Building a skeptic’s toolkit

  1. Communicate probabilistically. Tease out the assumptions buried under pronouncements. Instead of ‘This may not be the best idea’ it’s worth trying out ‘I’m 70% confident that a freemium model is the best way forward provided the underlying assumptions around the market size are valid. If however the market is much smaller, then your view may be the way to go. What do we know about the addressable market?’
  2. Announce the hand you’re going to play. Without priming, raising doubts can be seen as violating an unspoken social contract. Make explicit what you’re going to do before you do it. (‘These points seem well thought through. Let me do the necessary work of pushing back at a couple of places.’)
  3. Keep your mouth shut. This takes some self-restraint, especially for those who call it as they see it. Sometimes pointing out room for trivial improvement causes non-trivial erosion of motivation for the idea owner, which leads to poorer execution. Under such circumstances, staying silent is the best trade-off.
  4. Offer to help out however you can. Points 1–3 notwithstanding, just expressing skepticism may not suffice. You may be seen as a problem dumper. If danger was not on people’s minds, and now is thanks to you, they will appreciate your help (or sometimes not but you’ve to make the offer).

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Satyajit Rout

Satyajit Rout

I write about decision-making, mental models, and better thinking and things in between