he said, you ever hear of him? And I said, no not really. And he’s like, all right, well, do a
quick Google search. He’s not going to be harder to find. I spent some time with him that long, maybe 15
minutes, I got a call back from AJ and said, Listen he likes you, he want’s to have dinner with you. You know,
don’t take that too lightly. His times is pretty valuable and we had dinner and he said that James, I want to
create a $500 million independent integrated international communications company. Can you help me do it?
And I said, yeah, I actually think I can. So he was like, all right, well, don’t take one of those other jobs.

James Orsini (8m 21s):
You’ve already had that step on a cloud and do this with me. And I did. And, you know, he has certainly been
successful Before since, and it continues to be, I like to think I had played a small role and help a piece of his
vision come to life.

Dr. Anthony Orsini (8m 37s):
And that’s an important point. You mentioned in one of your interviews, the Gary asked you one simple
question. So what is it that you do tell us about that?

James Orsini (8m 45s):
He said, could you describe what you do in one sentence? And I said, yeah, I take dreams and visions and
put them into action plans. And he was like, you’re hired. So I got a lot of dreams. So it does good.

Dr. Anthony Orsini (8m 55s):
Well everybody needs someone to see the big picture and then somebody who facilitates. So I think that is
certainly you, it sounds like its a perfect match.

James Orsini (9m 3s):
Yeah, yeah. Has been, we’ve got an absolute blast and I’ve had several positions and is running the VaynerX
world and the newest of them right now.

Dr. Anthony Orsini (9m 10s):
So lets start moving towards difficult conversations and I asked Claude Silver the chief heart officer at
VaynerMedia the same question I’m gonna ask you. Of all the years you have been in leadership and all the
types of conversations that you’ve had with board members, CEOs, workers, employees, what do you think
is the most difficult conversation that you have had and that you continue to have to have that you really
thought that you needed to master?

James Orsini (9m 36s):
Well, its so many people unfortunately define who they are by their work it’s said definition, but it is factual
and removing someone’s work while not removing their soul has always been a difficult situation for me. And
as you read from that bio, I have had a lot of senior roles with those senior roles come, a senior
responsibilities, many of which was unfortunate in all different times, right?

James Orsini (10m 7s):
Or removing people who are simply out a position and I’ve had to do that around the world. I’ve done that
with bodyguards. I’ve done that with translators. I’ve done that in different cultures and it’s always difficult
when you’re removing the people who was used to removing to people. So I’m talking about CEOs,
founders, businesses that I bought and then remove leaders really, really difficult situations. And you know,
we need to do it because you know, the needs of the many outweigh the needs a few and what you are
trying to accomplish.

Dr. Anthony Orsini (10m 41s):
Any advice that you have to the young executive out there who needs to remove somebody’s or separate.
We had Dr. Larry Barton on a few weeks ago, Dr. Barton is the world’s leading expert on workplace violence.
He has a brand new book that talks about the way you separate someone from employment can really
predict whether they’re gonna come back and shoot the place up. Or, you know, I mean, those are rare
instances, but they do happen. So what advice do you have that for that manager whose got to remove
somebody’s that you could help him do it in the kindest most compassionate manner?

James Orsini (11m 14s):
Well, one, it shouldn’t be a surprise. So make sure you’re taking the time to properly communicate, to
evaluate over a period of time to, you know, having an ongoing dialogue. I believe Claude calls it “radical
candor”, you know? So by the time you get to that closed door office, nobody should be sitting on the other
end of that desk, thinking that it was a surprise. To, you know, be as fair and reasonable as you possibly can.

This is not the time. You know, at that moment to try and save an extra week, salary are pay or whenever,
you know, try and be as fair as you possibly can within the policies of your company and as reasonable as
you can in a, you know, not making it a choking situation.

