Legacy Planning: How Will You Be Remembered?

Your legacy has the power to shape the way you lead today — long before you retire by Robert M. Galford

Even by the standards of the educational leadership world, Mel Klein has had more lives than a cat. Like many others, he climbed a traditional ladder: high school math teacher, basketball coach, vice principal, principal, superintendent of schools.

But then, after a successful tenure as a superintendent in suburban New Jersey over 15 years, he retired and then quickly un-retired to add a few more lives. He served for almost 20 years as an interim superintendent in more than a dozen New Jersey communities and capped his career teaching leadership dynamics at Seton Hall University’s graduate school, where he also directed the online masters program in education leadership, management and policy.

Considering all that experience, one might naturally expect someone like Klein could give a reasoned, if not a rapid, answer to the question of what his legacy has been. But articulating your legacy — or your intended legacy — can be harder than you think, even for someone like Klein. What Klein learned was that thinking about your legacy can help you better understand your strengths and weaknesses and help you steer your legacy in the right direction.

Whether you’ve been a superintendent for decades or are just stepping into a new role, it’s the right time to ask yourself whether you know what you want your legacy to be — and whether you’re on your way to achieving it. Your legacy doesn’t appear out of nowhere at the end of your career. Your legacy is today.

A Deep Reach

Over time, you’re going to amass a broad track record. You’ll be graded or reviewed on a host of factors, probably including student performance, teacher performance and schoolwide or systemwide performance. But your leadership legacy — how you balance the short term and the long term and the influence you have on the thoughts, actions and lives of the people you lead — is being built now. It already is reflected in the individual faces of each person you come in contact with at work.

What will these people do today (and tomorrow and next year and after you’ve changed jobs or retired) as a result of having worked with you? Will they think about anything differently? Behave differently? Will they be better, happier educators and leaders as a result of the way you conducted yourself at work?

Your legacy is, quite simply, what people will do differently because they were part of your district leadership. Superintendents’ legacies have an especially deep reach. Not only do they affect those with whom they work, their sphere of influence includes the student population, parents, school board and the entire community.

Most people think that a legacy is something you worry about only when you’re close to retirement. But waiting to think about your legacy until it’s time to pack your desk means you’re only left with a host of unsettling “could haves” and “would haves.”

You don’t need to wait until your legacy sneaks up on you. The truth is, the impact of a legacy comes into play long before you retire or leave your school district for another. Your legacy has the power to shape the way you lead today — not just the way you are remembered tomorrow. It is a catalyst for action, rather than a result considered after the fact.

When school administrators engage in this kind of thinking, the concept of legacy becomes much more personal. At its best, legacy thinking marries the one-to-many nature of leadership with the one-to-one reality of day-to-day work, reinforcing the notion that the time to start thinking about it is now.

The Present Tense

So is thinking about your legacy like writing your obituary? Not at all. Obituaries are written when it’s too late. Legacy thinking gives you an opportunity to make a difference earlier on. If you want to be remembered for a certain reason, what do you have to do now?

Thinking along those lines has all sorts of implications for how we spend time now. Are we spending it most efficiently? Are we spending it in the right way?

Nor is legacy thinking the same as setting long-term personal goals. Setting long-term personal goals is a forward-thinking process. Legacy thinking is a process where we take that retrospective view as our lens: What do I want to be remembered for — not what do I plan to accomplish.

Michael Wood, who’s in his fourth year as superintendent of the Nashoba Regional School District in Bolton, Mass., believes he first started to consider his legacy when pondering a career switch.

“I knew when I was in elementary school that I wanted to be a teacher, but I knew that my legacy was important when I left my first teaching job for my first administrative job,” Wood recalls. “At my going-away party, my colleagues talked about how they were going to miss me, the person. I learned then that the sum of what you do and how you do it is key to having an impact. I knew then that all that I did, consciously or unconsciously, had an impact — so much so, that a year later I wanted my old job back and they gave it to me.

“Ten years later in my second superintendency, I hired two of my colleagues as principals and one is still there as the new superintendent,” Wood adds. “That is an important part of legacy, too — who you bring along with you for the journey.”

Legacy thinking is about you — as an individual. How you interact with others on a one-to-one basis every day. Someone with personal hopes, goals, desires and expectations. You want to do your best for the school district, but you also want to be at peace with yourself. Have you found satisfaction in your job? Are you doing the things you want to be doing? Are you playing to your innate strengths? Are you in your natural role? Or are you constantly pushing or pressuring yourself far outside of your comfort zone to achieve the organizational goals before you? Legacy thinking calls all of these questions into play.

Valuable Outcomes

For many people, thinking about one’s legacy is triggered naturally when a crisis occurs. A districtwide budget shortfall. A building project that goes awry. An act of violence on school grounds. The kind of thinking that follows a big crisis often tends to be driven by emotion and, while it is powerful, the behavior changes it inspires are often not sustainable.

On the other hand, engaging in legacy thinking in the absence of a crisis can foster cleaner insights and result in changes that are sustainable. Said one of my more reflective executive clients: “You shouldn’t need a crisis to get that kind of clarity.”

Nor should you wait until you’re in the midst of making sweeping changes. As those in school administration know, change can be difficult.

Brenda Finn, superintendent of the 3,200-student Concord-Carlisle Regional School District in Concord, Mass., says: “We all work with what we have, what we find when we walk in the door. School districts are conservative by nature so change is a challenge. I’ve found that districts that face the greatest needs are often the most innovative. They do not invest their energies in defending the right to argue that, since they are the best they do not need to change.”

The more people reflect on the impact of their leadership, the less often they describe it in professional terms. They speak of the aspirations they have for the entities they manage, but attribute ever-greater importance to the one-to-one influence they might have on colleagues, direct reports and the people in the organization at large.

