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Dan's Insights and Inspirations for Empowered Leadership

The Surprising Reason Leaders Don't Learn from Experience

Why do some people make the same mistakes, over and over again? If you're like me, there are few things more frustrating than watching someone get into the same bind, year after year. But when I don't learn from my own mistakes, it becomes infuriating!  

The first time you misstep, it's easy to give yourself a pass. 

"It's my first time"

"I've never been in a situation like this"

"I didn't see that coming."

But the second time around, it's harder to blame the mistake on events around you. Whether it's as big as financial mismanagement, poor hiring choices, failed product launches, or as small as a constant lack of punctuality. Over time, repeated mistakes become less about the circumstances you're in and more about your character.  

As a leader, repeated mistakes become harder to detect. Because the more influence you hold in an organization, the harder it is for colleagues and direct reports to bring your mistakes to your attention. In turn, you could lead for decades without understanding how your choices undermine the goals of the organization. 

Now, if you've read my book, “Authentic Leadership” you know I believe that mistakes are an indispensable part of your growth as a leader. However, every leader should aim to make new mistakes, and grow from their old stumbles.  

We all know people who have been in leadership positions for decades, but simply don't grow past their mistakes. When that happens, you don't have a leader with 20 years of experience. You have someone one year of experience, repeated 20 times. That's a scary thought. 

So why do some people make the same mistakes, over and over again?

This famous thought from John Dewey brings some clarity:

"We do not learn from experience... we learn from reflecting on experience."

In other words, we don’t learn from our mistakes. We learn from reflecting on our mistakes!

Reflecting on 2019

Think back to 2019. Think about the whole year, and answer this quick question: What did you learn? You had 365 days of experience. Specifically… what did you learn? 

The best leaders could answer that question with specifics. 

"I learned ______ about my team."

"I learned ______ about my industry"

"I learned ______ about my family." 

Our most profound growth comes from understanding how external events shape our inner world. In 2019, events didn't just happen around you… events shaped things inside you. 2020 will be no different. And in order to be a leader that learns from your mistakes, someone who grows and improves year over year, you have to develop one thing: Internal Self Awareness.

There are two kinds of self awareness: Internal and external. In a previous article, I explained that external self-awareness is the ability to understand how others see you. It's essentially stepping outside your bottle in order to clearly understand how others see your label.  

Internal Self-Awareness

Internal self-awareness, on the other hand, is the ability to continually monitor your inner world.

It's the ability to clearly identify how your values, habits, weaknesses, biases and aspirations interact with your environment. When you become more self-aware, you learn to assess your leadership mistakes, making regular, small, course corrections. At any given moment you know what mistakes were made, what you are feeling about it, why you feel that way, and most importantly… what you really want to see happen. Internal self-awareness skills puts your personal growth into hyper-drive. 

Internal self-awareness helps leaders take control of their thoughts and actions. Early in my leadership, I understood how important internal self-awareness was, so I began to journal. I had a spotty track record at first, but I gained momentum after a few weeks. A few years after writing in my journal, I decided to look back to see what patterns emerged. I was shocked at what I read. I was shocked how clear the pattern was.

It turned out that every two months or so, I would write a long rambling essay about how busy I was. In each instance, I repeatedly claimed there was too much on my plate and that I didn’t think I’d be able to get it all done. I wrote about how fearful I was that I would miss deadlines. And, in each of those, and there were about eight or nine total entries, I would swear that I would get more control over my calendar. I would tell people “no” more often. I would become more organized. I would never let this happen again!

But then, you guessed it, I forgot. Just eight weeks later I was right back at the same place, writing about how I never wanted to be this busy again. After I read that, I had an epiphany. I understood that, without reflection, I could be driven by unconscious patterns of thought. It was humbling to realize I was more predictable than I thought. Since then, I learned to schedule time blocks, say “no” more often, and create monthly, weekly, and daily priority lists. I now have much more margin in my life. 

Each of those steps helped me control my tendency to spontaneously over commit and thus avoid the overwhelming feeling of busyness. But without that written record exposing my unconscious habits, I likely would have continued to make the same mistake, month after month, year after year. 

Here’s the bottom line: to become more self-aware, codify your thoughts. Start by writing them down in a journal. Some leaders take it a step further and create a personal vlog. That way you can reflect on your thoughts, while making a record of your tone of voice and facial expressions. Some people hire a leadership coach, meet with a pastor, or see a therapist.  

Regardless what you do, to become more self-aware, you need to add self-reflection to your life.