OP
Outspoken
gloves probably wouldn't be a bad idea, but maybe not a necessity depending what the material of the thing is he's holding, eye protection... why?
Considering the roof has a loose surface that can be kicked up accidentally I would suggest that all those on the roof should have eye protection with them and anyone actually working would be well advised to use it. I am not one for blindly insisting on the use of PPE regardless, but there are some situations where people be given it and they should be instructed to use it where there is an increased risk, failure to use it should make them liable and NOT the employer.