Episode 256: Rethinking Intervention and Tutoring with Jennifer Sheffield
School leaders everywhere are wrestling with the same challenge:
How do we support students who are behind — without overwhelming teachers or relying on systems that don’t deliver results?
In this episode of Leaning Into Leadership, Darrin Peppard sits down with Jennifer Sheffield, CEO of HeyTutor, for a grounded, practical conversation about what effective tutoring and intervention really look like in today’s schools.
Jennifer brings a unique leadership lens — blending her background in law, governance, and education — to help leaders rethink how tutoring fits into MTSS, Tier 2 and Tier 3 supports, and daily school operations.
In this episode, you’ll hear about:
- Why “tutoring” means very different things — and what defines high-impact tutoring
- The biggest barriers schools face when implementing interventions
- How districts can address the human capital challenge without adding strain to teachers
- Creative push-in and pull-out models that work in middle and high schools
- Why relationships and student champions matter as much as curriculum
- How tutoring can become a pipeline for future educators
- What it means to lead with purpose, trust, and whole-person leadership
Jennifer also shares a powerful personal story that shapes her leadership philosophy — reminding us that great leadership is ultimately about people, belief, and opportunity.
Learn more:
- HeyTutor: https://www.heytutor.com
- Contact Jennifer directly: jennifer@heytutor.com
If you’re a school or district leader searching for intervention strategies that actually move the needle — this conversation will help you think differently.
Episode Sponsors:
This episode is sponsored by digiCOACH — an easy-to-use mobile platform that empowers school leaders to provide teachers with positive, actionable feedback tied to research-based instructional practices, with real-time data to support fidelity and instructional decision-making.
Learn more at digicoach.com (mention the show for special partner pricing)
This episode is also brought to you by HeyTutor - HeyTutor delivers customized, evidence-based, high-dosage Math and ELA tutoring to K–12 school districts nationwide. Their focus is on in-person tutoring, while also offering flexible online options — all tailored to meet diverse student needs and aligned with state standards.
Head over to HeyTutor.com to learn more - tell them you heard about them on the Leaning into Leadership podcast.
Darrin Peppard (00:00.088)
that, welcome into episode 256 of the Leaning Into Leadership podcast. My guest on the show today is Jennifer Sheffield, CEO of HeyTutor. We'll get to that in just a minute. You just heard her talk about how every context has their own unique needs and how we have really, in education, moved away from, no, I'll take that a step further, in leadership.
We have moved away from the one size fits all, the this is the ultimate solution to everybody needs that thought partner. Everybody needs someone to help them to ideally shape the interventions, programs, and work that needs to be done specifically in their context. And I'll be honest with you, so many of the leaders that I work with now are asking pretty much the same question.
How do we actually close learning gaps without burning out our teachers or layering on one more initiative that never quite delivers? Because, hey, if we're being honest, most of us have tried interventions. We've tried tutoring. Far too often, it's built on the fly. It's driven by urgency instead of being driven by strategy. I mean, a school that I was in just this week.
right into an intervention specific to reading and basically had to build it on the fly from the start of the school year, simply driven by here where your reading scores, this has to improve. Ultimately, programs, efforts, initiatives that are built on the fly don't really move the needle the way our students deserve or the powers above us want.
to see. So what does high impact support really look like? How can it genuinely be shaped? What does it take to align intervention, staffing and instruction in a way that actually works inside real schools with real constraints? That is what we're going to dig into today. Now, before we do that, I would like to take a moment and thank our two incredible partners who do this work the right way. Now let's talk
Darrin Peppard (02:29.334)
about my friends at Digicoach. At Digicoach, they help school leaders transform walkthroughs and observations into meaningful, growth-focused coaching conversations. Instead of stacks of notes or disconnected feedback, Digicoach allows leaders to align what they're seeing in the classrooms with their instructional priorities. And they do it in real time. It's simple. It's efficient. And it helps leaders coach with clarity rather than coaching for compliance.
If your goal is to support your teachers, to strengthen instruction and to stay focused on what matters most, Digicoach is a powerful tool that can help you make that happen. Go to digicoach.com and check out what they have and make sure you set up a time to visit with the team at Digicoach. While you're there, make sure you let them know you heard about it here on the Leaning Into Leadership podcast for special partner pricing. Once again, that's digicoach.com.
