Let me ask my boss. Then again, my boss’ boss.

There are so many variables that a strict rule of thumb may not apply. But assuming you have a good relationship with your manager, almost any issue at any time is fair game. If you don’t have a good relationship, almost no issue at no time is advisable.

For our discussion, let’s assume good karma (not a Catholic concept, but you get the point). Here are three categories of “escalation,” from the most modest to the most severe:

• Standard advisement. Many scenarios or problems are worthy of seeking advice. And from an ego point of view, most bosses are flattered and pleased when asked for advice. “I’m struggling with communication with the finance department.” “How do I best win over Stacy to cooperate with me on our new vendor?” These are issues that aren’t super sensitive or confidential, and don’t have major repercussions. While you don’t want to be running for help all the time (personal competence and confidence are valued), occasional inquiries are appropriate.

• Serious counsel. Other situations are dicier. They might involve people’s reputations, discreet or confidential information, layers of complication and /or weightier consequences. These matters are usually few and far between, but they do beg for higher-up help. “I’m stuck in a serious conflict with Bob.” “I depend on Gail, but she seems incompetent.” You want to cue up such discussions with discretion. Before you get into details, it’s best to secure your bosses’ agreement to confidentiality – just between you and him/her, unless and until you both agree it should go beyond.

• Intervention. Here we are dealing with serious cases like sexual harassment, alcohol or drug abuse, cheating, lying, stealing, etc. These are hot, hot, hot. So, handle with care. Hopefully your company has guidelines on how to report these issues. If not, your first inquiry can be theoretical. “If I ever become aware of a clear-cut ethical violation, how should I handle it? To whom do I take it, and how?” Above all, be careful, because these situations can be unfairly turned against you.

Needless to say, tap into one of the seven gifts of the Holy Spirit, which abides in you. The gift of counsel is a divinely bestowed power which perfects the natural virtue of prudence, or right decision-making: “Let your good Spirit lead me on a level path.” (Ps 143:10)