James Orsini (11m 56s):
You know, as a global CFO, I was the guy that used to have to remove global CEOs. The CEO didn’t do it,
he put me on a plane and say, you know, you’ve go to Mexico city or your going to Tokyo, you know? So that
was always hard and difficult. They kind of knew when I was flying in this sort of grim reaper type of analogy,
I’ve removed people who was companies’ I bought, we then absorbed a company and there was no need for
the founder anymore. That was difficult. But you know, I’ve done it in such a way, in one particular example
where I called years later in a different company.

James Orsini (12m 30s):
And I said, listen, I know I’m not the voice you want to hear on the other end of the phone, but I had the right
opportunity for you now I’m in a different place and I know what it is that you do well. And if you’re willing to
trust me, come and join me here in this new role. You know, I made lifelong friends that way. Obviously when
you do something like that in the Sito Mobile situation, I was brought on as the CEO, the founder was moved
to a chairman role. We worked for a couple of years together and then the board told me, listen, you have to
remove him.

James Orsini (13m 4s):
It was his, yeah. It was really, really, really difficult. Two grown men crying on each side on the phone, you
know, their thinking about it. It, it was his baby birthed that company. Now, if he was removed from it. So that
is a really hard,

Dr. Anthony Orsini (13m 17s):
Yeah. You know, it’s interesting that your first thing you said was they should already know it’s coming and
I’ve been training doctor’s as you know how to break bad news, how to give tragic news. You have cancer,
your baby is passing away. Your child’s gonna have neurological deficits. And what I teach and I use this
acronym called program PROGRAM and the G is for gradual and its the number one rule of breaking bad
news in healthcare and business. There’s so many parallels. That’s why I’m having you on also that there’s
so many parallels that when someone hears the bad news, that their husband just died in the emergency
room, et cetera, I always tell the doctors, they have family members should already know what’s coming.

Dr. Anthony Orsini (13m 56s):
So you want to plead your case first. And this is what happened. There is a heart attack was worse than we
thought it was by the time he got to the emergency room in his heart was a very low, his blood pressure was
low. We had to give him an adrenaline, etc, etc, etc. And this is neuroscience based just allows people to
brace themselves for that news. That’s coming in your case, you’re talking about over a period of time where

your giving them feedback, et cetera. But it’s interesting that the parallels, that was a first thing that you said
and that’s number one rule in medicine too.

James Orsini (14m 26s):
Yeah, no surprises. I mean, but at a time some of this difficult and hard conversation is coming. It’s horrific
when it’s cold water in the face, you know, it’s never easy, but it’s a little more acceptable. When this is the
third time you’re talking about this particular topic and this is going to be the last time.

Dr. Anthony Orsini (14m 44s):
In a small way. They appreciate that you took the time that you gave them the chance and that you did in a
compassionate manner. And so that whether you’re a separating someone from a appointment or you are
doing it in medicine, it’s really, really the same thing. There’s so many parallels. And as you know, I’m a big
student of communication. Well, I know you very well, but knowing each other, since, since we were
children, I know you have a very even temperament. And in medicine I had a mentor when I was very young
training, I think he was doing a neonatology fellowship and he told me this thing, he said, the higher you are
up on the ladder or the softer you speak.

Dr. Anthony Orsini (15m 21s):
And that was probably the best advice that I ever got. And I routinely get thrown into situations where there’s
a child or a baby who has no heart rate and the team whose very, very good and their very well trained. They
are trying to resuscitate. Then they called me and I can get in there. And although they are very good,
there’s panic in the air or there’s and I’ve seen Physician to start barking. You see it on TV, right. They
started barking orders, right. That doesn’t happen. Not real. And I learned very early on from this mentor that
when everybody is screaming and yelling and get this and grab the oxygen and do that, And I walk in and I
just say, okay, what are we have here?

Dr. Anthony Orsini (15m 58s):
That’s what’s going on. The level of tension in the room goes down. So you mentioned how you’re even
temperament helps. Can you expand upon that? Just again, to join another parallel?

