Emotional leadership is the Achilles’ heel of Entertainers. They tend to lose control of their feelings and inner core values. As a result, they may derail by becoming highly competitive and growing fonder of image-building than of building meaningful relationships and inspiring people. How can leadership coaching fix that?

“I always knew I was destined for greatness.” – Oprah Winfrey.

The Entertainer leadership trait describes an emotional leadership style fixated on success. Nothing is more important to an Entertainer than being successful or appearing successful. This basic need is the source of most of the Entertainer’s leadership strengths and weaknesses.

Entertainers fear failure. They also fear their accomplishments going unnoticed, resulting in others not recognizing their greatness.

Being preoccupied with appearing successful may derail Entertainers, causing them to focus on appearances instead of leadership substance.


Entertainers love to sparkle and dazzle.

Immature Entertainers often compare themselves to others. While they understand that they should measure their success and accomplishment against more objective criteria, they can’t resist the lure of competition. Derailing Entertainers like to triumph over others, thus proving their mettle to themselves first and foremost.

By understanding their leadership style, leaders, with help from a leadership coaching specialist, can define steps they can take to improve. Specifically, they can identify the traits they can develop to become better versions of themselves.

Understanding the Entertainer Leadership Type

The Entertainer feels compelled to achieve great things.

“I love that synergy between being entertainers and having people respond. There’s no greater reward.” – Ming Na-Wen.

Leaders with predominantly Entertainer traits must elicit a response from people. And from their perspectives, this response should be admiration, appreciation, and respect.

The basic motivation of an Entertainer is to get to the top and stay there. For an Entertainer, improvement is a means to achieve greatness and elicit admiration.

Failure is the ultimate fear of the Entertainer. For an Entertainer, to fail means to earn contempt and perhaps sympathy instead of adulation and respect.

The greatest thorn in the side of successful Entertainers is when people fail to acknowledge and recognize their accomplishments. Such leaders care as much about being successful as they do about how others perceive their success.

The almost compulsive need to be recognized and appreciated is the greatest weakness of Entertainer leaders. It can cause them to spend more time selling an image to others than crafting the success that should be the source of that image.

Mature Entertainers learn how to deal with this weakness. They learn to accept their limitations and find ways to develop as leaders without comparing themselves to others and treating leadership as a race.


Effective leadership is not a race, but Entertainers often treat it as such.

The Drive to Succeed: A Double-Edged Sword

“Success is almost totally dependent upon drive and persistence.” – Denis Waitley.

Entertainers’ unparalleled drive to succeed is an asset in the hands of mature leaders. Mature Entertainers inspire their followers through hard work, dedication, and persistence. They know how to harness their insatiable appetite for success. Using the energy the drive to succeed gives them, these leaders can accomplish things others may consider impossible.

From the perspective of emotional leadership, however, Entertainers don’t fare well unless they possess adequate levels of leadership maturity. Immature Entertainers are out of touch with their emotions and feelings on the level of their inner cores. This vulnerability causes them to derail. They end up pouring more energy into image-building than meaningful undertakings that forward their leadership and their organizations.

The trigger of immaturity-based derailing is a deep-seated fear of inadequacy. Immature Entertainers cannot suppress the feeling that their true identities are unworthy of the respect and admiration they need. As a result, they hide behind their successes and focus on image-building instead of genuine leadership.

As they get more and more embroiled in useless image-building, Entertainers lose sight of their inner cores. Instead of focusing on their feelings and the impact they have on their leadership behaviors, they redirect their energies outward, engaging in fierce competition with others.

Winning takes on such significance that Entertainers become willing to sacrifice everything on its altar. They’ll use illegal or unethical practices. And they won’t shy away from pouring resources into projects that have already failed or will obviously do so.

The drive to succeed can be a strength and a source of inspiration. It can also lead to misplaced and misguided attempts to create fake leadership identities and useless images.

The Mature Entertainer

Leadership maturity is always the difference between successful and derailing leadership habits and behaviors. Aware of their tendencies to lose connection with their feelings, mature Entertainers won’t hesitate to enlist the help of a leadership coaching specialist to restore and shore up their emotional leadership abilities.

