UVA-BP-0425

A GREAT LEADER:
A CREW MEMBER’S PERSPECTIVE

What makes a great leader? How does he bring a group of individuals together to create
a unit that is capable of achieving far more together than would ever be possible if the abilities of
the members were simply summed up? Leaders that have the uncanny ability to do so seem to
consistently conquer goals that would seem almost impossible otherwise. As author and world
class sailor Peter Isler wrote recently in an article, “The teamwork and leadership required to win
yacht races at the highest level can be easily transferred to the business world.” He goes on to
add, “It is no coincidence that some of the most prominent and prosperous CEOs and executives
in America are extremely successful yacht racers. In both business and at the highest levels of
competitive yachting racing, only the best-led, best-trained, and mostly highly motivated teams
win!”

In my career as a professional yacht designer and yacht racer, I have been fortunate to
experience both extremely effective and ineffective leadership. From a cursory point of view,
the leadership style of both the successful and the unsuccessful often seemed quite similar, yet
the results were dramatically different. Why is it that some leaders have been and continue to be
successful, while others have not been able to breed success? These are the questions that led to
the creation of this material.

In the America’s Cup, leadership has constantly proved to be the difference between
winning and losing. Great teams have been unsuccessful because they have not had the
appropriate guidance, support, direction, and leadership, while teams with less raw talent have
risen to the occasion when led by a true team leader. An America’s Cup team is an interesting
phenomenon to study. It is essentially a short-lived startup venture that lasts for only three to
four years. In its infancy it is similar to an entrepreneurial startup, with big plans and little
money. As the campaign matures it takes on the appearance of a high tech research and
development program. Not only does the campaign share many attributes of a medium-sized
business facing the competitive pressure of the real world, as it strives to bring its product to
market, on budget and on time, but it is obviously also a professional sports team aimed at a
world championship. It is begun from scratch, but is usually built around a leader whose vision
is taken on board by the teams. His goals become everyone’s goals, and his vision becomes the

This case was prepared by Drew Freides under the supervision of Professor Alexander B. Horniman. It was written
as a basis for class discussion rather than to illustrate effective or ineffective handling of an administrative situation.
Copyright © 2000 by the University of Virginia Darden School Foundation, Charlottesville, VA. All rights
reserved. To order copies, send an e-mail to sales@dardenpublishing.com. No part of this publication may be
reproduced, stored in a retrieval system, used in a spreadsheet, or transmitted in any form or by any means—
electronic, mechanical, photocopying, recording, or otherwise—without the permission of the Darden School
Foundation.
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team’s vision. A great leader/skipper will attract the most talented sailors and designers and lead
them to success.

Dennis Conner’s quest for the l987 America’s Cup is an example of the development of
just such a team that yielded incredible success. In 1983, Dennis was unfortunate to be the
scapegoat of the New York Yacht Club. He was the skipper of Liberty, the first yacht to lose
The America’s Cup in the 151-year history of the event. Much of the blame was pinned on him
for losing. In all honesty, he did an amazing job of putting up an incredible fight in a
competition in which he was totally out-matched. He and his crewmembers competed hard to
the very end, and went down with a huge fight. Dennis1 summed it up best when Australia II
crossed the finish line clinching victory, “We sailed well, didn’t’ we?”2 The entire crew had to
agree. When it was over, the emotion that he displayed was one of the key drivers that basically
forced all of the crewmembers to agree to race with him to help win the Cup back. He was a real
person with human feelings and understanding. He was tough and demanding, yet
compassionate and warm. He was a sailor’s skipper (a people’s leader). He was one of the first
skippers to be a part of the team. He never separated himself from the crew, yet took the blame
as the leader when the team lost.