Let them know I sent you, you will not regret it. Now let's talk about HeyTutor. I wanna talk about them. They are also a supporting partner here with the Leaning Into Leadership podcast. And HeyTutor partners with school districts across the country to deliver in-person high impact tutoring that is research-based, outcomes-driven, and it's designed to work inside the school day. This isn't homework help.
This is actual strategic intervention with trained tutors sourced from local communities aligned to your district goals and embedded into your MTSS, your tier two and tier three supports. HeyTutor helps districts solve real challenges around staffing, scheduling and student support. You're gonna hear exactly how in today's conversation, which brings me to today's episode.
My guest, as I said earlier, is Jennifer Sheffield. She is CEO of HeyTutor. And Jennifer and I sat down just before the holiday break and talked about intervention. We talked about the challenges that schools face with human capital, with finding those people, staffing those people, paying those people. We talked about creative scheduling. We talked about so many of the things that go into creating a high impact.
Darrin Peppard (04:54.09)
intervention that's genuinely going to move the needle. What is it that truly makes a difference and gives students a fighting chance to succeed? That's what we're going to talk about in today's episode. So let's get right to it with Jennifer Sheffield.
Darrin Peppard (00:01.159)
I think back often to my days as a high school principal and one of the biggest challenges that I was faced with was how do we put meaningful interventions in place so that our students have a genuine fighting chance of reaching proficiency. There are so many wonderful different programs out there that can help you
bring your students the opportunity to close the gap. And tutoring was certainly something that we explored. It was kind of something that we made up on our own, kind of created it on the fly. And it probably wasn't as effective as it could have been. We certainly could have used some outside partner who could come in and say, hey, this might help you.
here's some curriculum, here's some training, those kinds of things. And I know that many of you as listeners who are sitting in those school and district leadership seats, you're faced with a lot of those same challenges when it comes to how do I get the interventions that are really going to move the needle for my kids? Well, you're in luck because today on the program, I have Jennifer Sheffield joining me. Jennifer is the CEO of Hey Tutor.
And we're going to talk not just about, tutor, we're just going to talk about those intervention programs, that process and how some school leaders might consider leaning into ways to close the gap. before we get to any of that, Jennifer, thank you so much for joining me here on Leaning Into Leadership.
Jen Sheffield (01:48.937)
Thank you for having me. It's a pleasure.
Darrin Peppard (01:51.721)
Yeah, absolutely. obviously, you you and I have had a chance here over the last couple of months, we've gotten to know each other a little bit. We've had a handful of zoom calls and Google meetups and those types of things. But my listeners probably don't know Jen Sheffield. So tell them a little bit about you and maybe a little bit about your background.
Jen Sheffield (02:14.018)
Yeah, absolutely happy to do that. So.
Thank you. So yeah, Jen Sheffield. I am actually a lawyer by trade, believe it or not. I was a practicing attorney in Seattle, Washington for a little over a decade and had the opportunity after that practice to move to Los Angeles and really get involved in my kids' And I'm a mom, proud mom of two children, ages 12 and 10. And I've served on boards of directors for their schools.
I myself was a passionate learner. If I could have stayed in university and college forever, I would have. And so be able to get in the ground and be involved in their schools, not only kind of as a parent volunteer, which many of us in this country are.
which is an incredible resource schools have to draw upon, but then also to be involved on the governance and leadership side at the director level. And so really got in on the ground of K-12 education, understood a lot of the needs, priorities, the pain points for a number of schools in across this country and understanding what they would need to draw upon to really ensure student success. And so...
Fast forward to 2022 and an opportunity came to the table to join HeyTutor as its chief legal officer. So I did that for the first 14 months or so of my journey with HeyTutor and then was asked to step into the CEO role. And it's been really a pleasure and an honor to be able to work alongside school districts across this country in partnering to figure out.
Jen Sheffield (03:53.442)
how we solve the crisis that many schools face nowadays between teacher shortage and student proficiency lagging behind where we would all love to see it be.
Darrin Peppard (04:05.832)
Yeah, absolutely. So I'm curious, I'm going to squirrel here for just a moment, which I have been known to do. Coming from a legal background, working in a legal practice and now working to support schools and some of the stuff that you did to just dive in to support your kids and their schools. What are some things that you've learned in kind of that crossover from that
that legal background now into more of a K-12 space.
