Moving from teaching English and journalism to becoming an assistant principal at age 25 (3:03)
How Robert decided he should make the move from teaching to administration (4:29)
Robert’s most difficult moment on the path to becoming a school leader (5:40)
What it was like being an assistant principal on 9/11 (7:40)
How his early experiences in administration have made him a much better listener (9:31)
The importance of prioritizing as an administrator, while also maintaining a long term perspective at all times (10:10)
One of Robert’s greatest moments as an educator (12:28)
Teachers and principals both have tremendous impact on students, but in different ways (14:29)
How Robert strives to build a “culture of yes” at his school (15:15)
Robert describes a “culture of yes” and explains why it’s so important (16:15)
The biggest changes that have come about from Robert building a culture of yes (18:20)
The best leadership advice Robert has ever received (21:28)
The importance of being courageous and refusing to compromise your principles for administrators (21:50)
His top book recommendations for school leaders (22:25)
Why teaching students how to properly use and learn from video is crucial (23:22)
Robert’s favorite quote about education (24:12)
The importance of recognizing and learning from different cultures (24:25)
Always assume your teachers and other staff members have the best of intentions (25:25)
What advice Robert would give the younger version of himself – the importance of listening to veteran teachers (27:05)
Books mentioned in this episode
Make Space by Scott Doorley and Scott Witthoft
The Art and Science of Teaching by Robert J. Marzano
Between the World and Me by Ta-Nehesi Coates
Apps and tools mentioned in this episode
Connect with Robert Dillon
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Podcast Session #8
Consistently Believe and Invest in Your Students and the Other Teachers in Your School
Show notes: educatorslead.com/bobdillon
This is the Educators Lead podcast with Jay Willis, Session #8. Let’s go!
Intro: Dr. Robert (Bob) Dillon is currently the Director of the Research Institute at BrightBytes, a national education think tank dedicated to promoting innovation and best practice in all classrooms. Prior to this role, he served the students and community of the Affton School District as Director of Technology and Innovation and has served as an educational leader in several public schools throughout the Saint Louis area over the past twenty years. Dr. Dillon has a passion to change the educational landscape by building excellent, engaging schools for all students. He looks for ways to ignite positive risk-taking in teachers and students and release trapped wisdom into the system by growing networks of inspired educators. Dr. Dillon serves on the Leadership Team for Connected Learning, a Saint Louis based organization designed to reshape professional development to meet today’s needs. Dr. Dillon has had the opportunity to speak throughout the country at local, state, and national conferences and to share his thoughts and ideas in a variety of publications. He is the author of two books on learning best practices called Leading Connected Classrooms and the other is called Engage, Empower, Energize: Leading Tomorrow’s Schools Today. He is supported by his wife and two daughters, and spends the remainder of his time running, reading, and cycling. That’s just a brief introduction Bob, but tell us a bit more about yourself.
Dr. Dillon: Well, yeah Jay thanks for having me and it’s a, it’s a pleasure to talk to all of the leaders as a part of this and you know I always talk about classroom leaders, building leaders, district leaders and we don’t all wear that leadership hat. Yeah my career has been a great one and I’ve got a chance to serve you know folks not only here in Saint Louis and kids and teachers and leaders but it’s just been, it’s been a great path. I’m a learner at heart and so I cannot take on that role of kind of learner and servant no matter what I’m doing.
Jay: That’s great. So tell us a little bit more about the journey itself to becoming a school administrator.
Dr. Dillon: Yeah, I worked in a, as a high school English teacher and Journalism teacher and I really loved that for a number of reasons as I looked back 20 years ago and say the kids were really engaged and something they were passionate about was they were putting together the school newspaper. They were taking pictures, they were out gathering stories, they were writing about things they were passionate about so I think that’s why I loved that job so much but more than that I found that there were other teachers that truly were begging for someone to listen to them, take care of them and kind of remove friction from the system and I have a strength in that area, so very quickly after teaching for 3 or 4 years; I had an opportunity in that district to be an assistant principal and I jumped into that role. And I don’t know why someone hired a 25 year old assistant principal but they did and you know I never looked back and so I was very very blessed that first year to have a principal and 2 others assistants in the middle school with a thousand kids. That all had about 20 years’ worth of experience and so they really were incredible mentors to me those first couple of years.
Jay: So did you kind of always knew that you were gonna go in to school leadership or is that kind of the point I guess just seeing the need was that the point in which you decided or what was that point?
