Jessica Gamble graduated from Howard University, which is located in Washington DC. Mrs. Gamble is a huge supporter of Historically Black Colleges and Universities. Mrs. Gamble is married with two children, Kevin and Kai. Mrs. Gamble’s favorite place to visit is Jamaica. She loves it so much that she has been there five times! Mrs. Gamble loves to get her nails done. She always uses unique colors and she NEVER matches her fingers and toes. When Mrs. Gamble was growing up her parents owned a balloon event decorating company so now she can make any space into a party place! When Mrs. Gamble lived in D.C. she worked for the Washington Wizards and the Mystics. She was the captain of the fan patrol for five seasons. She loved to get the crowd engaged in all sorts of outrageous ways!

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Show Highlights

You’re a character in your students and staff’s stories. Hear tips on how and what to narrate.

A Hard Conversation Series on the roles schools play in discussing inequities and bias.

Navigate an uncomfortably hard conversation we all must have.

A process and protocol for facilitating conversations surrounding the topics needed at your school.

Appreciate the diversity in your student body by inviting open communication and visibility.

Cause friction and the tips on how to deal with it.

Interesting ways to increase family engagement so people feel welcomed and at home in your building.

“I would say bet on yourself. Don’t be afraid to be bold and jump out there. You’re sitting in that seat for a reason and so bet on yourself. You are the best person for the job for a reason.”
- Jessica Gamble

Madeline Mortimore

Jessica’s Resources & Contact Info:

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Read the Transcript here.

How To Have Hard Conversations At Scale

Daniel (00:02):
Hey, there were multiple times during today’s podcast that I almost had to pause, I did take a deep breath. I was about to choke up. This was such a meaningful conversation, and it’s our second installment with one of my favorite Ruckus Makers out there. Jessica Gamble. She really unpacks her Mastermind experience. That’s something that we’re doing more and more often on the podcast because the Mastermind is this special space. It’s transforming professional development for school leaders. It’s helping them become even more effective, but it’s connecting them to a powerful network. You don’t have to lead alone. You don’t have to look at your colleagues and peers or your supervisor when you see the future of education and the exciting things we can do. I know we can do it too, but it’s in those spaces with colleagues, peers, supervisors.

Daniel (00:54):
They look at you like you are crazy. Have you ever felt that way? You won’t feel that way in the Mastermind. We’re your people, we’re Ruckus Makers. It’s really cool just to hear her story, how she’s grown, and if you’ve ever thought about joining, I think you’ll have a little more clarity about what that experience is like. Hey, it’s Danny. I am a principal development and retention expert, founder of Better Leaders, better Schools, which I started in 2015. And this show is made for you, a Ruckus Maker, which means you invest in your continuous growth, you challenge the status quo. You design the future of school now, and we’ll get to the main content of today’s episode right after these messages from our show sponsors.

Daniel (01:49):
Learn how to recruit, develop, retain, and inspire outstanding individuals and teams to deliver on the vision of your school in leading people. A certificate in school management and leadership course from Harvard. Get started at BetterLeadersbetterschools.com/harvard. Last year, teachers using Teach FX increase their student talk by an average of 40%. Teach FX uses AI to help teachers see the power of high leverage teaching practices in their own classroom level data. It’s like having a personal instructional coach on your phone, your tablet or laptop. Start your free pilot@ teachfx.com/betterleaders. Why do students struggle? I’d argue that they lack access to quality instruction, but think about it. That’s totally outta their control. What if there was something we could teach kids? Then what if there was something within their control that would help them be successful in every class? And it’s not a magic pill or a figment of your imagination. When students internalize executive functioning skills, they succeed. Check out the new self-paced online course brought to you by our friends at Organized Binder that shows teachers how to equip their students with executive functioning skills. You can learn [email protected]/go.

