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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100 ways of solving a problem

Part of my daily routine is to listen to podcasts – when I’m walking to lunch, or in transit without a seat, I usually open up Stitcher and load up my podcast list.  At the top of that list nowadays is Stanford’s Entrepreneurial Thought Leaders series.  If you’re interested in starting your own business, or in high tech startups more generally, this podcast is a must listen.  Every week or so, this program brings in either a successful founder, executive, or investor in high tech related businesses to spend an hour sharing their story, lessons learned, and answer questions; guests have ranged from Ben Horowitz of Opsware and Andreesen Horowitz fame, through to Sal Khan of Khan Academy.

While ETL is a treasure trove of interesting lessons, one of the most interesting exercises was the idea of generating 100 ways to solve a problem, featured in Tina Seelig’s talk. What’s so brilliant about this is that it forces a deep understanding of both the problem, the mechanisms that cause it, and all of the levers one might pull to create change.  All of the simple answers and platitudes (which likely haven’t been implemented for a good reason), melt away in the face of the sheer volume and depth required to generate 100 different solutions.  This approach also forces orthogonal thinking, which leads to the kinds of disruptive innovations we all chase (along with many bad ideas).  The exercise achieves many of the same ends as Google’s 10x philosophy  – avoiding incrementalism, and being willing to reimagine the entire thing from the ground up, but provides a system to help spark the necessary frame of mind.  Definitely something I want to store away for future use.

Any other ETL listeners out there?  Would love to hear your thoughts on your favorite episodes.  If not, let me know what some of your favorite problem solving techniques are.