James Orsini (16m 6s):
You know, that’s been both a blessing and a curse for me because for some high strung people, it was like,
Listen, James, you’re not sensing the urgency that I’m trying to relay to you. And I said, I am sensing the
urgency, but if we’re all running around, like our hair is on fire, you know, nobody’s gonna have to see
through it and understand how important it is. Right. I’ve wrote a great book called the six fundamentals of
success by Stuart Levine, who is the ex CEO of Dale Carnegie. Now, if you know anything about Dale
Carnegie in business, it’s they train CEOs and it was about knowing what’s on your bosses dashboard.

James Orsini (16m 41s):

Some meaning like know what’s important to your boss and make sure that’s important to you. You know, for
a lot of what it was that I did with Gary in the earlier years, I was more like a decoder ring to him because
you know, the people that were around him were he used to Gary barks and out in an order and they run
100 miles an hour. Sometimes they smashed into a wall. And I was like, Listen I heard what he said, I think
this is what he means. You can go in a direction like this. Where do you know what let’s put some, we didn’t
necessarily call it process. We called it is scalable organization because when you are in hyper growth
mode, like most of his companies are, you know, process by nature sounds lethargic and slow.

James Orsini (17m 21s):
So we were just trying to organize enough to be able to scale. And a lot of times it gets tense in those rooms.
He’s just such a passionate individual that it comes out with a sense of urgency. And I just have a way of
seeing the dots in the room and understanding how they connect and come together. So I’m a much better
and a crisis situation. And I am a, it’s so funny. Because anytime I get very emotional in happy situations,
you want me as your pallbearers, but you know, because I’m gonna be no problem, but like they give a toast
at your wedding.

James Orsini (17m 55s):
I’m crying. So, You know, that’s a familial. And in fact, I just interviewed, I have a niece she’s gonna be on in
a couple of weeks, probably before this even airs. She was a premature baby survive that then, when she
was 16 years old, she got lymphoma, went through chemotherapy. She survived that. And now she’s a
pediatric oncology nurse and she takes care of kids with cancer. So I’m so proud of her. And I thought she
was going to be perfect. So I had her on, she was really a great interview.

James Orsini (18m 25s):
And during the interview or the introduction to my niece’s interview, I said in that introduction that please
forgive me because I think it’s familial that I might cry outt of pride and your gonna hear my voice quiver.

Dr. Anthony Orsini (18m 43s):
And my father is the same way. I think your father was the same way. Sadness, stone cold. But when their
kids graduating high school, they’re bawling their eyes out.

James Orsini (18m 54s):
Yeah, absolutely. Absolutely. That’s it. That’s the way it is.

Dr. Anthony Orsini (18m 58s):
So I don’t know if this is an Orsini thing anything or an Italian thing or what, but we were all the same and
let’s move on. So you, once said, were talking about More Difficult Conversations and sometimes you have
to have difficult conversations with clients, in the Sasha Group and I want you to tell us a little bit about that.
You’re really into mentoring and consulting and people are coming to you to help, but you once said a big

idea is not a business Hope is not a strategy and expand upon that. And I would think that sometimes you
have to have those difficult conversations with clients, with the Sasha group were people that come to you.

James Orsini (19m 28s):
Yeah. And that’s all, it was interesting when Gary pivoted and said, Hey you ready to start something new?
And I said, yeah, would you have a mind? He said, well, come on the cover of entrepreneur magazine, I got
14 million followers and we built a company to service Fortune 500, I don’t have a company for the smaller
and medium sized businesses. So he said, I want to start a new company. I want to name it after my dad for
legacy purposes his Dad was from Belarus, a Russian immigrant, who came to the United States worked his
way up. Bought his own liquor store? I, you know, the story there are, Gary helped out with that to help to
grow or whatever.

