10/01/2018 by Ben Bolte |

Pathways to School Leadership

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Not long ago, I read a quote attributed to a female Fortune 500 CEO that said, in effect, “If you want an exciting career, always take a job for which you’re not yet qualified.”

After 30 years of working with emerging leaders in independent schools, I know that actually getting a job you’re not yet qualified for only works some of the time. In the field of education, while administrators occasionally get hired with little or no leadership experience, the market typically favors those who have earned their bona fides and are ready — or at least appear ready — for the next-level role.

In my work, I’m often asked by teachers or graduate students (generally in ed schools) about the steps they should take to become a lead school administrator, or what the best professional pathway to a headship looks like. Newer administrators often ponder the path to future administrative positions with more breadth and responsibility. If one takes a position as an admissions director, for instance, is it likely that one can jump from there to headship?

While experience matters, there’s no simple or single answer. Department heads have indeed on rare occasions become school heads — and more commonly, vice-versa. Directors of admission and development sometimes do become heads and even occasionally a dean of students does. What’s important to know is that there are many possible pathways and they are usually quite personalized — based on experience, skills, interests, timing, and, of course, context. The location, mission, composition, challenges, vision, and governance of a school all play a role as well. If you are contemplating your own advancement in school leadership, here are some strategies that will help prepare you and position you for advancement:

Find Your Mentor 

A number of longtime heads of school — such as Bill Polk, Earl Harrison, Chris Berrisford, Ray Robbins, Bruce McClellan, Glenn Ballard, Reveta Bowers, and others — have considered it part of their job to be shapers of future leaders. Actually, most heads appreciate that opportunity — it’s just that some have been more prolific than others. Together, these influential school heads account for somewhere in the neighborhood of 50 women and men who have risen through the teaching and administration ranks to become successful heads of school. Many more have left those graces to become successful administrators at other schools.

No doubt, those homegrown leaders all displayed multiple talents. Some of them can likely attribute their success to their hard work and initiative. It’s also likely that the relative prestige of their schools played some role in their appointments to a headship or administrative post. But you can’t argue with the pattern and example they set. Along with their talents, they have had engaged mentors who have given them the support and autonomy to grow as leaders — and encouraged them to take the steps to lead schools on their own. When the opportunity arose, these influential mentors also gave them excellent recommendations.

Supportive heads such as these are serving in schools today and building future leaders. If you are a teacher looking to step into administration or an administrator looking to become a head of school, you could wait for someone to tap you for leadership. Better yet, you can let your head of school know of your interests. Ask about opportunities. Volunteer for committees. Connect with those who can mentor you and, when the time comes, support your candidacy and career advancement and development.

If you don’t feel you can find a mentor in your current school, you can also find mentors in the larger independent school community — especially through state and regional associations. NAIS also offers its members a formal mentorship program that connects current or former heads of school with aspiring heads.

Become an Expert 

There’s an adage that says if you become an expert in something, sooner or later the market will find you. As noted, mentors help. But so does expertise. If you have a deep interest in an important area of school work, cultivate it into expertise. Whether it’s a deep interest in STEM-related programming, faculty evaluation, school scheduling, inquiry-based learning and pedagogy, curriculum design, education technology, brain science and learning, student affairs, strategic planning, diversity and cultural competency, or some other relevant topic, it’s wise to pursue it, develop your knowledge and skills, and share your expertise as often as you can. Doing so will create opportunities for you to lead, advise, write, promote, and build on what you know.

If nothing else, this is a great way to fend off burnout — to keep your own enthusiasm for self-education high. But it’s also a great way to make a name for yourself, connect with other like-minded educators, help your school improve, and help you develop some of the skills that will serve you well as you step into administration. School leadership certainly demands having more than one skill-set and specific area of expertise. But being a master of one critical area of leadership can help set you apart in a crowded field and get you rolling.

Diversify Your Experience

On the surface, this piece of advice seems to contradict the suggestion above that it’s good to be an expert in one area. The best way to think of this is as an alternative pathway for the restless.

There have always been younger, ambitious types who want to build their administrative careers quickly. Because they are young and hungry, they change jobs often and always ask for more responsibility. In many instances, they tend to be seen, pejoratively, as “climbers.” However, as workplace practices and demographics shift, and roles have become more pressured, politically charged, and complex, I have seen more acceptance of those willing to seek out and shoulder the responsibilities of running a school — or part of one.

In other words, it’s more acceptable today to be a high-energy risk-taker willing to jump into new roles that both help a school and advance a career.

I maintain it takes about three years to get most major initiatives accomplished in a school, so hopping around jobs too often and too quickly still doesn’t make sense. But, for the right personalities, intentionally and strategically changing roles, and even schools, can be a way to build a résumé and develop a wide variety of valuable skills.

