TLDR;

• Insecurity is one of the most damaging leadership traits and is harder to fix than many other personality flaws.
• A story recounts working with a $15M company whose CEO’s insecurity and obsession with being liked prevented the tough decisions needed to do what’s needed.
• Insecure leaders often appear agreeable but are actually skeptical of advice that requires change, because change could expose their weaknesses.
• They tend to be paranoid, seeing capable employees and new ideas as threats, which leads them to avoid developing strong talent.
• They create a culture of indebtedness where loyalty feels manipulated rather than earned through genuine leadership.
• They rely heavily on titles and hierarchy for authority instead of influence or competence.
• They crave affirmation and use flattery rather than meaningful praise, which ultimately frustrates high performers and drives top talent away.

As a leader, insecurity within people is the hardest weakness you’ll face when trying to develop them.

There are 5 damaging attributes of insecure leaders.

They are listed below if you’d like to avoid this illustrative story.

I have been developing people for a long time. Over the years I have invested in many difficult personality types in effort to develop them: stubborn, obtuse, arrogant, impatient, dismissive, skeptical, and many more.  But about 10 years ago I encountered a leading attribute within somebody that was causing so much collateral damage I deemed “insecurity” the most difficult leadership dysfunction to work with. And the most damaging.

Let’s introduce ourselves to the 5 attributes of insecure leaders through a quick story…

It was a $15 million service company. I was acting consultant and working with the CEO and senior leadership team. After some simple discovery due diligence, what began as a scaling mission became a, “let’s keep this company from going bankrupt” mission. Their core company was losing 8% a year and was being kept artificially afloat by a very profitable, but small, wing of the organization.  The discovery was a shocker to the CEO.  When the dire situation was discovered, the CEO became rightfully alarmed and moved into a moderate panic. This accelerated my involvement and put us into a three-year engagement.

The CEO was a very nice guy. He had a huge heart. And he had genuine concern for his people, his customers, and his company. But I learned of his insecurities when he was presented with the aforementioned dire situation … and he was subsequently and abruptly faced with leading his company (a company he thought was healthy) toward recovery.

This is where the disaster started.

The CEO had built his company on one skill set… forming relationships. That’s all he knew. With no formal education, and through pulling himself up by his bootstraps and leveraging every dollar he ever had, he had found a way.  And his way was…be relational.  His leadership style was even a bit pastoral, primarily caring for the feelings and emotions of others. My mission was to help him become a transformational leader to save his company.  This would require bringing new skill sets. Ultimately, he was unable to do so.

We ran smack into his insecurities.

He had a deep need to be affirmed and liked.  He simply could not make the decisions necessary to rebuild his company for fear of receiving critique.  That was years ago.  He has since lost some of his top talent.  His company is marginally profitable, but is smaller than it was and is missing huge market opportunity.

As we unpack the calamity caused by leadership insecurity, let’s view this through two lenses. One, we must look at ourselves; are we the insecure leader? And two, are any of our people suffering from this malady? Let’s dive in.

There are 5 obvious symptoms of leadership insecurity::

• Skepticism

• Paranoid

• Indebted

• Title-driven

• Need affirmed

A leader who suffers from these five symptoms cannot be an effective leader. It’s impossible.

And I learned this the hard way.  An insecure leader…

…is skeptical. They are very, very slow to trust. They may lead you to believe you have their buy in, because they are very polite and nod their heads a lot. It will appear as though you are in perfect agreement. But truly, they have not changed their belief systems to align with yours. They are not metabolizing what you are telling them. Intellectually, they agree. But behaviorally, they don’t change. They are skeptical of any advice that would challenge them to change. Because change is terrifying to insecure people.  They are scared of change, because it will put them in discomfort and could expose their weaknesses. It truly is a situation where the Emperor has no clothes… they don’t want to be discovered. They know they are weak leaders with one skill set, so they are very, very slow to allow advisors into their life for fear of being viewed as weak or not enough.

…is paranoid. They are scared of their own shadow. Things that should not be threatening, are viewed as a threat. This is why they don’t develop people. They do not want to see others succeed beyond their own skill level or their leadership aptitude because if they do, they will be threatened by that person’s success; they fear they may no longer be able to lead them.  They don’t want people to “pass” them.  Someone excelling in leadership beyond them may expose them, and it’s terrifying for them to imagine being discovered. When you are insecure, you don’t have confidence. So things that should not be scary, are scary. And things that should not be threatening, are threatening. This is why they are hesitant to listen to new ideas, go into new markets, expand horizons, and hire outstanding talent.  If you look closely, most of the talent insecure leaders surround themselves with are below their skill level. From time to time, they will hire an outstanding producer, but that producer won’t stick around long. And insecure leaders are even paranoid of their own company – it’s terrifying for them to know the company needs more from them but they can’t provide it.  So in some cases, they even sabotage their own success to ensure they are never asked to become something different.  That’s what the CEO did in our story up above.

…is going to bring a microculture of indebtedness around their brand. There will be a strange obligation to respect them and follow them. But it won’t feel right. You may find yourself wondering, “have they led me or have they manipulated me and placed these weird conditions on our relationship to get my loyalty?”  There is sometimes a shaming or a strange undercurrent to get followership.  It feels disingenuous. This is a difficult byproduct of insecurity to explain, but for those of you who have felt it, you know it.

…will tend to place weight on titles. Titles offer security. Without a title, we are left only with our ability to influence without any positional levers. Without a title, we have no leverage and there is no cultural expectation for followership. A title brings a cultural expectation and even an organizational expectation. If I am a CEO, the title will demand a certain amount of followership and will buy me grace. And if you are a manager under the CEO, you are below them so there is a professional safeguard for the CEO. If I give great attention to the formation and boundaries within an org chart, I protect myself and my insecurities can remain in my own mind.  Titles give me safety.

…is fueled by affirmation. Insecure leaders do not affirm…they flatter. There’s very little substance behind their compliments. However, their entire self-worth is built upon receiving affirmation. So, they flatter.  They emphasize feelings and they emphasize culture so they are perceived as a very nice person. And in return, they will be told thank you and they will be affirmed – they expect you to return the “affirmation favor.”

Today’s main point is to shed light on perhaps the most costly dysfunction of a leader… insecurity.

An article for another day is to unpack the collateral damage this causes. But very quickly, it breeds a paranoia within the team. Employees know the culture is an empty shell. It is a mirage. Under an insecure person’s leadership, typically the lowest performers are the most protected, and the highest performers are the most frustrated. Anyone who values equity, accountability, and justice will be extraordinarily frustrated. And top performers will be held back to the point they must either compromise their ambitions or leave the company.

If you are a leader who struggles with insecurity, the secret is out. Everybody knows it but they might not know how to label it. But they know the symptoms, and they know how they feel. The best thing you can do is begin the hard work of dealing with it. Again… an article for another day.

If you are a confident leader but have identified an insecure leader within your organization, do not ignore it.

There is collateral damage. Sometimes it is subtle. And insecurity is rarely the identified culprit but it is often the guilty party. Insecurity needs called out.  If your culture, your profits, or your operations are a disaster, an insecure leader may be to blame. Something to think about.