Dennis Conner and his experienced crew aboard Liberty did a masterful job throwing
every wrench possible at the fast and nimble Australia II, building a 3-1 margin in the best of
seven series before Australia II came back to even the match at 3-3. Conner refused to buckle
against the quicker boat, opened up a lead in the final race, but was unable to hold off the
charging Aussies, as they passed him just before the last mark and went on to win the most
coveted prize in yacht racing, by a slim 43 seconds. From the moment the Cup was lost, Dennis
was driven to get the Cup back for the United States. The New York Yacht Club had always
defended the Cup their way. No questions asked. An incredibly strong culture had been
developed over 132 years. It was always done their way successfully (24 straight times in fact—
dating back to 1851), so no one questioned it. A group of “men with red pants” as they were
referred to, made all of the decisions behind closed doors. No one had any say and no one
questioned their decisions. Crewmembers were decided less by how good they were and more
by whom they knew. There were no tryouts. A crew was chosen by the committee and then
raced on behalf of the New York Yacht Club.

When they finally lost in 1983, Dennis had the opportunity to do it his way. He had the
opportunity to build an incredibly strong team of hard-working individuals. They weren’t
necessarily the best in the world, but they were willing to make a three-year commitment to
winning “The Cup,” as he called it: “These men should be committed for their commitment to
the commitment.” He wanted people who could work together for three years and function as a
team of equals. Everyone’s input was valued. Dennis was unable to get the New York Yacht
Club to change their ways, so he created the Sail America Foundation that represented the San
Diego Yacht Club in the 1987 America’s Cup, not just the stuffy yacht club members.

1
Everyone refers to Dennis Conner as Dennis or DC-once again showing his personal approach.
2
Quoted in Bruce Stannard, Stars & Stripes—The Official Record, (San Diego: Dennis Conner Sports, Inc.,
1987).
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Dennis proceeded to change a gentlemen’s sport into a full-time business. Many didn’t
realize it at the time, but Dennis was creating a value-based leadership.3 Respect, integrity, trust,
and listening composed the baseline principals that the team was built upon. Dennis was a leader
who almost didn’t want to be a leader but was forced to because of his charismatic personality.
People were automatically drawn to his leadership. He never asked for respect, he earned it. As
told from a crewmember who joined the team for the first time:

From the first moment I stepped aboard Stars & Stripes in Hawaii and sailed with
Dennis for the first time, he had my complete respect. It is hard to explain why. I
am not sure if it is because of the way he treated me and the other crewmembers
or because of what he so unassumingly had accomplished. It was basically
everything about him.

I was blown away by the way he would ask me, the youngest member of the crew,
what I thought about different things. I would wonder why Dennis would ask me.
I am not sure if he even intended to actually take what I had to say into account,
but he sure listened intently. He was an excellent communicator. He would talk
candidly about almost anything with all of us. Everyone always felt comfortable
discussing even the most embarrassing or personal issues with him. He had an
ability to speak, yet listen and understand. He could be our father one minute, and
our brother the next.

The sense of mutual respect and a sense of belonging that he created was what
drove all of us to succeed for not only ourselves, but for Dennis. I have never met
anyone in my entire life who was more driven. He was always the last to leave
the compound in the evening, and always the first to show up the following
morning, often before 6 AM. He brought the meaning of the word leading by
example to new heights. He would always tell us that he did not have time to
sleep. He was too scared that someone else would get ahead of him.

It was difficult to get indoctrinated into the ‘team.” To do so, each crewmember had to
prove themselves. Not to Dennis, but to the other team members. Dennis delegated most of the
everyday responsibilities to the rest of the crew. He wanted to create an autonomous team that
could function without his guidance. He thought the crew was composed of individuals who
were well capable of performing their jobs and could motivate themselves. He knew that, just as
he knew how to steer the boat and lead the team better than everyone else, that the crew knew
their jobs better than he did. During the crew tryout period, the crew (more than Dennis) mostly
tested the drive and the ability and desire of a potential crewmember to back up his other

3
In James O’Toole’s book, Leading Change, values-based leadership is described as a leadership style that is
based upon integrity, trust, listening to your followers, and having respect for your followers. One of the key
components to this method of leadership is that the leader cannot compromise the team’s goals and principles.
Individuals who employ this management style typically listen to their peers, encourage opinions, grant ample
authority to their subordinates, and lead by example rather than by power and manipulation. These leaders also
usually are recognized as masterful teachers who inspire trust and hope in their followers, who in turn in most cases
become encouraged to serve, to sacrifice, to persevere, and to lead change.
 -4- UVA-BP-0425

teammates. This was probably the most critical attribute of a team member. The best
crewmember was someone who would always be thinking how not only to do his job, but also to
help the crewmember next to him when things hit the fan. This was a direct reflection of Dennis
and his values. In yacht racing quite often events take place or situations develop that the team
cannot practice in advance for. Therefore, it was critical that the crew could think on its feet
rapidly and work together through a tight situation with very little notice and no preparation.
Everyone on the crew needed to be 100 percent confident that they could count on the backup
and support of every other team member in the hairiest of situations. Dennis kept reminding the
crew that a team could possess power that a group of individuals could not.

