CHICAGO -- David Ross attended Joe Maddon's annual charity event in Pennsylvania in December. Days prior, at the Winter Meetings, when a group of Cubs writers erupted in laughter at a Ross one-liner, Maddon, now manager of the Angels, leaned back at his neighboring table with a smile and asked what he missed.

It's clear that there's no awkwardness between the two as the Cubs transition into a new era under Ross following arguably the greatest five-year stretch in franchise history on Maddon's watch. And it's more than a changing of the managerial guard. Ross had an edge as a veteran leader during his playing days, and he plans to stay the same in 2020 and beyond.

"I want to work. I want to do things the right way," Ross said recently. "But we're going to have some fun, too. I learned from one of the best ... about how to have fun, how to keep things loose. And I also have some of my own ideas that I'll implement for this group that I think will carry the day."

The Cubs' equipment trucks have already arrived at the team's spring headquarters in Mesa, Ariz. Pitchers and catchers will report on Tuesday, with the first official workout taking place the following day. Barring a major trade, the group of players Ross and his revamped coaching staff will have will look very similar to the 84-win, third-place cast from last year.

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Although the changes to the Major League roster have been slight -- outfielder Steven Souza Jr. and reliever Jeremy Jeffress are the only additions via MLB contract to date -- the alterations to the organization's operations have been dramatic.

Chicago underwent changes in the front office, hired and promoted new leadership for its amateur scouting arm, overhauled the player-development department, poured more funds into research and development, and built a new Minor League hitting and pitching infrastructure. It was the result of the Cubs taking a hard look in the mirror and realizing that the status quo was not cutting it.

"We looked at things," general manager Jed Hoyer said, "and decided that the game is moving incredibly fast when it comes to player development, when it comes to research and development, and we made a lot of big changes. We thought it was time. This is our ninth [year here]. We've been here a while, and sometimes it's time for kind of a sweeping change."

Although the bulk of that change has been from the ground up, with the long-term health and growth of the franchise in mind, it will be Ross who now sets the tone at the top. With that in mind, Ross went about building his first coaching staff by combining voices from last season's group and injecting some new leaders into the mix.

Pitching coach Tommy Hottovy will still have Mike Borzello (associate pitching, catching and strategy) at his side, but now Chris Young (bullpen coach) and Craig Driver (first base and catching) are on board. Hitting coach Anthony Iapoce remains in place with assistant hitting coach Terrmel Sledge, and Will Venable makes the move to the third-base coach's box.

To aid Ross' first year at the helm, the Cubs hired former Padres manager Andy Green as the bench coach. Green impressed Ross immediately during the hiring process and has been integral to helping Ross map out Spring Training. Ross will also have a former teammate, Mike Napoli, with him as the quality assurance coach.

"You see the guys I’ve kept from Joe," Ross said. "A lot of the things will be the same as far as the environment. I think we'll all create our own unique identity. I don’t know exactly what type of manager I’m going to be yet. It’s going to take a lot of input, a lot of conversation. I don't believe in autonomy."

And although Ross will borrow from Maddon when it comes to giving players some room to have fun, it will also be very much back to business and structure. During the Winter Meetings, Ross went as far as saying he hoped some of the core players experience a little bit of shock this Spring Training.

Atop Ross' list of priorities is having the players get back to a more collaborative approach to their routines and workouts. He wants to empower such veterans as Jon Lester and Anthony Rizzo to show the way for younger players. Ross wants more players working together -- rather than individually -- to generate more conversation to spur growth. He wants on-field drills to better simulate game action.

"We talk a lot about how things relax and change and a lot of good environment was created here," Ross said. "I also think there's a little bit of, from the players' perspective, holding them accountable to their structure, and creating that routine at an early age, that just kind of got pushed to the side with all the success they had had.

"I just want to get back to the things I've seen on the winning teams I've been around and I've been on. Knowing these guys and where their heart's at, I just think that attention to detail will create such a culture and bring these guys back together. It's easy in today's game, with all the information, to get kind of on your own plan and do your own routine.

"We all have our own individual workouts in the offseason, our own personal trainers and how we take care of our body and how we go about our individual cage work. I want to bring a lot of that kind of back together and doing that as a unit."

As is the case with Lester, Jason Heyward and a handful of others, Rizzo and Ross were teammates on the 2016 Cubs team that won the World Series. The two are friends, but Ross is now also the boss, so Rizzo has taken to jokingly calling him "Manager David."

Cubs fans learned to love the "Grandpa Rossy" persona, but Rizzo knows that the same edge Ross had as a teammate will be present now that he's in the manager's chair.

"He'd be the right guy no matter what," Rizzo said, "because of his knowledge of the game, his leadership skill set, the way he can talk to guys and communicate."