CHAPTER 8

Understanding the Heart Leader Triad: Helpers, Entertainers, and Artists

Heart Leaders—whether Helpers, Entertainers, or Artists—share certain character traits involving how they feel about themselves and others. Both their greatest strengths and greatest weaknesses are their emotions.

Type Two: The Helper

Leaders who are predominantly Helpers have strong feelings for others. Ironically, this very positive attribute can also be the source of many of the challenges they encounter. Helper Leaders can tend to overexpress their positive feelings toward others and dismiss their negative feelings in their attempt to deal with the challenges they face at work. Their sense of self is that they are sensitive, caring leaders, yet when they are derailing, their acts of kindness and care are not free; they want something in return. At some point, Helpers who derail come to believe they should get back in respect and kindness what they gave out. This is why leaders who demonstrate the derailing side of the Helper type often come across as needing to “buy” respect and admiration; they will see to it that others admire and respect them. Not only are they effective in getting others to accept that they have no choice but to show them admiration and respect, but they are also very good at making others feel guilty if they don’t reciprocate. Derailing Helpers are also unaware of the pressure they can put on others; there always seems to be a silent expectation; they are always looking for more attention, a bigger response.

Mature Helpers, on the other hand, are considerate and genuinely the most sensitive and caring of all the personality types. Because they have strong feelings toward others, they will go out of their way to help their employees, their team, their boss, their clients—everyone. They are passionate about selflessly serving others. As they derail, however, Helpers can become dishonest about the presence of their aggressive feelings; consequently, they rarely see themselves the same way others see them, namely, as manipulative. Derailing Helpers respect and admire others but always with strings attached. Even though they have strong needs for inclusion and affection, they are careful not to overexpress this need.

At their inner core, Helpers can have a problem with their identity. Derailing Helpers often deny their aggressiveness toward others and frequently conceal their hostility even from themselves. In fact, the only time they act aggressively is when they have convinced themselves they are behaving this way only for someone else’s benefit. To admit their aggressiveness contradicts their self-image and potentially alienates the people they may need later. Derailing Helpers therefore deny their selfish or aggressive motives or interpret them as appropriate. As they perfect this mode of leadership behavior, the distance between the Helpers’ motives and behaviors becomes significant. The result is that they tend to force others into situations in which the Helper controls everything, which can cause those who are being controlled to become frustrated because of the control and the sense of being obligated to show the Helper gratitude. The major focus of derailing Helpers, then, is on themselves, although they never want to think they are giving this impression to others or think of themselves this way.

Mature Helpers

• Prefer close relationships.

• Support and actively listen to others.

• Are warm, accepting, and friendly.

• Work slowly and cohesively with others.

• Tend to be agreeable, steady, calm, and supportive.

• Share personal feelings.

• Demonstrate effective coaching skills.

• Handle conflict effectively.

• Encourage support from others.

• Prefer to be on a first-name basis.

• Are more relationship oriented than task oriented.

• Are generous, unselfish, and show respect and care for others without strings,

Average Helpers

• Tend to talk more about their own feelings than those of others.

• Talk more about care, respect, and admiration than truly executing these traits.

• Are emotionally demonstrative.

• Give attention to others to the point of flattery.

• Can be solicitous to the point of meddling.

• Interfere a lot under the guise of caring.

• Try to control those they have “invested” in.

• Want people to depend on them.

• Want to be informed about everything.

• Like to be sought out for advice.

• Expect to be constantly thanked and honored for the good they bring.

Derailing Helpers

• Complain a lot and are often resentful.

• Disguise their motives behind friendly gestures.

• Are manipulative and self-serving.

• Try to make people feel guilty.

• Undermine others by disparaging them.

• Control others to the point of being domineering.

• Feel entitled to get what they want.

• Are disappointed when favors are not repaid.

• Feel victimized and used.

• Rationalize their responses to others’ ingratitude.

To move toward increasing levels of executive maturity, Helpers need to follow the sequence presented on the Enneagram as: 2 4 1 7 5 8. In other words, if you are coaching mature Helpers, one of your objectives is to help them create a compelling and rewarding path that enables them to start to take on the mature attributes of the Artist (Four). Mature Helpers already accept the presence of their negative feelings as completely as they accept their positive feelings. Because they have become emotionally honest, they are able to express their full range of emotions. They do not play the conditional respect game; they have learned to accept others unconditionally. Respect and admiration are given to them because of who they are, not what they have done for others.

