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Five Mistakes I Made as a Leader in 2016

I spend time each January processing the mistakes and progress I made the previous year. Like many, I find January is a great month to make adjustments and course corrections on my life. Below, I’ve included five mistakes I made this past year. I hope my transparency will benefit you and prevent you from some of the same mishaps.

Five Mistakes I Made Last Year:

1. I focused so much on outcomes, that I missed some “outcasts” and “outliers.”

Like most leaders, I’m motivated by results. In fact, we use a phrase in our office: “manage by fact.” This simply means, we must make our decisions based on the best data so we can achieve the best outcomes. There’s nothing wrong with this, but I found it easy to be so consumed by outcomes that I missed some staff or students who may have been in the shadows—but loaded with potential.

Sometimes, the best student leaders aren’t the likely ones—who make a 4.0 GPA, who sign up to volunteer or who run for student body president. If history teaches us anything it is that world changers are often outsiders.

This year, we’ve engaged with colleges and high schools around the world, and we focused mostly on those “most likely to succeed” adolescents who look good, behave well and excel in the classroom. Certainly, those early bloomers should be tapped into, but I was reminded (once again) that I need to keep my antennas up for those disenfranchised kids who are angry—but whose anger could be transformed into positive action with the right guidance.

2. I assumed I could do more than possible in a day but less than possible in a month or a year.

This is something every leader needs to comprehend about themselves. Where are you overly optimistic and where are you unduly pessimistic? I re-discovered I think I can do more than is humanly possible in a work-day. I am the eternal optimist when it comes to crossing items off my “to do” list. Too often, I get to the end of my day before I get to the end of my “to do” list. Ugh. I am always a bit frustrated.

Similarly, when I look out a month or several months into the future, I tend to be more realistic, perhaps even pessimistic about what I can pull off in a fiscal year. I can’t explain it. One would think I would be equally optimistic about both a day and a month, or a year. But, alas, it’s not true for me. So—I must enter my items on the daily and annual “to do” lists knowing this quality about myself. Then, adjust my expectations accordingly. This lessens my frustrations and heightens my motivation.

3. I become enthralled with the new and novel, but drop some essential habits.

I am a creature of habit—but I am like most other people. Anything new or novel can capture my attention. This year, it seemed so many new innovations and products were released and they showed up on social media. I got a bit distracted by my Apple Watch and the Apps I purchased on my phone. By the way, they’re all good and they helped me to do good things, like eat right, focus, breathe, and keep track of my tasks.

The irony of it all is—I became so enamored by the new “stuff” that helped me become a better person and a better leader that I neglected some of the fundamental disciplines I have practiced for years. So while the new technology was supposed to help me be a more disciplined person, I both added and dropped some disciplines I genuinely believe in. Hmmm. Life is, indeed, a trade off.

Going forward, I recognize I can probably practice a handful of daily disciplines, regardless of how many tricks I know or devices I learn to use. I must choose the most important ones and “marry” them. Not date them, but marry them. Then, if there is an App or a program that helps me master the habit, all the better.

4. Failing to balance my vision and my blind spots.

This year I did a study on how all leaders possess both vision and blind spots. By this I mean, we all work off of an ideal, a vision of a preferred future. My vision drives me. However, because we’re human, we all have blind spots to our vision. There are realities we cannot see because of our limited perspective. Because we want our vision to come to pass so badly, we neglect to see what others may see.

My solution to this, of course, is to surround myself with people who see life differently than I do. I now have three people who hold me accountable to my vision but also ask me about my blind spots. Sometimes blind spots can be good. It’s why some entrepreneurs make it; they experience rookie smarts because they didn’t know enough to be afraid. So, blind spots are not all bad. I must simply work to ensure they don’t prevent me from achieving my vision.

5. Allowing some routines to become ruts.

I endured a season in 2016 where I became worn out. I was on the road constantly and became an emotional zombie. I continued in my daily rituals and routines, but they became ruts. I stopped growing. My passion waned. I didn’t excel.

We all need routines in our lives in order to survive. They wake us up in the morning and carry us through most of our days. At times, however, those routines can become ruts. They can certainly feel like ruts—bland, blah and boring. We stop thinking on our own. We stop questioning our methods. There’s a fine line between routines and ruts. We need routines but we must avoid ruts. The key is to stick to our routines long enough that the repetitions of our routines become grooves of grace—brilliant, healthy habits. Habits are actions that burrow their way into our subconscious and we can do them without thinking. The key is to continue thinking in those habits and finding meaning in them.

So, I’d like to hear what you learned from 2016. Please comment below.


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  • williamdparker

    Tim, Thanks for sharing so transparently. Good food-for-thought on areas where I need to grow. Your comments on missing out on potential of others reminds me of a great talk by Margaret Heffernan on the power of teamwork by studying research on laying hens. I’ll link to a summary here: http://www.williamdparker.com/tag/laying-hens/ Best wishes on a great New Year!!

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