We ran our first official family 5km barefoot with our 11 - year old kid. He did try running barefoot on smooth surface around a local mall's paved roads but his run on shoes earlier made him complained a lot because of the discomfort from wearing shoes.
So, after runnning a kilometer, he had to remove his shoes and ran barefoot with us. He had to complain though on the rocks he stepped on.
We just had to tell him to spring faster as his feet would land and to run with shorter stride but with faster cadence.
Running barefoot can be not at all appealing for everyone. In fact, it can be quite uncivivilized compared to runners on full running apparel but one can correct his running form, becomes economical and more efficient.
I could have run nicer with my barefoot accessories including of pearl necklaces except for carrying my son's shoes.
With regular practice, barefoot running can be his way of running.