The Sheffield United midfielder, who made nearly 60 appearances for Rangers before heading south of the border, also knows a thing or two about taking on the establishment after leaving the 54-time Scottish champions during the newco saga seven years ago.
The knowledge he acquired after progressing through their youth system should serve him well as Chris Wilder's side, second in the table with only eight matches remaining, enter the final phase of what they hope will be a promotion winning campaign. Indeed, with Leeds, Norwich City and a resurgent West Bromwich Albion also hoping to nail down a top two finish, Fleck believes mirroring the values of their home city represents United's best chance of success.
"Sheffield is a working man's city," he said ahead of Saturday's home game against Bristol City. "It's a down to earth place where people don't get ahead of themselves, they just get on with things and work hard.
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"We've been trying to bring that attitude to the club and for the fans. We're not a team full of household names or big stars so, as a group, we just try to work as hard as possible."
Fleck, aged 27, is expected to make his 39th appearance of the season when Lee Johnson's side arrive at Bramall Lane having spent the international break traipsing around Europe with Scotland but failing to get a game. Alex McLeish, whose refusal to select him appears remarkable given some mind-numbingly pedestrian performances of late, might not be fully convinced of Fleck's talents. But Wilder, whose side are unbeaten in their last 10 outings, is a fully-paid up member of his fan club having selected him for all but one of United's league matches so far this term.
The coaching staff appreciate Fleck's cultural sensitivity too, with Wilder himself underlining the importance of reflecting Sheffield's personality on numerous occasions since taking charge.
"The connection with the fans is huge," Fleck said. "And it's definitely helped us along the way.
"I think the fans appreciate it, even in the games where we haven't won, because they can see we are trying out best and giving everything out there. That's the most important thing they want to see."
With only five points separating the division's leading three teams, while back to back wins under caretaker James Shan have seen West Brom consolidate their grip on fourth, Wilder and his counterparts at Elland Road and Carrow Road are aware of the need for strong hearts and cool heads.
Fleck recognises the challenges set to confront United between now and May's visit to Stoke City, after winning two SPL titles at Rangers and one Scottish FA Cup during his spell with Rangers. Together with his midfield partner Oliver Norwood, who is chasing a third successive promotion from the Championship, that experience makes Fleck a vitally important figure both on and off the pitch.
"The only pressure on us as a group is to give our all," he said. "That's the only pressure we are under. If we do that, then we've always got a chance of winning games."