12 Most Gold-Mining Questions to Ask in a Pinch

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Still waters run deep. And so can the choppier waters. Deep is deep, no matter what you find on the surface.

After two decades of diving into these depths, asking literally hundreds of questions in the context of hiring interviews, satisfaction surveys, focus groups, and needs assessments, I have found this one thing to be true: people are endlessly interesting. People also like to talk about themselves, given the right provocation.

A good content-generating question tends to have a few basic qualities:

• Easily asked and easily understood — but not necessarily easy to answer
• Respects the answerer — doesn’t put them on the defensive, but gives them credit for being able to think by asking challenging questions
• Requires more than a yes/no response
• Is specific — e.g. instead of “how do you feel” ask “what do you think about [fill in the blank]?
• Focuses on the positive — we all want to tell the good stuff
• Reciprocity — don’t ask a question you’re not willing to answer yourself

Not only can you ease uncomfortable silences at parties (see my previous post for my fellow introverts), you will generate rich content for numerous blogs, essays, white papers, and even novels through timely application of any one or more of these questions. You might even learn something new about someone you have known your whole life.

1. What’s in your IN box?

This is a good ice-breaker question and lets other people know that you respect their busy schedule, that you are grateful that they are taking time to talk with you, and that you are genuinely interested in what matters to them.

2. What are you reading lately?

This is another good warm-up question that is not hard to ask or answer, but can generate interesting conversation.

3. What do you love about it?

A natural follow-up question to number 2, this question also can be asked after any topic that seems to enthuse the teller. I prefer to say “love” as opposed to “like,” because even with the “can take it or leave it” things, it’s too easy to find something to like. It’s more challenging to name something you love about it, which makes the response that much more substantial.

4. Who has had the greatest influence on your life this year (month/week/etc.) so far?

Most people can name a boss, teacher, uncle, friend, or mentor that has been influential over the course of their whole life. But what about in the present? Awareness of current influences is at least as important as lifetime heroes.

5. If you could have a superpower, what would it be?

This is the “Wizard of Oz” question, with the response nearly always pointing to a strength or quality already present in the individual. I have found that it is also fun to ask six-year-old boys, who already think of themselves in super-heroic terms.

6. How has (fill in the blank) changed your thinking about yourself?

I credit Dan Rockwell (Leadership Freak) for inspiring this gem of a question through his post from over a year ago: The Question That Changes You. I have adapted it to several different conversational situations, interviews, surveys, and focus groups, and it always comes back with gold. For example, a friend of mine recently left a teaching position at a community college to lead a new initiative at a university half-way across the country. When I asked her how leaving changed her thinking about herself, she told me about a newly discovered confidence that caused her to radiate that same confidence as she spoke of it. Talk about a question that changes you!

7. What makes you really good at your work (art/sport/craft/fill in the blank)?

I have found this a very useful question in preparing a search for a new employee. When you want to know what qualities are important, ask the people doing the job (especially those doing it really well).

8. When was your last awesome failure?

We all fail. When we do it spectacularly, we really ought to share. Besides being, potentially, a good laugh (which is good medicine), a fail story is a great connector and a wealth of hard-won wisdom.

9. What is the most important room in your house, and why?

Thanks to Cyrstal Hurd for sharing this writing prompt from her creating writing class. It is one of those questions that translates well from writing to conversation, and can lead down many interesting hallways (so to speak!).

10. When in the last three days did you surprise yourself?

As with spectacular failures, good surprises are worth sharing and generate great conversation.

11. How would you do (fill in the blank) differently?

This is a good follow up question to either the failure or amazement questions, but it’s also very handy to keep on hand when someone on a work team vocalizes dissent from a current plan or project. The key with using it effectively in cases of dissent is to really mean it. If you don’t intend to weigh their insights seriously, don’t ask.

12. What should I ask you about (that I haven’t asked yet)?

My conspiratorial coach and friend Jen Roberts asked me this question after forty minutes into a coaching session. Before responding, I sat silent for at least thirty seconds, which can feel like an hour in a conversation. When I finally answered her question, what came out was energized, productive, and truly game-changing. Ask this question only after you have developed a strong base of trust and sense there is more to the story worth pursuing.

With any one of these questions, the response could very well warrant a follow-up “Tell me more about that” type of question. A good listener will be sensitive to when the teller has reached their “telling limit” or if there are further depths to plumb.

What are your surefire content-wooing questions?

Featured image courtesy of seier+seier licensed via Creative Commons.

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