Jen Sheffield (04:37.962)
You know, I think the legal background, what that empowered me to be able to do is to truly understand a lot of the priorities that a district has to consider when implementing programs. So everything from, you know, strategic planning to priorities set by the board to parent concerns. And so I think a lot of my legal experiences really helped inform my understanding of what a school district is faced when, you know, not only doing kind of the
day-to-day teaching that has to be done, but also setting kind of that strategic direction and figuring out what's going to really move the needle for kids.
Darrin Peppard (05:16.872)
Yeah, for sure. think that's a lot of the, maybe the hidden work that a lot of people don't understand or know about the actual happenings, the going ons, if you will, in the K-12 world. Certainly for me, know, transitioning from teacher to school administrator, that was kind of an eye-opening experience. And then transitioning from school leader to a superintendent role, even more so, just understanding the, just that next level of
of strategy, of being intentional, of really thinking several moves ahead rather than just being reactive. And I think you bring up something that's really, really important and something that certainly our listeners who are in those chairs and those assistant principal and principal and district level leader seats, they've certainly been learning those lessons as well.
So let's dive into this a little bit. I mentioned it a little bit kind of in the opening for me as a high school administrator, even before I was a principal, to be honest with you, one of my assistant principal roles, I was in charge of curriculum and instruction, which interventions became a part of that focus early on. And again, this is at the high school level. Early on, think intervention and high school
really didn't go together. People thought, no, that's an elementary thing. Tutoring at the high school level, I think that did make some sense. And that's where we were able to lean in a little bit. But my elementary colleagues, they understood intervention, but tutoring didn't necessarily like, like jive. So I want to talk about Hey, tutor eventually, but but right now, let's just simply talk about that intervention piece and, and from
your experience now with HeyTutor and the schools that you're supporting all over the country, what do you see as some of the barriers or some of the challenges that connect to putting the right pieces in front of students to help them close the cap?
Jen Sheffield (07:29.89)
Yeah, absolutely. You know, I think when we think about tutoring, it is an immense umbrella of a lot of different types of services. On one end of the spectrum, it's more of kind what you experience as a parent. Finding a private tutor for your student to help them. Maybe it's in math, maybe it's in science. All the way to the other end of the spectrum, which is more of what we do here at HeyTutor, where you're talking about in-person.
tutoring where tutors sourced from your local community are pushing into your school districts, pushing into your school site classrooms, or pulling students out to work in a library. And even within that lens, it can vary too. It can be something as simple as homework help, which is absolutely a much needed service. And I will tell you, as a parent of two school-aged children, I love when they get the help with homework at school. But when you're talking about Darren with the
Darrin Peppard (08:19.881)
Yeah.
Jen Sheffield (08:27.28)
thoughtful intervention, though, when you're thinking about MTSS, know, tier two, tier three supports. Tutoring has a role to play in that, and I think that's what a lot of school districts are really working through right now, is how to embed something like high-impact tutoring into their existing MTSS, tier two, tier three structures, to provide that level of intervention that a lot of their students who are two or more grade levels behind, or perhaps even their
multilingual students could really benefit from the structure that high-impact tutoring could provide. And so certainly that's something we're hearing from a lot of school districts. And I think the other thing to really keep in mind, and it probably is not news to your audience, is it's not a one-size-fits-all solution.
High impact tutoring can be customized and it can very much vary from one school district to another. And so I think part of that process, both at a district leadership level, but then whoever perhaps they're partnered with in the community to execute upon tutoring intervention.
It's about trying to figure out what is it, how does it need to be designed thoughtfully in order to really support the specific student needs in that school district. And again, yeah, that varies wildly across the country.
Darrin Peppard (09:49.77)
Yeah, and I think you bring up two things right there that are really, really important. One is simply the personnel challenge. I think a lot of schools would love to have high impact tutoring as a part of their tier two and tier three interventions without question. And they may even sit strategically and have conversations about this. And then somebody eventually, you know, addresses the elephant in the room of, but who's going to do it?
You don't want to ask more of your teachers, teachers already have so much on their plate. You may or may not want to lean into your instructional assistants or you know, paraprofessionals or IAs, whatever phrase a school district might use to describe those paraprofessional individuals. But oftentimes they get stretched pretty thin and they're really, really hard to hire right now. That is a tough position to fill. One of the most
That's not the right way to say that. me try that again. The least filled position, the most still open that school districts have are those paraprofessional positions. Hard to find people to fill those roles. So the number one thing you bring up is the personnel piece. But the second piece is simply having a thought partner of how do I customize it for my setting? Because I mean, you're based in California.
