A few years ago, I found myself uncomfortably witnessing a painful breakup. But it wasn’t a couple struggling through a divorce; it was the unravelling of a friendship, complicated by the fact that the two people in question were also a boss and his subordinate. They were once so close that the boss, Jason (not his real name), and Martin (also not his real name), took family vacations together. Because they also frequently commuted to and from work together, the rest of us came to understand that Martin had unique access to our boss and that he was in a position of power because of it.

Now Martin was reduced to hovering in the office hallways hoping that he’d “casually” bump into Jason on his way home and that Jason would offer him a ride. We never really knew what led to the splintering of the relationship, but it was clearly not a good thing - for either person or for the company. They soldiered on in a kind of forced formality - reporting lines were rejiggered under the guise of a larger restructuring - but eventually, Martin left the company and it seemed that Jason was relieved.

When I think back to this situation, it’s clear how complicated a boss-employee friendship can be. I’ve been fortunate to have had great relationships with all my bosses — though they never fully crossed into the friendship category. Can it ever be wise to befriend a boss when that person has the power to fire you, refuse you a raise, or generally make your work life miserable?

Of course, there are perks to being friends with your boss. Though we’d like to think we work in a truly egalitarian system, if your boss considers you a pal, she’s more likely to trust you with information, say yes to your vacation requests or a flexible work schedule, and perhaps most importantly, pick you for high priority projects and assignments. After all, it’s human nature to treat people you like better than those you don’t. “If you are closely connected to someone at a higher level in the organization, they may be able to promote you, spread your reputation, [or] provide you with access to information that is useful to use,” says Monique Valcour, a professor of management at EDHEC Business School in France.

So how do you know when it’s a good idea to be friends with your boss — and when it’s just too risky? The answer, experts say, depends on a number of factors.

1. Were you friends before you became the subordinate? “It’s easier to have your boss turn into your friend than to have a friend turn into your boss,” says Ben Dattner, an organizational psychologist and author of The Blame Game: How the Hidden Rules of Credit and Blame Determine our Success or Failure. If a friendship predates a new reporting relationship, you have to make a concerted effort to maintain some degree of role clarity. Self-awareness – on both sides — will be key. Ask yourself, “What is my relationship to this person now? How should we be relating to one another?’” suggests Valcour. “Follow your sense of what’s comfortable and what’s not.”

2. Are you friends because you genuinely get along or did you try to develop a friendship because it might serve you? “If you have a natural affinity, genuinely like each other, and want to have a social bond, I think that’s worth cultivating, as it would be with other coworkers,’’ suggests Dattner. ‘’But I wouldn’t make a special effort beyond what you’d do with any other coworker. That would take on a Machiavellian tinge, which I think you don’t want.’’ A relationship that’s based on you making a power play isn’t likely to be a strong one, and you run a higher risk of it ending in disaster, especially if your boss senses that you’re getting close to her to advance your own career.

3. Are you willing to talk with your boss about boundaries so that the friendship/boss line doesn’t get blurred? If the relationship has shifted from being friends-colleagues to being boss-subordinate, have a direct conversation about how to make sure the lines don’t get blurred. You can even articulate the lines you’re drawing in the moment: “I’m speaking as your friend here…” or “As your employee, I’m telling you…” It may seem artificial to do that, but it helps. There’s no escaping, however, the fact that a superior-subordinate relationship comes with complications that you might not face in other friendships. You might tell your buddy about the highs and lows of your personal life or whine about a colleague who is getting on your nerves. But should you feel just as free to vent to your boss? “Anytime you provide your boss with a piece of information, think about the fact that you’re both friends and he’s your supervisor. Keep it as uncomplicated as possible.”

4. Will you face backlash from your peers if you’re perceived as being the boss’s favorite? It’s possible that your colleagues will be wary of you getting special treatment so you have to make sure that your peers don’t end up resenting you. “Monitor the decisions the boss is making to make sure you’re not given all the plum assignments, all the easy trips,” says Dattner. “Get feedback from other people in the workplace on whether your relationship is a problem for others.” If it does seem to be causing resentment, discuss this with your boss. You might say, “I really appreciate you’ve given me some of the softball assignments, but I’m concerned my colleagues might perceive this as favoritism.” Work hard to be a good team member, independent of your relationship with your boss. One person I spoke with recalls that working for a friend actually made him up his game. “We both had to go to great lengths to make sure things appeared to be on the up and up,’’ he recalls. “My performance had to be exemplary so it didn’t look like she’d just hired her friend.”

It’s possible your boss will go to the opposite extreme, too. He might end up giving you the short straw so as to not be accused of favoritism. Monitor the decisions from that perspective, as well, Dattner says, and don’t be afraid to confront your boss if that’s the case. “You might want to say to your boss, ‘I understand you’re not trying to give the appearance of favoritism, but this is out of whack.’”

5. How old are you? Ask a Gen Y worker what she thinks about forging a friendship with her boss and she might give you a look of bewilderment. Because younger generations tend to relate to parents as friends, there’s less separation between generations than previously existed, says Tammy Erickson, an expert in managing across generations and author of What’s Next, Gen X? “The rise of mobile technology has shifted the role traditional authority figures play in their lives,” she says. “Teachers (and parents) used to know more stuff than younger people did. Now, access to facts is equal; the older person becomes more of a guide or coach and less of a source of authoritative answers. This also adds to the shifting relationship.”

So where should the lines be drawn — if at all? Having a positive, constructive, and trusting relationship with your boss is always a good thing, says Erickson, and everyone should work toward that. But whether it should cross the line to genuine friendship is less clear. As Erickson says: At the end of the day, it’s a personal preference.