Daniel (03:20):
Ruckus Makers, I am so excited to speak today and to introduce you to my friend and a really inspirational leader, Jessica Gamble, and she graduated from Howard University, which is located in Washington DC. Jessica’s a huge supporter of historically black colleges and universities. She’s married with two children, Kevin and Kai, who are maybe unofficial Mastermind members and some of our favorite people to see on the screen. Jessica’s favorite place to visit is Jamaica, so I know where I need to host the the next live event. She loves it so much. She’s been there five times and she loves to get her nails done. She always uses unique colors and she never matches her fingers and toes. When Jessica was growing up, her parents owned a balloon event decorating company, so now she can make any space into a party place. While she lived in DC she worked with the Washington Wizards and the mystics, and she was the captain of the fan patrol for Five Seasons. Loving to get the crowd engaged in all sorts of outrageous ways. Jessica, welcome to the show.

Jessica (04:29):
Thank you.

Daniel (04:31):
Well this is super, super exciting to have you on the podcast, and next week we’ll feature you as a Mastermind case study too. And there’s so many things to talk about. I think one of the interesting things about you is how you incorporate family into the school experience. And not necessarily like, obviously you connect with families of your students and of your staff, that kind of thing. I’m talking about blood family like Kevin and Kai and then your parents. Can you talk to me a bit about how you do incorporate them into the school experience?

Jessica (05:14):
Both of my children go to Riverside with me. Kevin is in fourth grade. He’s been here since kindergarten, which was my first year. Kai is in first grade and she’s been here since pre-K. So before getting married and having kids, I always knew I wanted to be a teacher. So even as a little kid, like if people ask you what did you wanna do? I wanna be a teacher. As I get older, I would say, I wanna be a teacher and a principal and a superintendent, like literally my entire life. I’m living exactly the dream that I had as a kid, but also as a dream. I always wanted my kids to go to school with me to go either in the building that I was teaching or the building that I would lead.

Jessica (05:53):
It’s kind of cool. Both of my parents are retired and my father-in-law moved here from Washington, DC about two and a half years ago to be closer to us. I completely have my family roped into everything that happens here at school. My parents and my father-in-law run the book there. Twice a year, they run the winter holiday gift shop. Both of my parents are currently mentors for a program we have here in Cleveland called True to You, where we mentor eighth graders on their path into high school. So they’re mentoring one of my eighth grade classes. My dad participates in any class event that either of my kids have going on as a volunteer, and he is a well sought after volunteer. Every year we do a winter giving tree and my mom does all of the wrapping and tagging for those events. They had a field day for me. Typically whatever I need my family to do, they do happily and graciously. I think part of it is my parents are watching their own child’s dreams come true. And how could you not wanna sit there and watch that from the front row? And my core value is family. I preach that to my staff. Actually today, one of my staff members’ daughters was here helping out. I allow my staff to bring their children all the time to be here in the building. I’m very lucky that my family lives close and they’re willing to support. My students are obsessed with my parents and my father-in-law, absolutely obsessed. They like to know stories, what I was like as a kid, what did I do that was wrong? I’m biracial and mixed. My father’s black and my mom is white. It trips my students out to say that’s my mom because my mom is a redhead. They’re like, you’re Mrs Gamble’s mom. What? And so it brings me absolute joy to have them here in the building with me as often as possible.

Daniel (07:59):
Yeah. What a gift. I want to learn a little more about the True to You program because in my mind, it’s amazing that you have both parents with you. That’s certainly not my reality. The fact that they’re so engaged. They have so much wisdom and experience to share with people. And I was curious if you could leverage that. I’m gonna ask you a question but I wanna share my story. I would bring my mom, she’s been to every school where I’ve worked. Maybe I shouldn’t have done this, but when I was a teacher, I mean, they’re kids, so they weren’t like, oh, that’s obviously his mom. They probably just thought like a sub or some type of assistant. But I remember my first year teaching mom’s in the back. She might even be doing something quintessentially like mom, like knitting or something in the background. But I remember there was a kid, I don’t know the kid or what the situation was, but I remember like this kid not responding to redirection. So I’m thinking, what am I gonna do? Like, this is not going well. Instead of the principal’s office, I sent the kid to the back of the room, I said, you have to go sit by my mother. And all the students, it had dawned on them, they didn’t realize that’s my mom. But once they realized, Mr. Bower’s mom, nobody in my class was perfect. For the last like three days she visited. I think you called it true to true to you. Is that true to you? Yeah. Amazing. Here’s your father and father-in-law. I think you said helping out, I could be wrong. Talk to us about that mentorship program and what’s going on there?

