Two Questions on Leadership

“Why do you wish to lead?” That’s a common question one is asked to write about when applying for any leadership job. Lots of people want to be a leader, but what does it mean to actually lead? Lead what? Lead whom? Lead where and how? And, of course, the Why?

Leadership is also not always about a position. There’s leading the work and leading people. Which one do you want? Which one is the job?

Leadership is about character more than anything else. Can you lead without a title? Can you show leadership when it’s not in your job description? Often, we expect responsibility before we’ve demonstrated accountability. We want the job or title before we’ve shown we are capable of doing it, and doing it well.

I ask aspiring leaders and mentees to consider these questions, to reflect deeply on them because leadership is as challenging as it is rewarding. There’s nothing easy about asking others to follow you…

…Which is why I ask those who want to work for me, and those who aspire to more than just a title or position and want to learn the character of leadership, “Why would anyone want to be led by you?”

The first question, “Why do you wish to lead?” is about you. The second question, “Why would anyone want to be led by you?” is not about you, even though you will have to talk about you. How does what matters to you also connect to what’d matter to others? What will your leadership offer someone else? There are probably more average, mediocre and poor leaders than good and great ones. So how do you improve yourself to improve others?

Great leaders make others better in the course of bettering their institutions. The second question is a more complex question than the first one and, therefore, a better one in my opinion. It’s about the whole and not just the individual; it requires deeper reflection on community and its people, on the ethics of leadership, not just the mechanics of it.

So, why would anyone want to be led by you?

Read More:

No Regrets.

If you wait until you’re ready, you’ll be waiting the rest of your life.

You’ll never be fully ready for the things that matter. Most of the time, waiting until you’re ready is the fear talking. We’re scared that if we put our heart and soul into something it might fail. How you respond to this fear is often the difference between living a meaningful life and one filled with regret.

Good opportunities appear suddenly and disappear rather quickly. Beyond a certain point, which most people reading this newsletter have reached, outcomes matter less to life satisfaction than minimizing regrets. While the pain of trying something and failing sucks, it’s over rather quickly. The pain of regret, however, lingers forever.

You don’t control the outcome. You control your actions. Are you moving toward success or avoiding failure?

Shane Parrish, “Brain Food” newsletter, Farnam Street, 02/23/20

I’ve shared a few times on this blog my doubts and my fears about my next step. It’s not my brain that needs reassurance; the brain knows I’ll be fine. It’s the rest of me. Whether it’s my age, or our title-asset-follower-status-driven culture, I find myself more concerned at times about achieving outcomes, instead of minimizing regrets.

I don’t know what’s next after June 2021 and whether I’m “moving toward success,” but I won’t stop now because I’m terrified of failure. I may not control my success or failure, but I control every step I take. No regrets.

What are your fears? What’s your meaningful life, and are you living it already? What regrets will you choose to have?

The Two-Year Anniversary of Parkland

I’m breaking the norm from my usual two posts a week, every Sunday and Wednesday, to share this letter I wrote to The Children’s School families two years ago, on Feb. 21, 2018. I end with the lament, “Growing up should never be so hard to do.” Two years later, it’s still hard. This afternoon, I talked to one of our teachers, S, who had a really difficult day yesterday. Her daughter, F, is eleven years old and goes to one of the local public middle schools. Since August:

  • She has witnessed three fights at her school;
  • A few weeks ago, some students in her class were held at gunpoint outside the school;
  • Another student comes to class every day, curses the teacher and throws stuff around, threatening to kill everyone.

S is wondering why this student is still allowed at her daughter’s school. What does she tell her eleven year-old? How does she protect her childhood? Growing up should never be so hard to do.

Dear TCS Families:

I can’t stop thinking about the shooting one week ago in Parkland, FL. I don’t know why that is; something feels different now. Maybe I can’t put it out of my mind because I’m not supposed to; because it’d be wrong to ignore, again, why these tragedies continue. Schools are the strongest and the most vulnerable places of any neighborhood; where families bring their most precious parts of themselves, their children, and their dreams and aspirations and hand them over into the trusting hands of strangers who quickly become an extension of the family.