Once an individual became part of the team, it was understood that he or she was part of
the family. As one grinder4 was heard saying, “Everyone knows that Dennis would run through a
brick wall for you, so everyone in turn has the same attitude towards him.” This was the flattest
organization structure most crewmembers had ever experienced. A relatively inexperienced
college student was on the same level as some of the most experienced and successful yacht
racers in the world. What each individual said counted! Each member gave the team everything
they had because they felt that they owed it to them. It was everyone’s responsibility as part of
the team.

When the Stars & Stripes team went down to Australia during the fall of 1986, after
almost two years of intense training and practicing in Hawaii, they were a cohesive team with a
leader whom they trusted their lives with. Dennis could have asked any member of the crew to
jump off a cliff and they probably would have done so because everyone trusted his judgment so
much. The team showed up in Freemantle on a mission. Most team members had never seen
such determination as they had in Dennis’s eyes when they landed in Australia. There was a
billboard near the airport that read, “Dennis, if you think you are going to win the cup, keep
dreamin.” That billboard only fueled the fire. By the way, when they left (with The Cup seven
months later), the billboard read, “Dennis, if you dream long enough, dreams come true!”

Stars & Stripes had problems early on in elimination trials. The boat was designed for the
heavier winds forecast for later in the trials. In the light air during the early fall they were
vulnerable. Instead of pointing fingers and creating tension, as was developing in many of the
other camps (such as the NY Yacht Club entry, America II), with Dennis’s encouragement,
direction, and leadership, the defeats only forced the crew to work harder to overcome the
weaknesses. In the press conferences, Dennis was often taking considerable heat. When Stars &
Stripes lost it was always his fault. Never once did he blame it on the designers or the crew. In
fact, the press was giving him a bad rap because he wasn’t comfortable being in the public
limelight. He was more comfortable being with “the guys” than being a public figure. His
response was to shy away from the press, which was interpreted as being rude. Dennis was
never totally comfortable with being “Da Man.”

4
A grinder is a crewmember responsible for supplying the horsepower for turning the winches, which in turn
pull in the sails. They are the brawn behind powering America’s Cup yachts.
 -5- UVA-BP-0425

A brief recount from the bowman of a memorable instance in Australia:

On one occasion, during an elimination race against the team from New Zealand,
I made a major mistake and not only fell overboard, but lost a sail over the side in
the process. Dennis did not say even a word. He realized that the disappointment
on my face said enough. The silence almost killed me. How I wished someone
on the boat would have yelled at me! We of course lost the race because of my
mistake, yet during the press conference when questioned, Dennis refused to
answer. He said ‘As a team we sailed less than satisfactory, and that you (the
press) saw what happened, why do you need to ask me?’ That day was the
culmination of my respect for Dennis. He sat me down that evening and told me
not to worry about what had happened. He knew how disappointed in myself I
was, and how I felt that I had let the team down. He went on to tell me of a few of
his major blunders on the racecourse. He knew how to relate to each and every
one of us.