James Orsini (19m 59s):
It was 3 million in sales to 60 million in sales. So servicing the small businesses and is why we kind of
positioned ourself more like a consultancy on the front end in an advertising agency on the back end, you
know, fortune 500 has a brand manager’s from Wharton MBAs and, you know, understanding the real side
of marketing. And the folks that I serve are founders and owners and entrepreneurs, you know, who has a
passion for something and saw an opportunity could have been as a family owned business that they are
now taking to another level.

James Orsini (20m 30s):
You know, it could have been something that they saw on the marketplace and saw a way to pivot and they
be learned something new and they need guidance, not only marketing guidance, but business guidance,
but I was fortunate at this week to be included in a campaign, the magazine’s 40 over 40, it celebrates
wisdom and experience. Really, if you think about it, there’s no substitute for that. And in this space, I
happen to have that.

James Orsini (20m 60s):
So there are, are difficult conversations there. Like I know you’re birthed in this business in you and you
loved it, but the pivot the has to be here, or I know this guy has been along side of you for umpteen years,
but he’s not doing you any favors in the role that he’s in. And he’s simply not a chief operating officer or is it
not financially savvy? So there are difficult conversations with people who, you know, are passionate about
what is that they birth in a business, but don’t necessarily have a plan, but I spent a lot of time giving them
outlines to a business plan.

James Orsini (21m 35s):
Here’s how your idea becomes a business. Now remember the four pillars that Gary gave me, I wanted to be
integrated international independent communications company. Those four pillars, help guide the decisions
that we were making. They did two things. One, they enabled us to hit the gas and directions that aligned

with that. But more importantly, they enabled me to push back and challenge him.

James Orsini (22m 5s):
When, it didn’t align. Why are we doing this? I don’t understand how this fits. Remember the pillars that you
gave me. You know what I mean? So and Gary, by his own admission, says that he’s a moldable dictator,
right? So their buddies, a moldable, a dictator, meaning that you can have a conversation with him. And you
know, he’s going to make the ultimate decision as he should, but you can reason with him to understand why
things should be the way they are.

Dr. Anthony Orsini (22m 30s):
So you have to approach that conversation with at CEO because as you said, it’s his, baby, its her baby.
Then you need to tell them I have to train a bunch of physicians sometimes who are referred to me from their
hospitals saying that this guy’s is a great surgeon. He’s the great obstetrician. We were getting so many
complaints about his bedside manner. His, we call them H cap scores. Our patient satisfaction scores are
really low and it’s my job to coach them. Sometimes I put them through improvisational role playing with
actors.

Dr. Anthony Orsini (23m 1s):
I’m getting someone already. Who’s got an attitude like he or she does not want to be there. They’ve been
sent by daddy down there to get trained. And I can say, Because, I’m a physician. I mean, doctors have egos
and that I’m sure CEO’s have egos. And I’ve learned through my coaching that you do have to spend a lot of
time stroking that ego. And as they say, lead the horse to water in, when I teach conflict resolution, you kind
of steer them until they go, you know what James I think we should do this way. And that’s exactly what you
wanted them to do with it.

Dr. Anthony Orsini (23m 33s):
Is that a problem with CEO’s too? Stroking the egos a little bit?

James Orsini (23m 36s):
Well, I, you know what, the interesting thing, when I was going to Sito Mobile to become a CEO, you know, I
had never been a CEO. I was never been in a publicly traded company. And at the time I didn’t know
anything about technology and a, I resigned from Saatchi and the then global CEO, Kevin Roberts said to
me, so your going to be the CEO of a small, publicly traded company. He said three things. He says one
lonely job. He said two-hard job because when it gets to your desk, as this stuff that nobody else can figure
out.

James Orsini (24m 7s):
And he says three, where is it trading now? And I said, it’s trading on the bulletin board and were going to
bring it up to the NASDAQ. And he said, you are going to be asked to compromise your morals and integrity

on a daily basis. You know? And I shook his hand, it sounds like a Hallmark card. And six months later I went
back and I said, wow, those words were so deafening because it is exactly what I was feeling. So the
interesting part is in any room, there are so few people who even, you know, I’m sure as publicly traded
companies CEO is I’m honored to have held that title.

