Building a skeptic’s toolkit

Satyajit Rout
6 min readDec 24, 2021


At some point in my job, I started functioning in two modes.

This surfaced some years ago when I was helping incubate a new business unit. I would happily hear out ideas from the team I was managing. I would encourage people to chip in and try and decentralize idea generation as much as possible. Many in my team were young designers, illustrators, and content creators, and few ideas would be put to bed without being entertained first. We would talk often about and run small experiments, be it how to hack voice-overs or how to short-circuit the animation process.

Elsewhere, I assumed a different role. I tended to be skeptical of suggestions coming from my superiors, at times even when I wasn’t directly involved. It could have been a change management initiative, a restructuring exercise, or other strategic decisions. I would look for holes in the argument first. I would question the evidence, or ask for more. I was the doubter in the room.

Why did I switch between being open-minded and skeptical around the two groups?

I don’t have a clear answer but this is my best guess.

I thought it was my job to play those twin roles in the company of said groups. Around a young team, I needed to be receptive first and foremost and help build their confidence, before gently nudging them in the right direction. And the results were promising. The reduction in emotional friction helped push out intellectual and ownership inertia.

Around leadership, my thinking was, Here’s a seasoned bunch that doesn’t need confidence-building. What they need is for someone to shine light on any blind spots so that it helps make the plan better.

I assumed my superiors knew the role I was playing and gave me sanction for it, explicitly or not. I did not bother to check this assumption. It is only with time that I got a sense that my hold-a-mirror approach was not working as I thought. Annual feedback suggested this. It was only much later when I sought out my ex-boss for an honest appraisal that the role-dichotomy penny dropped for me. He conveyed that sometimes I bore the impression of being a contrarian (he used the word ‘activist’). We went on to discuss why that may have been.

Upon reflection, these are my suggestions for 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).

On the side of open-mindedness too, with experience it has dawned on me that not all ideas are equal. Once the price of admission for an idea drops below a threshold, people get lazy. It is important to develop good filtration skills to quickly separate possible signal from noise, else we may simply feel good about being open-minded but little of that will translate into tangible progress.

Getting the labels right

While these are lessons I hope to assimilate, there’s an important detail in nomenclature that needs airing, without which it is possible — and I’ve seen it happen — to mis-diagnose the problem. It is one of mis-labeling. Think of it as a child saying she’s sad when she may feel rejected or embarrassed. And the mis-labeling I’m talking about is this: the opposite of open-minded is not skeptical.

It is easy, almost intuitive, to think that the two modes of skepticism and open-mindedness are in direct contrast to each other. That if you’re not one, you’re automatically the other. But to my understanding that is not the case. They are on two separate gradients. It is not uncommon to mix up the two, notably to start on one and end up on another.

Consider a spectrum that captures willingness to consider. At one end is unwillingness to consider ideas (close-minded), and at the other is willingness to consider ideas (open-minded). Consideration is not outright acceptance or dismissal. The tension that exists between two people on this spectrum is reflective of the difference in their willingness to consider. The greater the difference the stronger the tension. This is not to say anything about the validity of their reasons. Someone with prior bad experiences or with deep social conditioning may be closed to consideration of the same prospect. Think about how avowed non-smokers react to smoking.

Now consider another spectrum, defined by a willingness to accept. At one end is an unwillingness to accept ideas without evidence (skepticism), and at the other is willingness to accept ideas without evidence (gullibility). Acceptance (or lack of it) of an idea signals a deeper investment than merely tossing an idea in the head. It is natural, to those with an independent mindset, to question what they are told. What drives them to clarity is evidence. Be that as it may, we’re all sometimes guilty of gullibility — of treating reputation, rank, or relationship as proxy for evidence.

Neither of the two spectrums have anything to do with belief per se. They are indicative of stages in thinking pre belief formation. It is possible for someone to start out tolerant of an idea (being open-minded) and then conduct a process of inquiry (being skeptical) before they are convinced enough to accept or reject it (forming a belief).


Seeing claims as falsifiable and questioning them is healthy. Otherwise we would fall prey to conspiracy theories all the time. Making a judgment to form a belief is not a problem. Making a judgement before we have looked at the evidence is. In Carl Sagan’s words, we are then guilty of prejudice.

But to stop ourselves here is only a job half done. We need to develop specific skills to communicate what we see to others constructively. These skills make up a skeptic’s toolkit. With my personal struggles as a parable, lacking the toolkit to weigh the merit of new ideas communally is likely to trip us up. It may trick us into questioning skepticism itself when what we need is a better delivery mechanism for it.



Satyajit Rout

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