The short answer
You're asking soft questions because the real ones feel risky. But the whole point of an informational interview is to get honest intel you can't find elsewhere. Write down the one question you've been avoiding, then ask it first.
When people ask safe questions in informational interviews, they usually already know what they're afraid to find out. Research on interviewer-respondent interaction shows that the person asking the questions shapes what comes back — vague, polite questions get vague, polite answers. You're not getting useful information because you're not really asking for it yet.
Marcus wrote that the mind doesn't have to make trouble for itself by fearing what it might learn. The fear lives in the anticipation, not the answer. Your understanding — your actual judgment — can handle what you hear. The discomfort you're dodging is almost always smaller than the cost of staying in the dark.
This week, before your next conversation, write down the one question you've been circling around but haven't asked. The one where the answer might change something. Make that your opening question, not your last. Ask it plainly, then stop talking. What you hear will be more useful than everything in any safe conversation you've had so far.