Derailing Helpers, on the other hand, when they are not able to spiral toward greater maturity, run the risk of taking on even more immature characteristics, starting with the derailing traits of the Driver (Eight). Their negative progression on the Enneagram runs like this: 2 8 5 7 1 4. The major issue with derailing Helpers is that they have not come to grips with their aggressive feelings. They resent those who are ungrateful to them and are quick to strike out at those who have not responded to them the way they wanted.

Helper Leadership Style

When they are mature, Helper Leaders enjoy compatible relationships with their employees, team, peers, boss, and clients. They show patience and staying power, and they are motivated to make relationships work. Helpers are generally uncomfortable with conflict unless they are moving toward greater maturity. They are vigilant about how others complete tasks but will rarely say anything negative about what they observe; this is typically seen with average Helpers. When they are mature, Helper Leaders are great coaches and teachers because they are selfless in their need to help others. Helpers seek inclusion and desire to work with people on a first-name basis. Mature Helper Leaders tend to seek more in-depth friendships at work than the other personality types. They are also great listeners and expect others to listen as well. They are open and expressive about their thoughts and feelings, and likewise they expect the same from others.

Tips for Coaching Helpers

• Take the initiative to show you are interested in them as people. Ask about what’s important to them as leaders and individuals; then support them in terms of their stated needs.

• Mature Helpers want to work with you because they know they can increase their chances for even greater success, but, because they sometimes will understate their goals and passion for achieving them, you may have to work closely with them to learn the specifics of who, what, when, where, why, and how. As a coach, be careful not to exaggerate the extent of interest you have in helping them. If Helpers sense you are coming on too strong, they can become disappointed and distant.

• Be patient and encourage the Helper to open up about unstated goals. Helpers tend to verbalize spontaneously about other people’s goals, such as their own boss’s. It is critical you keep them focused on articulating their own goals so that you can be in a better position to help them achieve their goals.

• If you agree on a development goal and action steps and they begin to take action, make sure to check back in soon to see how they are progressing and if they have any hesitancy about the validity of the goal or action steps previously agreed to. Sometimes, Helpers will agree prematurely in order to avoid a potential conflict. Use these opportunities as a way of showing that airing disagreements can be done effectively up front, in an open, honest, and professional manner. Helpers need to develop a reference reservoir where they see that mutual respect can be given and received, even in the face of conflict.

• Helpers tend to be less disciplined about time. Make sure you give them enough time to execute their development actions. Be patient, and don’t force them to make decisions too quickly about anything during your coaching engagement with them. You will have more success as their coach if you move slowly, cautiously, casually, and informally.

• Show you care. If you listen and are responsive to the Helper, you will sometimes get them to share their negative feelings. Remember, Helpers tend to overexpress their positive feelings and underexpress their negative feelings. Your candid openness and honesty will bring you what you really want to hear, and this can be highly motivational to the Helper.

• Be patient. Helpers use opinions as opposed to facts to avoid the risks associated with making important changes. If you have built rapport, trust, and credibility as their coach, influencing their commitment to action should not be difficult. Helpers sometimes will ask for a personal guarantee that the action you want them to take is the correct one. You cannot offer a guarantee because the guarantee is much more the result of Helpers’ decision and commitment, but they want your support and expert guidance.

Type Three: The Entertainer

Leaders who are predominantly Entertainers are perhaps the most driven to succeed. Believing that they will be admired and respected only if they deliver results, Entertainers become fixated with success and appearing successful. In essence, success becomes the central component of Entertainers’ self-concepts. Everything else becomes a secondary priority. Their singular focus on fame and recognition allows Entertainers to thrive in organizations where style is seen as more important than substance and where symbols win out over reality. If an Entertainer is in charge of an organization, he or she may try to create such an organization.

Mature Entertainers gain the respect of others because of their drive, determination, and hard work. Other people become inspired by the dedication and energy of mature Entertainers. Through their own efforts and their effects on others, mature Entertainers can accomplish tasks that were thought to be impossible. As they begin to derail, however, Entertainers direct more effort toward image building than task accomplishment. Instead of accepting who they are and focusing on working hard, derailing Entertainers focus their efforts toward appearing like winners. They study how to dress, talk, and network like a winner. However, at the end of the day, derailing Entertainers have neither achieved success nor developed an authentic inner core. Given the precariousness of their image, derailing Entertainers become jealous and hostile toward anyone who challenges their success. Incapable of producing any tangible evidence of their success, derailing Entertainers may resort to hostility and manipulation to deal with anyone who challenges their projected image.