Jessica (09:45):
So true to you is a district initiative. I’ve been in the district for six years, so at least it’s been going on for six years. Part of Cleveland has a portfolio high school model. So many of our high schools have models so students can and have the ability to pick high schools that are more aligned to their likes and their desires or what they see themselves doing in the future. So through true to you, the students take a variety of what’s called Naviance assessments. It kind of helps categorize like what are you kind of into and like, what do you see yourself doing in the future? And then through the True to You program, they talk about financial literacy, they talk about high school choice. The mentors engage with them in a variety of SEL l activities once a month for two hours.

Jessica (10:32):
They go on a college field trip. My students are going on a college visit in the next couple of weeks, I think it’s in April, to see a college campus. The mentors kind of help guide what their likes are into potentially what might be the best fit high school for them within our district. They do form a partnership, a relationship with the students and the adults. The mentors have an opportunity to recommend three students every year that they think should participate in a summer work program at Cleveland State University, where they’re kind of involved in some leadership opportunities and it’s a paid summer internship. And so the district is always looking for tru 2you mentors. They do frequently partner with companies like Sherwin Williams or you know, Marriott or some of companies that have philanthropy goals or give backs.

Jessica (11:24):
They also take just regular volunteers that are interested. And so my parents were business owners in the city of Cleveland for over 25 years. They ran a very successful business my entire childhood and adult life in the city. And I thought that they would be wonderful mentors for my eighth graders. They did raise two kids that they both sent to college and our wonderful grandparents currently to four amazing kiddos. And they completely love being mentors. I love it because my dad’s always preparing like, “I’m getting my PowerPoint ready for the students.’ My students get a complete trip out of the fact that they’re looking at my parents every month. And typically that day they see your parents were here today. Like I knew their stuff was in my office, I saw them. Your mom’s coming tomorrow. Like I know It trips them out because I am very similar to my mom in mannerisms or like I really pattern her. I never think twice about involving my family in school. It turned out to be a good thing and another like a passion avenue for my parents who are retired. Like what a cool way to give back to students and talk about your successes and how you got there.because neither of my parents have a college degree. I think it is important for my students too.

Daniel (12:48):
Schools these days especially sort of frame college is the only way to success, but that’s not true and so that’s cool that they can share from experience okay, we didn’t go to college but we ran these businesses very successful and obviously they had these dynamic personalities because the kids are so interested in what’s going on with mama and Papa Jessica.

Jessica (13:11):
The Better Leaders, Better Schools podcast is proudly sponsored by Harvard’s Certificate in School Management and Leadership. I know many Mastermind members and many Ruckus Makers who listen to this show that have gone through the program and have loved the experience, but don’t just take it from me. Let’s hear how some of the Harvard faculty describe the impact and their heart for this program. I Deeply believe that every single person on this planet has superpowers and it is our job as educators to tap into them and unleash them. Learn more about the program and apply at BetterLeadersbetter schools.com/harvard. You know what student engagement sounds like? Students ask questions, they build on each other’s ideas. The classrooms are alive with conversation. Creating that kind of classroom is much easier said than done. Teach FX helps teachers make it happen. Their AI provides teachers with insights into high leverage teaching practices like how much student talk happened, which questions got students talking. Teach FX is like giving each teacher their own on-demand instructional coach to help them boost student engagement and learning as well as their own. It’s eye opening for teachers and scales. The impact of every coach and principal. Ruckus Makers can start a free pilot with your teachers today. Go to teach fx.com/blbs to launch a free pilot for your school. Again, start that free pilot by visiting teach fx.com/blbs. Today. As students progress through their K12 experience, schoolwork only gets harder and more complex. Yet at the same time, students are asked to be more independent in their learning. Young people struggling with executive functioning skills will fall further and further behind the pandemic. Let’s be real, it’s only made things worse. The remedy is found in equipping students with executive functioning skills. Our friends at Organized Binder have released a new self-paced course and it teaches you how to teach these executive functioning skills and set up your students for success. Learn [email protected]/go and start setting up your students for success today. Again, that’s [email protected]/go.

