Follow your mundane questions with a form of "do you like it?". It will usually break the conversation right out of 20-questions mode.
Example:
A: What is your major?
B: English
A: Do you like it?
B: Well, yes, but what most people don't understand about English majors is...
I picked this up on Reddit, and it really works. Give it a try! A: What is your major?
B: English
A: Oh, cool, I took an English course in college. Probably nowhere near as detailed
as your studies, but I enjoyed it.
B: Oh? Which course?
A: Science fiction.
B: Never took that one. Which books did you read?
A: A bunch of Heinlein, some Ursula LeGuin.
B: I never liked Heinlein - thought he was a sexist pig. I love LeGuin though.
The problem with asking a lot of questions is that there's unequal emotional investment between a question and an answer: the answerer is putting themselves out there a lot more than the questioner. (This is one reason why he who asks the questions controls the conversation.) If you're trying to build a relationship, this feels very awkward. Instead, the point of most conversations is to find & build a connection between the two people, one that lets both of them feel safe simply volunteering information and knowing that the other person is interested. By relating topics back to yourself, you a.) give both parties a chance to ask questions, and b.) show that you're in the same boat as them, and so they can feel free to open up to you.Notice that conversations between close friends rarely have questions - they consist of people taking turns volunteering new information, often rather animatedly if they have good rapport with each other. Also look at Hacker News comment threads: people rarely ask direct questions, they just contribute additional information along the same lines as the original comment.
And I presume there are other such people in the industry.
My experience with developer-type leaders and sales-type leaders really breaks down to this: the developer builds a solid foundation and finds the product-market fit for it, the sales-oriented person projects the future they want others to believe in. One is slightly more logic-based, the other emotional. Some people can do both. That's rare.
(To borrow terminology from "Thinking, Fast and Slow"):
In my experience, more socially-inclined people are able to rely easily on System 1 -- whereas the more awkward ("engineer" types) attempt to engage System 2 continually, and thus the experience of talking with them often feels effortful and lacking in "flow."
EDIT: A quick primer, from Wikipedia (http://en.wikipedia.org/wiki/Thinking,_Fast_and_Slow#Two_sys...)
"In the book's first section, Kahneman describes the two different ways the brain forms thoughts:
System 1: Fast, automatic, frequent, emotional, stereotypic, subconscious
System 2: Slow, effortful, infrequent, logical, calculating, conscious"
"Turning off your brain" sounds like a good summary of that. I don't think one need a particular "skill" to act stereotypically, subconsciously, emotionaly, automatically, at least... If one is inhibited and thinking too much, just give it some wine.
In the book's first section, Kahneman describes the two different ways the brain forms thoughts:
System 1: Fast, automatic, frequent, emotional, stereotypic, subconscious
System 2: Slow, effortful, infrequent, logical, calculating, conscious
http://en.wikipedia.org/wiki/Thinking,_Fast_and_Slow#Two_sys...
On the other hand, I ask the most questions when I am genuinely curious about something in which case I am inclined to talk out of natural curiosity than social necessity.