If he is really your Rebbi, ask. You will get sagacious advice and his heartfelt Tfillah as a side benefit. It also helps if you run into problems, he is connected with the matzav and can provide more comprehensive direction.
In addition, sometimes you don’t see a second side to an issue anad he may see a few more. Why not utilize your resource? If you were investing $$$$ and you thought maybe reuvain has some possible info about the company, you’d call …… call your Rebbi!