Daniel (15:48):
One of the things I wanna say to the Ruckus Maker is listening too. So this is like an ideal situation. And maybe maybe your relationship with parents is troubled or maybe they’re not even around and could come to the school whether that’s location or age or whatever. But even if that’s the case, what your story highlights Jessica, is that Ruckus Makers don’t realize that they’re a character to their students and to their staff. Your parents are a part of your story obviously, and the character that’s Jessica. I want to encourage people to be intentional about how they get to know you. They’re able to get to know you better through your parents a little bit, because you’re a very, very open and authentic leader too. If you’re not telling your school story, the community who will tell that story. It seems true about you. If you’re not telling your story, they’re gonna tell the story about you. So it can be brought in your parents, but it could also be like, what are your values? What do you stand for, stand against all this kind of stuff. And that’s all I’ll say there, but that, that is that’s pretty fun. I almost like it, I wish it was a TV show to be honest. I think that would be fascinating just to watch and I would totally subscribe. If you start a YouTube about that or start a TV deal, let me know. I’ll be the first subscriber. Gonna write it down as an idea and we can jam about that as an idea too later. The last thing I’ll say is that we’ll probably go on a break and bring you back. But again, so if this is sort of a popular topic with your parents, like with the students and maybe even with parents in the community and that kind of thing there could be so many creative ways to tell that story that people would wanna tune into. And now people who might have been a little less engaged in the school or whatever might be tuning in to like what you need to be telling them public service announcements and here’s what’s going on. Just because you really amplify that really sweet relationship you have with parents and then the students and everyone. Alright, place a pin if you wanna do a coaching call with me on that, we can totally do that.

Daniel (18:03):
We’re gonna get a message from our sponsors, but when we come back, I want the Ruckus Maker to stick around. Because you’re really good at navigating hard conversations and you’ve been focused on that since covid with your staff and obviously the Ruckus Maker listening could benefit. We’ll be right back.

Jessica (18:23):
We’re back with the amazing Jessica Gamble, one of my favorite leaders of all time, and we’re talking about family and really, we really riffed on that for the first half of the podcast. But I think it was a rich conversation. I know it was. And so where I wanna take things now is, I don’t wanna necessarily say it’s negative, but you have to have tough conversations. As a school leader, it’s gonna happen. And to be honest, it’s a weakness of mine. I’ve had to really work hard at it because it doesn’t come naturally. But you’ve been hosting these hard conversations series since Covid started. Could you just sort of talk about what that series is and like some of the topics you’ve covered and that kind of thing?

Jessica (19:10):
Obviously the year that we were out for remote my district was remote for almost the entire school year until March. You have to find all these interesting ways to connect to your staff through a Zoom call. Every single week. But one of the biggest things that Covid highlighted in Cleveland and typically Cleveland bounces between number one and number two of the poorest cities for children in the country in how inequitable, covid exasperated so many things. So how many of our families had no access to the internet, our families had no access to school supplies, desks, computers, food, housing, insecurity, all these things were hyper-focused. It was glaringly obvious in a remote setting more than it ever was when we had students in the school building. Obviously when we had students in person, you could visibly potentially see the families who struggled.

Jessica (20:09):
But when you’re looking into people’s living rooms every single day, it is obvious how many families are struggling. And I just think that brought up a lot of conversations when people were making comments about why families weren’t doing certain things. Like what’s happening in our homes in the suburbs is very different from what’s happening with some of our families and in their homes. And so we started just having conversations about just inequities and bias in general. We did quite a few staff meeting sessions on bias. We took the Harvard implicit bias test, we did anonymous padlets so people could respond on how those tests made them feel, and did some background on how those tests were developed and really stretched the staff to think about beyond racial bias. That we have bias about everything and all of our bias comes from how we were raised in our traditional environment and that we’re not here to pinpoint everyone’s bias because I have bias.

Jessica (21:10):
Even as the school leader. But it is for us to stop slowing down and recognize that maybe before we make a comment or we make a decision that we check our bias and we think about is that coming from a place of like love and care or is that coming from a place of like my previous kind of my previous experiences. We did a lot around that that year, January 6th happened and we engaged in quite a few conversations with our students around that and frankly had some parents that were very upset with the conversations that our students were having with their teachers. And so we kind of did some talks around Black Lives Matter around that movement about what January 6th meant to all of our school community, because we also had a group of students whose parents never talked about it, but they literally were not having that conversation.

