Leicester Crown Court heard that between 16 and 25 January 2008, Pope, trading as Westwise Demolition, was demolishing the former Manvers Arms public house on Monks Road in Lincoln. The demolition involved piece-by-piece removal of the two storey pub's roof tiles.
One man sat on the roof, removing tiles and passing them to the son of the defendant, who was standing in the upturned bucket of an excavator positioned level with the edge of the roof.
Once the bucket filled with tiles, Pope's son climbed onto the roof before the bucket was lowered, emptied and raised back up; he then climbed back in and carried on the task.
There was no scaffolding to prevent the men on the roof from falling and nothing to protect those working below from any tiles dropped or dislodged during these activities.
Pope, of Hassock Hill Drove, Gorefield, in Wisbech, Cambridgeshire pleaded guilty to two counts of breaching Section 3 (2) of the Health and Safety at Work etc Act 1974 for failing to ensure people not in his employment were not exposed to risks to their safety.
He was today fined £6,000 and ordered to pay £13,483 costs by Leicester Crown Court.
The Health and Safety Executive have reminded employers of their responsibility to protect their workers following the case.
After the hearing, HSE inspector Martin Giles said: "This was foolhardy to say the least and could so easily have resulted in serious injury or even death. It is particularly disturbing that Mr Pope was willing to risk the life of his own son by failing to put such basic safety requirements in place.
"Working at height remains one of the greatest dangers to construction workers. Many incidents can be avoided if contractors identify a safe way of tackling a job, provide all necessary protective equipment and ensure that workers, sub-contractors or casual employees are fully trained and properly supervised.