Throughout the series the team was amazing. They pulled off maneuvers in 30 knots of
breeze that were unheard of in a 12-meter yacht (the yachts raced in the America’s Cup). Eleven
men acted as a single unit. Each maneuver was choreographed like a ballet. At times they even
amazed themselves. Twelve-meter yachts were incredibly undermanned in the heavy conditions
of Freemantle. The boats sailed with 11 crew, while needing 14 to 15 for some situations and
maneuvers. The Stars & Stripes team got around this by switching people around in ways never
done before. Dennis would always question why things were done a certain way. He would
always pose his suggestions as questions. “What do you guys think of this?” If he came upon
resistance he would reply in his usual inquisitive tone, “Why don’t you humor me and try it just
once and see what happens?” Never as an order, but as a request. Ninety-five percent of the
time he was right. He could have just told the crew to do it that way, but instead he wanted them
to figure it out on their own. He always wanted the team’s buy-in. During the race Dennis
would continually ask for input from almost every crewmember. No one was sure whether or
not he cared what they had to say, but it always kept everyone on their toes. He always made the
final decision, and was willing to bare the responsibility of the consequences, but never did so
without the crew’s complete faith and trust.

The crew aboard Stars & Stripes obviously went on to dominate the 1987 America’s Cup
and brought the Old Mug back to United States soil and the San Diego Yacht Club. As one crew
member notes:

The sense of accomplishment that we all had was a feeling that I may never feel
again in my life. It was all due to the efforts, strategy, foresight, and leadership of
Dennis Conner. We were all just along for the ride of our lives. Dennis had
orchestrated a detailed plan that we had to help him execute. We knew that as
long as we did our part and accomplished our jobs properly, our leader was going
to bring home the silver for us.
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The crew aboard Stars & Stripes truly learned what it was like to be a part of an
organization that exemplified value-based leadership. With almost everything that he did,
Dennis exemplified those principles. Even though he created an organization from the ground
up, he did it by changing the rules in the process. He changed the sport of sailing forever. He
was the first to treat it and run it like a business ought to be run. He brought in corporate
sponsors and television. He was nominated as both Time Magazine’s and Sports Illustrated’s
“Man of the Year” for 1987 for his efforts on behalf of the sport of sailing and for bringing The
America’s Cup back home. He knew what it took to change The America’s Cup, and was keenly
aware of what it would take to win. As a leader, he was, and continues to be in the eyes of
everyone who has crewed for him, near perfect. He has many faults, such as a major drinking
problem, a weight problem, and constant problems with his family, but these never seem to get
in the way when duty calls. They only illustrate that he was human just like everyone else.

How Dennis built the organization depicted how an innovative team should be
developed, unlike how it had been done with any America’s Cup team (or any yacht racing team
for that manner) in the past. Everyone on the team had a ton of responsibility and autonomy.
When most crewmembers of the ’87 Cup campaign look back, they note the interesting changes
that took place. Many noted that it was weird the first time for everyone. Everyone had to go
through a distinct period of change, both as individuals and as a team. When each crewmember
began they were looking for direction, as they had experienced in the past. As one crewmember
noted:

I can only speak for myself, but judging from the reactions of others, I think it is
safe to say that each and every one of us had never before been involved in a
racing program or America’s Cup campaign where we were not constantly being
screamed at and told what we should be doing. We were lost at first, with each of
us walking around almost as an unguided missile, not being used to the
responsibility and autonomy that each of us had been given. After a month or so
passed, the changes began to take shape. We all began acting and thinking on our
own, but you could still see the hesitation in everyone’s actions. We each slowly
began to act on our own, doing what we felt were in the best interests of the team,
but still with some hesitation.

As Dennis reinforced our behavior with support and encouragement, soon this
developed into the only way we knew how to act. We instinctively took on
responsibility and went about our business without direction. We no longer
questioned our judgment, whether it was what project we were to be working on
in the morning in preparation for the day’s practicing, or on the racecourse during
a maneuver. Dennis must really have known what he was doing because he took
each and every one of us to a new level.

Approximately three quarters of the way through the ’87 Cup campaign Dennis had a rare
meeting with the entire team, including the shore crew and the sailing crew. This intrigued the
team because this had never happened before in the history of the campaign. This turned out to
 -7- UVA-BP-0425

be one of the most memorable moments of an incredible campaign. As Dennis began to describe
his concept of “commitment,” it was obvious it was coming from his heart. This was the real
Dennis Conner. He explained how everyone had unknowingly raised their own comfort level
day by day. By training hard, day after day, for months on end, in the strong winds and rough
ocean off Oahu, everyone had learned to feel comfortable sailing a fifty thousand-pound 12-
meter5 sloop in 25-30 knots of wind. Despite the man overboards, the sail blowouts, the broken
gear, and even the bruised and battered bodies, the team had made real progress. Dennis pointed
out that each of the crew, by making “a commitment to the commitment” had worked harder as a
group, and together had raised the game to the point where the team was on the verge of winning
the America’s Cup. He added that that was not a position that any team, no matter how talented,
could just walk into. It was a result of an awesome team effort made possibly by the mutual
commitment of the entire team.