I’m wondering, and worrying, right now about all of you: what are you telling – or not telling – your children about what happened in Parkland? Are they asking about whether it can occur at our school? Why someone, anyone, would want to harm anyone who looks like them or their friends? I wonder and I worry about each of you.

Shortly after I started at TCS in spring 2013, Neeti asked me whether I had accepted the reality of what it means to be a head of school. I said yes. I felt responsible for the livelihoods and the lives of several hundred children and adults and, directly or indirectly, their immediate and extended families. We don’t have children of our own, but I come to work every day knowing and accepting the responsibility of keeping your children, and those that surround your children, safe and secure as if they are our own.

I left my own immediate family when I was 16 and came several thousand miles away to a small boarding school in Asheville, NC. While my parents supported me and loved me, they couldn’t really “parent” me from so far away. When I graduated from college, I joined schools as a teacher and then administrator because being in schools helped me compensate for the void I felt in my life of a family and my parents. Until the age of 16, I had a normal and wonderful childhood. But, my childhood ended when I came over to the United States, and I had to grow up, sometimes against what – looking back now – I’d have wished for myself. To steal from Christopher Robin in the movie, “Goodbye, Christopher Robin,” my childhood was wonderful, but growing up was hard to do. The childhood of so many children in Parkland and schools across the country has ended. Growing up now will be hard to do.

A few months ago, I read an article that the founder of Amazon, Jeff Bezos, obsesses over the customer experience and has made that the cornerstone of Amazon’s culture. I wondered then what I obsess over as head of The Children’s School. What would I say to anyone who asked me that question? My answer didn’t take long. I obsess over childhood, to ensure that every child’s joy, creativity, and passion for life; their can-do, will-do attitude; their sense of invincibility; their wonder and curiosity; and their limitless imagination that builds castles in the air and reaches for the stars are at the center of everything they do or experience, to embed it all so deep into their consciousness that it becomes inseparable no matter what the world tells them or inflicts on them. I obsess over that kind of a childhood; and I see it happen at TCS every day.

Adults who have been adults for too long naively call all of the above a child’s innocence, implying that our children don’t know better. Reflecting on the events of one week ago, it seems to me that it’s we – the adults – who don’t know better. Let’s build those castles in the air and reach for the stars like our children do. They show us every day that they have power. Why, then, do we act so powerless? Others may call it naive, but perhaps that’s how we will protect our children and their childhood. Growing up should never be so hard to do.

For all children,

I’m Excited, Also Terrified.

So many in my personal and professional circles have been encouraging and supportive of my move to India this fall to join Enabling Leadership (EL). They are happy for me, even proud, and called me, or the work I’m going to do, “noble,” “brave,” and “bold.” They are impressed with my “courage.” A few have wondered or asked, however, if I’m also scared. I quit my position at The Children’s School (TCS) without another in hand, and I’m taking a job across the world in a different hemisphere, culture, community and industry, with little to no experience with the people I’ll work with or serve, at a scale I can imagine but not yet understand, and without the same pay and benefits of a head of school. That’s just on the professional front. Personally, Neeti and I became American citizens two months ago, she’s happy in her job and her business is growing, and she will remain in Atlanta for the ten months I’ll be abroad. I’ve mitigated every risk I know, but it’s still enough to scare me. I could have said yes to EL in May 2019 but it took me another five months to do so. And, I’d wake up panicked even after Neeti and I made our decision in late October. I’d panic inside every time I told people what I’m going to do. A lot of self-talk and self-doubt would start and repeat itself: What have I done? It’s not too late yet. I can say no. I can do something else. This other opportunity just popped up; it’d be perfect for me. Yes. No. What have I done?

We are terrified of vulnerability. I can be not-great in front of my family and friends, who will not take advantage of my vulnerable moments, when I’m doubtful or doubted, scared and anxious, imperfect or just mediocre. Put me in front of strangers and I’m careful about what I will share. I don’t want you to think less of me, question me, or not respect or admire me. I don’t think I’m that different from you. Brené Brown didn’t develop a whole industry just around my fears and anxieties.

So what am I terrified of, really, and why?

As August draws closer, I have more days when I’m excited than scared, and I’ve accepted that neither feeling is going away for a while.

