Like many of the soft skills necessary to be a successful project manager, there's no silver bullet that will guarantee effective escalation but here are some tips that might help:
1. As part of your stakeholder analysis, find out what their escalation requirements are. Similar to risk bias, stakeholders are likely to have differing views on what kinds of decisions or issues need to be escalated to them for resolution and while you may not be able to tailor your approach to exactly meet these expectations for individual stakeholders this up front requirements gathering can reduce the likelihood of your being far off the mark.
2. Document escalation criteria and processes within your project's communication management plan. Such criteria should be objective or at least be supported by examples of the types of events that merit escalation.
3. Leverage an external observer who can provide you with unbiased feedback on a situation. Obviously you should not abuse this resource with each and every decision or issue that emerges on your projects unless a formal mentor-mentee agreement exists, but having the support of an external advisor can reduce the likelihood that your own intuition is invalid.
4. Make sure you've done some analysis. For example, when faced with a decision or issue you can ask your team to perform a quick expected impact calculation (combining maximum impact and probability of occurrence) based on the question "What's the worst that could happen if we choose to deal with this without escalating?".
5. "Once is happenstance, twice is coincidence, three times is enemy action". If repeated attempts to resolve an issue or make a decision within the team have failed, escalation can at least reduce the likelihood of further project impacts.
Communication is the most important project management knowledge area, and the ability to effectively escalate is a critical competency for any project manager.
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