Leadership: 7 Unintentional Lessons I Learned from Failure

Q: What can school leaders actually learn from failure?

The most useful lessons from failure are specific. An unsuccessful interview, for example, can reveal which competencies a hiring group emphasized, where an applicant's answers were weak, and how effectively the applicant communicated their values under pressure. Writing down those observations while the interview is still fresh can turn the experience into a practical professional-development plan.

Q: Should a principal talk to students about a failure of their own?

It can be appropriate when the example is age-appropriate and the focus remains on learning and what happens next. Students observe how school leaders respond to setbacks, and a principal who acknowledges a mistake or disappointment, remains composed, and explains what they will do differently can model persistence and reflection.

Q: How do you keep a failed interview from ending your ambitions?

Treat an unsuccessful interview as one hiring decision rather than a definitive judgment about your ability. A search committee selects one candidate based on the needs and priorities of a particular position at a particular time. Review what you learned from the process, address areas that could be improved, and continue applying for positions that fit your experience and goals.

Q: What should you say to a colleague who just failed at something?

Acknowledge the setback rather than avoiding the person or pretending it did not happen. Ask how the colleague is doing, recognize what they have done well, and give them room to talk about what comes next. Support does not require finding perfect words; straightforward and respectful acknowledgment can be enough.

Q: Does failing hold you back from moving into district leadership?

An unsuccessful application or interview does not by itself prevent advancement into district leadership. Hiring committees consider factors such as preparation, experience, demonstrated competencies, and fit for the position. Candidates can use unsuccessful searches to identify gaps in their experience or interviewing and address those areas before pursuing future opportunities.

By Jon Konen, Last Updated: August 25, 2026

Rodeo rider being thrown from a bucking bull in a dusty arena as a bullfighter moves in to help

Failure can teach leaders lessons that success doesn't, especially when they reflect on what happened. After losing a superintendent bid, I came away with seven lessons: flip your perspective, find the win, model failure for students, learn about yourself, set up your future, have hard conversations, and pay it forward.

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1 - Flip Your Perspective

Failure arrives in a variety of packages that people internalize, and many use it as an excuse to stop trying. When someone fails, I wonder what goes through their mind. It's a topic that's been picked over quite a bit lately, and you'll find no shortage of articles and research on it. The theme that comes up again and again is the same: many successful leaders describe failures as important learning experiences. To get there, we have to flip our perspective.

We could live and wallow in anger and sadness knowing that we failed at something. One productive response is to reflect on what happened and decide what to change next time.

Developing a workable light bulb is one of the most famous inventions of all time, and it did not happen overnight. Thomas Edison could have stopped after each failed attempt and said he was done. Instead, he kept learning from the failures by flipping his perspective. The mantra in his head could have sounded something like this: "I almost got it. What if I experimented with this filament, or used this material?" He kept going by changing his thinking. Edison had grit.

In much the same way, when the school board called me late on a Tuesday night while I was enjoying a sausage and mushroom pizza at a local place, I was shocked. My first thought was, "I failed." I spent roughly five minutes in that state, then started reflecting on what I'd do next time. I flipped my perspective almost immediately and started treating the failure as a learning experience.

Notepad with a handwritten note about adopting a new mindset

2 - Win-Win Mindset

In every failure, there is a win. That win may be hard to see in the moment. How can we adopt an attitude that lets us find the positive in every failure?

Many people who went on to lead in their fields did so only after failing first: in an election, in a bid for a higher position, or in a tryout for a team. That failure set them up for bigger accomplishments, creating a win-win.

Take the basketball GOAT, Michael Jordan. Trying out at Laney High School as a 15-year-old sophomore, he stood 5-foot-10 and wasn't among the players chosen for varsity. He was assigned to junior varsity instead, and he went home, locked himself in his room, and cried. He kept working. He grew, made varsity as a junior, had a monumental senior season, and earned a scholarship at the University of North Carolina. You know the rest: six NBA championships, a stack of MVP awards, scoring titles, defensive honors, and Olympic gold. Jordan's win-win moment came when he changed his mindset and set new goals for the following year. His failure turned into a win.

My pursuit of the superintendent position was a win-win too, if without the same athletic prowess. Had I been hired, that would have been a win for me and for the district. When I didn't get it, I won something else. I now know what I need to do to get the position next time. I understand more about myself, which areas I need to improve, and how to communicate what I believe in a future interview.