Dr. Dillon: Yeah it’s funny you know, its 20 years ago, 10 years ago when people said you know, “Did you love being a teacher” I said “I really liked being a teacher, I wasn’t very good at it yet” But what I did know was that, I brought people together well. I facilitated conversations; I got people excited about things. Kind of some of those real rudimentary things that school leaders need to do and so you know just like I tell anybody else these days, go work and have a career where you have strength and I just it fit and the timing was right and so I don’t know that I always knew that I was going to be a school leader but once I saw what a school leader did, I saw some of my strengths overlap there and so I looked back and now I’m not this reticent to tell teachers that I was really really excited to be a leader and so I’ve enjoyed that role ever since and kind of worn that hat you know whole bunch of different ways.
Jay: Yeah, so somewhere along the way from teacher to administration. I’m sure there were some ups and some downs. What would you say was one of the most difficult moments on that journey like as you were pursuing that school leadership?
Dr. Dillon: Yeah you know I kind of learn on the job. So I almost kind of count my first years as assistant principal as part of my journey to becoming a leader but I remember walking into a staff meeting and there was about a 30 minute conversation about whether we should have kids chewing gum in classrooms. And I was getting frustrated and frustrated and frustrated and I said something like “You know we have spent so much time talking about instructions around here as we did talking about gum” and about that time that came out of my mouth, all I wanted to do is suck the air back in and like you know hit the button on time and reset things and I was definitely overzealous like you know we know calling people out telling people how I thought it was supposed to be with zero wisdom, kind of early administrator and got me in this trouble and so that those were some of the early downs I would say and so that were part of that.
Jay: So were there any specific moments that stood out like, I’m sure that you know between, I mean where were you at in life at that point I mean was that you know after you made the decision, were there more classes that you had to take and how did you juggle that with everything else you’re doing, you know with your day job you know as you were pursuing that.
Dr. Dillon: You know I was really lucky ; I did my masters and my doctorate while I was still single and didn’t have kids and you know two of my really good friends just earned their doctorates this week you know both of them have 3 kids and a house. Both of them have a loving wife. Both of them have jobs that have ongoing and I really was able to avoid that. And so that worked out ok. But you know I think back also Jay, like in those first couple of years, there were really some incredible moments that I latch unto, I was an assistant principal during 9/11 and I remember that day very specifically.
Jay: I bet.
Dr. Dillon: And having to walk around and talk to teachers and let them know what was going on and figure out communication strategy and you know make sure that kids got home and were safe and you know even in Saint Louis you know certainly not what was happening in New York City by any means but you know where the home of Boeing, lot of folks in the defense industry. A lot of folks in the military, a lot of folks weren’t certain what was going on but I just remember that being the part of leadership that has nothing to do with learning but everything to do with people. And I think that that taught me a lot about the fact that good leaders have to take care of the stuff but really nurture the people. And I looked back on that day as being kind of a transformative in one of my leadership career.
Jay: Yeah so kind of backtracking just a bit, when you’re talking about that some of the struggles and you know being overzealous I think all of us can relate to because you know I don’t know if you’d coin it like the rookie syndrome or what it is but sometimes when you just when you’re passionate about something you really excited and like I’m sure some more seasoned people kind of look at you and roll their eyes and are just like ok yeah let’s just wait until you got a few years of experience and then we’ll talk about that you know. But what are some things I mean maybe that specifically you want to address or maybe just something else but what are some of the biggest lessons that your learn from some of the struggles on the path to becoming a school administrator that maybe you wouldn’t be the same person if it hadn’t been for those struggles like can you kind of mention some of those?
Dr. Dillon: Yeah sure I think one of them has to do with listening and I have become a much better listener over time before I think I was always in that mode, what is needed by the other person to stop talking so I could reply. Ok I’m not listening; I’m just waiting for you to stop talking.
Jay: Right.
Dr. Dillon: But that is maybe become a better leader and I give my wife a lot of credit for that. She’s a licensed social worker and I’ve watched her work her magic with our kids and then her work and being able to really facilitate growth through listening and so that being a piece of the puzzle and then I think a couple other things, I think that I‘ve learned how to make time for both things that are urgent but also things that are significant. I think a lot of leaders can get caught in the to do list but never get to the vision, never get to the important conversation, never get to the informal conversation that’s important that day so that that’s a piece of a puzzle and then realizing that knowing that this conversation may not be the one that changes someone long term. As an assistant principal, you’re meeting with the student, they’re excited. They’re mad. They’re angry and things happen at home, things happened at school that moment may not be where you make change but that could be the moment were you never able to make change in that student. If you just put that relationship, if you respond in a way that’s hurtful and without compassion, sometimes you have to play the long game with students and I think given that first year I go back and think; man I talked to some really really tough students and that they really were struggling and there was a moment where I threw a whole bunch of file foldersand all these discipline reports across my office and then a higher level administrator came in and said “Well I guess today wasn’t a good day because we’re gonna have to do better tomorrow” and it was just that, like there’s gonna be a tomorrow. Yeah you’re right so you know I need to get my act back together and so I definitely remember that as I grow in piece too.
