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My Five Biggest Leadership Mistakes and What I learned

My Five Biggest Leadership Mistakes and What I learned

The Success Train that Made Only One Stop

I am an incredibly naive person. It’s one of my most endearing traits (according to my mom). It’s what made me once believe that humans could float on clouds and that there was a pot of gold at the foot of a rainbow. As a kid, I believed anything people would tell me. I was so naive that when we traveled under overpasses, my dad told me he could magically switch off the sun by turning the air conditioning switch in the car. It took me 8 years to learn that this was merely a trick, and no, he did not possess magical powers.

I approached leadership with the same naivete. I assumed that a wild imagination and unyielding optimism in things unknown would make everything turn out alright.

‘Futures Academy’ was borne out of this naivete. It started with a belief that three people, given enough optimism and belief, could ultimately disrupt and transform the way in which we school kids.

As an adult, I was just as naive as I was as a kid.

Perhaps that’s why my success train made only one stop before it experienced an enormous amount of failure.

Here is one of my biggest:

It was late September, only a short month after we launched 'Futures Academy,’ the unique ’school within a school’ program designed to connect students to their passions and the world outside of school. After an early exhibition of student work, it seemed everyone was on board with what we were trying to do. Our students were enthusiastic to share their learning, our parents were proud of what their kids had accomplished, and other kids from the school were eager to sign up.

Naively, I assumed this had to do with our incredible leadership and communication of the program. After all, we were only 2 months into the program and already had generated excitement. Out of the students that came to that exhibition, many wanted in the program.

Like rookies, our teacher team celebrated way too soon. We exchanged high fives, pats on the back, and congratulated each other on a job well done. And so rather than work hard to build off off that success, we assumed our work was complete. In only a few short months, we would realize just how short lived success can be.

Fast forward to January, month 5 of the program. It was in this month that we begin to watch the students we admitted for the 2015-2016 school withdraw just as quickly as they signed up. It was like a terrible cold that had spread to all corners of the school. On some days, we had up to five students withdraw from the program all at once.

We all scratched our heads in disbelief. What had we done wrong? How did a program that was embraced with such positivity, excitement and optimism, turn to one that was viewed as being ’too easy’ and for ’the special students.’

In desperation, we tried to regain what we lost. We put together campaigns to advertise the success of the program. We held lunch meetings with pizza and drinks to regain momentum. We even allowed 1 on 1 meetings for curious parents to express their concerns and gain reassurance that the program was right for their child!

None of it worked. It was too late.

During the next two months we watched helplessly as nearly 50% of our new student applicant pool withdrew their applications one by one.

It would take the rest of that school year and countless phone calls, e-mails and other communication methods to get a few of those students back.


Perhaps you have had the same struggles with leadership. Perhaps you have experienced early success and have not done enough to keep the momentum.

I learned that perception begins with expectations. Without a clearly defined start, we had no way to quantify and celebrate progress. We had not asked for enough feedback; showcased enough of our student’s work; reached out regularly to our parents; or invited skeptics to voice their criticism and give them a space to share.

How could we even say the program was successful?

There was a big elephant in the room that we refused to acknowledge. We assumed that because we had a positive perception of what we were doing, therefore everyone else would as well.

As the team leader, I had failed my team. I assumed enthusiasm and optimism were enough to get us through the tough times. They weren’t.

What I learned

I learned that you have to work tirelessly to maintain a positive perception when undergoing any massive change. Change is uncomfortable for several people. It is only natural for people to view it in a negative light. The only way to change that perception is to communicate with humility and honesty your successes and shortcomings, and maintain an open stance to criticism.

This is only one of several mistakes I have made as a leader. Here are four more failures and the lessons I have learned. I hope they resonate with you and offer you some tips for your own leadership roles.

Leading the way you like to be led

“Leaders who don’t listen will eventually be surrounded by people who have nothing to say” - Andy Stanly

This is a leadership make I consistently make. I remember a leadership consultant coming to our school and asking leaders to stand in the corner of the room that best represented how they built trust in people. One corner was reserved for ‘openness,’ one was for ‘honesty’, one was for ‘caring’, and one was for ‘competence.’ I stood in the corner reserved for ‘openness.’ Much of my team stood in the corner of ‘competence.’

