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Leadership and Facing Dragons

  • Lydia Richards
  • Nov 5, 2025
  • 5 min read



They may be lurking in your HR conference room, or nesting under the Boardroom table. Some have been known to inhabit the cracks between departments, while others can be spotted along their migratory path during annual review time. They are Dragons: the unresolved internal issues that haunt nearly every human being. But when that person is a leader, Dragons can be particularly fearsome. 


We have all seen them. You’ve seen the leader who surrounds themselves with fawning, flattering suck-ups, or the CEO who will justify complete incompetence, so they won’t have to fire anyone. You’ve seen it in the fearful, or boastful, or under-performing leader. 

Rarely do leaders fall short because they lack technical or management know-how. Instead they fall short because they are unknowingly captive to their unresolved personal issues. They are pushed around by their Dragons. 


To make matters worse, when leaders have dragon problems, entire organizations suffer. Gallop reported that, “Three out of every four people report their boss is the most stressful part of their job.” In fact, Clifton points out, “None of the other expensive programs a company institutes to increase employee engagement — excellent rewards, well-thought-out career paths, stimulating work environments, EAP programs, health insurance, and other perks — will make much difference to the people stuck with bad bosses."


Dragons might show up as a leader who refuses to give up on a bad idea until it’s too late, or the one who is unwilling to risk failure, or the leader no one trusts (not even enough to let her know she isn’t trusted). If you take a close look at most leadership gaffs you will find a Dragon or two skulking about. These unhealthy dynamics are present every day in business and industry, and the impact of unresolved personal issues causes significant turmoil, loss of productivity, and costly missteps. 


Consider this case-study:

Ryan, was a gifted marketing director for a global wine company in California’s Napa Valley. He is a hard-working, smart, likeable man in his 40’s, yet he’s on his third position in as many years. He lacked nothing in pedigree and experience, graduating with an advanced degree in Wine Marketing and Management.  Twice Ryan was hired into positions that seemed perfect for him, yet about nine months in, things started to unravel. His teams would underperform. Relationships would sour. Twice, he chalked it up to a “poor fit”.  Then, for a third time, Ryan got that familiar sinking feeling.  It was happening again. 

Ryan came to leadership coaching confused and determined to understand what was happening. It didn’t take long. True, Ryan was positive and likable. In fact, he was ONLY positive and likeable. He struggled when the conversation turned to hard truths. Through coaching Ryan realized that he believed he needed to stay positive all the time, to “rally the troops.” He had spent his life accompanied by an ever-present Dragon, which he named his Be Nice Dragon. While being nice may have helped is some parts of his life, it was simultaneously sabotaging his leadership. He rarely gave people direct, honest or critical) feedback either at work or at home. He gave lots of atta-boys, believing that would encourage people. Instead, it taught them that the truth is not safe to speak. Ryan’s Be Nice Dragon had caused him to avoid giving his team the feedback they needed to grow and he had avoided receiving feedback himself. 


Overcoming Dragons is a complicated and messy business. We continue looking for solutions where they will not be found, while talent, time, and profits are squandered. The only solution to a dragon problem is to face them.


Ryan faced his Dragon. By doing the hard work of soliciting feedback, and processing his reaction, he realized that his Be Nice Dragon had bedeviled him since his earliest years. As with most dragons, it had been given to him by well-meaning adults. Ryan began to see that the Be Nice Dragon was not nice at all. In fact, it was undermining his leadership and his authentic connection with others at work and at home. He went back to his team, shared his learning, and enlisted their help. Ryan and his team began (slowly at first) sharing low-risk truths with one another. Their candor and accompanying trust grew. The change took time. New habits always do. 

Today Ryan is a gifted leader.  His genuinely positive outlook remains among his greatest assets yet his Be Nice Dragon is no longer calling the shots.  Ryan still catches glimpses of his dragon but he has learned to face it and make intentional choices about his leadership style. 


Perhaps you have a Be Nice Dragon too. Many of us do. If so, you are likely creating walls between you and those nearest to you. 


What are YOUR Dragons? 

I’m-Not-Good Enough Dragon - You may tend to play small, needing to be certain of success before playing at all – or spend your life with an obsessive drive to be good enough. And while one can become monetarily successful with that kind of drive, leading well requires a generous spirit focused on others, rather than self.

Shame Dragon - You see it rear up when others try to give you feedback. Shame may cause you to deflect, defend, or attack others to avoid receiving any feedback that could help you grow. Or it may cause you to seek-out ONLY negative feedback, so you can wallow in it. Either way your Dragon is in charge. 

Jealousy Dragon - You may feel threatened by others’ intellect, charisma or success.  Great leaders surround themselves with the most brilliant people they can find. Yet jealousy prefers the safety of being surrounded by mediocrity. As David Ogilvy, the business legend, writes, "If you ever find a man who is better than you are – hire him. If necessary, pay him more than you pay yourself."

Fear Dragon - You may be controlling or micro-managing.  Fear often shows up not as specific and warranted caution, but free-floating, global anxiety. It’s impossible to be a great leader if you are unable to let go, effectively delegate, collaborate, and empower others. 

We have so many Dragons!  Hubris, Martyr, Left-Out, Defiant, Self-Focused, Offended which will cause otherwise gifted leaders to stumble again and again. 

How do you slay a Dragon? 

In short, you don’t. 

People do try and sometimes succeed. Common acts of someone trying to slay a dragon including devouring self-help books, undertake years of psychoanalysis, trying self-actualization, craniosacral therapy, energy healing, or even seeking out a shaman or guru to teach the art of dragon slaying. Some emerge victorious. Many return disappointed, with their dragons still in tow. 

So what are we to do about our dragons?

The good news is: to be a fine leader (and a happy person), you don’t actually need to slay your dragons  (in fact that might be a waste of precious energy). That said, you do need to learn to face them. You will need to learn their movements and tendencies, and become practiced at sniffing them out. Only then will you be able to powerfully choose how you want to lead and how you want to live. 

The key to successfully facing your dragons is self-awareness…. deep, searching, fearless self-awareness. 

Six steps to dragon-size self-awareness:


  1. Pause – Every day, for two or three minutes, morning, noon and night even if it’s tough

  2. Question – Think about what is making you uncomfortable and look even deeper when you try to defend yourself

  3. Reflect – Use a journal before the dragons erase the freshest learning.

  4. Discuss – Find someone whom you trust completely and won’t shy away from the hunt and bring them on the journey 

  5. Experiment – Observe your dragons’ habits. Notice when and where they are most likely to show up and don’t be afraid to laugh at yourself.

  6. Control – Create strategies that put YOU back in charge even when dragons are on the prowl.


So, what are your dragons? 


You have the power to face your dragons.

You also have a responsibility to do so, for you good, for the good of those who work for you, and for the good of your organization.



 
 
 

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