Make two column array of text boxes for the Job Information and two columns for workers and use the subscript for the box as the pointer to your data list. That way when you enter data in one of the text boxes, the subscript of that box will be the subscript in the list. Done that way, you can loop from one to 10 and manipulate it however you want.
For the random job assignment, look at the function for the Random Number Generator in your textbook. It will return a random ordered list of numbers from 1 to 10. Suppose the list is 6,2,8,9... Then loop through the workers and assign worker 1 job 6, worker 2 job 2, worker 3 job 8 etc.
To display total time you need to record the beginning time and ending time. You should have a Timer function that will return the number of seconds since midnight. Put buttons up for Start and End. Set a start variable to the timer when the button is clicked and an end variable when the end button is clicked. To determine the time, subtract the start from the end and divide as
Result (in hours) = (Difference / 60) / 60