Jay: Yeah so much of what you’re talking about, when you were talking about this communication, I’ve learned a lot, just in my wife and I have been married for 10 years now and so many times when you’re talking earlier just about waiting for the other person to stop talking just so you can kind of say what you want to say and just the, especially in a marriage just in order to have that healthy relationship and for the other person really most importantly for that other person to feel heard and then also a lot of times you’ll miss something if your just constantly thinking about what you want to say and so yeah that’s been a lesson kind of, I’m constantly learning that actually. It’s not something that I’ve kind of arrived in.
Dr. Dillon: Yeah I don’t think I’ve arrived, either in. None of us have arrived in that one I don’t think.
Jay: Yeah, so what, I know you’ve been in school administration for a while so I’m sure you have some really amazing stories to share but what has been one of your, if you could just kind of take us to one point in time that was one of your most, one of your best moments as a school administrator, just one of the most memorable ones that stand out to you?
Dr. Dillon: Yeah, I actually, it actually happened recently which is kind of interesting. You know often times we look to the fruits of our labor right like kids come through a middle school. They think we got them on track, you don’t know. You know I have students now that in their thirties, you know they have children. They’re teachers and I’ve walked into a Panera the other day and everybody knows when you’re walking the Panera you don’t look at the person at the cash register often you’re looking up like I what am I ordering today and so you look up and you’re like I want to pick two and I want this. So I do that I look down at the student who was actually one of my former students standing there and we both have this look on our face like, “I know and I know you” and she smiled then it was this, she didn’t have to say anything and she was like, “I made it, I survived” Really really tough student. I always tell the story that I spent 3 years trying to figure out a job where you just yelled at people because she was really good at yelling at people. And like adults, kids she yelled at a lot of people. I can just find a job where she yells at people. I’m gonna find the right place for her. And you know, lot of anger, lot of this, lot of that were like, it was just great to have that a moment to say like, “I’m ok, I made it” and there was a little bit of a thank you and that smile too and so those are really good moments that we don’t get enough as administrators.
Jay: Yeah, that’s great. I love Panera by the way.
Dr. Dillon: Yeah.
Jay: That’s a good place. What do you think is the difference between the impact you has as a teacher versus the impact you have now as an administrator?
Dr. Dillon: Yeah, well I go back to say like, I don’t ever think I was a very good teacher. I never really honed to that craft. I feel like I was still in that survival mode of that first couple of years of teaching. I do think that I have a passion, deep passion for writing. I shared with you teaching journalism and so I want to give that gift off to students and I really really enjoyed the classes where I got to teach writing and teach that process and so I do think that a lot of students grew in enjoying writing andbeing able to do that. As a leader and actually my latest role here as the Director of Innovation for the Affton School District. I’ve really been able to see what is possible if you do a couple of things, one if you tell people yes. And I really talked about building a culture of yes. A lot around here and then also sticking almost ad nauseum with the idea that we are going to integrate technology for the purposes of kids to create, make and design and over the last 3 years, we’ve been able to get friction out of the systems, say yes to people and really create this culture where kids were creating, making and designing. And I couldn’t be any more proud of the team I worked with and the folks that leaned into that philosophy here. It’s been really really really good and as I moved on in July officially to a new role, you know I this place is gonna be great for the next decade because they bought into culture. So that’s the difference I think between really helping kids be passionate about something and really being able to shift an entire culture. I think it’s the difference.
Jay: So kind of, digging into a little bit, if you could expound on what is the culture of yes and then what’s the significance there?
