Asking good questions

As I mentioned my recent post about Quora, I believe a lot of value is created by asking really good questions. It’s a skillset that’s not only core to my work as a VC, but one I think is important in nearly all facets of life, both personal and professional. In that spirit, I thought I would share David Jackson’s (CEO of Seeking Alpha, who maintains an excellent blog) post about how to generate them (excerpt below):

Step 1: Find a white board or flip chart where your team can do its question-centric work. (For what it’s worth, standing up seems to jumpstart better questions than sitting down.)

Step 2: Pick a problem that your team cares about intellectually and emotionally. Double check to make sure that the problem (or opportunity, for the optimists of the world) is one that you honestly don’t have an answer to.

Step 3: Question everything. Engage in pure question talk, with one team member writing down each question verbatim. This gives everyone the chance (especially introverts) to see each question, reflect a bit, and then create even better ones. Don’t give preambles to the questions and don’t devote any time or energy to answering them. Just ask as many questions as you can. Go for at least 50, perhaps 75. But don’t give up when your mind goes blank around question 35. Savor the momentary dead space and continue the search for even better, more provocative questions, which will come with patience and persistence. It usually takes 10 to 20 minutes to exhaust a group’s questioning capacity. Push for exhaustion.

Step 4: Decide which questions on your list seem most “catalytic,” or which ones hold the most potential for disrupting the status quo. Focus on a few questions that your team honestly can’t answer but is ready and willing to investigate. Winnow your questions down to three or four that truly matter.

Given its importance, continually improving on what questions I ask and how is something that I’m constantly working on. Tweet at me @ablordesays if you’ve found other interesting ways (or relevant resources) to generate good ones.

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