And most people I think think of California and they think of these massive school districts, You know, like, you know, LA public schools, one of the, you know, one of the top three, four, you know, size districts in the entire nation. But there are a lot of small rural districts. There are a lot of K five districts, K eight districts, high school districts in California. And we see them all over the country. So I say that because
You've got the groundwork right there in California to say, hey, you know what, what works in this rural K-8 school may not work in San Bernardino County or something like that. So two different elements that I'd love for you to address. Thought partner, personnel piece, dealer's choice. Jen, I'll let you choose where you want to go first on those two things, but you brought them up. They're super important.
Darrin Peppard (12:17.405)
Those are the challenges I think our leaders are faced with right now.
Jen Sheffield (12:20.59)
Absolutely, and I think let's start with the kind of the human capital side of it because it does blend into the larger piece around thought partnership and execution of a program with fidelity. So on the human capital side, you're right Darren, absolutely.
huge teacher shortage crisis across this entire country. Same thing with the filling of instructional aid positions or paraprofessional positions is a huge pain point for school districts.
Typically school districts have an incredible HR team, but they have to juggle a lot of competing priorities. And so, you know, certainly that's where others like us in the field and ourselves as well can really step in and partner with a district to help offset some of those pain points and bring more resources to bear. I think the other piece that is a challenge on the human capital side
is also the time necessary to stand up a program like this. And so even if you have the right kind of tools in your bench, right, that you...
may not have the time to actually have them implement with fidelity. We've talked about teacher burnout. And so when you think about having your teachers take on the additional challenge of curating a tutoring intervention program, it's too much. It's too much to ask of our teachers who already have a lot of really important work to do. And so, yeah, I think that does blend into where certain types of partners can be really, really helpful in relieving some of that
Jen Sheffield (13:58.592)
administrative burden, taking some of that off the plate. But it's got to be a cohesive partnership where both are coming to the table with ideas, an expression of what the concern is, an understanding of what student need is, and then kind of bringing to bear that partner's experience in implementing tutoring across the country to say, you're right, it isn't going to look the same in a large top 10 school district as it looks in a
school district, but how can we use our learnings to inform how to customize it, how to tailor it to those specific students.
And you're certainly right. It's been our experience here in the state of California, as well as other states across the country, that it isn't a one size fits all. A rural school district needs something different than, say, a high school school district, and then say a top 10 school district in this country. And so I think what you are looking for ideally is someone who will partner with you as a thought partner, as a thought leader in terms of shaping that goal. And I think the other thing that's been really important
for us and certainly something I convey to all of our teams is don't shy away from the conversation.
come to the table with ideas of how we shape strategic goals in the tutoring program. What do we want to see at the end of, three months, six months, a year of tutoring? And obviously that can change as we go along too. And so I think being at the table with our district leadership, with our school site principals, our school site interventionists, even all the way down to our teachers to understand what they're seeing in the program and being responsive to that. And so I think it's
Jen Sheffield (15:43.712)
very much an organic process, but I think it's really dependent on ensuring at all times that we're all operating under the same set of goals and also the same set of strategic priorities. And so, you know, certainly as we have a conversation with a new district partner, we spend a lot of time getting to know what's in their strategic plan. How do they think about MTSS, tier two, tier three? How can we make sure we're embedding side by side with them in a way that's going to ensure fidelity?
to their overarching goals as a district.
Darrin Peppard (16:17.894)
Yeah, so I'm curious. I think about tutoring and I think a lot of school leaders probably think this way too, that this is something that needs to be done in an after school or before school setting or a lunchtime setting.
What are you seeing out there in the field? Are there some creative solutions with tutoring where we can find ways to intervene with students during the normal course of a day? And I honestly, in this question, I'm not talking about elementary, there's so much more flexibility in how you can do that in the elementary school. But a middle school administrator or high school administrator might be saying,
Well, that's great, but I'm locked in on my seven period day or my four by four, you know, two day rotation or whatever their whatever their master schedule dictates. I was a master schedule builder. I know what it feels like to feel anchored to a master schedule. So I'm just curious what what might be some other ways that school leaders could look at this, whether whether they partner with Hey, tutor or not, how can they think differently about
flexibility in their schedule to make this happen during the day.
