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.


Questions about Quora

Quora is one of my favorite products on the internet.  So many times, learning new things is the product of asking the right questions – and Quora is a crowdsourced repository of really interesting questions and answers, from the tactical (e.g., what is a cool / useful skill that only takes five minutes to learn?), to the philosophical (e.g., “How can one make the most of one’s youth?“). The vast majority of the times I visit the site, I emerge 30+ minutes later, having clicked through so many related questions that I’m multiple degrees of separation from the initial topic (very much like Youtube’s related videos).  Most other people I talk to who have used Quora are also similarly impressed by how addicting and high quality the content is.

However, one common observation I’ve heard (and experienced) is that, despite really enjoying the product, people don’t find themselves headed to the site of their own accord very often (note: based off my own small sample size) .  I typically visit Quora only when I receive their weekly digest email (which, by the way, is incredibly well targeted).  I’ve done a bit of thinking as to why, and the answer I’ve arrived at dovetails well with two questions we commonly ask startups:

  1. What “job” is your product helping a consumer complete?
  2. What alternatives will your product displace and why?

I think Quora struggles to answer these two questions, largely because there are so many alternative ways to acquire knowledge and wisdom (from in person conversations, books, articles, podcasts, etc.).  For the first question, while Quora might answer with “Getting smarter”, this is such a diffuse need, with so many alternatives that it’s hard to create a strong association in a user’s mind for a particular goal.  Without that association, building and retaining a network of users that come back regularly of their own accord is a challenging task (part of the reason why focus is so valuable for a company).

These challenges are not unique to Quora – on the surface, Facebook had a very similar set of difficulties to overcome.  However, Facebook was an incredibly low-friction, reliable way to complete an emotional “job” – feeling connected to your friends and community.  Going to the site was much easier than texting, calling, or arranging time to meet up with that broad circle of people, and required significantly less commitment (and cognitive load, vs. Myspace) than the alternatives. In Quora’s case, it’s not clear that going to the product is much easier than cracking open a book (nowadays, opening your Kindle app), reading an article on Pocket, Feedly, or clicking on link from your timeline. Quora finds itself competing for time and mindshare with all of these alternatives, without an immediately clear advantage. And so, even for Quora-lovers like myself, I don’t think to use the product, even in cases where it might be relevant.

Though the questions seem basic, I think companies should devote the time to developing a clear answer to each – it’s often the simple things that are deadly.

Reach out with your thoughts – would love to hear other perspectives on Quora and the framework above.