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For the Aspiring Leader

I’m a big fan of the tv show How I Met Your Mother. The character development is just fantastic and you really feel a part of Ted’s little circle of friends. One of my favorite episodes is from Season 4 episode 1, The Leap. Marshall has wanted to, and claimed he could, leap from their apartment rooftop to the neighboring building, where a hot tub sits on the balcony. For a long time, Marshall has found excuses not to take the leap. Ted is very much at a point in his life where he is ready to leap into something new. What about you? Are you preparing to ‘take the leap’? You know what I’m talking about…leaping from the classroom into administration, leaping from assistant principal to principal, or leaping from the school level to a district level leadership position.

Each school year, like a regular calendar year, has its seasons. And February typically marks the beginning of hiring season across the country. Each year teachers and administrators move on from their current assignment to another for a variety of reasons. Among the reasons for transitioning, moving into a first administrative role or to the next role is quite common. But how does one go about this process? There are so many different ways to approach a career leap. As someone who has made the leap many times (from assistant coach to head coach, from teacher to AP, from AP to principal, from principal to superintendent, from superintendent to entrepreneur), let me share a few ideas, thoughts, and resources that may help you to be successful in the career leap. Understand, everyone’s experience in this is quite different. But there are some things that should not be overlooked before taking that big first step.

  1. Survey the landscape: what is out there and available for your consideration. Leaping for the sake of leaping is not always a wise decision. Looking for openings that are a potential good fit, both for you and any significant others in your life, should not be overlooked. When I left my teaching position to become and AP, the move was coupled with a return to our home state of Wyoming. There were other positions available near where I was located at the time, but for us it was as much about raising our daughter near family as it was about changing positions.
  2. Do your homework: not all openings are created equally. When contemplating a leap, it can be very tempting to look at potential salary placement and homes available on the market in the search area. A little bit of homework on district culture, employee turnover rates, and resource allocation plans (curriculum adoption, capital maintenance plans, etc) can go a long way in letting you know if you’d be happy in this new location. What are the advancement possibilities? It is unlikely you’ll be looking for your last leap, so do you have the potential to grow in the perspective district? Researching the community in which an opening exists is just as important as the district itself. How do the community ideals align with yours? All of this homework done on the front end can make a big difference when you land in the interview chair.
  3. Know your strengths, don’t fear your limitations: I have talked with so many prospective candidates who are looking for some advice. The number 1 thing I tell them, quit worrying about the experiences you don’t have. Focus on the experiences you do have, they are unique to you. Imposter syndrome can jump at you quickly when you’re preparing to leap. Don’t get freaked out by it – embrace it as your chance to focus on all the great skills and attributes you are bringing to the table. The list of ‘requirements’ on the job posting are typically the same for most roles. Rarely do you find the candidate that checks every box and is a good fit. I’m not saying to ignore areas of limitation, rather be mindful of them when the opportunity arises to sit in the ‘hot seat’ and sell yourself to a committee.
  4. No decision exists until the job is offered: I was given this nugget of advice early in my leadership career. So often, people get themselves all worked up over whether or not to apply for a position. Folks, applying does not guarantee success. However, not applying does guarantee you won’t get the job. Every chance you get to put yourself out there, to learn about someone’s interview process, to refresh your resume and brush up on your interview skills is good for you. Don’t let yourself go round and round in your brain about an application. You don’t actually have to make a decision unless they offer you the job. Take that one for what it’s worth.
  5. Get ready: I once interviewed for a position without doing any research on the district, the school, or the leadership team. It was a nightmare. I was so unprepared and essentially relied upon my charm and general knowledge to make it through the interview. I would suggest you find a resource that can walk you through the process. The very best one on the market (in my opinion) is a book titled Taking the Leap: A Field Guide for Aspiring School Leaders by Robert Breyer (link: This book does a great job of walking you through the homework around community, data, interview prep, and more.

If you are ready, or think you are ready, to take the leap – think the process through and be brave!! You might just land the ideal position for you!

Have a #RoadToAwesome Week



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