Why it is difficult to handle escalations?

Sometimes the people to whom a PM must escalate a problem are the cause of the problem. This makes it very difficult for a PM to escalate the truth, especially when retribution is the only likely result of doing so. Anyone who has worked for incompetent or lazy superiors can probably relate to this.

Very good feed back from the group.

As a general rule it's better to escalate to be transparent and not coverup anything. If it's turns out to be an non issue just move on.

All excellent points already above.

I would add that a periodic stakeholder review meeting is a must in proper escalation management. Especially in conjunction with robust risk management.

These approaches allow the stakeholders to be aware of risks that may require escalations and such escalations do not come as a surprise.

This is important because, much like everything else, sour escalation experiences arise from a gap between expectations and reality. Periodic reviewing of risks minimises the chances of this gap occurring - and when it does occur, it is usually due to unforeseen or external factors.

good comments above. Periodic meetings with upper management from beginning of project will make it easier to escalate if situations occur. Especially keeping them in loop of known and unknown risks that occur and ask for the input if any.

I have seen both too fast at escalating and other who refuse until it is impossible not to escalate.

The right timing is better