Watching the team aboard Stars & Stripes perform on the racecourse was something of
beauty. Often the boat would be racing for minutes with not a word spoken by anyone. Dennis
would tack the boat, and not a word would emanate from his mouth. Stars & Stripes would go
around marks and change sails without a sound from anyone’s mouth. Everyone was thinking
about the next step and what needed to be done to accomplish the task at hand. The
crewmembers often focused on what could go wrong and how to help out the fellow teammates
if need be. One instance that has been indelibly etched in many people’s minds was during a
race against Team New Zealand when a jib that Stars & Stripes had up literally exploded. It was
blowing 25-30 knots, 6- to 8-foot seas, and pieces of the jib were everywhere. In less than two
minutes the crew had a new jib flying and were able to maintain a slim lead over the New
Zealand.

Most crewmembers got goose bumps every time they saw the television footage of this
event. Three crewmembers (one of which was the navigator—which is almost unheard of for
him to be on the foredeck) were up helping the bowman and the mast-man wrestle the old
shredded jib to the deck. The sewer man was already below passing up a new headsail. When
the bowman saw that the others had the old sail under control, he began hooking up the new one.
This was truly a team effort, and clearly illustrates how empowerment and involvement can
enable people to think and react in a way that is incredible. What was more amazing about the
entire ordeal was that not a single scream could be heard. Later the bowman mentioned that he
did remember glancing back at Dennis at one moment and seeing the agony on his face. It was
obvious that he wanted to jump in himself, but he had to continue to steer.

Many don’t realize the level of preparation that went into the campaign. Dennis had the
team practice every maneuver possible (and that he could dream up) and accomplish each with
as little talking as possible. He always accentuated the fact that talking was removing energy
that was required to achieve peak performance. On many other boats, needless chatter could be

5
12-meter yachts are the type of yachts that were raced in the America’s Cup in 1987. Twelve meters is not
their actual length, but the result of a complicated formula that all competing yachts must measure into. It uses the
length of the boat combined with the sail area and a width measurement, and then divides this sum by a coefficient
to arrive at 12 meters. The boats in actuality are approximately 67 feet long.
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constantly heard. Dennis was very critical of this. He felt (and rightly so) that for everyone to
reach “their zone” that concentration was key, and all energy needed to be channeled into useful
actions, not useless talking. When watching the races on television, the difference between a
quiet boat and what is referred to as a “noisy” boat was painfully obvious. The quiet boats were
continuously thinking, while the noisy boats were being needlessly distracted. The level of
confidence was also noticeable. The quiet boat had a felling of control, while the noisy boat
appeared to be very nervous and chaotic. This seems to have been a constant theme for success.

Very few are aware of the fact that the crew aboard Start & Stripes had actually practiced
the genoa failure/replacement maneuver that the team had performed flawlessly. In fact during
the practice when first arriving in Australia, it was a dismal failure. Everyone was giving their
two cents instead of working as a team. In the process, the jib that was being lowered was
tangled in a complete mess, blocking both forward hatches and making it impossible to bring a
replacement sail up from below. Dennis became so disgusted with the performance and actions
of the crew during the practice that he called off the practice and turned the boat home, without
uttering a word. Needless to say, when the crew arrived at the dock, they had thoroughly
discussed what went wrong and decided upon an action plan for future failures/disasters of a
similar nature. It was decided that right or wrong, the decisions (and temporary control) would
be placed in the hands of the bowman. This gave the team direction and organization to solve
the problem, hence avoiding the anarchy and chaos that resulted in the practice. Once again, this
exemplified how Dennis had organized the team. Dennis was not involved in the process at all.
Frankly, he didn’t want to be. He just wanted the crew to do what it took to succeed and think
for themselves at all times. That genoa failure in many ways culminated how the team had
developed.

