Are you questioning your operating assumptions enough?


I have a hunch that one the key ways to maximize the probability of startup success is periodic and consistent questioning of operating assumptions.[1] For example:
  • What are the premises that underlie your vision/mission/strategy/etc.?
  • Are these premises still valid?
  • How valid are they?
  • How will you further validate them?
  • Are all underling assumptions fully enumerated?
  • Is current thinking on these assumptions in-line with your current vision/strategy/tactics/etc.?
Of the many wannabee and first-timer entrepreneur symptoms, a lot of them can be cured by periodically and consistently answering these hard questions.[2] It helps you steer your heat seeking missile towards success.
The trouble is that it is very hard to fully ask and answer these questions solely among the executive team. There are many reasons for this but paramount among them is that it is just simply hard to escape the thinking of day to day operations.

I personally seek this higher-level analysis through conversations (sometimes one-way) with users, critics, journalists, investors, mentors, family (mainly my wife), team members and peers. It doesn't always flow naturally, however. I have to work at it, including acknowledging piercing questions in plain sight when the natural response is to ignore them or rationalize them away through cognitive dissonance.

Perhaps the best advice though, especially for first-timers is to find a good mentor. The more I mentor/actively invest, the more I think my role is to ask these hard questions.

P.S. I haven't been blogging a lot because I'm putting all that extra time (it's not much, but it is some!) into finally getting out Traction Book.

[1] One of the tricky things about analyzing startup success in general is there are really no necessary or sufficient conditions. You can always point to counter-examples. So I rather like to focus on more probabilistic thinking on how to maximize your likelihood of success. That said, this hunch and my general approach are probably products of my analytical personality and so take everything I say from that perspective.

[2] For the opposite viewpoint of the top entrepreneurs check out the recent article by Aileen Lee analyzing trends of The Unicorn Club, tech startups with billion dollar valuations. If you read it, also check out Fred Wilson's response. These articles got me thinking about startup success because the first one talks about ingredients that often make up these startup unicorns, e.g. # of co-founders, their backgrounds, ages, etc. I couldn't help to start thinking about the underlying mechanisms and how a lot of these ingredients (experienced founders, technical backgrounds, etc.) are all probably highly correlated with critical thinking and an established processes to enumerate and question assumptions.


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I'm the Founder & CEO of DuckDuckGo, the search engine that doesn't track you. I'm also the co-author of Traction, the book that helps you get customer growth. More about me.