Jen Sheffield (17:35.576)
think it's about creativity around the implementation. So I think the biggest concern we hear is the one you've just expressed. How do I fit it into the school day? You're completely right. It is often a concern we hear in the middle school and the high school implementations that we do across the country.
What we recommend always and what we've seen work really, really well in practice is flexibility in the implementation style. So for instance, what we would really recommend in those secondary school contexts is a hybrid model. You're not going to be able to pull out into small groups all the students who need tutoring intervention in a secondary school system. You're right. You'll never fit it into the schedule. You will never find a way to shoehorn it in. And so what we've done and I,
I can't imagine we are the only ones in the country. I'm sure there are many secondary school districts who have stand up their own programs and have figured out this secret sauce as well. It's about finding ways to do a combination of a push-in model and a pull-out model.
And so I'll give you an example. We work with a high school school district here in California. We've been with them for four years and we do a combined approach. And so the way that works is tutors would push into core instruction, observe the teacher, deliver the lesson. There is some small...
time set aside for breakout group sections or one-on-one work, and at that point the tutor can circulate with the students that have already been identified for tutoring, providing that additional reinforcement of the core instruction lesson of the day. But then the other piece we've been able to embed with that high school school district is some set-aside time for pull-out sessions. So that tutor almost really becomes embedded into the ecosystem of that school district in a way that they don't necessarily
Jen Sheffield (19:28.24)
if it's just a pull-out only model. And the great thing about that is you start seeing students who actively want to volunteer to be part of tutoring because they know they get to know that tutor in their classroom. They get to see them in the hallways and I can't even fully express the impact that has. You know, I was watching back one of your more recent podcasts with Miguel Salazar and he talked at length about the importance of every
kid having a champion.
At the end of the day, that's the value of high impact tutoring when it's in person is you give students an opportunity to have a champion in the classroom. And so I think if we're all aligned at a partner level, a district level, a site level for how we can implement creatively, creatively in order to fit it into the school day, you're going to see better student engagement. You're going to see better classroom management and behavior. You're going to see student performance, obviously improve.
but then you also are going to give your students the opportunity to connect with someone from their local community. Maybe they didn't have that relationship with their teacher, so it's bringing another adult into the room who might make a difference in that kid's life. And so, you know, it's certainly something we are very passionate about here at Hey Tutor, because it makes a difference. You know, I've had people in my life, Darren, I'm sure you've had people in your life as kind of through your educational journey as a kid and even
as young adult and there's just so much value you can get out of those relationships.
Darrin Peppard (21:07.368)
Oh, absolutely. Yeah. You say that and it makes me think back to, you know, a handful of people that certainly, you know, made a difference for me both, you know, in my K-12 experience as a student, but then also, you know, as I as I made my way through my, my odyssey of getting my undergraduate degree, which wasn't just the routine four year deal for me, it was a little bit more of more of a challenge.
I'm curious, I want to ask one more question before we get to the penultimate question, the one I ask everybody here on the show. We talked a little bit about human capital, but maybe let's talk a little bit about finding creative solutions for that human capital challenge. And this is one of the things that really attracted me to Hey Tudor that maybe say, man, I really want to learn more about you guys. And then ultimately, you know, now we're
You guys are a signature sponsor here on the podcast and then all that kind of stuff. And then I don't do that if I don't believe very, very strongly in the work that you do that, that ability to help schools solve that human capital piece, I think is really interesting. So maybe, I I don't know, you, can, can go where you'd like with this, either give us an example of a way you've done that, or maybe just talk about philosophically how
Hey tutor says let's let's find the right people to help with with the solution that you're helping to create
Jen Sheffield (22:40.084)
Yeah, no, I think where I'll start with it is kind going back to what we talked about a few questions ago.
When an HR team at a school district is looking for teachers and instructional aides, they're looking for people who are already looking for those roles, right? And I think the unique thing we can bring to the table is we're looking broader than that. Admittedly, our tutors, some of them may be teachers, some of them have been retired teachers who still want to be in the classroom and have an impact in student lives. The majority of our tutors actually aren't. They often are folks who have a master's degree.
a bachelor's degree in a related subject, so maybe it's in English history, maybe it's in geometry, maybe it's in math generally, and we're able to then effectively figure out are they qualified to serve as a tutor? Are they able to meet the needs of a student in a classroom? The great thing about being able to draw on a bigger pool of candidates though
is you give the chance to give people an experience inside of a classroom when maybe they never thought about being a tutor, maybe they never thought about being a teacher.
