I will make the assumption that the Boss buys if no one picks the number that he wrote on the board.
In that case, he effectively has five chances to pay for coffee and each person has 1 chance out of 10.
So the probablity is that your Boss will pay 50% of the time and that each of the five of you will pay 10% of the time.
Another way to look at this is to say what is the probabilty that your numer will not match the hidden number
for the first person it you be 9/10 or 90%
for the 2nd person it you be 8/9 or 88.8%
for the 3rd person it would be 7/8 or 87.5%
for the 4th person it would be 6/7 or 85.7%
for the 5th person it would be 5/6 or 83.3%
now if you multiply these probabilties together you will get the probability that none of the five people match the number
when you multiply these percentages the result is 50%
so chances are that 50% of the time one of the workers will pay and 50% of the time the boss pays
so there is no advantage