Here are a few ways I chain questions together
Move from facts, to reasons, to speculation: “What happened when you sent the file for ingestion?” “Were you able to identify the specific differences in that file, and to link it with any logs?” “why do you think it behaved like that?”
Move from speculation to action: “why do you think it’s not getting through?” “Can we try a different proxy, or a different tool?”.
Narrative - “what led to this situation?” “what happened next?” “How did we get here?” “ What are your options?". One might see this example as a time-going-forward collection. Constrast with the "Five Whys" approach, which goes the other way, from observed symptom to possible cause(s).
Consistency – as I build a model of what’s going on, I try to note what no longer fits, what has changed at a significantly faster/slower rate from the rest, what is extra or missing.
Specifics from Generalities - as I hear general information, some might trigger my interest: “You said that you prioritise by risk – can you tell me about the risks that have influenced this release”. ‘Obviously’ is a great detector word for these.
Get Examples - “could you show me an account with this issue?”, “do you have a document for that?”
Some details are big questions in themselves - “Tell me more about finding that you had different properties for the same identifier”
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