Dr. Dillon: Yeah and you know, I know that’s again I don’t think I coined that phrase but I really have bought in to the idea that you know ideas that aren’t good would die on their own and as an administrator, the first time someone brings you an idea and you say, “No I don’t think we can do that or Hey can we unblock that site?” “No we can’t do that” Or “Do we have the budget” “No….” if that’s the prevailing attitude of what goes on, then that has a huge ripple effect because not only does it kill that idea, but that teacher’s gonna go back to their department. They’re gonna go back to the teachers’ lounge and someone’ll go “I have this great idea” and they’re gonna say, “Don’t even ask he’s gonna say no” and bad ideas, if you just keep asking questions like, “Tell us more about that” “How did you do that?” They die on their own. They don’t have to die in the beginning and so when people bring me idea and the answers is always “Yes”. You know, “Can we go visit this school” “Yes, let’s figure out when you make that happen” “Can we try this out” “Yes, let’s have a pilot, let’s do that” and so you know you don’t break the bank, you know certainly we all have budgets to deal with but we can build that culture of yes and really genuine excitement around people’s ideas. I think that in too many places, folks feel like they are carrying out a script of how things are supposed to be and they can’t insert anything into that they care about. And that just isn’t the case here anymore. I took you know with the help of a lot of folks…our district felt a very kind of inferiority complex like “Hey we’re good, we’ve always been good” and “Why we can’t be the best in the state? Let’s go for it” and that energy and enthusiasm and just saying “Yes” just made a big big difference.
Jay: What’s the greatest impact that has developed as a result of that culture or just like their willingness to be innovative and trying new things you think?
Dr. Dillon: Yeah and you know on 3 things you know I certainly brought a new layer of technology to the whole district. But that isn’t it at all. It’s when you walk through our “Maker Space” for kindergarten and 2nd grade that they all have as a special right next to art, music and PE. They have “Maker Space” and those kids are playing and being creative and solving problems. I know that 5 years out, 10 years out when those kids are juniors and seniors, that’s going to make a huge difference in how things work. And then the 2nd piece to that is we were really intentional about changing our learning spaces and that’s the big passion for me and actually doing a lot of writing. My next couple of books are about learning spaces. So but they’re coming out and saying like, “You know what we have to have brain friendly classrooms” we have to have places that spark curiosity and so if you walk through all of our buildings now, we have summer library spaces. Some are old computer labs; some are classrooms that people are going wow! I want my space with more like that and we’ve been able to do that on a budget which I think is also a piece of the puzzle. That those two things I really really think have made is different than just another district that’s added technology to the mix.
Jay: Yeah, was this you’ve able to do some things through that culture of yes that other people probably they just they just just dismissed it so one of the advantages I would guess for developing that culture is like lets you know instead of just shooting down every idea or one that maybe sounds crazy. Let’s explore that, like let’s see, maybe that is possible and let’s see if we can figure out a way to make that happen instead of just automatically saying, “Oh it sounds like a crazy idea there’s no way that would ever happen”
Dr. Dillon: Exactly, the other piece that is so central and you know, it’s called “Tall Puppy Syndrome” and if you don’t know that, my friend in New Zealand said “Oh yeah, we’re a whole country that does that” if someone sticks their head up and does something wonderful we chop it off and I think that in schools, if you’ve ever been a part of the “Teacher of the Year” process and how uncomfortable that is in building whether it before, going or after the selection. Healthy cultures point the people that are doing awesome things and everyone celebrates that. No one says, “Oh they need to get back in line and they’re making me look bad” or “You know they need to knock it off trying to show me up over there.” They’re genuinely supportive of really incredible outstanding teachers and projects and things that are happening and we’ve been really intentional about communicating that. Telling that story and making sure that that’s in our social media feed all across the district as well.
Jay: Yeah, that’s great. So I am about to roll through some rapid fire questions, if you’re ready?
Dr. Dillon: Ok. I actually have it in front of me; I thought there’s no way…I need to have this in front of me to be ready so…
Jay: So first one is what is the best leadership advice you’ve ever received?
Dr. Dillon: That it is truly about being a servant and your job is to serve other people and putting that into everything you do is super important.
Jay: What would you say is your biggest strength as a school administrator?
Dr. Dillon: I think I’m courageous. I think I’m willing to take risks. There are things that I’m willing to get fired for. That is so important to me that I would not compromise on those including lots of issues around education equity.
Jay: I love that. I love that. So aside from your own books, obviously which you know of course everybody that’s listening should go out and buy those but in addition do you have a book or two that has helped shape you or that you would recommend for other school leaders?
Dr. Dillon: You know one of those is Make Space which came out of the Stanford designs school and talks about learning space designs so I think that’s a really really important book. And then a book that I go back too and I’m surprised that I mentioning this by going back to it was The Art and Science of Teaching, the Marzano book. I really really now truly bought to this idea that we have to cultivate both the science of teaching and knowing the research in doing that piece and understanding best practice but also cultivating the art of teaching and being able to allow people to have the space to create. Just like we’re creating those spaces for kids are great making those times, we have to create spaces for teachers to be able to raise their level as an artist and as a teacher.
Jay: Right. Instead of like you’re talking about earlier instead of everything seems like it, it’s gonna be scripted right?