The thing we've seen and I think is one of our big success stories is a number of our tutors who have worked with us for a couple of years have actually gone on telling us, know, I never thought about being a teacher, but I love working with these students every day. I have been grateful to have this opportunity with Hey Tutor. It's nothing I would have ever considered doing with my degree, but they develop that passion. They see the impact they're making and then they've gone on to get hired by the
Jen Sheffield (24:20.592)
school district as a teacher. So for us, although we've lost them as an amazing tutor, we celebrate the win for our school district partners that they then get to bring on board this amazing teacher who started with them as a tutor who got
experience in seeing what classroom structure is like, what it's like to lead a class, what it's like to work alongside other teachers, other interventionists, all, you know, driving toward the main goal of student success. And so, you know, just this last year, I believe, we had with one high school district partner, actually, five.
of our tutors go on to become hired by the district, either as a full-certificated teacher or some other role within the district. So for us, it's a big win. It's what makes us really excited because those folks are going to continue having an impact at that school district, which is, it's amazing. And so, yeah, it's...
It's an interesting area that we can partner in with the school district in a way maybe you don't necessarily think is possible. But as we think about creative ways to tackle the teacher shortage crisis in this country, certainly partnering with tutoring providers is a great opportunity to bring some folks to the table who may never have considered a career in education.
Darrin Peppard (25:43.056)
Yeah. I love that so, so very much. You know, it's, it's interesting. You know, we, I've talked a whole lot of times on the podcast about this and a lot of times when I speak to just about that origin story that every educator has and not, every one of us started our way into education by, know, being a third grader and going home and playing school with, know, with our friends, right. Or with our, with our siblings, most of us in the education space.
got there through some other methods, some other way that we found the inspiration to want to go make a difference and work with kids. So I absolutely love that story. I think it's fantastic. So and that's going to take us to the last question that I ask here on the show, the one I ask everybody. Jen, this is the Leaning Into Leadership podcast. So tell me how are you leaning into leadership right now?
Jen Sheffield (26:35.278)
I'm gonna start with a story first because I think it informs kind of how I think about leadership and how I'm trying to lean into it myself.
So I am the proud, very proud granddaughter of a man who was a parks director here in Los Angeles County for many, many years. And he did something really extraordinary in the 1950s. You know, he was parks director in Lincoln Heights, East LA, where there was a ton of gang activity. And he saw a number of kids who really needed help, who needed a mentor, who needed a coach, who needed guidance.
to stay away from the gangs, to get out of the gangs. And so he created a community boxing club. And through that boxing club that was housed within the parks, started Lincoln, but then moved to some others, he saved a lot of kids. He made a difference. And so when I think about kind of leaning into leadership, I think about what he did there. And so he didn't put people in a box. He didn't label them. He took the time.
to get to know them, to know that they're whole person.
and help them set goals, help them stick to those goals, and they really take the time to make that difference for them and put them on a different course. And so when I think about leaning into leadership, I try to bring those same principles that he showed in his life, both here internally to how we kind of manage and set up our teams at HeyTutor, but then also how we partner with school districts. So certainly on the internal
Jen Sheffield (28:17.093)
hate tutor side.
We really lean heavily into developing a culture where there's no bad idea. We want you to bring innovative ideas to the table. We want everyone at the end of the day to bring their whole selves because with kind of the diversity of thought, with the diversity of skill sets, that's where we'll really be able to be the best partner we can possibly be for students across this country. And so certainly I think it's in order to create effectively that cycle
logical safety for people to feel safe to do that, to feel safe being creative in a work environment, you have to take the time to get to know them. And so, you know, certainly I tried to get on as many team calls as I possibly can, getting to know them not only as employees, as part of Hey Tutor, but to get to know who they are as a person. and I kind of share one other anecdote and Darren, you and I have talked about our love of football before.
What really resonates with me is how Pete Carroll set up the Seattle Seahawks team and how he approached leadership during his tenure as the head coach. am, as I mentioned, former Seattle resident, so we are huge Seahawk fans. But I think what always resonated with me with Pete's style is he took the time to get to know every single one of his players off the field, on the field. And what you saw as a result of the time he invested doing that is team performance.
performance skyrocketed. saw people who were passionate about the mission, passionate about the work, even when it was hard. so, you know, certainly within HeyTutor, that's what we really hope to develop. You know, we want people, even though it's hard to do tutoring intervention, it's not easy work. We want people who are committed to it because they're passionate about who they're working alongside. They're passionate about the mission. And I think that translate, that same passion translates to
Jen Sheffield (30:19.16)
our partnership with school districts. You they feel that they know that this is a true partnership. It's you've got someone in the trenches with you. Yes, they're not on district payroll. They're not working in your schools as your teacher, but they're here to help you fight the fight and to help you see students succeed.
