Three leadership mistakes I made, and you should avoid

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Leadership. It’s not easy. As I reflect on the last 25 plus years leading, I know I have made several mistakes. Regretable mistakes.

But the beautiful thing about mistakes is that you can first apologize, and secondly, learn from them. 

In a recent journal entry, I wrote, “failure is not your enemy, it is your teacher.”

From moments lacking in emotional intelligence to arrogance, I have made my fair share of mistakes. 

Below are three mistakes that I made (there are countless more), that I hope you never do.

Not being present

One time, a staff member came to me after I had challenged him publicly about some recent mistakes he had made. 

He wanted to share with me about some deep pain that he was going through in his personal life, which was affecting his performance.

What he shared with me was affecting both his confidence and his focus. 

He then apologized for his recent mistakes.

Instead of taking the time to acknowledge his pain and encourage him, I abruptly accepted his apology. I said something about “personal life shouldn’t affect your work-life, blah, blah blah.”

I was such an idiot. 

Good leaders are always present. At the time I was not in a position to be someone’s counsellor. However, I should have kept the conversation about his personal challenges. He needed to know that I was there support him in any way possible as he worked through the circumstances before him. 

He needed some kindness on that day. Not criticism. 

As leaders, we can get distracted with all the goals, tasks and obstacles. Often, this keeps us from being present in all our interactions.

Leaders who are present are more attuned to someone who is struggling. 

This is one of the most simplistic ways of creating a culture that is safe and productive. 


One of the great longings of the human condition is to discover our value. Why do we matter?

This is an in-escapable reality. We desire to be valued. To be seen. 

As leaders, we want to make our mark in whatever environment we find ourselves in.

In my career, I was often promoted. Promoted before people with more experience, education and often, with more talent. 

Given my lack of emotional intelligence and combined with my own personal insecurities, this was a cocktail for an ego-collapse of epic proportions.

I had a personal administrator that had worked with me for several years.  

She was incredible at her job. I could tell she was always trying to go above and beyond. Consistently meeting my demanding standards and abrupt last-minute requests. Usually, because I wasn’t as organized as I should have been.

I was hard on her when she failed. Though her failures were few and far between.

She finally did the right thing. She went to my boss. Basically, stating that I was creating unreasonable working conditions. And then she said, and I am paraphrasing, “He always positions himself as ‘important.’ That he always knows what is really going on.” Ugh. Her assessment of me was right. 

This was a pivotal moment for me. I apologized, not just with words but in action. Determined, I started to deal with my false bravado of self-importance. I had to face my insecurities head-on. I have become a better, leader, husband and father because of it.

Not one of us is more important than the other. Healthy leaders humble themselves. We serve those we lead. It is on us to invest in the potential of others. And, never diminish others to make ourselves look better or important. 

The book Ego is the Enemy by Ryan Holiday is a must-read for all leaders.

Not delegating

As a leader, it is easy to fall into the trap of false belief. A false belief that many of us fall into; if you want something done right, do it yourself.

When we act on this belief, these are some of the outcomes that will begin to reveal themselves in various ways. 

  • Your team will not believe you trust them.
  • You will not pass on knowledge.
  • You will be perceived as arrogant.

An unhealthy work culture will be the result. You will not be able to create high capacity team members. 

Other possible consequences are team boredom-disinterest, loss of respect, and the ability to be taken seriously. 

Successful leaders know how to delegate to others. We need to be able to identify people who we are ready to take a risk on. Then we champion them regardless of failure or success. We need to cultivate a culture of learning and trust. Even when there has been a failure. 

We can’t just say, ‘i’ll do it myself.’

These are just some of the leadership mistakes I have made. My hope is that you will learn from them. 

Cheering you on,


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