Why Leaders fail

It’s usually not the technical skills where principals and other leaders have difficulty; it’s the human relations skills.

Don Kress,

Chief School Performance Officer

Together we can make the difference.

Betty Collins,

Elementary Principal

The union president was angry. Rebecca Newman represented the principals of one of the largest school systems in the nation and she wanted to know why some of them were failing and losing their jobs.

Granted, it wasn’t a lot of them, but even just a few was a few too many. With close to two hundred schools, only one or two principals each year were evaluated as not meeting standard or underperforming, education-speak for being ineffective leaders who had lost the confidence of their bosses – the associate superintendents who evaluated them. Less than one percent were in this negative category – but why?

It wasn’t their educational credentials. They all had undergraduate degrees in teaching and had completed graduate programs in school administration. Some had even earned their doctorates.

It couldn’t have been their work history. Almost all of them had come up through the system. They’d been good teachers who had been selected to head departments and when they demonstrated their effectiveness in that smaller arena, had been chosen to become assistant principals. During their first two years in this new job, they had participated in a rigorous training program where their work had been dissected by a team of system administrators and they had been provided with feedback and advice from a series of coaches and mentors. Then, in a rigorously competitive process, they had earned their final entry ticket – to a place in the coveted principal intern program – where they spent a year studying and practicing becoming a principal. It even included a two-month period informally known as the “take-over” in which the real principal left the building and the intern ran the school solo in an ultimate test of their decision-making ability.

So here they were – first-year principals with schools of their own – some of them elementary, some middle and some high schools. Yes, they were novices – but not completely green – not with all of their education and work experience. And they weren’t alone. They were each assigned a consulting principal – a kind of executive coach – a formerly highly successful principal on special assignment to support them through their first year in the new job – a job that no matter how well you are prepared still puts you on a steep learning curve. Decision-making is no longer an academic exercise in graduate school and there is no principal in the office next door to come to the rescue. For the first time, like President Harry Truman’s sign on his desk (Truman, n.d.) – The Buck Stops Here – with you.

And yet, with all of that training and experience, a few still weren’t making it, and the union president wanted to know the reason.

She wasn’t questioning the evaluation process or claiming that these principals were the victims of unfair treatment. Rebecca Newman had been one of the architects of a new way of evaluating principals in which a peer coach (the consulting principal) drew a conclusion independent of the principal’s supervisor (the associate superintendent) and both of their judgments were scrupulously reviewed by a panel comprised of an equal number of associate superintendents and principals.

“I want to know where these principals went wrong,” she stated. “I want to know if there are any patterns in their experiences that would teach us some lessons about how to better prepare principals. We don’t want to be sitting here a year from now having watched someone else lose their position and not know if we could have done something to prevent it. I want this to be studied and reported out soon. This is urgent!”

She made this demand at a high-level meeting of executive staff and union leaders. Everyone agreed it was a compelling problem and thought it was a reasonable request and a good idea. I did too, even though I knew that, as the director responsible for the training of principals, it would be up to me to figure out how to do it.

I brought my team together to brainstorm approaches. Clearly, it wasn’t going to be an experimental research study, since we weren’t going to come up with a bunch of variables and then manipulate them with a treatment and control group. Besides, it would be unethical to change the training program in a way that we thought would solve the problem and then withhold it from some of the new principals. It had to be a qualitative study in which we looked back at all the written evidence about the principals’ performance and figured out what had caused them such significant problems that their careers tanked.

We reviewed all their evaluations which luckily were written in narrative form, so there was a lot of rich language and detailed examples to draw ideas from. The evaluations were written based on standards that had been developed by a national group. They could be summarized in just a few key words: 1. Vision, 2. Instructional Leadership, 3. Management, 4. Collaboration, 5. Professionalism, and 6. Context (Social, Economic, Political).  (Professional Standards for Educational Leaders, 2008)

As I am sure you have guessed from the title of this book, all the evidence pointed to problems in one area above all others – the failure to collaborate. There were issues requiring improvement in some of the others too, especially modeling professionalism and reading the social and political context, but when you dug down more deeply, what you realized is that even these other problems either had their root in the principal’s lack of collaboration or were manifestations of this weakness.

It was pretty astounding to think that we had spent years training these administrators, learning about their strengths and habits, trying to understand their thought processes and shaping them into visionary instructional leaders for our schools. While we had taught them many skills which they had mastered, such as analyzing data, observing teachers, scheduling, planning, budgeting, we had missed one essential piece – the skill of working with others.

We did plenty of reflecting on this finding. If we wanted to be generous to ourselves, maybe we hadn’t missed it completely, but we had certainly underestimated its importance and underemphasized its place in our curriculum on school leadership. It was as if we had discovered a blind spot. And with all blind spots, what’s really interesting is not just discovering you have one, but figuring out what underlying assumptions caused you to think this way.

We had a theory that applied to our district – and now that I have had the opportunity to work with school systems, private and charter schools and university programs all over the country, I am convinced the theory applies to almost everyone in the business of preparing leaders (and not only in education). It’s simply this: People often think of human relations, communications and collaboration skills as soft skills and soft skills aren’t valued as much as technical or hard skills.

The irony is that you can teach most people to manipulate a spreadsheet or read a database to analyze student achievement data. It might be more difficult for some than for others, but these are technical skills that can be broken down into manageable and sequential steps to be followed in order to produce a school or department improvement plan, a set of recommendations or a report. It’s a teachable and learnable set of skills. In other words, the hard skills really aren’t that hard to learn. But think about the skill of building trusting relationships. It’s not so easy to break down this skill into linear steps because people are complex and situations vary, all of which requires nuanced interpretation and thoughtful application of strategies in order to know what to do under different circumstances. In other words, learning soft skills is hard.

Don Kress (personal communication, 2010), the Chief School Performance Officer of one of the largest school districts in the country, observed that, “It’s usually not the technical skills where principals and other leaders have difficulty; it’s the human relations skills.” He based his conclusion on years of observing administrators at work, both in schools and in central office. I once had a conversation with his successor, Steve Bedford (personal communication, 2007), about why some principals succeeded and others failed. He had formed a similar opinion: “If a principal is having trouble with raising student achievement, we can work on that; but if he or she is having trouble building relationships and collaborating with people, then that’s hard to fix and can be a career ender.”

The Power of Leading Together is about how to put collaboration skills to work for you and your school or organization. There are just three clear steps to follow, so it’s not so hard after all. But it does require a different way to think about leadership, not as an act of one person directing others, but as a person making strategic moves that model for everyone that WE are leading our school, office or team together. As Betty Collins (personal communication, 2005), an inspiring elementary school principal who influenced generations of school leaders used to say, “Together we can make the difference.”

Excerpt from Peface

The Power of Leading Together: Three Steps to Success (Brill, 2026)

by David I. Steinberg, Ph.D.