In late fall 2019, I sat down for breakfast with a TCS parent. She wanted to pick my brain on a work project. This parent was going through a transition of her own at work. She had quit her comfortable job and was striking out on her own. Her father, an immigrant to the United States, was a pioneer and entrepreneur, but now worried for his daughter. To him, he didn’t have a choice when he moved here, but he took on those risks so his daughter didn’t have to later. Now she had left a comfortable salary and benefits in a big company to try something new and less comfortable. I didn’t tell the parent what I was going to do next, but I empathized with her and shared with her the broad outlines of my next move. She told me something that had given her courage, a quote by someone else whose name she couldn’t remember at the time, that made me feel a lot better about my own decision:

We are kept from our goal not by obstacles, but by a clear path to a lesser goal.

Robert Brault

I know my goal for the ten months starting August, but I don’t know what I’ll do after next June. I don’t know if it’s the best decision I’ll ever make, or the most stupid. I don’t know what I’m gaining and I’m scared of losing what I leave behind. I’ve always been a planner and, in a long time, I don’t know what my plan is beyond the next 15 months. I’m not 21 anymore, but I also have decades of work still ahead of me. I’ve bet on myself before, and I’m making that bet again. The path isn’t clear and that’s okay; I choose this discomfort to allow a few surprises in my life now.

Note: My fears, at least some of them, are irrational. I know that. I wrote this to respond to the few who’ve wondered whether I feel any fear. The Brené Brown fans will understand that courage and fear are not mutually exclusive; the vulnerability and discomfort that will stretch me also contain immense possibilities.

“Who-Luck” and How We Measure the Impact of Our Lives

“A bookstore. That’s what I want to build after retirement, but it’s going to be really hard to leave school.” Liz was ruminating three nights ago over dinner on her career, and upcoming retirement in the next couple years. While I no longer work at the same school as Liz, we’ve stayed in touch, infrequent as it is, and we catch up on schools, marriage, educating and raising children, family, books, TV shows and movies, and future plans when we get together.

Liz is right, of course. It will be hard on her, and it will be hard on her school. We are all replaceable, but the better schools create more than just the professional or the position, and the better teacher and administrator does more than just her job. The person breathes life into the profession, makes it her own, molds it to her style and leadership, her way of being and relating, and defines the job or position in a way that is uniquely hers. When she leaves, the position will be replaced but the person cannot be. What is replaceable is the job, not the person. We miss the person, not the job because the job will be done again and again, just not by the same person or in the same way anymore.

Liz, too, will miss the job and school, but I suspect it’s not the job that will be hard to leave; it’s the relationships and friendships, the ones who’ve cared for her and allowed her to care for them, those who pushed her and also gave her grace, befriended her and shaped her. She has seen many of them leave her school over her two decades, and with each departure of someone good, she has mourned not just their leaving but the gaping hole they leave behind in her community and in her life, irreplaceable by anyone else.

As I come to the end of my tenure at The Children’s School, I wonder about legacy and impact. I wonder about questions like, “How do we measure the impact of a life?” Is it in buildings I’ve built, programs I’ve implemented, or the grants and accolades we’ve received? I’ve never put a lot of emphasis on those tangibles. They are important, but buildings disintegrate, programs end, and yesterday’s news is yesterday’s news. I have left many places and will join others and then leave those too. What continues are the people I leave behind and the ones I take with me, in message and in relationship.

Every transition is an opportunity to contemplate the past, present and future. The choices we make, when we are confronted with a fork in the road, determine and define who we are and who we become. In 1998, I dropped out of the school of engineering, transferred to the liberal arts college, and decided to major in philosophy. In 2001, I chose a middle school humanities job in Dallas over other possibilities like law school or a job on Wall Street. In fall 2004, I postponed graduate school to take on administrative roles, and co-chair the NAIS People of Color Conference. In 2008, I turned down an opportunity and more pay in San Francisco to go to Alexandria, closer to a cousin and family on the east coast. Now in 2020, I’ve turned down several comfortable and familiar options to go home again and try my leadership reach and impact on a bigger platform.

