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Following on from newbie mistakes, I wanted to know what mistakes the leaders themselves have made.

Remember, these are all successful serving or retired school leaders. But they are not perfect. Wisdom doesn’t come from having no weaknesses; it comes from knowing your weaknesses and addressing them. Those weaknesses are often revealed in our mistakes.

The ability to reflect on our mistakes, to learn from them, to move on from them, and to grow because of them are traits of an accomplished leader — traits of a wise Head.

In their responses, the school leaders demonstrated reflection and wisdom. They demonstrated that their mistakes have formed the leaders they are today.

For ease of reading, the responses are grouped into themes.

Get recruitment right

“Assuming new hires were settled when they needed more support. Now I spend more time and energy onboarding staff, regardless of their level of experience.”

“A poor appointment — based too much on skills and not enough upon personal qualities — caused lasting and ongoing problems. When interviewing, I now require each candidate to convince me of their good character, rather than assuming that it’s the case.”

Be consistent, be clear and celebrate success

“Making exceptions — early in my career I made an exception for a child to participate in a football camp that was not open to their year group. When other parents found out I had a whole group in my office wanting to know why their children could not also participate. I am now extremely reluctant to make exceptions.”

“I didn’t celebrate all the work being done behind the scenes enough. Now I make a point of being consistent in celebrating our successes, no matter how small.”

“I regretted not formalising my expectations, assuming conversations were adequate. Now I follow-up with written confirmation of what has been agreed. Or, at the very least, close meetings with a clear summary of who has agreed to do what.”

Avoid micro-management

“Too closely monitoring staff did cause me problems. There are often extenuating circumstances as to why teachers don’t perform; over time, I developed a more understanding and caring attitude towards issues among teaching staff.”

But, you can’t do it alone

“I had to learn to coach staff and, even more importantly, delegate, so I didn’t burn out!”

“I was promoted to a position where the previous incumbent had micro-managed. I made a commitment that I would prioritise servant leadership; I didn’t want to add work to other school leaders and aimed to make their lives and work easier. However, in an effort to not encroach on their busy schedules I took on too much. As a result, and because I lacked the confidence (and desire) to delegate, we made far less progress than we should have.”

“Working all night for weeks on end as a Housemaster and suffering illness as a result. Sleep is vital, you won’t help anybody if you can’t focus.”

“Realizing that I alone could not secure the aspirations for my team and our students and that, in terms of leadership agility, as the Kenyan proverb has it: sticks in a bundle are unbreakable.”

Though sometimes you will wish you had

“Being too friendly with staff and then losing respect as a leader.”

“When I started out, it was safer and easier to make alliances with like-minded people. It led to some alienation of certain members of staff and blinded me to some of the issues with the people I was allied with. In my new post I have aimed for greater neutrality and it has paid dividends.”

Trusting the wrong people.

“I overestimated my colleagues’ loyalty; when their jobs were threatened they threw me under a bus. At the end of the day, on some matters you have to fight alone.”

“I once thought that creating friendships at work was important when in fact it was detrimental.”

Don’t make assumptions

“Assuming new hires were settled when they needed more support. Now, I spend time and energy onboarding new hires, regardless of their level of experience.”

Slow down, zoom out

“There are a number of mistakes that all would have benefited from not making decisions too quickly or seeking to impose myself too prematurely. I try to give things more time to play out these days.”

“When I first moved into senior leadership, I was still so focused on the immediate instead of looking at the big picture. I had to learn to stop focusing on one class or team and begin to think of all the moving parts of a school.”

“A number of times I have acted without getting as much of the big picture as I needed (or could have accessed).”

“Trying to teach too many (any) timetabled lessons — you are not always doing the students in your classes any favours.”

“Don’t make hot headed decisions.”

“Saying yes to too many things and moving from one innovation to the next without giving time for the last to bed in.”

“Missing one or two key details. Don’t overlook small stuff.”

Trust is hard earned, and easily lost

“I reacted to something I had been told by an adult, telling a child off without getting the full picture — and I made the wrong call. I now make sure I have a good understanding of all sides before I decide what response is appropriate.”

“I broke a student’s confidence once to her mother. It took months to get her trust back. Now I listen to people more and don’t treat them as problems to solve.”

Keep an eye on your own career

“Staying in one school too long. To avoid a fixed mindset, school leaders need to be experience as many different ways of delivering education as possible. As Charles Darwin said:

It is not the most intellectual of the species that survives; it is not the strongest that survives; but the species that survives is the one that is able to adapt to and to adjust best to the changing environment in which it finds itself.”

“Walking away from the dream job because it was in the wrong country.”


In the previous article I asked you to reflect on a mistake you had made.

For this challenge I want you to reflect on a mistake you have seen a leader or colleague make.

Given the same circumstances, and the same information at the time, would you have made the same decision and the same mistake? Be critical but honest in your reflection. Was the mistake caused by a value judgment or was it a result of insufficient information, poor timing or factors beyond the individual’s control?

It is all too easy to sit on the sidelines and criticise decisions, rarely though do we have the full picture. Leadership is conflicted and compromised. The decision-maker is often a victim of circumstance.

Some ‘mistakes’ are, therefore, decisions we, the onlookers, don’t necessarily agree with. The decision-taker may have had few options — they may have been caught between the proverbial rock and the infamous hard place.

As a leader you will make your fair share of decisions that other people will consider mistakes. As a leader you will be critiqued and complained about. As a leader you are exposed and vulnerable.

The challenge then is to empathetically reflect on a ‘mistake’ you have seen somebody else make.

Consider the mistake from their perspective. Could it have been avoided, mitigated, better-handled or managed differently? What can you learn from their mistake about the way decisions are made? What does the situation tell you about the compromised nature of school leadership?

Focus your reflection on:

Process: Could the mistake have been avoided? What can you learn about decision-making processes, communication, values and/or compromise that will assist you in a future leadership role?

Empathy: As a leader you will want staff to be empathetic towards you. By taking time now to reflect on mistakes made by others, and by seeking to understand those mistakes rather than criticise, you will be better placed to make decisions that invite empathetic responses.

The full ‘Wisdom of Heads’ book can be purchased here (Amazon US), here (Amazon UK) or here (iBooks).




on education, by educators, about all things educational

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Dr Denry Machin

Dr Denry Machin

Educationalist. Writer. Sharing (hopefully wise) words on school leadership and management.

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