We use a company to fix our swimming pool, these are usually small fixes and don’t cost a lot of money,
The owner is very successful and these small amounts don’t make a difference to him
We will often have to ask two or three times for a bill or ask him to come collect the money because he often forgets to come
How much obligation do we have to make sure he gets his money ? Are we responsible for his bad business skills ? (He is Jewish)
You are not obligated to tell him to come get his money more than once, and once you informed him that he can get his money you are not obligated to do any more than that. This is because it is obligation of the worker to come get him money. On the other hand, you don’t want to be left owing him anything. Therefore, I would suggest that the next time you use his services, you can pay him for the last time that he worked. You can also add that if he does’t come for the money you assume that he forgives it.
ע’ אהבת חסד פ”ט שאם השכיר תבע מעותין ולא היה לבעה”ב אז, ואח”כ קבל כסף שצריך להודיעה לשכיר שיש לו עכשיו את הכסף. וז”ל בנתיב החסד אות לא ד”ה או להודיעו “ודי בזה שאינו עובר עוד בבל תלין, אם מתעצל השכיר לבא וליקח מעותיו, דלא מצינו לענין פרעון שכיר בעלמא שיצטרך בעל הבית להוליך המעות לביתו אלא דהשכיר צריך לילך וליטול מעותיו“.