Dr. Dillon: Yeah, right.
Jay: Is there a technology tool or an app or software that you’d recommend to other school leaders?
Dr. Dillon: Oh so many, the one that popped in my head, I really like Ed Puzzle lately and there’s a couple of things to do that but we have to teach kids how to digest video in an intellectual way. A lot of passive ingestion of video for kids and there’s a couple of sites for that one that popped in my head that allow teachers to slow kids down inject that ideas while kids are watching videos, we’re such a video driven society. We have to be able to figure out how to learn that way as well.
Jay: It’s called Ed Puzzle?
Dr. Dillon: Ed Puzzle, yeah. There’s a few things that do what Ed Puzzle does but I like that one.
Jay: Ok. What is your favorite educational quote?
Dr. Dillon: This one is hard for me. I’m not a quote person but I’m looking for a quote on my desk. So I’m gonna go with the fact that there are no limits but the sky and Cervantes said that.
Jay: Ok. Great. What advice you have for working with the students that you serve and you know in your school?
Dr. Dillon: Yeah, you know Affton is a very unique place. We are one of the largest homes of Bosnians outside of Bosnia and so we’re one of the few schools, maybe the only school in the country that has a Bosnian studies program in high school. So I just think like there is unique beautiful culture in every school if we allow ourselves to lean into it and we have so much to learn about culture and about the way that kids live and I think we don’t lean in, even when we try to lean into it and I’m not sure we will lean into it as much as we can. Just finish reading the book Between the World and Me. That’s just one a bunch of awards but it talks about school in Baltimore and what that student had to go through just to exist in the community and so I think that’s a really really important piece of a puzzle.
Jay: What one piece of advice would you have for working with the educators that you lead like the other teachers?
Dr. Dillon: Yeah, assume best intentions always. That people are working really hard every day for kids. And that the change that needs to be made is oftentimes about things that they don’t know yet. And so if you can assume those best intentions and really feel like you were helping to help folks do things different instead of asking people to do things more. Because no one has time to do more but I think that folks have time to do things differently and probably a responsibility to do things differently and so I kind of take that one into my work with all the adults that I worked with.
Jay: What’s the best way to connect with you?
Dr. Dillon: Yeah, two things; all of my work and my blog and my website is drrobertdillon.com and then also I’m @ideaguy42 on Twitter and so I’m close to giving that up. I think it needs to change but I’ve been there since 2009, so it’s hard to give up 7 years of being @ideaguy42.
Jay: Well, I was apparently not the first Jay Willis to ever use most of the social media platforms that I’m on. So unfortunately I had to be jaywillis1 in lots of places.
Dr. Dillon: Yeah, it works you know, as long as people know where to find you.
Jay: That’s right. That’s right. So last question and this one is kind of, you know it might catch you off-guard a little bit but it’s , I think it’s a good question for our listeners to just be able to hear the answer too just if you could go back and to when you were a teacher and had just made the decision move into school leadership. If you could talk to your younger self, what advice would you give yourself?
Dr. Dillon: Yeah, I didn’t take time to listen to the wisdom of the veteran teachers. Even folks that are in their final years and may not be knocking it out of the park in the classroom, even though I’ve worked with some great final year teachers, take those folks to lunch, take a walk on the track with them, whatever that is, but be willing to humble yourself to the potential that their story holds wisdom for your career.
Jay: That’s great. Learn from the experience and wisdom of others. That’s great.
Dr. Dillon: Yeah. You know I feel like I was a little arrogant at that time to be able to know that nugget.
Jay: Yeah, I think most of us are; you know like when we’re first started off and we’re just were young and think we’re invincible and just that willingness to be humble enough to admit, you don’t know everything and learn from like the wisdom and the experience of others, such a valuable thing.
Dr. Dillon: Yeah.
Jay: That’s great. Well, thank you very much. Edu-leaders this has been a great interview today. For the show notes of today’s show and other resources visit educatorslead.com and type the word bob into the search tool to find his show notes. Bob, thank you for sharing your journey with us today! And that represents another episode of Educators Lead.
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Educators Lead is a podcast created to help launch educators into the next level of leadership. This show is for you if you are interested in educational leadership as an assistant principal, principal, superintendent, teacher or someone who hopes to be a school leader one day. Educators Lead offers inspiration and practical advice to help you lead more effectively. Jay Willis interviews school leaders weekly to discuss why and when these educators made the decision to move into school leadership, challenges along the journey, and stories that made it all worthwhile. Educators Lead is a great resource for any educator looking to make a greater impact.
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