Another example of the depth and commitment of the teams that Dennis developed was
illustrated in the 1992 defense. The team had tried a full-scale test of an experimental keel in the
defense tails and it was a total disaster. The boat was miserably slow, and to top things off,
Denis had extreme difficulties steering the boat (it was a unique design with a rudder in the bow
and one in the stern with a keel). The Stars & Stripes team obtained permission to change keels
but had to do so overnight in order to race the following day. It was usually a full three-day
project. The team was amazing. All of the shore crew and sailing crew worked side by side
from the moment the boat hit the dock. They worked through the night, and had the change
completed just 15 minutes before the boat had to leave the dock to race. Dennis himself was
there right along side the crew, wet sanding away. Ted Turner would have laughed had his crew
asked for his help. Everyone was so pumped (even though no one had slept) that Stars & Stripes
went out and destroyed the competition in the race. Events like that one continually brought the
Stars & Stripes team together closer than ever.

Dennis had developed an organization that concentrated on people, not policies, systems
and structures. There were times when he did step in, and some would say that this may
illustrate some “situational” leadership, but this point could be argued. When he did so it was
because the situation totally warranted it. No one would ever contradict the fact when Dennis
would momentarily take charge. If he chose to do so it was because an immediate decision was
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required, and the leader, who always had our best interests in mind, had to make it. To prove his
sincerity and integrity, if the decision was correct, he would say “the team this” or “the team
that.” If it was one of his occasional mistakes, it would be “I made a mistake, don’t blame the
guys!”

In discussions about how the team operated and functioned both on and off the water
people have been astounded how the team was organized. Many old-time yachting greats do not
understand how a yacht could be raced with, as they call it, “anarchy.” Many would respond
with, “Who was in charge?” “If Dennis didn’t tell the crew what to do, then how did everyone
know what their jobs were?” This clearly explains how Dennis has changed the sport of yacht
racing and why he has been as successful as he is. This also shows why Dennis Conner
continued to be one of the most successful skippers of all time. He has gone to the next level of
leadership in competitive sports.

Talks with many crewmembers since the’87 Cup campaign reveals the importance that
the culture, atmosphere, and structure of the organization that Dennis created Since that time it
has been safe to say that a team that functioned as the Stars & Stripes crew did has not been
created (aside from other Dennis Conner teams). There was an incredible lack of real leadership
ability displayed by many supposed leaders. Maybe it was because it was their pleasure instead
of their work, but many CEOs are terrible leaders/skippers on the water. They feel that they
must take control of the boat and bark orders at the crew. They may have felt that was the way
that boats were supposed to operate because of yachting folklore. They couldn’t be effective
leaders in companies that way. One would expect actions like that from sailors, but successful
businessmen should know better. It was amazing how this approach creates an immediate rift
between the skipper and the crew. It emulates the management/employee conflicts that develop
in many firms. In racing yachts these issues emanate from a lack of trust and mutual respect.

There is no substitute for a values-based leadership approach, especially on an extremely

competitive racing yacht. Situational leadership6 may bring results in the short term, but they
will not prevail over the long haul. The organization must have complete buy-in, and everyone
must have the same overall goal in mind. Individuals can not be in it for themselves, separating
themselves from the team and weakening the organization. Once people are aware that they
cannot count on their cohorts to back them up, then the structure begins to break down, and the
power of the team is reduced. The feelings of satisfaction that the Stars & Stripes team had were
incredible. Each member was truly an integral part of the team and became part of a crew that
dominated the competition in every sense of the word. From the ground up, begin with a strong
value-based structure that empowers team members to think for themselves and help each
individual attain a level as a team that would not be possible if we were just a group of
individuals.

6
Situational or contingency leadership is what is considered to be the counterpart of values-based leadership.
This leadership style is characterized by doing what it takes to get the job done. The end essentially justifies the
means with this type of leadership. Proponents of this style state that it is difficult to lead with a values-based
approach because situations often dictate that decisions have to be made and that there is not an opportunity for the
democracy of a values-based system.