I’m an “impact junkie.” I didn’t know my next move in the spring of 2019. It wasn’t simply about going to a bigger school or bigger budgets. Volume was one piece of the puzzle, but it wasn’t my primary or only motivation. I went into teaching in 2001, against my parents’ judgment and wishes, because of the two years I had spent at a small boarding school in Asheville, North Carolina. I was surrounded by teachers and administrators who took more than a professional interest in their students, and cared deeply for their personal lives and the people we’d become. Other jobs felt like a job, but I saw those teachers live more than a job. I wanted their lifestyle and their impact, so I chose teaching too.

I’ve been fortunate in my career. At 32, I became head of school and, at a time, when less than 5% of heads nationwide were heads of color. Success is a combination of many factors, luck being an important one. As Jim Collins would say, I’ve had incredible “who-luck,” people who placed a bet on me, like Jay who moved me to his honors-level English course in my first year at Asheville School; Shaun and Susie who gave me not one but two leadership roles at 24; Jay and Caroline at NAIS who assigned me to the POCC, SDLC and DLI faculty; Tony who’d call and check in on me regularly; Billy who’d make time mornings, evenings or weekends to guide me during any number of crises; Rich who believed I could do something before I did it; and Ray who listened, prodded and sorted through my jumbled thoughts. The list goes on. They were conscious of my future before I was; they felt my needs and wants before I did. Impact is not unidirectional; it’s measured by my reach, and also by those who took time out to reach me.

I will carry Liz, as I will so many others, to India too. We leave jobs behind when we move; but the people we need come with us.

Developing the Leadership Muscle

We practice leadership every time we meet.

As head of school, I consider my weekly executive team meetings as my classroom. In the time I have with them as a group and in their 1:1s, I see my primary responsibility as developing their leadership capacity. Our muscles atrophy due to neglect, so our “leadership muscles” also require the same attention and intention. I assign the team an article to read every Sunday, two days before our team meeting. The article is drawn from any number of sources. It could be HBR, The New York Times, Fast Company, NAIS, and so on. I don’t limit myself to lessons from just education or nonprofits. We study leadership and leaders of all kinds across all cultures and industries. I’ve even recommended the first episode of season one of “Chef’s Table: France.” Becoming a student of leadership is a non-negotiable for me.

When I talk about my team meetings to others, folks are curious, amazed and wonder if they can do the same thing. They frequently ask how I can afford to spend 45-50 minutes of a two hour meeting just discussing an article. I wonder now, after having led meetings like this for almost five years, how my team and I can afford not to. My team is better because of it, and each individual is a better leader. We use the articles to question each other; question our vision and our processes; we interrogate past events or conversations in our community; who we hire and how we promote; what systems require change; what’s priority; and what is resilience and how do we look for it in others and in our school. We spend more time on culture than strategy, and use those cultural and team norms to then inform, engage and question our strategy. We clarify what is confusing and align our intent and impact at every meeting. We are more efficient and effective because we prioritize the “Who” instead of the “What.” Using those two hours every Tuesday for reflective engagement is essential for our growth as leaders who lead other “Who’s.”

I spend more time with new hires to my executive team during their first few months. We learn one another, each other’s rhythms, personal and professional histories and values, experiences that define who we are as leaders and how we lead, and then align all of that to our own community and relationship. Instead of one weekly 1:1, I schedule two. I also have other informal check-ins during the week. We go on walks around campus and off-campus to get coffee, breakfast or lunch. I make myself available to their questions and needs. Leadership is practice, leadership requires attention and alignment, leadership is relationship, and leadership is continuous learning with a mindset and a work ethic for continuous iteration and improvement. That investment of time in the person and team has usually paid off for me. They become more independent of me as the head of school, yet aligned with my vision and direction. The team begins to anticipate my questions and my responses, what I’d think or advise, and who would we talk to so we can create agreements and manage our risks.

