according to the gatekeepers℠…

Nobody really wants to have to go above their boss’ head. But sometimes it seems necessary. When it is clear cut, you have no choice. But where should that clear cut line reside?

Earlier is my career, my boss, who was the CEO at the time, gave my assistant a single rose. He left it on her desk before she got in one morning and then took credit when he came to see me later in the day. Corey, my assistant, told me the rose made her uncomfortable.

She’d previously asked me if it bothered me when he touched my arm and shoulders. I had seen him do it to others, as well as Corey. It seemed “alpha dog” behavior to me, so I ignored it. Even though Corey did not want me to say anything to him at the time, it seemed to bother her more. Now that she had the rose, I understood.

I spoke with my boss. I told him it wasn’t wise to “appreciate” an employee in that way; others may misunderstand his intentions. And while on the subject of making people uncomfortable, I told him that his “innocent touching” had bothered some employees, even though I wasn’t offended. He said he understood and would do his best to stop.

“I am just an affectionate guy,” he shrugged.

About a week later, I was in a meeting with the executive committee, all males except me. Corey came in to give me a note. When she was headed out the door, my boss said, “I wonder if Corey will go out with me if I ask her in front of all of you.”

There was a lot of nervous laughter in that room, but I wasn’t smiling. Without thinking, I quipped, “She’s out of your league,” just in time for Corey to hear more nervous laughter as she walked out the door.

Clearly what I said was not enough.  

In the wake of the revelations about Harvey Weinstein’s behaviorand all the other executives and celebrities that are being exposed in the moment, but have been lurking in the shadows for years, the “line” obviously isn’t clear cut at all.

We recently asked the gatekeepers℠—a consortium of 80 CEOs, board members, C-suite executives, executive search consultants, venture capitalists, private equity managers and talent executives—to give us their advice about when going over your boss’ head is the right thing to do.

Here’s what they had to say

If the issue is illegal or unethical behavior, it is clear cut, just do it.

Fede Barreto, chief financial officer and EVP at Sony DADC, thinks that going over the boss’ head should be something of a last resort.

We should all strive to achieve our goals with help from our bosses — instead of trying to go over their heads. But there are still instances where going over the boss’ head is definitely the right move.

“In my opinion, it’s the nuclear option,” Barreto says. “One should take the approach only in situations of fraud, corruption or likely damage to the company’s finances or image.”

Jim Daly, chief human resources officer at the Affinion Group, agrees.

“It is usually best to discuss most issues with the boss directly, seek HR’s perspective if they are trustworthy or gain the benefit of an advisor or mentor to determine how best to process,” Daly explains. “If it is not a legal or ethical issue, going over the boss’ head could backfire and cause further conflict.”

What about some of the less clear cut areas? When does it make sense to do it?

Kaivan Desai, CFO at GE Power, believes that there are other situations when going over your boss’ head is warranted.

For example, if you have a fiduciary responsibility to your company as a finance leader which your boss doesn’t necessarily understand or agree with, you may have to raise your concerns to the appropriate decision maker.

“If you believe a decision made by your boss negatively impacts your team, it’s your responsibility to stick up for them,” Desai says.

And what if your boss consistently ignores your ideas or concerns?

You may also want to consider going above your boss’ head when you’ve given them an adequate amount of time to respond to an idea or concern only to be greeted with silence, according to Pam Chandor, global sales vice president at IBM.

This doesn’t necessarily mean that you should always go outside the hierarchy when your boss doesn’t seem to consider your ideas. You should definitely think twice before going above your boss’ head.

But when you’re confident in your ideas—or you think your concerns need to be addressed—by all means do what you think is best.

Definitely go to the next level, when your company’s reputation is at stake.

Most of the gatekeepers felt that you should go above your boss’ head “when it becomes clear that a critical mission is at risk and when the consequences will cause either financial loss or reputational risk—or endanger employees.

Patrick Fay, chief operating officer at Mizuho Securities, agrees.

Go above your boss’ head “when the issue at hand poses a critical risk to the firm’s financial or reputational well-being —and your boss has repeatedly ignored or has not responded to the risk,” Fay explains.

Nigel Hurst, executive VP at HEI Hotels & Resorts, also believes it’s important to defend your company’s reputation.

Hurst recommends going over your boss’ head “when you are asked to do or not do something which will create a conflict with company policy or company values and you have not been able to convince your boss otherwise.”

Tell to your boss first; they might endorse you. 

Some gatekeepers believe that good bosses might relent or even will be okay with allowing you to talk to their superiors.

“If you have a good relationship with a superior, start by asking for advice in confidence before any true escalation,” says Val Rahmani, a board director at Aberdeen Asset Management, Computer Task Group, Rungway, and RenaissanceRe. “Otherwise, unless you feel that your boss is about to be removed soon, going above them will almost always hurt you.”

Tom Geisel, an executive vice president at Sterling National Bank, agrees—assuming the concern or conflict is substantively material.

“If it is and you feel that you have the factual justification for a different decision, then the professional process would be to let your boss know you disagree and you would like to have an opportunity to speak with their boss,” Geisel explains. “Most of the time, a secure leader will say yes. If they say no, you have to review the risk-reward or doing so.”

The bottom line is to exercise caution before going over your boss’ head. When certain behaviors or actions are illegal or unethical, your concerns need to be heard by the next level of management or at the board level. In other circumstances, you must weigh the risks and rewards, and be clear about the potential consequences to your career.