VP of Devil’s Advocacy

It’s a little known secret that the best time to scour Tech Crunch for content that’s actually worth reading is during the weekend. There’s not a lot of “real tech news” going on during the weekend so you’re more likely to run into a thought-provoking post. I found this one about three weeks ago:

The VP of Devil’s Advocacy

Though I resent MG sinking as low as using quotes from a disappointing zombie movie as the “hook” for the story, the gist in compelling nonetheless: often times the biggest product catastrophes/flops seem almost “bound to happen” to the common man. At least in retrospect. Which then begs the question: how come these companies, with all the amazing resources at their disposal, keep making these mistakes?

Answers to this question often leads back to a dysfunctional decision-making process, stemming from very human pitfalls such as groupthink and being trapped in the wrong paradigm.

MG’s advocating for adopting similar lessons to the ones implemented by Israeli intelligence after the ’73 war and creating an official position of “VP of Devil’s Advocacy” – only if a product can withstand all the honest feedback and worst case scenarios prevented by this person – it is allowed to launch. This can also be tied to addressing Lencioni’s 2nd team dysfunction – fear of conflict – head on, by appointing a person responsible for creating (healthy) conflict.

But having someone in that role full time requires scale and organizational maturity that many companies don’t posses. The good news is that there are smaller structural investments that can be made in order to make the decision making process less error-prone on these fronts. A lighter-weight more commonly used variation of this concept is the formation of Red Teams. Red teams don’t necessarily have to exist on a permanent basis, they can be formed ad-hoc whenever a big decision with strategic significance needs to be made.

Do you have a good example of using a red-team-like structure in Tech effectively?


VP of Devil’s Advocacy

Goldilocks Management

Dustin Moskovitz and the folks at Asana have created some great pieces of thought leadership on org design which should merit a post on this blog. I want to spend this one on one of my favorites: 

Goldilocks Management

The gits: the traditional, hierarchical, command-and-control approach to management clearly doesn’t make a lot of sense in the modern work environment. But the allergic reaction of swinging the pendulum all the way to the other extreme and eliminating management altogether (a-la Valve Handbook) clearly doesn’t work either. Instead, Moskovitz proposes the following approach: aim to distribute decision-making authority as much as possible to the relevant domain experts. Management still plays two key roles: 

  • Backstop for all decisions – filling in the whitespace where decision authority is unclear 
  • Drive and guide employee’s personal growth through mentorship

What do you think: should the pendulum start swinging more in this direction? what’s still missing? 

Goldilocks Management