Jessica (22:04):
Then we had a group of kids whose parents were having the conversation from one political view and a group of parents were having that conversation with their children with another political view and then help them navigate the how, what is our job and what is our role when something like this comes up. We’re not here to sway kids’ opinions, but we are here to give them both sides of the story. That kind of then turned into conversations about pronouns and conversations in support of the LGBTQ community. We partnered with the LGBTQ Center of Greater Cleveland on a variety in a series of sessions and safe zone trained our entire staff, but then also took it a step further and realized we have a very large Arabic population and did a special session with some community members from the Arabic and the Muslim community on what being in the LGBT community means to them and, and, and so that we can get a better grasp and understanding of how it affects our staff and our students.

Jessica (23:03):
We have pretty much tackled every conversation, some much easier, some much harder. I think we always say about hard conversations that some hard conversations for people are very easy, some people love talking about race and that’s an easy conversation. But then we switch over to talking about pronouns in l the LGBTQ community and that’s a very uncomfortable hard conversation. And so we have been very dedicated to continuing that work at this point. The topics don’t come from my co-leader and I, they come from the staff and what bubbles up with them or concerns they have. I have a list on my board actually right now next to my desk. We just tackled hair and hair culture in the black community. We have code switching coming up next gracious assumptions and doubling back to some safe zone reminders as we’ve had some things kind of pop up that we need to double back on. Uncomfortable. Yeah. Empowering and challenging.

Daniel (24:04):
Yeah, I wasn’t a joke. It doesn’t sound like any topic was off limits and you’ve really done a great job digging into that and leaning into it. It’s way better than sticking your head in the sand, clicking your heels together and wishing the stuff reality didn’t exist. But that’s not, that’s not the path of the Ruckus Maker talk. Talk to me about format. So obviously on Zoom during Covid in the early days, but now is it in person with staff?

Jessica (24:33):
Great question. So even last year we did Zoom staff meetings because we were still in a post covid e world. That’s even the yeah, phrase this year. We’ve done a combination of the two, some I know most recently in hair and the hair culture. We started one week on Zoom and we watched a video and last some reflection questions out there. And then last week we joined in person and we mixed the whole staff up to answer those reflection questions at about 16 different groups. They had about 12 minutes to discuss the questions and kind of like dig in and, and think about what the video, what they saw and what they’ve been thinking about. I think it’s just a combination. I do feel like in this regard, doing it on Zoom happened to be actually a very safe space because you went around your peers, you could sit and you could think in a private place to you and really have some time to kind of sit in your uncomfortable feelings if it was a topic that was uncomfortable for you.

Jessica (25:28):
The anonymous Padlet I think was beyond beneficial because you could say exactly how you were feeling without fear of people knowing what the comment was. So you could be very open and transparent. We did some group breakout rooms on Zoom where they would get into rooms and speak with their peers and we always really try to stay out of those spaces. We tried to allow them to dialogue with their colleagues and their peers and their friends without putting ourselves in that space with them. I think sometimes when we’re not there, they can have more of a transparent conversation where if we are there, they don’t wanna say something that we might judge them on. And so it, I would never change anything that we’ve done. I wish we could do it more because new topics are always coming up.

Daniel (26:22):
Speaking of that, so you have your list on the whiteboard. How do people submit a topic? Is it like Google form or something, or how do you get those from staff?

Jessica (26:30):
So most of the time people either send us an email or come talk to us directly. Most of the topics up there were people who came and spoke to us directly. I consider us to be a very transparent leadership team and so we did have a Google form a year ago where we asked people to submit topics for hard conversations, but to be honest with you, nobody really submitted anything.

Daniel (26:51):
Interesting. Do you have some sort of protocol to follow or some, these obviously can be highly charged topics and I’m sure the staff might not always agree. On what the best approach is. And so how do you facilitate a conversation where there’s real dialogue and real understanding and real listening versus people yelling at each other?