I tell new heads of school at the NAIS Institute for New Heads that they are always accountable and almost never responsible. Members of their community will make hundreds of micro and macro decisions in classrooms, meetings, emails and texts that will either move the school forward and create positive outcomes, or generate a negative reaction. They do not direct the vast majority of those micro and macro decisions, yet they are accountable for every single of them. The investment in the executive team, and the individual and team culture and capacity is almost critical to create the necessary intentionality and discipline. Slowing down every Tuesday when we meet, or spending more time with every new team hire, creates alignment, and alignment creates momentum. We move faster, we speak openly, we engage with vulnerability (the Brené Brown kind), and we don’t get bogged down in unnecessary politics or betrayed by egos. We also laugh with one another, and go out to dinner or drinks after work. Like any relationship, we have our issues too. I wouldn’t want my leaders and team any other way.

Four years ago, I read an article in Business Insider about Satya Nadella, at the time the recently appointed CEO of Microsoft. In just nine months, Satya had aligned the company around a few clear norms and values. I wondered whether my team, exponentially smaller than Satya’s team or company, could articulate my vision or norms. Most of them had worked for me for at least a couple years and had heard me speak at events, write letters to the community and lead team and staff meetings. Could they answer the question with the same clarity that Satya’s team had for the BI journalist? We read the article for the next team meeting and I asked the question. Silence. Some spoke up and gave versions or stories of stuff they had heard me say or write recently. There wasn’t clarity or consistency. I wasn’t surprised. We were learning but without purpose.

At the same meeting, I offered three principles to focus our priorities and execution:

  • Align values and pedagogy;
  • Break down silos;
  • Develop a culture of learning and leadership.

I picked our readings accordingly too, and we used the discussions to interrogate what we meant by silos, what we observed as the difference between our values and pedagogy, what was the culture already and what did we want it to be?

Not too long ago, one of my senior administrators was struggling with the hard lessons of leadership. She wanted to be better at it. Discouraged, she wrote me one evening. I replied:

Consider what you’re doing right now your apprenticeship. And while that includes daily, rigorous practice, it also needs a dose of perspective and inspiration. So study leadership. Become a student of leadership. What leaders, living and dead, do you admire? Read about them, anything they’ve written, that you can get your hands on… As you’re developing a leadership philosophy, you also want to – and will, with intentionality – develop a personal philosophy that demonstrates your values. The answer to why you want to lead has to speak to a better something… What calls you to do this work that will improve lives or outcomes for all of us? … For a great leader, the personal and the professional are intertwined. I won’t stop doing this work or leading people even when I’m no longer the head of The Children’s School (TCS). It’s a calling, it’s a movement and TCS was my platform for seven years.

Leading people is exhausting, frustrating and rewarding. It’s slow, inconsistent, and demanding work. About six months into my tenure at TCS, Neeti asked me if I felt like a head of school. This being my first headship, I had no comparison, but I said yes. I felt responsible, I told her, for the lives and well-being of hundreds of families of the children who attended and the faculty and staff who worked there. The buck really stopped with me. Until then, even as the assistant head of a school in Alexandria, I didn’t own the final decision or its consequences. Now I did, and the impact of my leadership would be deeply felt across all the Who’s. Becoming better at it was not just a necessary lesson anymore; it was a moral one too.

Note: This is another theme I will return to frequently. In future posts, I’ll share my weekly selections too, starting with a list of some recent ones.

When is it Time to Move On?

This is not ‘Nishant’s school.’ I’m a temporary keeper of the flame.

This has been a common refrain of mine since my first year – 2013 – at The Children’s School (TCS). I would bring it up at board meetings, in parent forums, and faculty and staff conversations. No institution or program can risk becoming fully entwined with the identity of any one individual. The same is true for the individual leader. Who I am, and what I do or where I do it are not the same.

I’m fascinated by leadership transitions, and I’ve pondered the question – When will it be time for me to go? – since day one at TCS.

I didn’t start in 2013 with a clear end point for my tenure. I knew, however, that the longer I stayed, the school and I would become synonymous with one another. “Oh, TCS? That’s Nishant’s school.” I committed to myself, and spoke of it openly to my team and our board, that on my departure, I wanted to be just another puzzle piece to be replaced. My legacy would not be dependence but independence.

