My nephew was on the same Little League team with Will Venable one year (age 12) and they played on All-Star teams together. We used to tell the other manager before the game to make sure his 1B played DEEP because Venable (then about 80 pounds) could just rip the ball down the RF line (LH hitter) before the infielders moved a muscle. Saw him hit a ball in All-Stars at least 50' over the RF fence!
His Dad, Max, was a MLB player for many years and a really good guy. You would never have known he was a MLB player. He would ask if he could help when he was able to attend practice, but never acted as though he knew any more than any other guy.
Just a GREAT family and Will was articulate, rather quiet, always smiling, as a youngster. Not a surprise when he went to Princeton and played basketball (fabulous athlete), not a surprise when he started playing baseball again as a junior there and not a surprise when Sandy Alderson (who lived nearby and knew Max) drafted Will in the 7th round. Also not a surprise when Theo picked him up for the coaching staff. Will is a class act!
Will almost certainly lacks the experience to get selected as manager by Theo and he seems more like a front-office type to me; however, I'm sure he has everyone's respect in the Cub org and I'll bet he communicates very well with players...maybe down the road.