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Here are a few tactical approaches to consider as you design your testing efforts -- these are not in any particular order intentionally, as you'll need to think through each and then revisit how these tactics work together.
Risk analysis. Web analytics. Priority levels. History. Exploratory testing. Issue tracking.
A risk analysis is a great step in trying to determine what's important. It is found that a risk analysis when shared with stakeholders might bring tough topics out into discussion as we hash through what is a risk and what ranking we might assign to each risk. Sometimes the risks are obvious and sometimes I've uncovered surprises just by hosting the conversation about risk.
Explain to project stakeholders that not all testing will be addressed but that testing will follow the results of the risk analysis. Both of these facts are important and as obvious as it might sound to a tester, this isn't always obvious to project stakeholders. Risk analysis drives priority in testing. Sometimes people -- upper management and stakeholders especially -- will falsely believe all testing will somehow be accomplished. It is best to communicate that testing will likely never be done but will be executed in order of priority and that a risk analysis is not just a process but an important way to determine that priority order.
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