A couple years ago, I came across an article in “The Chronicle of Higher Education,” written by a college president, Janet Dudley-Eshbach of Salisbury University, on the eve of her resignation from her post. It was titled, “It’s Time for Me to Go.” In it, Janet asks the question that I’ve asked of myself and other school heads:

When is it time to go? When has a college presidency run its course? I’ve always wanted to be sure not to overstay the period in which I can be most productive.

I didn’t want to overstay my welcome or relevance either. Leadership in academia and our schools today is increasingly complex with external and internal forces that shift unpredictably and at an accelerated pace unsustainable for many except our most resilient institutions. Our schools require of the person in my job to be the pastor and the CEO, the teacher-coach and the manager, the gentle soul and the tough talker, the best friend and the aloof leader, the visionary and the operations executive. Under these circumstances and expectations, how is any leader expected to know or forecast when it’s time for them to leave, and leave well and on a high note? The question – When is it time for me to go? – has an easy answer when times are bad or poor. A change could be good or necessary. The answer is almost invisible or fuzzy, however, when times are good. Who’d want to leave, or be asked to leave, when things are going well?

When I asked other heads about their decision timeline or rationale, some common themes emerged:

  • The decision is individual to each person, but as Janet says, “‘You’ll know when it’s time’ – and it turns out they were right.”
  • There’s really no good or perfect time to jump off a moving train.
  • I shouldn’t expect most others to understand it.
  • It’s like timing the stock market. Whatever you choose, you’ll wonder what the future would have held had you done the opposite.
  • You want to leave when they still want you to stay, and you have two more years of good work left in you.
  • There will be those who think you left too early, and there will be others who think you’re leaving too late. Hope that you’re leaving behind a bigger group in the former category.
  • It will feel like an intimate relationship coming to an end.
  • Seven years was the magic number at least four different heads shared with me in separate conversations. It takes seven years for a thoughtful assessment and analysis; build relationships, one’s team and board; advance strategic and master plans, a feasibility study and a capital campaign; and complete any campus construction and renovations. At the end of the seven-year mark, it will be time to either get off or recommit to the same cycle.

Many have wondered or asked why I’m leaving. Because I didn’t have my next job lined up at the time of the announcement, a few wondered if I was unhappy or disgruntled, if I’d been fired or asked to leave. Why would I choose to leave such a great job and city where Neeti and I are home, have friends and colleagues we cherish, and a comfortable life we’ve built over seven years? Or, who in their right mind would make such a decision without knowing the answer to what’s next? None of those assumptions are true. I’m happy and I wasn’t asked to leave. The job is hard; I haven’t worked harder at anything else. It’s also the best job I’ve had.

The decision to leave, when it came to me, was not a single event or epiphany. It was a feeling that started somewhere in my gut and developed over time. There were also markers I had set for what I wanted to leave behind and how I’d calculate or assess my impact. I reframed the question for myself from “When is it time to move on?” to “What do I want to leave behind for my successor?” There’s stuff I’ve built and stuff I’ve probably broken; my legacy, like every other leader’s, isn’t going to be perfect. But my impact will be measured in not just what I did when I was here; it will be measured also by whether I’ve set up my successor for success. A few days ago, one of my administrators asked me about my confidence in the future. I told her I had confidence in the people I’ve hired and who are, like her, leading the programs and people under them. No head of school or CEO should ever become irrelevant to their organization, but an exceptional team can maintain momentum as it leads and initiates the decisions and changes necessary for a confident future. For whatever I’ve built or broken in my seven years, my confidence isn’t simply in what I’m leaving behind, but who my successor will inherit.

Giving up power or authority is not natural to us as a species. Washington didn’t have to step down as president after two terms. He’d have been easily reelected to a third one. His farewell address was written to decline another term in office. Every president since, except FDR during World War II, followed Washington’s example until 1951 when the 22nd Amendment established a two-term limit for presidents. His decision reinforced our republican identity; we wouldn’t be defined by any one person.

I leave TCS after seven years knowing that it stands on its own two feet. My successor will have lots to do, but she won’t be alone. I was never the entire puzzle; I was just one puzzle piece.

Note: Leadership transitions, as I’ve already said many times above, fascinate me. I expect to return to this theme over the next several months. Feel free to leave your questions, comments or feedback, and I will try and incorporate them in future posts.