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School Cultures Built on Relationships - A Conversation with Jon Gentile

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Today, I'm having a conversation with Mr. Jon Gentile of Educational Wingman.

Jon is a gifted school leader with an uncanny sense of how to build trust. Many of us have similar stories of being thrust into roles for which we are wholly untrained, sometimes unprepared.

It forces us to call upon a well spring of raw talent, to sink or to swim. Jon pulled several Michael Phelps-esque performances that still impact school communities by virtue of the the cultures he built.

Unconventional. Brash. Sometimes a lot like a bucket of ice cold water in the face, albeit on a hot summer day, Jon brings love to the equation. Love for potential, for people.

Jon: Dr. J, you asked me for possibly three scenarios, so lets see if I can separate.  But I’m going to start with what I call my Big Picture:

First, let me talk about my fundamental key points on relationships


  1. Be genuine. I know who I am, I am loyal to my sense of self.  I am aware of gaps in my abilities. I am confidently humble.
  2. What does this mean?  I know what I bring to the table and what I don’t.  I know how I can deliver and connect.
  3. Nothing matters if THEY DON’T HEAR YOU. So while I’m confident, I have to be humble because I want to facilitate the optimal opportunity to hear me.  Otherwise, we are wasting resources. 

Dr. J: How do you balance confidence and humility?

Jon:  Don’t downplay you.  But own things that don’t matter so that others feel empowered.

Dr. J: Is that also like picking your battles?

Jon: Not battles, just being accountable for the things that matter to others, but also minding the things that they aren't paying attention to. 

This is universal for all levels of cultural stakeholders:  staff, parents and kids.

I keep bringing up humble confidence.

Helping parents see that they also have influence and credibility, even though I'm the principal. That title is like a judge robe or an officer's badge. It comes with some perceived authority, not always the right kind. So knowing that this exists, honoring it, and acting accordingly can really be helpful.

We can all be successful when we toss away the ego.

Not every parent or community member had a positive experience with public education. I might be the first person with whom they've had a conversation.

One way to do this is to call attention to the fact that we all want the same thing.  We want what's best for the children for whom we have responsibility. I build relationships by establishing that.

Dr. J: Sounds nice, but how do you do this. I'm frankly tired of clichés that feel good but are not followed by actions.

Jon:  Okay. I try to empower them..... I've been compared to a figure skater.  I’m allowing my partner (the parent or the student) to feel as they are leading, but I’m going to the destination I want the entire time.

Dr. J: That feels a little dishonest, doesn't it?

Jon: No. It doesn't to me. As I said earlier, I am completely loyal to who I am. Confident that I am doing what is best. Maybe that transfers to the people with whom I am working, that they pick up on it, and like that feeling we are on ice, and we are together in the situation, and we can work together.

Great school leaders take risks others wont take, because to us, they aren’t risks at all as we already rigged the deck in favor of the kids.

Dr. J: Okay, more clichés. Give me another example.

Jon: When I taught I asked the class what they wanted for rules.  You could imagine the the 100 rules on the board by the end of it.  I would say, awesome.  Let me see if i can condense these at all and still get it all in there.  I already knew that I was having three rules no matter how many they all came up with.

1.  Pride
2.  Respect
3.  Responsibility 

Everything, in my opinion fits into those. The greats have an ability to simplify complexities.

Dr. J: So, synthesizing the desire for someone to tell them what to do, or all the rules, into three simple approaches. Not simplistic, but simplified, so that everyone can get on the same page?

Jon: In bringing people into my circle or into my network, like I said, I know where I am strong and where I need work or have gaps. I don't have to have all the answers or know all the subjects, I do need to know where to go to get them or hire them.

Ones and twos hire 1's and 2's and threes and fours hire 3's and 4's.  Man, I know I’m never teaching that Chem teacher more about Chem.  But I’ll make her instruction better by fundamental strategies; by recognizing her work, respecting her professional skill, and promoting responsibility through accountability.

How's that for an example?

Dr. J: That's money. Thank you for breaking it down for me.

Jon: Finally!

Let me wrap this up by sharing that I'm also pretty focused on providing feedback. It's something most leaders are afraid of, afraid of hurting someone's feelings.

People have to know that your criticism is coming from a good place.  That we are genuine and do as we say and aren’t trying to set them up.  Feedback is empowering. It makes us all better.

Dr. J: I'm so appreciative. I know you're a busy Dad, and a professional who's in the mix of several projects. Thank you for taking the time to talk about leadership and relationships.

Onward!

Dr. J

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