James Orsini (24m 40s):
I know what I don’t want to be ever again. And its a publicly traded CEO but once you have the badge, you
have the bage. So while Gary has 900 people in VaynerX, I don’t know anybody other than me, who’s been
in a publicly traded company CEO. So there are decisions he makes that you no, in the earlier times when I
was able to send him a text and so I know how to difficult, that is how you handled it eloquently I’ve been in
that situation. Well done.

James Orsini (25m 11s):
And that’s what happened with some of the CEOs, nobody want’s to come in and you know, and then they
were like, James, what do you know? What, what do you know about retail furniture? What do you know
about insurance? What do you know about law firms? And I said, absolutely nothing. I said, but I will never
know as much as you know about your practice, but you’ll never know as much as I know about the people
who are purchasing your services. Now that’s where the two of us come together. So that’s what I have. And
I don’t profess to know what it is that you have, but what you have becomes better when you mix it with what
I have,

Dr. Anthony Orsini (25m 45s):
It’s all about credibility. I have the same issue when I’m coaching physicians or when I’m doing workshops
and big hospitals about improving patient experience. We do exercises about how you sit down. When you
speak to a patient, how to be a genuine person, et cetera. Many of the other companies that do what I do,
they are taught by masters in education. Maybe they are taught by a nurse and as a physician, I know this to
be true. So even when I started my workshops, they are sitting in the back with their arms crossed, going. I
don’t really want to be here, but once I say to them, listen, I work in the world’s largest neonatal intensive
care unit.

Dr. Anthony Orsini (26m 22s):
We’ve adopted these practices. Our patient experience scores have gone up and I still go home at four or
five o’clock then all of a sudden, everybody sits up a little bit straighter. So when you were alluding to is it’s
all about the credibility. And I think that’s really important, but you still have to be careful with egos, right?

James Orsini (26m 38s):
That’s right. You, you definitely have to play with egos and it can get to your head. Just you read in bio. You
know, I was kind of cringing and looking around and I couldn’t even look at you reading it. I mean, if not done
properly, it will go to your head. You know? And now we had a 40 over 40 accolades somewhere in the

bottom of that, my wife does a good job of helping ground me. You know, they say Einstein’s wife thought he
was an idiot. Right,

Dr. Anthony Orsini (27m 6s):
Exactly. Right. I know you. well, your very grounded, your genuine people wouldn’t even know you do what
you do. Because you just loved to laugh. You enjoy life. And so I think that really goes a long way. Tomorrow,
“I’m going to be interviewing Stephen Covey, the speed of trust author. And he talks about building trust and
building loyalty, the best bosses I’ve ever had in my life. I walked through a fire for them. And that if you said
something poorly about them, I’d be very angry at you. No matter what. And some bosses I’m not happy
with.

James Orsini (27m 37s):
Yeah. That’s really, really important. You know, when I left the Sito Mobile I read a book called “Consigliere
ruling from the Shadows” and it was about being a great number two. When I read that book, I’m like, Listen,
that’s who I am. I don’t need to be the guy on the stage. I don’t need to be the number one. God, I think I
would of been a better CEO if I had a number two, like me behind me, I know most people have a number
two who is trying to shoot them to be number one. And that’s kinda, you know, what the realities of the
business world are.

James Orsini (28m 9s):
But I think that’s kinda where even when the, and this is, this is a funny one, Gary was like, alright, so you’re
going to be the CEO of the Sasha Group. I said, nah I think I would like to be the president. And they said,
you should be the CEO it’s, you know, you should be the CEO of VaynerMedia. You should be a CEO of The
Sasha group. And he’s like, wow. I never really had somebody get back a title. No, but it was like, that’s
kinda what was, I knew what was going to be doing. I didn’t really need any bigger title than the one that I
had to do, what it is that I knew I can do. And there’s a lot of trust there you know, there’s a lot of trust there.