Jessica (27:18):
It’s a great question and we definitely have had some heated conversations. So when we first started having hard conversations, we used a model, I know my mind, I’m pretty sure it was called the Flex model, but I’m sorry, the first one was focused on within. So the first set of conversations we had were all based on focusing on you, like thinking about your background, your upbringing, things that you’ve encountered, your life experiences, and then it was like listening about others. So now that you’ve kind of focused on within, you’ve identified some of your own biases, your conscious and unconscious biases, then we were gonna listen about others and then we were gonna explore and experience what others were going through. I do feel as though the staff is very respectful and transparent with one another.

Jessica (28:08):
I do have some staff members that share more than others in a setting we’re it’s open to talk, they share more. We have found that when the groups are smaller, they share more. So when the groups are like three or four, the dialogue can be extremely, not, I don’t even say passionate, but the dialogue is a lot more than when there’s 6, 7, 8 or nine people in a group and people’s voices get lost. And so we have not had any screaming matches. I’m very happy about that. I think that everybody here respects, but I also think I have a staff who’s very much open about learning about others. Especially when you’re in a diverse building like our building. Anytime we have conversations regarding things like our Arabic community or our Muslim community, it’s so empowering to our staff and we learn so much about that culture that they wanna participate so that we can best support those families and those students.

Daniel (29:05):
Awesome. If you haven’t submitted a proposal to speak on this topic at a conference, I really think you should consider that because it’s certainly fascinating. I’ve got a million more questions, but we’re short on time and I know the Ruckus Maker listening will be really interested in what we’re talking about too. Let’s say you could put a message on all school marquises around the world for one day. What would Jessica’s message be?

Jessica (29:31):
If you love them, they will come.

Daniel (29:33):
How about building your dream school. If you were doing that there were no constraints in terms of resources, your only limitation was your imagination. What would be the three guiding principles?

Jessica (29:47):
Three guiding principles on building this dream school. I would definitely be focused on equity, making sure that every student had something that they needed to be successful. I am in a building right now where I have students with a variety of autism and I’m always looking for more things so that the playing field is level. So equity would be a guiding principle. This sounds kind of silly, but I think that colors are such an avenue to happiness. And when you see colors that you connect to it makes you happy. And the last would be Green Space.

Daniel (30:26):
Awesome. We covered a lot of, well, we went deep on I think actually two topics, but of everything we discussed today what’s the one thing you want a Ruckus Maker to remember?

Jessica (30:38):
I would say bet on yourself. Don’t be afraid to be bold and jump out there. You’re sitting in that seat for a reason and so bet on yourself. You are the best person for the job for a reason.

Daniel (30:55):
Thanks for listening to The Better Leaders, Better Schools podcast Ruckus Maker. If you have a question or would like to connect my email, [email protected] or hit me up on Twitter at @Alienearbud. If the Better Leaders, better Schools podcast is helping you grow as a school leader, then please help us serve more Ruckus Makers like you. You can subscribe, leave an honest rating and review or share on social media with your biggest takeaway from the episode, extra credit for tagging me on Twitter at alien earbud, and using the hashtag #blbs. Level Up your leadership at BetterLeadersBetterschools.com and talk to you next time. Until then, “class dismissed.”



Transform how you lead to become a resilient and empowered change agent with Harvard’s online Certificate in School Management and Leadership. Grow your professional network with a global cohort of fellow school leaders as you collaborate in case studies bridging the fields of education and business. Apply today at http://hgse.me/leader.


Last year, teachers using TeachFX increased their student talk by an average of 40%. TeachFX uses AI to help teachers see the power of high-leverage teaching practices in their own classroom-level data. It’s like having a personal instructional coach…on your phone, tablet, or laptop. Start your free pilot at teachfx.com/betterleaders .


Why do students struggle? I’d argue that they lack access to quality instruction, but think about it. That’s totally out of their control. What if there was something we could teach kids there was something within their control that would help them be successful in every class? It’s not a magic pill or a figment of your imagination.

When students internalize Executive Functioning Skills they succeed.
Check out the new self-paced online course brought to you by OB that shows teachers how to equip their students with executive functioning skills.

Learn more at organizedbinder.com/go


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