What Every Baseball Coach Struggles With During the Season (How Coaches Fix It)

High school baseball seasons rarely fall apart because of talent. More often, it’s the challenges that show up during the season that quietly pull a team off track.

So we asked four experienced coaches one question every coach eventually faces: What is the toughest in-season challenge, and what actually helps when it happens?

Coach Jeff Boulware explains how off‑the‑field distractions—prom, school breaks, graduation events, and the chaos of spring—can slowly derail a team’s focus, and how returning to preseason goals and leadership training helps players stay locked in.

Coach Jeff Mielcarek dives into the reality of time management, sharing how the hidden workload of running a program—paperwork, facilities, fundraising, and planning—can drain a staff’s energy, and the simple weekly system he uses to stay ahead.

Coach James Grandy tackles one of the toughest problems coaches see in the dugout: players losing confidence. He explains how positive coaching and a return to fundamentals can help athletes break out of slumps and regain belief.

And Coach Jimmy Fillingeri discusses the constant tension every coach feels: developing players while still trying to win games, and how to design practices that solve game problems without abandoning the basics.

Four coaches. Four different challenges. And practical ideas you can use with your own team this season.

Join the Baseball Coaches Unplugged podcast where an experienced baseball coach delves into the world of high school and travel baseball, offering insights on high school baseball coaching, leadership skills, hitting skills, pitching strategy, defensive skills, and overall baseball strategy, while also covering high school and college baseball, recruiting tips, youth and travel baseball coaching tips, and fostering a winning mentality and attitude in baseball players through strong baseball leadership and mentality.

Transcript

What Derails Teams Midseason

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Every coach hits a moment in the season where something starts pulling their team off track. One coach says the biggest battle isn't on the field. It's the distraction that players face off of it. Another says the real problem is time. There just isn't enough of it during the season. A third sees players slowly losing confidence in their ability, and a fourth wrestles with the constant tension of developing players while still trying to win games. Four coaches, four completely different answers, and their solutions might surprise you. Next on Baseball Coaches Unplugged.

Sponsor Message Netting Professionals

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Each episode features real conversations about high school baseball coaching, travel baseball development, college recruiting, player development, practice planning, teaching and winning development, and building a winning baseball culture. If you're a baseball coach looking for practical ideas on running better practices, developing players, navigating the recruiting process, and leading a successful program, this podcast showcases the best coaches from across the country with your host, 27-year high school, Coach Ken Carpenter.

Why Four Coaches Were Asked

Off Field Distractions And Ownership

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Baseball Coaches Unplugged is proud to be partnered with the Netting Professionals improving programs one facility at a time. The Netting Pros specialize in the design, fabrication, and installation of custom netting for baseball and softball. This includes backstops, batting cages, beefy turtles screens, ball carts, and more. They also design and install digital graphic wall padding, windscreen turf, turf protectors, dugout benches, and cubbies. The Netting Pros also work with football, soccer, lacrosse, golf courses, and pickleball. Contact them today at 844-620-2707. That's 844-620-2707. And you can visit them online at www.nettingpros.com. Check out Netting Pros on X, Instagram, Facebook, and LinkedIn for all their latest products and projects. Hello and welcome to Baseball Coaches Unplugged. I'm your host, Coach Ken Carpenter. Thanks for joining me today. And we're on to the next 200 episodes of Baseball Coaches Unplugged. If you enjoyed today's show, please be sure to share it with another coach. And if you get an opportunity, leave us a review. It helps us to grow the show. Today, I reached out to four different coaches to talk about what is one challenge that a coach faces during the season. And it was very interesting to get their comments on this because four different coaches came up with four different situations that they deal with during the season. I thought this would be helpful to any coach out there that's listening, and you could maybe take some of their ideas and attach them to some of the things you're doing at your program. Our first guest is the head coach at Bishop Waterson High School in Columbus, Ohio, and his name is Jeff Bulware, and he talks about it's the off-the-field distractions that are the biggest challenge because baseball in the spring is unlike any other sport during the high school seasons, whether it's football or basketball, because you have a lot of distractions that you have to deal with as a coach. And just recently, a team, a high school team out of Florida, lost its upperclassmen who chose to go to the prom versus playing in a state playoff game. Here's Jeff Buller.