James Orsini (28m 40s):
The thing as his father, his name on it, you know, he doesn’t want to screw it up in any way, shape or form.
He was involved in the vision. And then I sat the strategy for how to execute the vision.

Dr. Anthony Orsini (28m 49s):
And the trust has to go also downwards. So there are so many managers and leaders in bosses that I’ve had
where, I know the way that the way they stay up top, they believe in a way to stay up top is to keep
everybody down. And the best bosses I’ve had were ones that, you know, would hire Anthony Orsini and
then say, when I have another accomplishment, I’m going to take the credit because I hired him and there’s a
big difference. And as the audience knows my daughter Summer, she also works for VaynerMedia.

Dr. Anthony Orsini (29m 21s):

We had the episode with Claude on that atmosphere that Gary has started in that you are able to do that
people wanna work there. Right? I mean, how do you build that trust and loyalty for, with the people that
work for you?

James Orsini (29m 34s):
The interesting part about the Sasha group, is that we over index on senior people. So when I came to the
Sasha, I mean, I took me six VPs and SVPs is over to recognize people that I took over at each one of them
were running a portfolio of a business bigger than the Sasha Group. And I had a half a dozen and most were
like, Hey, how are you going to make any money? I, you know, all of these people making all of this, you
know, big salaries and, but I knew what it was that we were trying to build. And you know, the people that we
were servicing wanted to hear from senior people on the other end, a, a, a consultancy by it’s nature, you
know, Gary gave me the, the, the creative Liberty.

James Orsini (30m 12s):
They take the cream of what I saw at KPMG , Goldman Sachs, interbrand or Saatchi and pull kinda those
things together to form what it was that the Sasha group is and does for its clients, I’m big believer in a
succession planning. And you should have that or not feel threatened by it. You know, if I were to hit by a
bus and you know, one of those leaders is going to run this company. That’s important and you have to be
really comfortable in your own ability to do that.

Dr. Anthony Orsini (30m 41s):
That’s exactly right. The bosses that are worried about keeping people down are often insecure and worrying
about it, but I know you, and I think the reason why people stay loyal to you and you build so much trust, is
that even at work, I know this from my daughter, you’re just a genuine person, your James right? I mean,
everybody knows you, if you have to tell everybody you’re the boss, then you probably not doing a good job,
right? How do you build that loyalty with your employees?

James Orsini (31m 7s):
I tell people that I lead mostly because people choose to follow not because I get on the desk and say, Hey,
I’m the CEO or I’m the COO, and you need to listen to me. So that happens. I’m in touch with every boss I’ve
ever had. Listen to that statement. I am in touch with Every boss. I had ever had, and I left, although you
went through a line of Company. So obviously I resigned, left a lot on all of them, but it, my cell phone, I can
call even the first guy who hired me out of college, Larry Jansen from KPMG, you know, because I left on
great terms.

James Orsini (31m 44s):
And that is a lot of the advice I would give to people, even when there were resigning or looking to resign, I
would like, you know, I understand that the notice is two weeks, as Gary says, and I’ve really hung on to this
doing the right thing is always the right thing.

Dr. Anthony Orsini (31m 58s):
That’s what I tell my kids all the time, right? Is that right or wrong? As always, while you, you can rationalize
away from it,

James Orsini (32m 3s):
You know? And I can tell them from experience. I understand they want you over there. They will never want
you more than the first day that they want you. So just so you know that I’ll tell them that, you know,
everybody wants you today. There’s always the need today. And you need to tell him that you are going to
start there next month. The good news is you’re coming. The bad news is, is it’s the next month. And if they
want you that bad, they’re going to accept that. And I’ve done that time and time and time again, when I left
into a brand to go to Saatchi and I gave three months notice, and, you know, I left Saatchi to go to Sito
Mobile I gave three months notice, you know, three months was a long time, know your kind of leaving and
walking out the door, but it was the right thing.