Changing your position or school often also forces you to work with a new constituency, new colleagues or reporting structures, new challenges and goals, and new problems to solve. Business, they say, is about solving problems. To some extent, so is school leadership. Solve more, different, difficult, or varied problems and you’re likely to develop the skills — especially the people skills — and instincts to take on and handle more.

Just remember, you can also re-create yourself in one school multiple times and remain happy, challenged, and fulfilled for years. I’ve seen it many times.

Know Thyself

Once, when our firm had only a dozen people on staff, we all took the Myers-Briggs. All but two of us tested as different types. On the institutional level, this says something important about having a diversity of personalities and learning styles on staff. On the individual level, it’s a good reminder that we each have our strengths and perspectives — and the differences matter.

Some now argue that the Myers-Briggs test is of little value in the workplace. And there are other forms of personality and work-style tests one can take that may be more accurate. But the research also makes it clear that differences in perspective, work style, and life experiences have institutional value — and can lead to better overall outcomes and better decisions. So knowing who you are and what you can bring to the table matters. And sharing what you think and know will help you earn, and keep, your place at the table.

As you consider your career ladder and potential pathways, be clear about who you are, consider your preferences, style, level of EQ, and other personal qualifiers so that you’re focused on serving in the roles that fit best for you. In our ideal careers, we all want to be happy, productive, successful, and fulfilled. To achieve this, it’s best that our work aligns with our personalities and strengths. While different types can certainly manage against that, at least for a while, not everyone is suited for every role. You will thrive and grow best in roles that are suited for your skills and when you have colleagues that value and complement your strengths.

Also, knowing who you are and being able to delineate your strengths clearly will serve you well in job interviews.

Remember the Red Line 

The “red line” is one of those corporate terms — for reaching a point beyond which your current skills, abilities, vision, and/or experience won’t take you. The job or the challenge ahead requires more skill or ability than you currently have. Many people reach this point in a career, sometimes more than once. It can be sobering, humbling, frustrating, or, worse, career ending.

It can also be liberating. Just know that, if you are looking to climb a career ladder, the red line is out there waiting. Use your spider-sense to see it coming. Savvy leaders know that oftentimes, with the right preparation, movement, or determination, you can step over the red line and keep moving forward.

I’ve known or heard about talented educators who have risen quickly in schools only to hit the red line hard and without warning. It might be a newly-appointed head who doesn’t have the fund-raising skills to meet the board’s goals. It might be a new dean of students who doesn’t have enough knowledge of legal issues.

The best way to avoid the career-ending red line is to be honest about your ability and skills (see “Know Thyself” above) and not overreach. As noted, it can be OK to be a “climber” — but patience, as they say, is a virtue. You need to be strategic and deliberate about taking on new roles and positions. And if you trip over the red line and fall flat, it’s time to regroup, figure out what went wrong, and rebuild your career with greater wisdom, knowledge, and humility.

Perhaps another way to say this is that many of us have moments of crisis in our career, times when we feel we are just not up to the task. On the one hand, if your spider sense tells you you are closing in on the red line, you can ask for help and seek the sort of professional development that will enable you to thrive in your work. Alternatively, it’s OK to step down a rung on the career ladder — or even to change ladders — improve your skills, then start to climb again when the time feels right. The way ahead isn’t always forward.

Finding Your Path

I wish I could tell you that there is a single pathway to headship or a top leadership position in independent schools. But there isn’t. It certainly helps to have experience. It helps to have a master’s degree or, in some cases, a doctorate. It helps to take part in leadership programs such as those offered by Klingenstein, PennGSE, Vandy, and others. But ultimately, we must all find a pathway that works for us — that fits with our skills, strengths, interests, and personalities — and where we can be happy and productive.

I’ve seen people succeed on all sorts of paths. In all likelihood, some combination of the above will help you find your way. Maybe the best piece of advice I can give is: don’t be shy about it. Let the experienced educators in your life know of your interests and intentions. Offer to step up to the plate when you can. Take risks. Ask questions. Learn. Be ready. The world of education is in flux these days, and schools need all the help they can get to evolve wisely against the needs and challenges that face them. Smart school leaders know this and will welcome your interests and intentions.


Ben Bolté is the Practice Group Leader of CS&A's Key Administrator Practice. He can be reached at bbolte@carneysandoe.com.

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1 Comment

Nasreen Ikram Hussain 3/9/2019 at 4:27pm

Perhaps the most helpful words of advice I have heard in a while. Where are all these mentors you speak of?

Thank you for reminding us that the “ the way ahead is not always forward” .

Nasreen