Student sitting at a classroom desk looking discouraged over schoolwork

3 - Teach Others, Like Students, That Failure Is Acceptable

I'm lucky to be around a great group of people every day, from colleagues and staff to community members and friends. When I didn't get the job, I heard from so many of them. It usually started the same way: "I'm sorry you didn't get the position." My typical response was, "I'm good with it. I learned a lot." Sometimes I'd go into detail on everything the experience taught me.

The day after the school board's call, I was walking down the hallway of my school when a group of staff members surrounded me and gave me a hug. I almost lost it. From there, I went out to supervise morning entry on the playground. A group of fourth-grade girls came up and told me, "We're sorry you didn't get the job. But we're happy you get to stay with us." That's when I lost it. I began to cry, thanked them, and kept walking from the upper playground to the lower one.

I knew my conversations with kids that day, and in the days that followed, were going to matter. At lunch, several students were ecstatic that I didn't get the job. I understood what they meant, and I took it as a compliment.

I talked with the kids about staying positive and having a growth mindset. Some of the same thinking shows up in how we handle discipline, and I've written before about what I learned weighing in-school against out-of-school suspension. I told them how much I learned about myself and about my community. They saw me be strong, and they also saw me cry and stay positive. I'm not the crying type, but crying can be part of failure, and it's okay for students, friends, and the public to see it. It's a human emotion, and we shouldn't file it under weakness. So I kept telling them the same thing: what you do after you fail matters more than anything you did before it.

Person sitting alone and reflecting quietly on a recent setback

4 - Learning About Yourself

Reflecting on the words we use, the actions we take, and how we choose to spend our time tells us a lot about who we are. The moments right after failure interest me most. You can learn a great deal about a person from how they handle their emotions. Do they rage? Are they shocked? Are they offering excuses immediately? Are they calm? Are they sitting there cataloging how much of a failure they think they are?

Much like a death, failure can bring emotions such as shock, sadness, anger, and eventual acceptance, though people respond differently and not in any fixed order. Failure can mirror many of those emotions, obviously at a different scale than losing a loved one.

My 1985 Chicago Bears were elated after beating the New England Patriots 46-10 in Super Bowl XX. How did the Patriots handle that loss? It took them eleven seasons to reach another Super Bowl, which tells you that recovery is rarely quick and rarely a straight line. My 2018 Bears, meanwhile, were elated to move into the playoffs. The game came down to a field goal from kicker Cody Parkey. Parkey hit the upright, then the crossbar, and the kick was no good. Plenty of Chicago fans didn't handle that failure well, but true Chicago fans know we'll be better next year because we learned something about ourselves.

I learned a lot about myself in not getting the superintendent position. Most of all, I learned I have a lot more to learn. Being humble and staying humble matters when you're surviving a failure. There are always people smarter than me, people who could replace me in my own position. One of my takeaways from the self-reflection is that I need to communicate my confidence in doing that job more effectively than I did.

What I found difficult during the process was changing my train of thought fast enough. I had to start making decisions and having conversations as if I were already in the position. I learned that listening matters even more at that level than in any job I'd held before. As people interviewed me, I paid attention to the kinds of questions they asked. The questions tell a story about what each group values. The pattern shifted with every round: teachers union, leadership team, cabinet, community leaders, and school board. Each set connected their values to the superintendency. Before the interviews, I'd decided which qualities and values make me who I am, and I worked to make sure those came through in every answer. I can get better at this. Again, I learned so much about myself.

Person working through a problem with notes and diagrams spread out on a desk

5 - Setting Yourself Up for the Future

Failure, handled right, sets you up for a better future. If you keep a list of people who have crossed you, you'll live in retribution and resentment forever. Drop the list. Decide instead how this failure can set you up for what's next.

We learn from failure by finding the things we can improve. Sometimes failure exposes a gap in experience or preparation. Shaquem Griffin had his left hand amputated at age four and spent his career being told what he couldn't do. He went to Central Florida, was named the American Athletic Conference Defensive Player of the Year in 2016, and captained the 13-0 UCF team that finished the 2017 season undefeated. He wasn't invited to the NFL Scouting Combine at first. He earned a late invitation, ran a 4.38-second 40-yard dash, and became the first one-handed player selected in the modern NFL draft, taken 141st overall by the Seattle Seahawks in 2018.