James Orsini (32m 43s):
And they said, James why are you doing this? I said, because you would want me to do it to you. If it was
different, you would want the same thing. You know, I also think that giving them people or helping people,
and this is why get along so well, I think with Gary because he genuinely loves to help people as do I even
doing it, even when there’s nothing in it for you seemingly at that moment, there’s no quid pro quo, right? It’s
I happen to be in a position to help. And therefore I am, you know, now, is there an expectation if I were to
call you fourd months from now, you should be taking my call.

James Orsini (33m 18s):
Absolutely. But we don’t do it with that notion of a favor bank per se.

Dr. Anthony Orsini (33m 23s):
That’s a great answer. Or two more questions. Because I know you gotta go. So one of the questions that I
teach, communication skills, especially a conflict resolution, et cetera, we talk about active listening and I
saw quote that you wrote that somewhere. Listen more than you speak. Just expand on that. Just briefly.

James Orsini (33m 41s):
When I went to VaynerMedia as the oldest guy in the building, I think at the time, the average age was 26. I
didn’t really know anything about social media. Gary gave me great advice. He was like, I want you to just
kinda breathe. I don’t need you in every room or making a decision or telling us how to do it. I want you to
breathe my company is just take a few months and taken all in. I would learn a lot. You know what I mean?
That’s the other thing, like its just not too old to learn. Do you have this wisdom and experience?

James Orsini (34m 11s):

Yes, but I certainly became relevant in my kids’ lives because they’re all the sudden I was telling them what’s
coming up next on Snapchat. You know what you know, there is times to learn. So I do listen more than I
speak just so I could, you know, help connect those dots that we talked about earlier. I just wanted to see
how it comes together. And then I’d like to think that my input is a thoughful.

Dr. Anthony Orsini (34m 37s):
Speaking of they have 26 year old average age or the millennial and generation Z this leads, me to my last
question. And I asked Claude the same question. So there are a little different than we are. The millennials
generation Z is our kids are both. And most of those are little, in my opinion, in a little bit more impatient than
we are. Some of them may be more used to texting. Then they are speaking in communication. At least
when I’m training young physicians, I find that their communication skills or not what they should be.

Dr. Anthony Orsini (35m 9s):
I ask Claude this question. What advice do you have to the young person who really wants to do more for
the company who wants to speak to their manager or somewhat higher up and say, Hey, I’d like to do more. I
would like to move up, but not necessarily a raise, but you know, I want to advance a little bit. What advice
can you give them about that conversation? How should that go?

James Orsini (35m 30s):
Two things. One, I want to reverse it and the speak to the people who are getting those requests and
recognize my observations. I dispell alot of notions about millennials. Okay. I did not see them as lazy and
self centered. I mean they’re smart, they’re inquisitive, they’re collaborative, they’re hungry. So why not
harness that difference from our generation, right? Or rather, rather than stifle it. So one embracing the
differences and you know, not to get off on a tangent, but certainly we as a country or not doing that really
well.

James Orsini (36m 6s):
Like if you’re not like me that’s a really bad, bad, bad problem. Right? So embracing the differences two we
encourage an open door policy, you know, I probably spent more time with people putting in 15 minutes on
my calendar simply to try and figure out what it was that a chief integration officer did or what does chief
operating officer was there to do? Do you, you know, and in most other company’s those senior levels are
kept in a corner office. You don’t get access to them.

James Orsini (36m 37s):
Okay. You just, you just don’t, you don’t even go to The when I was at Saatchi, most people didn’t come to
the 17th where I sat next to the chief executive officer and chief creative officer or chief strategy officer and
me, and we had this glass off areas and you didn’t come there, you know, unless you’re summoned to be
there. Not here at VaynerMedia they had like scheduled 15 minutes. So like, I am just, you have to introduce
myself, find out what is it you do James you know, what do you do here to do so gathering that information is

important.