Executive coaching can also help leaders identify their leadership tendencies and establish whether they fall in the Entertainer category. You may be a mature Entertainer if you exhibit some or all of the following traits.

  • You are committed to what you want to accomplish and are fast-paced and direct in your approach.
  • Your listening and speaking skills are top-notch.
  • You are confident, and charming, and have no problems motivating and persuading people.
  • Your optimism is unshakeable, allowing you to embrace change successfully.
  • You are aware of your leadership vulnerabilities and understand how your inner core influences your behaviors.
  • You possess a genuine desire to improve.
  • Your drive to succeed and genuine leadership abilities make you popular.
  • You may express your opinions dramatically and take action in a similar fashion.

Executive coaching can assist leaders on their journey to maturity. In the case of Entertainers, this journey starts with self-acceptance and a glimpse into the inner-core shortcomings that facilitate emotional derailment.

With the problem identified, coaches can help leaders work toward maturity by adopting and solidifying some of the strengths of other leadership traits.

The Derailing Entertainer

Immature Entertainers do not have the self-awareness to recognize their inner-core emotional vulnerabilities. Losing sight of the true objectives of leadership, they allow their misguided emotions to lead them into competitive showdowns. As a result of the emotional leadership derailment, their values suffer. You may be an immature Entertainer if you have some of the following leadership traits.

  • You find yourself valuing appearances over substance.
  • You don’t think twice about resorting to manipulation for the sake of winning.
  • You are preoccupied with how others see you and whether they appreciate your accomplishments.
  • You bask in the limelight of attention and exaggerate your accomplishments to get there.
  • In light of your real or hyped-up accomplishments, you see yourself as superior to others.

artificial image

Immature Entertainers will often hide behind an artificial image.

Fierce competitiveness is often the first sign of derailment in Entertainer leaders. It is far from the only problematic behavior immaturity brings about in these leaders, however.

Without the intervention of a business coaching professional or an off-chance personal revelation, derailing Entertainers can engage in much more destructive leadership behaviors.

  • They can become utterly opportunistic and exploit others for personal gain.
  • They can grow resentful when others win.
  • They may try to sabotage those they see as more successful.
  • Stabbing others in the back may become part and parcel of the MO of such leaders.
  • They may become jealous, immoral, and unable to build meaningful relationships with anyone.

Immature, derailed Entertainer leaders surrender all alignment with organizational values. Through sabotage and backstabbing, they provide the worst possible example to their followers. They actively contribute to the creation of toxic organizational cultures that stifle individual growth to the detriment of the company.

Strengthening the Entertainer Trait and Working with Entertainers

Mature Entertainers should look to acquire some of the traits of mature Disciples. By doing so, they can shift their mental focus away from themselves and find additional avenues of self-expression through others. They can improve their emotional leadership through collaboration and cooperation.

Entertainers’ targets for collaboration and cooperation can include fellow executives, business coaching specialists, customers, and lower-level managers, as well as employees.

Entertainers should focus on defeating their competitive tendencies. By developing the necessary level of emotional intelligence, they can realize that no one likes people who one-up everyone all the time. With enough introspection, they may even find such self-aggrandizing behavior childish and embarrassing.

Some immature Entertainers model their behaviors after models they find successful and appealing. By helping them develop their own identities, leadership coaching can help such leaders avoid counterproductive behaviors.

leadership coaching

Leadership coaching can work with Entertainers and help them mature.

Despite some of the derailing tendencies of Entertainers, it is possible to work with them productively. Those who want to maintain productive relationships with mature Entertainers should involve Entertainers, seek their input, and discuss with them in an alert, upbeat, storytelling-focused manner.

Entertainers love success, but they often don’t care about the details of a promising plan. When working with them, iron out all the details and present them as factors that enhance the likelihood of success.

Be aware that arguments may trigger the competitive spirit in Entertainers. Instead of seeing disagreements as a means of expressing alternative perspectives, they may see them as challenges they feel compelled to win.


Entertainers are the rogue actors of emotional leadership. Immature Entertainers tend to be out of touch with their inner-core values and feelings. The objective of the executive coach is to help these leaders achieve maturity.

With enough emotional intelligence and self-awareness, mature Entertainers can identify and stifle their derailing emotions and feelings.


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