Darrin Peppard (30:40.262)
I just love that so very much and not just because you included a football anecdote. That's wonderful. Hey, Jen, people are going to want to get in touch with you. They're going to want to learn a little bit more. They're certainly going to want to know more about HeyTutor. So what are the best ways for them to do that?
Jen Sheffield (30:57.612)
Yeah, absolutely. So I am a roll up your sleeves kind of CEO. So I welcome people to reach out to me directly. So I am just jennifer at heytutor.com. Alternatively, you can go to our website, which is www at heytutor.com and just click on the book a meeting with us or contact us here. And we'd love to chat with you and see if there's ways to explore how we could help partner with you on student success.
Darrin Peppard (31:27.544)
Absolutely, we will put all of that stuff down in the show notes folks So it's easy for you to go and get to hey tutor Hey tutor again is a signature sponsor here for the leaning into leadership podcast So you'd see that stuff down there in the show notes anyway, and when you do reach out Tell them that you heard Jen here on leaning into leadership. It'd be awesome for them to know that That's how you made your way to hate tutor Jen. This has been so much fun. So informative
I genuinely appreciated the time with you. Thanks for joining me here on Leaning Into Leadership.
Jen Sheffield (31:59.032)
Thanks for having me, Darren.
Yeah, man, what a wonderful conversation. I cannot thank Jennifer enough for not only coming on the show, but for joining me with the Leaning Into Leadership podcast. Her entire team has just been absolutely wonderful. Make sure you get over to heytutor.com and check out their information. If you use the link in the show notes, that will let them know that you heard about them here on the Leaning Into Leadership podcast.
I know they would love to know how many of you are listening to the podcast and who had an opportunity to listen to Jennifer talk so elegantly today about how we create high impact, meaningful tutoring in our schools. And now it's time for a pep talk. So I mentioned at the top of the show that I was in a school earlier this week. Actually, I was in several schools this week. And one of the schools that I was in, towards the tail end of the day,
there was a bit of crisis. There was an issue with the health of an adult, and we were almost at dismissal time. And in an elementary school, you know dismissal time is a very coordinated effort. And all you have to do is throw one little thing in there, and it can cause complete chaos. And it got me thinking as I watched the leader and his team handle the situation honestly very, very well.
It made me start to think about chaos and about how leaders themselves are constantly thrown into situations where chaos can ensue. What is it about a great leader that can keep chaos in check? And what is it about a leader who's struggling a little bit, who's still trying to find their footing that allows the chaos to start to take over? I think that whole cycle of chaos
Darrin Peppard (07:09.194)
is what makes the difference between successful leaders and leaders who step away from the role. How do you handle chaos well? I would tell you number one, and this is no surprise coming from me here on this show, you've gotta have clarity. You've gotta know what's important. You've gotta know how you're going to communicate. You've gotta know what steps you need to take. And you have to have invested in the relationships and built the trust with the people around you so that when it comes time to step into a crisis situation,
everybody's ready to respond. Now, I will tell you this, this is a little bit of a different way to approach a pep talk. I am dropping a special midweek episode here in just a few days. It'll be episode 257, where I talk about what I have started to coin as the cycle of chaos. So many leaders get stuck in the cycle of chaos. I'm going to outline for you in episode 257 what is the cycle of chaos, and I'm going to give you some tips for how you get out of and stay out of
the cycle of chaos. Be looking for that. In the meantime, you step into some chaos, folks. It's okay to take a step back, to get up on the balcony for just a second, catch your breath and think about, okay, what do we need to accomplish? How are we gonna do it? Who's gonna be responsible for it? And what's my role? You don't have to do it all, but you do have to be the conductor inside the chaos. Hey, thanks so much for joining me here on episode 256. Once again, go hit HeyTutor.com, go and hit Digicoach.com. Check out our wonderful partners. They're doing incredible work to help you make a difference in your schools and in your classrooms. Get out there. Have a road-awesome week.