James Orsini (37m 8s):
Recognizing I asked them to do an SSP matrix, strength, skills, and passions. Okay. So it’s a reflective mirror
where you could look at yourself and you’re going to tell me honestly, with your strengths, skills and passions
are, and then I will tell you where that fits in our company as opposed to okay. James yeah, I think I’m ready
to be a creative today. And I said, aren’t you going to be in the strategy department? And they said, yeah,
yeah, I’m ready to try being a creative.

James Orsini (37m 39s):
I said, well usually you’re either born creative or you know you went to Miami school design or something.
You don’t just kind of flip a switch and say today’s today I become creative, right? This is where using your
strengths, skills and passions. If you are strength, skills and passions, don’t align with a creative director. I
don’t see a lot of hope for you finding your way there. So the NSSP matrix has really opened the eyes to
many of these younger people that say, Hey, you know what?

James Orsini (38m 9s):
I am passionate about that. And now, now I can find my way there because I have a skill in it. And I’m getting
stronger in that.

Dr. Anthony Orsini (38m 18s):
Let’s go with that. So now you are a young millennial. You want to talk to your boss, you look at your
strengths, your skills, your passion. If you think you’re in line and now you need to get up enough energy to
go into your boss. And you say, how do you think that conversation should go as the boss? If you said, well,
if he or did it really well

James Orsini (38m 37s):
In the SSP matrix, I just kind of lead them from themselves. I then help them position the conversation,
right? So there’s another form of advice. If your one of these millennials don’t go, you know, boldly in where I
would know, man has gone before, find yourself a mentor to help you are going to flesh this out. Now your
going to be like Listen I did my strength, skills and passions. I think I could align nicely with that position over
there. That’s open. And can you help me maybe even role play that you look your whole profession right now
is on role playing, right?

James Orsini (39m 12s):
So you know the importance of that and how much you could learn from that, would you mind role playing or
if I know, I know you’re not the one that I’m supposed to ask when I’m gonna run this by you and this way,
can you Q and a, this with me, I do this with my wife to, you know, hen she’s a looking to do something at
work, let her do a little role play and being honest, you know what? I don’t see it. I don’t see you. haven’t

made us strong enough compelling case for why this should be.

Dr. Anthony Orsini (39m 37s):
Great. That’s great advice that a young person, so James was, this was a lot of fun. And I want to thank you
so much for taking time out of your crazy crazy schedule, but it’s always fun talking to you. Can’t wait for this
to air because, you know, I promise my audience two things, every single episode in that’s to inspire, which
you certainly did because your career is inspiring. And you gave a lot of advice about communicating both as
a boss and as a young millennial who was trying to go to increase their career.

Dr. Anthony Orsini (40m 7s):
And I just want to say thank you. I think my audiences in a real treat when this airs, so thank you so much.

James Orsini (40m 13s):
It was great being on. I hope that they do find some value with it. You know, they can follow me or find a lot
of what we talked about. I wrote about in medium, whether it’s to delegation stuff or how to work with
millennials, it’s all on James Orsini in media, and James Orsinion LinkedIn and Instagram. And I am
@Jimmy the pencil on Twitter. Yeah. I wanted to ask you about the Jimmie the pencil thing. That’s it. We
have a story for another day or you actually do remember me with the pencil thin Clark Gable mustache.
When I combine with the fact that I started in accounting in the pencil.

Dr. Anthony Orsini (41m 12s):
Fantastic. All right. Great. Well, thank you so much. If you enjoyed this podcast, please go ahead and hit.
Subscribe to podcast is now available on Apple, Spotify, Amazon now, and Google podcast. If you like to get
in touch with me or find out more about the Orsini Way I can go through the Orsini way.com and you can
reach me through that. James thank you again. It was an absolute pleasure and I will see you hopefully
soon.

James Orsini (-):
Hopefully a Florida.

Dr. Anthony Orsini (41m 14s):
Yes, that would be great.

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