At their inner core, Entertainers are out of touch with their feelings. Connection with their true feelings and self is lost because their energy is directed toward building their social image. Entertainers fear that their true self is unworthy of respect and admiration, and as a result they turn to their successes and image to gain the respect and admiration of others. As Entertainers derail, the disconnect between their true self and projected self becomes greater. Instead of developing their inner core, derailing Entertainers become fiercely competitive for all forms of success and prestige, turning every situation into a competition. Entertainers become so focused on the outcome—winning—that they overlook how they achieve success, opening the door for unethical and illegal practices. Entertainers also have tremendous difficulty dealing with failure. Because failure directly challenges their self-image of success, Entertainers may devote enormous amounts of energy into trying to turn unsuccessful projects into successful ones. Instead of walking away from lost causes, Entertainers may pour more and more resources into a sinking ship. Immature Entertainers may also direct enormous amounts of energy toward sabotaging and attacking those who are more successful than they are. Instead of finding ways to be more successful themselves, they seek out ways to undermine the success of others. As derailing Entertainers deteriorate, they run the risk of becoming superficial, narcissistic, and completely incapable of empathizing with anyone’s feelings or needs.

Mature Entertainers

• Are self-assured, confident, and charming.

• Are direct, fast-paced, and enthusiastic.

• Listen and speak well.

• Persuade and motivate people.

• Can be influential and popular.

• Adapt well to changing conditions and remain optimistic.

• Desire self-improvement.

• Know their strengths and weaknesses.

• Can be dramatic in their actions and opinions.

Average Entertainers

• Are pragmatic, efficient, and goal-oriented.

• Are hypercompetitive and believe winning is the most important thing.

• Can be manipulative and calculating.

• Value style over substance.

• Constantly worry about how other people see them and the image they project.

• Constantly compare themselves to others.

• Have an inflated sense of self, which often leads to grandiose expectations and arrogance.

• Exaggerate accomplishments to draw attention to self.

Derailing Entertainers

• Are immoral, untrustworthy, devious, and jealous.

• Are opportunistic and exploit others.

• Do not tolerate others winning.

• Undermine those who have moved ahead.

• Often stab colleagues in the back for personal gain.

• Manipulate others to achieve their ends.

To move toward increasing levels of executive maturity, Entertainers need to follow the sequence presented on the Enneagram of 3 6 9. In other words, if you are coaching a mature Entertainer, one of your objectives is to help them create a compelling and rewarding path that enables them to start to take on the mature attributes of the Disciple (Six). By learning to commit to someone besides themselves, Entertainers learn that more can be accomplished by working together than against one another. Taking on the attributes of a Disciple also teaches Entertainers that commitment to others does not imply that their own self-image is diminished. Mature Entertainers accept who they are and no longer need to achieve success or appear successful to feel good about themselves. Because they feel good about themselves, they no longer feel the need to sabotage others who are successful. They realize that the success of others does not take away from their own success. This outlook enables Entertainers to gain the trust and commitment of others. The respect and admiration that Entertainers seek are now given to them because of who they are, not what they have achieved.

When derailing Entertainers deteriorate, they begin to take on the immature characteristics of Arbitrators (Nine). Their negative progression on the Enneagram runs like this: 3 9 6. When derailing Entertainers begin to take on the characteristics of Arbitrators, they further lose touch with their feelings. Whereas immature Entertainers are driven by their hostility, derailing Entertainers take on Arbitrator characteristics and lose touch of their hostility. They are left feeling nothing. Without their hostility to drive them, deteriorating Entertainers are without zest or energy. They are no longer motivated to accomplish anything or even to project an image of success, a task they were formally obsessed with.

Entertainer Leadership Style

When they are mature, Entertainers can win over people at all levels of an organization, whether they are subordinates, teammates, peers, bosses, or clients. Entertainers are goal directed, optimistic, and fast paced. Additionally, Entertainers are great at selling themselves and their ideas. Entertainers are also capable of leveraging ideas and innovations from everyone throughout an organization. Feeling that desks confine them, Entertainers typically move about the office talking to nearly everyone from the custodian to the boss. Entertainers are good at getting people to open up and prefer to be on a first-name basis with people. By brainstorming with everyone, Entertainers can bring out good ideas that may have never surfaced. Because Entertainers are naturally talkative and people oriented, they often seek out visible leadership positions where they can achieve popularity and recognition.

