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Leaders Look Back!

Posted by on in Leadership
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Leaders look back

On May 30, 1911, the Indianapolis Motor Speedway held the Inaugural Indianapolis 500.  Although there is controversy surrounding the winner of the race and methods taken by the winner, Ray Hourron's ingenuity and innovative idea transformed how we all drive today.  Among the other cars arriving that morning for the race, Ray's car had a device attached to the front of the car.  While other race cars arrived with a driver and an onboard mechanic, who also acted as a spotter, Ray attached a make-shift rear-view mirror to the front as a way to increase the weight of the car with one less person.


There was a much-debated controversy that a lack of passenger to spot other drivers could cause a pile-up, but Ray knew that he could look back on his own to be a better driver ahead.  As a result, Harroun won the first Indianapolis 500 averaging 74.6 miles per hour!

I am amazed by the number of articles and post that admonish leaders for looking back.  They claim that looking back creates doubt, insecurity, and a rut of living in the "way we've always done it" mentality.  Yet, we are surrounded by so many examples, both historically and your own life I'm sure, that declares, "Leaders gotta look back to look ahead!"

As educational leaders transition to the summer, it's vital they make conscious efforts and plans to look back over the past year in order to truly prepare for the year ahead.  Check out these 3 Strategies for Looking Back to Look Ahead:

Strategy 1: Look Back at Your Mission to Look Ahead.  Many organizations have a mission statement.  They are meant to point the way in providing clarity and purpose in the work.  Yet, a majority of people have not taken the time to reflect and create their own personal mission statement.  And, the leaders who do, unfortunately, don't take time to look back over the course of the year to see what caused them to move closer or away from their mission.  What helped in moving closer?  What prevented you from it?  What could be done next year to make it more of a priority? (Stephen Covey has a Mission Builder to help guide you in developing a personal mission.)  Take time this summer to create one and then post it on your wall to serve as a guide for the future.

Strategy 2: Look Back at the Relationship with Your Coach(es)/Mentor(s) to Look Ahead.  Take time this summer to look back at your relationship with your coach or mentor.  This does not necessarily mean the person you report to or evaluates you.  As I share about my coaching philosophy, I share that I actually have multiple coaches who I approach for various aspects of my life.  Reflect on how the relationships has grown stronger over the course of the year in building trust and openness to talk about growth.   Have you made it a priority this year?  What made the interactions worthwhile?  What could be done next year to make it more impactful?  Take time this summer to develop a plan to consistently meet with your coach(es) or mentor(s).

Strategy 3: Look Back at Your Positive Impact to Look Ahead.  It's easy to look back at all the missed opportunities and situations when you failed.  Reflecting on those moments is important and should be recounted in order to learn from them.  Yet, too often, we don't take the time to look back at the positive outcomes we had.  Like an autopsy, focusing on them can help us to better understand what caused them to be successful.  What parameters existed for it to take place?  What could be done next year to make them again and again?  Take time this summer to reflect on the environment that created the most positive impact and define ways to replicate them.


The Indianapolis 500 is coming up this weekend.  Race cars have improved since 1911 to now go as fast as 230 miles per hour! Today, all cars come equipped with a rear-view mirror to help us to look back, so we can do a better job moving forward!  In order for education leaders to be successful next year, they need to make sure to look back! 

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  • Guest
    Jonathon Wennstrom Monday, 23 May 2016


    Great post and excellent timing! It is so important to look back and reflect as we plan for the future. I am in the midst of teacher Evals right now and in all of them, we take time to reflect on the year before we plan for next year. Thanks for the reminder and the example!


  • Neil Gupta | @drneilgupta
    Neil Gupta | @drneilgupta Thursday, 02 June 2016

    Thanks, Jon. Great example in coaching up the teachers through reflection!

  • Errol St.Clair Smith
    Errol St.Clair Smith Monday, 23 May 2016

    Welcome, Neil! Loved your first post. It's as thoughtful as the one that sparked our journey together. Look forward to spending more time dancing with your wisdom!

  • Neil Gupta | @drneilgupta
    Neil Gupta | @drneilgupta Thursday, 02 June 2016

    Thanks for your support, Errol! I appreciate you taking the time to read it and encouraging me in my journey!

  • Guest
    AT Monday, 23 May 2016


    As always, you are spot on! The one characteristic I look for in people is their ability to reflect. It is an asset to an organization and allows for failure and improvement.

    Aric Thomas, Principal
    Groveport Madison HS

  • Jon Harper /  @Jonharper70bd
    Jon Harper / @Jonharper70bd Tuesday, 24 May 2016

    Neil, I really enjoyed this. We spend so much time looking forward in an attempt to find new ways to improve others and ourselves that we often forget that looking backwards and reflecting on the past can be just as valuable. Great piece.

  • Rita Wirtz |  @RitaWirtz
    Rita Wirtz | @RitaWirtz Friday, 27 May 2016

    Great post! I always advise we look back to see where we've been and what worked. Formative and summative evaluation at its best. Bravo.

  • Neil Gupta | @drneilgupta
    Neil Gupta | @drneilgupta Thursday, 02 June 2016

    Rita - great perspective in tying this to formative and summative! Love it!

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