As for me, I believe the failed interview has set me up for future positions. I understand more fully what I need to do to make it at the next level, and what experience I still need to get there.

Two colleagues sitting face to face having a serious conversation

6 - Not Shying Away from Hard Conversations

When someone fails at something, we sometimes don't know what to say. It feels similar to searching for the right words for someone who has lost a loved one. Just being there and letting the person know you're there goes a long way when failure happens. I found that plenty of people would walk the other way when they saw me. Most often they'd steer the conversation away from the failure entirely. We can't shy away from these conversations.

In a failed relationship, friends have to decide how they're going to talk with you about it. Some comfort you, some give advice, and others won't engage at all. A few decide not to be around you afterward. It's interesting to me that they're there for all your successes leading up to the failure and absent once it arrives. You'll also find the true friends who stay with you through the whole thing, whatever the outcome.

We can't shy away from having these conversations with kids either. We let them know it's okay to fail, and that we're judged more by how we get back up. We have to model that and use descriptive language when we teach it. Most of all, we have to stay positive in spite of whatever obstacles show up. We have to show them that when we fail at something, we don't stop and we don't give up.

Hands passing along a handwritten pay it forward note to another person

7 - Pay It Forward with Grace, Compassion, and Encouragement

So much of what we talk about is how we handle failure in ourselves. We also have to step outside our own shoes and show grace, compassion, and encouragement to the people failing around us. As we try not to judge others, we have to acknowledge that when they fail, it's okay. We can show kindness and start a conversation. Too often in our society, we attach a negative connotation to failure and read it as weakness. Maybe that comes from our fascination with sports and competition, but it's a mindset worth changing.

When a close friend didn't receive an award recently, I had that hard conversation. We talked about what they've accomplished so far, everything they have going on now, and what's coming up for them next. Then I told them how much I believe in them. Then I bought them a drink.

We need to reach out to people whether they succeed or fail. We need to be compassionate and let people know we care about them either way. Then we encourage them on to the next thing.

Frequently Asked Questions

What can school leaders actually learn from failure?

The useful lessons are specific, not general. A failed interview tells you which competencies a hiring group weighted most heavily, where your answers went thin, and how well you communicated your values under pressure. Write those down within a week, while the questions are still fresh, and you'll have a development plan instead of a bruise.

Should a principal talk to students about a failure of their own?

Yes, when it's age-appropriate, and the focus stays on what happens next. Students spend most of their day watching how the adults around them respond to setbacks. Seeing a principal name a failure, stay steady, and describe what they'll do differently teaches more about persistence than any lesson on the topic.

How do you keep a failed interview from ending your ambitions?

Separate the outcome from the verdict. Not being selected means one group chose one candidate on one day against one set of priorities. It isn't a ruling on your capability. I interviewed for seven principal positions before I was hired for one. Apply again when the next opening fits.

What should you say to a colleague who just failed at something?

Say something. The most common mistake is avoidance, and the person notices every time someone crosses the hallway to dodge them. Acknowledge it plainly, ask how they're doing, and talk about what they've done well and what's ahead. You don't need the perfect words.

Does failing hold you back from moving into district leadership?

Not on its own. Search committees look at preparation, experience, and fit. Many administrators encounter unsuccessful applications or interviews while pursuing district leadership roles. What tends to hold candidates back is repeating the same interview without addressing the gaps the last one exposed.

Reflect, don't ruminate - The gap between a failure that teaches and one that lingers is how quickly you move from replaying the loss to planning the next attempt.
Failure is curriculum - Students learn how to handle setbacks by watching the adults in the building handle theirs, which makes an honest response part of the job.
The interview is data - The questions each group asks reveal what they value, so tracking the pattern across rounds is worth as much as the outcome.
Don't dodge the conversation - Colleagues who fail notice who stays and who avoids them, and showing up matters more than finding the right words.
Apply again - Seven unsuccessful principal interviews came before the job I have now, and that record is an argument for persistence rather than against it.

If a failed interview convinced you that the gap was preparation rather than ability, that's worth acting on. Depending on your state's requirements and your career goals, a graduate program in educational leadership may help build the preparation needed for district leadership. The sponsored programs on this page include online and hybrid options built for people already working full time in a school.

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