The further they think, the more they also begin to talk about their desired work legacies in personal terms. Says Finn: “Legacy is a word that has a resonance with family and personal connections for me.”

As a result, focusing on one’s legacy has a second valuable outcome, and that is to help leaders leave positive legacies.

Looking at this in terms of the business world, we see that successful companies almost always have strong leaders, but sometimes organizational success comes at a personal price. We all can name people who built financially successful companies at the cost of personal relationships or their own satisfaction. We also can name people who excelled at driving a company forward yet left peers and direct reports vowing, “I’m never going to behave that way.”

Positive results, in terms of the organization’s success? Yes. But they may leave negative leadership legacies.

Creating Community

No one leads a district in a vacuum. As you think about your legacy, you may find yourself realizing it’s not just how you lead that matters, but also how you have influenced your colleagues to lead and work together.

When thinking about planting the seeds for his legacy, Wood says the steps he took are rooted in developing the district’s leadership. “We have leadership throughout the teacher ranks and they give voice to the work that we are doing,” he says. “Sharing the leadership in deciding our goals and how to achieve them is the best fertilizer. I can’t do it alone, and there are days when I think I am, but then there are days when I hear a comment from a teacher, a parent or a student and I think, ‘Wow, that began since I came here,’ and I feel warm with pride.”

Finn points out that legacy thinking includes the hope that one’s work will continue over time, transforming others and getting better with each progression.

“In each district, we identify the critical work that needs to be done, involve those closest to the situation in finding solutions and shaping progress, encourage new leadership that will keep the work alive and improving, and walk out the door knowing and hoping that someone with some of the same ideas and some very different ones will walk in the door,” says Finn, a superintendent for eight years.

“This is the beauty of organizations — they flourish with all kinds of leadership. It’s just plain goofy of us to believe that any one of us as an individual can work to set the direction of an organization. Our work succeeds or fails because of who we work beside and how we have supported and directed their efforts to move the organization forward in a like motion.”

A Direct Self-Exam

When faced with the day-to-day challenges of leading a school district, it can be hard to start thinking about your legacy. There is no exact blueprint, but there are guidelines to follow. To begin considering your leadership legacies, ask yourself these questions to help generate the insights that legacy thinking demands.

  • Who were the last 10 people to come into your office, to call or send you an e-mail (for reasons other than expected, routine contact)? What did they want? Did they seek advice on personal matters? Did they want you to mediate a dispute? Did they want you to help them brainstorm about something?

If there is any common theme in your answers (and there may well be), that is a strong clue as to your natural tendencies as a leader, and as to the positive legacies you may be seeding.

  • Consider the parts of your job you find most enjoyable. Do you see any overlaps with the needs that others come to you to fill? If so, there’s another clue. What parts of your job do you enjoy the least? Are there aspects of your job you dread? Are these things formal responsibilities — responsibilities you take on because you feel you must?
  • Ask what you have you carried forward from your first job. What impressions are still with you? What did you learn there?
  • What about yourself as a person? Are you the same at work as you are outside? Do you wear a “game face” a great deal? If so, why? What are the threads and themes that permeate both worlds? Are there things you want to do, but you keep saying “soon,” or “next year?” What are those things, and how will you feel if you never do them?

These questions can help you establish the beginning of a portrait of your own leadership landscape. They can help you think about where you might be leaving a negative legacy (and why) and where, by contrast, you might be having a lasting and positive impact.

Half Dozen Roles

In looking back to the legacy he left as a superintendent in his previous school district, a small rural system in Maine, Wood says he believes his lasting contribution was about building systems “so that work could get done, decisions could be made and people knew how things were going to get done. I would guess, though, that my legacy was more about the tangible differences like bringing technology into the district and putting computers in the classrooms and lab.

“I think my legacy was the leadership that I hired and nurtured and then helped to take over after I left,” Wood adds. “I still see the strategic plan on their website and see that it is a living, breathing document and that is a strong sense of accomplishment.”

At times, it can be difficult to answer the “what will your legacy be?” question without just a bit of prompting. And in our work, we have observed that leaders generally fall into one of six different legacy roles. Sometimes they fall into more than one category, but just like in college, people usually have a major.

These six roles include: Ambassadors, Advocates, Builders, People Movers, Truth-Seekers and Experienced Guides. While these merit more explanation than just a mere mention, it can be said here that people often find their roles naturally. It’s what they’re good at, what they like, what they’re rewarded or admired or suited for. (See related story, page 12.)

After all, your leadership legacy — the influence you have on the thoughts and actions of the school district you lead — already is being reflected among the administrators and teachers on the staff, students and community members. To the extent you can influence your course — by being more aware of your own strengths and weaknesses and by probing why certain aspects of your job are more or less desirable — you will be able to seed positive legacies that will start bearing fruit today.

Future Talent

As for Mel Klein, the veteran school executive in New Jersey, he was a people mover if there ever was one. He’s especially proud of the number of people he has steered over the years into educational leadership roles: principals, superintendents, administrators at schools, colleges and universities. He told me stories about people now in those roles. He sent me their bios, links to their schools’ websites. He described the e-mails he receives, saying, “My greatest pleasure is seeing all the others who have become leaders as well. For me, there’s no greater reward, no greater legacy.”

Even if you’re not a people mover, but are instead an ambassador or a builder or something else, don’t you wish you’ll be able to feel the same way? It’s up to you. And your legacy is today.

Robert Galford is a leadership/organization consultant in Boston. He adapted this article from a book he co-authored, Your Leadership Legacy: Why Looking Toward the Future Will Make You a Better Leader Today (Harvard Business School Press). E-mail: galford@yourleadershiplegacy.com