Tips for Coaching Entertainers

• Ask questions about their opinions and ideas. Letting Entertainers share their vision shows that you respect them enough to give them your time.

• Look for ideas they find exciting, and work with them to shape their ideas into successes.

• Discussing your ideas in a stimulating, entertaining, fast-moving, storytelling manner is the best way to get the attention of Entertainers. Motivational stories about people and situations that support your ideas in a positive way are effective ways of influencing Entertainers.

• Supporting your ideas with the opinions of others is more effective than facts and details when trying to convince Entertainers of your point. Show how other people and organizations have benefited from the actions you are asking them to take. Entertainers respond well to actions that lead to recognition.

• Be sure to work out the details of an idea. Entertainers tend not to focus on the details. Focusing on the who, what, when, where, why, and how can strengthen their ideas and increase the probability of success. If they are not interested in the details, summarize what’s been discussed, and make suggestions for improving the idea. You may need to pin them down on details later.

• Ask what you can do to help them come up with a plan of action for implementing their ideas.

• Don’t compete or argue. Disagreements threaten Entertainers to the point that they often become fixated with winning an argument rather than finding a solution. Rather than saying “I disagree,” opt for, “Here’s another alternative” or “Here’s another option you might want to consider.”

Type Four: The Artist

Leaders who are predominantly Artists are perhaps the most creative leaders. The creativity of Artists is driven by their deep understanding of themselves. Unfortunately, this tendency to engage in deep introspection can lead to many problems. Derailing Artists often feel they lack self-worth. This, in turn, makes them uncomfortable in their social roles and relationships with others. As a result, derailing Artists may avoid carrying out their leadership responsibilities and let their subordinates direct themselves. Artists can become so self-involved that they lose touch with everyone but themselves. They stop paying attention to the needs of others and exist in their own world. Artists in this state can make illogical, unrealistic, and counterproductive demands of their subordinates, teammates, and bosses. Artists may not even realize how off the wall or unreasonable their demands are. Although Artists can produce works of beauty on their own, they have difficulty working with others to produce works of beauty. This is due to their intense self-focus. By spending so much time and energy diving into themselves, Artists have little left to devote to others. Consequently, Artists may not notice the needs of others and neglect coaching and developing people. In the end, they may resort to doing things themselves.

Mature Artists have the potential to bring out the most in people. Because they can sense in themselves the depths to which people can descend as well as the heights to which people can ascend, Artists are perhaps the most aware of the potentials and predicaments of human nature. Their ability to understand what is at the core of each person enables Artists to move people deeply. This in turn allows Artists to be effective champions of causes. As Artists become increasingly mature, they draw less inspiration from themselves and more from others. By forming meaningful and deep connections with other people, Artists become more grounded in reality and are better able to shape it into what they imagine. As Artists derail, however, they direct increasing amounts of energies toward themselves and less toward expressing how they feel to others. Instead of channeling their feelings toward building things that can move and inspire people, Artists escape into their imaginations. The more withdrawn Artists become, the more they lose touch with reality and their ability to shape it.

Like Helpers and Entertainers, Artists face problems with their identity. Artists believe that they are different from other people. This desire to understand why they are different fuels their deep introspection. If Artists cannot determine why they are different, they run the risk of self-hate. Seeing themselves as defective, they become hostile to themselves. Derailing Artists are highly self-destructive leaders. Their constant focus on themselves and their defects leads them to lose touch with other people. With their inability to focus on other people, derailing Artists often alienate other people. They allow whatever emotions they experience at the moment to surface. Although Artists believe this is a sign of their being genuine, others interpret this as a sign that they are prone to frequent mood swings. The tendency for Artists to have manic highs and debilitating lows puts their subordinate on edge; they never know what to expect. This instability also makes it nearly impossible to present a clear vision and direction to subordinates, teammates, colleagues, and clients. Derailing Artists frequently shift their priorities. Consequently, a million projects may be undertaken, but none are completed.

Mature Artists

• Are creative and intuitive.

• Are introspective and comfortable being alone.

• Are sensitive to themselves and others.

• Respect others and show compassion.

• Accept their feelings and act authentically.

• Can reveal their feelings through other media.

• Can openly discuss their fears.

Average Artists

• Are moody, easily hurt, and not very practical.

• Are imaginative to the point of fantasizing.

• Can be self-absorbed to the point of shyness.

• Express their emotions indirectly.