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You know, you've got um things that fall and winter sports don't have to deal with, like prom and, you know, we've got Easter break in the Catholic schools in Central Ohio that, you know, we have five days off, we're not allowed contact, which opens up a whole new kind of can of worms there. Got graduation and baccalaureate and the graduation parties, you get the senior tag. Um, and if your season's going really well, the season's still going and school's out. Some brains can be going in all sorts of different directions there. So, you know, how do we address that? We we try to go back to our goal setting in the preseason, and then we're constantly reviewing, you know, what the behaviors that the players set that would help us reach those attainable goals. You know, and with that comes the leadership training. And I think the more that you involve players in those discussions and setting behavior expectations, and you show that you value their opinions and and their input, the more ownership that they, you know, take over those behaviors and and and hopefully, you know, as you know, behavior um produces results. So that's kind of what we do at Watterson to avoid the off-the-field issues. Good to be with you, Ken.

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Time management is one that every coach probably wishes that they can get better at. And the challenges now that every coach in America that's coaching right now faces is not having enough time in a day. Between paperwork, working your job, coaching the team, everybody only sees you out on the field coaching the game, but there's so much more to it. And Jeff Melcarrick at Toledo Central Catholic explains how he prepares for the upcoming week each season.

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Coach Carpenter, great question about uh biggest pain point or challenge that as a coach, high school baseball coach, I face during the season. You don't want to look at it as a pain point. To me, that's a negative. It is a challenge, and and I would think to me, the biggest one after doing some uh soul searching to answer the question. Um, the one that kept coming back to the to the forefront is time management. Trying to do everything that's required um to be successful in running a high school baseball program, it has become more and more um detailed and more and more time consuming each and every year, whether it be preparation, uh paperwork, spring trip planning, um, facility preparation, daily and weekly, um fundraising, and the list goes on and on. Um I try and sit down on Sunday each week and put together, looking at our schedule, and put together what tasks I need to accomplish personally, and if there's any of those that I can delegate to anybody else to get them done so that we can have a successful week of whether it be training or games. To me, the training sessions and the games each week are the fun part of the season.

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Up next is Division III head coach at Bluffton University, James Granty, discussing when players feel like they're in a slump and things aren't going their way. He talks about the benefits of positive coaching and going back to the fundamentals.

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So what we try to do is remind them of times they when they have done things well and the things that they do well, and also get back to doing the fundamentals really, really well. And then if in baseball, if you can do the fundamentals well, usually the game takes care of itself.

Development Versus Winning In Practice

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Finally, our fourth coach is Jimmy Fillingerry. He's at Duchess Community College in New York, and he's also host of Clearing the Bases podcast, talks about focusing on working on things that weren't going well during games and having meaningful practices.

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The first thing that I want to do is I want to thank you for asking me to be part of this. If I had to say what my biggest challenge is during the season, is trying to balance the development portion versus the winning games portion. So as we know the baseball season is very, very short. And, you know, you you jam act with games, but you still need to practice and you have to make your practices meaningful. So, I mean, we still have to, you know, get in our catch play. We still have to get in some situational hitting. We have to get in situational alignments, we have to work on our skill sets. There's just so much stuff that we have to do. On top of working on the things that we see are not working during games. Um, you know, I could use as an example, like, you know, maybe rundowns aren't going good, uh, cuts and relays aren't going good, the boys aren't communicating well, uh, you know, pop-up priorities, all of those things that maybe didn't go right during a game. We need to work that stuff into the practice along with our rudiments of the game. And I find that to be a little challenging.

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Special thanks to Jeff Bulware, Jeff Milkerrick, James Granty, and Jimmy Fellingerry for joining me on today's podcast. Be sure to look for a new episode every Wednesday where I sit down with some of the best coaches from across the country. Today's show was brought to you by the Netting Professionals Improving Programs One Facility at a time. Contact them today at 844-620-2707, or you can visit them online at www.nettingprose.com. As always, I'm Coach Caden Carpenter. Thanks for joining me for baseball coaches unplugged.