Does he have any injuries? Any conditions that may make him not suitable for certain movements?
I'd actually not recommend going barefoot for the beginning. This is a person who has likely been in shoes for 50 years - if any barefoot stuff is done, I'd limit it to 5-10 minutes a day on grass or carpet for at least 3 months. Is 3 months a long time? not compared to 50 years.
DaveS - the good habits should be in place, but even Justin who just went 28 days straight without shoes said that as soon as he put on shoes he caught himself heel-striking. So I feel that it is a long time and a lot of practice and focus to break the bad habits.
IMO I'd start him with some light conditioning - 2 pullups is good, maybe get him doing 3 sets of 5 jump pullups - see how he does with breathing and heartrate (and I don't mean with a monitor - I mean with common sense) after 3-5 minutes of moderate exercise.
From there I'd have him start on squats, and I'd measure strength and flexibility to see where his needs are.
After maybe 2 weeks of 3 X (5, 10, 25) squats, then basic running, cadence, start stop, and the progression DaveS mentioned - but with shoes.
From the start he can try safety vaults, and work on cadence by jogging and trying to hit targets and plan his footing.
Balancing on objects is also great, I really like balance boards as they work strength, mobility, and coordination all at the same time in a very safe way, and the skills that you develop transfer well.
After a few weeks of squatting, measure broad jump and vert, and see if he can touch his toes and see how far down he can squat without lifting his heels. Report back or feel free to email me