• Withdraw from conflict.

• Have difficult expressing their feelings to others.

Derailing Artists

• Are depressed, overly negative, and angry at themselves.

• Constantly feel drained and fatigued.

• Can’t discuss their ideas or feelings.

• Remain detached from people with no strong connections.

• Avoid any kind of responsibility.

To move toward increasing levels of executive maturity, Artists need to follow the sequence presented on the Enneagram of 4 1 7 5 8 2. In other words, if you are coaching a mature Artist, one of your objectives is to help them create a compelling and rewarding path that enables them to start to take on the mature attributes of the Perfectionist (One). By taking on the characteristics of Perfectionists, Artists move out of a world of subjectivity and self-absorption to a world of objectivity and principled action. Focusing on objectivity and action will enable Artists to build real and tangible success. Success, in turn, produces positive feelings and emotions and counters the tendency of Artists to experience negative emotions. As Artists take on the characteristics of Perfectionists, they accept that they must submit to values and expectations. This will enable Artists not only to feel a sense of connection with others and decrease their sense of isolation, but also to remain focused on objectives. The more Artists take on the characteristics of Perfectionists, the more self-disciplined they become. By not being controlled by their emotions, Artists learn how to perform consistently despite personal ups and downs.

When derailing Artists deteriorate, they first take on the immature characteristics of Helpers (Two). The deterioration of Artists follows the path of 4 2 8 5 7 1. Artists who derail have an overwhelming desire to escape themselves and their introspection. They accomplish this by becoming dependent on another person who provides them with the direction and understanding they need. The problem with this dependency is that they are no longer capable of leading others. Instead, they become the enforcer of another person’s will.

Artist Leadership Style

Mature Artists are good at stimulating creativity. They are able to see how each task fits into the greater whole. As a result, Artists are good at mixing things up and altering tasks to create novel products and services. If innovation is needed, mature Artists can help stimulate it in others. Artists are also cautious and methodical leaders. They tend not to make decisions based on impulse. Instead, decisions are made after much deliberation and introspection. Artists are very good at asking themselves questions and exploring problems from multiple angles. Additionally, Artists tend to lead based on their own ideals and conviction. This offers other people a sense of stability because knowing the values of an Artist enables others to predict their likely actions. Artists, however, are not perfect leaders. Due to their deep deliberation, Artists tend to be slow decision makers. As a result, they may not be the most suited for leadership positions in time-sensitive industries or operations. Furthermore, Artists fear failure more than other personality types and are quick to become negative when faced with setbacks.

Tips for Coaching Artists

• Build a supportive, safe environment. Artists tend to be warm, approachable people when mature, but distant to the point of being uncommunicative when immature. If your Artist coachees are not fully mature, take time to make them feel accepted and adequate. Don’t force them to take action too quickly, or they will reject you and your ideas. Patience is the key when dealing with Artists.

• Take your time. Because Artists tend to act slowly, it may take longer to build a relationship with them. Demonstrate that you support the Artist’s feelings and ideas. Because immature Artists often have negative self-worth, they may interrupt criticism of their ideas as an attack on their self-worth.

• Build their confidence. Immature Artists tend to view themselves as inadequate. Consequently, one of your primary objectives as their coach is to build their confidence. There are a number of ways to accomplish this objective. First, Artists can be reminded of their past successes. Often, Artists become so negative that they focus only on past failures. When you draw attention to successes, Artists begin to see that they can be successful despite previous failures. Artists can also be given small developmental exercises, something as simple as “Brainstorm 10 possible ways of dealing with X problem.” By giving Artists more focused, proximal goals, you can better direct their efforts. This will prevent Artists from trying to solve big problems out of the gate. Instead of becoming dissuaded by their inability to solve large-scale problems and getting caught up with their grandiose visions from solving them, Artists are actually able to solve a problem. This helps build their confidence because, instead of getting caught up in their imagination and inaction, Artists begin to learn the importance of breaking bigger problems into smaller, more approachable problems.

• Acknowledge the importance of their intuition, but identify other factors that help their decision making. Because Artists tend to rely on introspection, they often base their choices on intuition. Consequently, it is important for you to initially support their gut feelings. Discuss times in which their feelings guided them to the correct decision. Also identify the cues that likely affected their feelings. This way, Artists begin to see that their intuition is a reaction to cues in their environment. By doing this, you can help Artists become less dependent on their feelings. Artists learn the importance of supplementing their feelings with additional information when making decisions.