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All “Whys” Need a “How” to Succeed

By Starr Sackstein — January 28, 2019 5 min read
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Excitedly I listened to Simon Sinek’s book Start With Why and loved it so much that I followed it up with Leaders Eat Last. Both have me thinking a lot about my learning and leadership. Often, I find myself lingering on things that I hear long after I’ve heard them, prompting me to buy the text as well, in order to go back and really dig deeper into the texts.

One idea that really struck me, though, was about how some people are inherently “why” people - big ideas, focused on big pictures and some people are “how” people; focused on the way to achieve those big ideas. Sinek suggests that “how” people can function well, but uninspired without “why” people, but “why” people have a hard time functioning without “how” people because they often can’t get things done.

Earlier in my teaching career, I started a print-journalism program at one of my old schools that ended up growing into an online media outlet. The program took years to nurture, and by the time I was making the decision to leave, students fully ran the two classes and media they produced. For several years I worried about leaving the program because I was certain it would fall apart without me being there.

One of the positive aspects of the program was that it was a two-year sequence, with additional time for meetings as a whole staff, but largely, the seniors were the editors, and the juniors were the reporters. I did more directed teaching in the junior year, but the editorial leadership did the vast majority of leading once we got rolling.

Classes ran efficiently whether I was in school or not, as my students knew what they were doing and knew how to reach me if something that was out of their wheelhouse came up. Everything was electronic so we could communicate on a variety of platforms, and students understood how the system worked.

By the time I decided I had to move on for my career growth, although very sad that I was leaving something I was so passionate about, I knew that I had trained the students well and that the current junior class (who were very strong) could survive a new teacher and keep things as they were. And when I first left, they did. Plus, the editor-in-chief was regularly reaching out to me when her new teacher didn’t have the answers. The new teacher, however, never reached out.

This made me sad, too.

So what’s the point of this story?

I thought that I had firmly implanted both the why and the how for the program to continue to run, but I clearly didn’t. And although the program is technically no longer my concern, and any students who would have known me are long gone, I still feel responsible. A lot has changed at that school since my departure: new leadership, new teachers, new students, but it is still a journalism school.

It had me wondering how I could put structures in place in my new position that would long outlive me and could help the school community thrive regardless. If there is one thing I have learned from these leadership books, it is that great leadership shouldn’t be contingent upon one particular person, the ideals espoused should be embedded in the culture, and the people should feel blanketed and secure by those beliefs.

So how do leaders, great ones, help to foster and nurture environments that help people thrive and can exist without their presence?

This I’ve been reflecting on a lot. I consider the relationships I’m building with our team, always wanting them to know that I know what they go through and respect their knowledge and expertise. It is important that they understand I have their backs and never want to do something that makes them feel like I’m looking for a reason to metaphorically lynch them. Each of us is so important to making the school run well, and our department must see each other as a team.

Communities can only thrive when they work together, not when they compete. There are places where competition is appropriate, but I don’t believe classrooms and schools are those places unless they are in sports, and that even requires good sportsmanship. Teammates shouldn’t compete, they should work together to compete against other teams. Internal competition only weakens the overall impact of how strong a group can be, and that is so with educators, too.

Instead of judging each other or competing with each other, teachers need to be building each other up. We need to work together for our kids and we need to be clear about what the end goal is. When we have our “why” in place and design a “how” that works for all those involved, we have a winning combination.

So as I continue to ponder my shortcomings in the classroom that allowed my program to languish as it was, I wonder how I can learn from that and do it differently in my new situation. Leaders leave, but cultures should thrive.

Here’s what I’m thinking:


  • What did I inherit in my position from those before me, and how can I shift older perceptions to no longer have them associated with the role I’ve stepped into?
  • How can I be a part of the positive changes happening, to organically repave the path without it being exclusively tied to me, as the person in this new role?
  • Who can I further empower to distribute important leadership roles so that they can build deeper structures that can outlive my presence?
  • Are there implicit fears that I haven’t uncovered yet about myself that force me to cling to control?
  • How can we work together to shift perception to make real the necessary changes in our culture so that our new, bigger, more diverse team see themselves like that, instead of discrete departments, segregated by content and different needs?

Sometimes when we think we are doing a good job at something, we miss important details. I have to listen better, observe better, and keep building relationships. My words aren’t enough; my actions need to support what I say in an unwavering sort of way.

Leaders need vision, but they also need a plan to keep everything manageable. We need to know who our “why” people are and who our “how” people are so we can better utilize everyone’s skill sets for the benefit of the team.

What can you be doing to ensure the growth you enable in your organization continues to thrive long after you leave? Please share

*Photo made with pablo.com

The opinions expressed in Work in Progress are strictly those of the author(s) and do not reflect the opinions or endorsement of Editorial Projects in Education, or any of its publications.

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