. A recent article I read focused on whether it is good for a manager to throw their employees under the bus. I was thinking about this and turned it around to employees throwing their manager under the bus. The two situations are not quite the same. However, I think it is an excellent way to view the case when you have to go to the boss of your boss.
The Last Resort
I think that it needs to be clear up front that this sort of escalation should only be considered after exhausting other options. A boss that is either not communicating or not understanding is not a good enough reason on its own. There should be a thorough and patient effort made to break through these sort of failings. We all have our bad days. If you escalate a situation merely to avoid frustration, then you might find yourself in a worse situation.
There is no way your boss will not find out what has happened when you choose to go over their head. Thus, escalating a situation in this way is not something you can do halfway. They will most likely ask you why you chose that path so be prepared with a thoughtful and easily-defended explanation.
Be aware that a step in this direction will bring scrutiny to you as well as your boss. I have seen minor misunderstandings bring projects and teams to a grinding halt due to the attention brought on by an escalation. Yes, your boss will probably not appreciate your action. However, their boss may not be too happy in getting involved either. I have seen a rookie mistake in this area a couple of times. A junior staff member that was sure of their position ended up looking for a job after they were shown to be woefully wrong.
How To Proceed
Now that the warnings are out of the way, we can look at when this might be a needed step. The best situation is when you are only escalating a situation due to absence. This can occur when your boss is on vacation or otherwise unavailable. That allows you to open the conversation by saying that you are only bringing the item up because you cannot reach your boss. You will also find that to be easier for your boss to handle when the time comes for an explanation.
In marriages, there is the idea of irreconcilable differences as a reason for ending them. Sometimes this can happen with you and your boss as well. The difference is that your boss does have the option of pulling rank. I find that the only reason for going around your boss after a decision is made is when that decision is either illegal, immoral or easily shown to be damaging to the company. These situations may cost your boss their job so treat them with that level of seriousness. The step of escalating must be shown as done for reasons that are not self-serving. You also will want to have a long paper trail of conversations or decisions by your boss. These will be useful to support your escalation.
When in doubt, I would tell my boss before escalating a situation. That avoids surprises and allows for the situation to be defused or corrected before bringing in the “big guns.” The job you save might be your own.