What I learned was that in order to build trust as a leader, you have to meet the needs of your constituents. My team didn’t need a cheerleader who supported them when they had tough days, or a visionary who helped them see the bigger picture. They needed a fully competent leader who demonstrated a level of expertise that gave them the confidence that what we were doing was backed up by academic research and a track record of success.

Feedback= Failure

“There is no failure. Only feedback.” -Robert Allen

I used to be terrible at receiving feedback. This was painfully obvious when first working with the school's leadership team. I remember showing the leadership team a trailer video of what they could expect in ‘Futures Academy;’ fully expecting it to be received with a round of applause and adoration. Instead, it was met with specific feedback for how the video should be changed to better align with their vision. Like a beaten dog, I hung my head with disappointment, feeling that I failed.

It wasn’t until later learned that I learned that feedback is perhaps the greatest gift I could be given. This free advice was the only way to improve my practice! As I got better at receiving feedback, I naturally because better at leading my team. Being receptive to feedback allowed us to regularly adapt student schedule’s, re- organize poor units, ditch unsuccessful projects, and reach out to more collaborators for our work.

Sharing responsibility is a sign of weakness

“Unity is strength. When there is teamwork and collaboration, wonderful things can be achieved.” - Mattie J.T. Stepanek

I used to have this Superman mentality. I said “yes” to everything, took on way too much work, and tried to do everything on my own. As a result, I worked on ‘Futures Academy’ in isolation. Because of my background, I believed I knew what it needed to be successful, and as a result took responsibility for early development of curriculum structure, marketing, project design, and presentation building. Although I had a team of experts only a phone call or short walk down the hall away, I thought reaching out for help was a sign of weakness.

I learned later that building a team is the only pathway to success. When I was able to admit that I couldn’t do it all, and allowed other team members to step up, it helped the program improve. Our school’s communications team took up the marketing and outreach for the program; our leadership team took responsibility for communicating the program to the rest of the middle school; and the curriculum team helped facilitation the design of different units.

Leaders need to receive credit for what they do

“A good leader is a person who takes a little more than his or her shame of the blame and little less than his share of the credit.” - John Maxwell

I have this unnatural need for justice that was counterproductive as a leader. If someone did something admirable, it was only fair and just that they were acknowledged for it. I viewed Futures Academy in the same light. In the development stages, I treated it like a company distributing its stock. Like a company, ownership of its development should be distributed fairly and according to time spent. When someone got credit for something they didn’t do, I was the first to speak up and make sure the admiration was given to the correct person. This righteous indignation of justice caused a lot of friction in the leadership team, and slowed the development of the program.

It took me a whole year to learn this lesson. Futures Academy was about kids. Period. It was about improving their experience, and designing projects that connected them to what they care about most. When I was able to release my need to receive credit for every little development of the program, I was able to focus on the bigger picture and design more meaningful experiences.

In Closing (Have a call to action….as you read this sign up for SLACK. It’s free and join the #wagnerPR channel to share XXX and create….

Leadership is one of the toughest jobs in the world. I once saw a quote plastered to someone’s desk that read, “A leader only gets remembered for the times they mess up.” This may be true. You are asked to do incredibly challenging work on a daily basis with little acknowledgement of what you were able to accomplish. You may never get the accolades you deserve. But I want you to know that I appreciate you and your incredible resilience! I hope you are able to take the lessons from above and apply them to your own practice. Here are some places to go for additional support...

More ideas for school leadership and transformation:

The lessons above are represent a few of my experience with coordinating Futures Academy at The International School of Beijing. My book, Power of Simple,’ offers several more ideas for transformational leadership in addition to simple and concrete strategies to help lead your school in that direction. You can get that here.

Meet with me at SXSWEdu

I will be conducting brief 10 minute mentoring sessions at SXSWEdu to help school leaders work through transformative ideas for their schools. I would love to meet with you there! Below is the information for my session in addition to information about the book signing I will conduct immediately after. I hope to see you there!

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Kyle Wagner
School Transformation and Project- Based Learning Coach

I coach school leaders on how to lead change and improve student learning through simple, innovative srategies and teaming structures.

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