A Spoonful of Healthy Skepticism

Celine Wee
3 min readJul 29, 2023

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“Just a spoonful of sugar helps the medicine go down
In a most delightful way”

- Mary Poppins “A Spoonful of Sugar

I’ve been struck recently by how spoonful of healthy skepticism is necessary and valuable, especially in how a listener reviews a pitch/claim/assertion. I’ll dive into it by:

1/ Comparing two types of reactions to a claim/pitch assertion

2/ Defining what a Spoonful of Healthy Skepticism means

3/ Explaining the costs of NOT having a Spoonful of Healthy Skepticism

Photo by Ana Municio on Unsplash

Comparing two types of reactions to a claim/pitch/assertion

Here’s how to read the table below.

  • In column (A), you’ll see an example of a pitch, claim, or assertion.
  • Then let your eyes move right, to the next two columns (B) and (C), where you’ll see two different responses. Column B is for a “green/inexperienced” listener, and column C represents a “seasoned/experienced” listener. A listener could, for example, be someone in product, engineering, partnerships etc.
An imaginary conversation.

Energy and enthusiasm (as demonstrated by the listener column B) is appreciated. Expressing praise over something delightful is an enjoyable human experience. But there’s immense value in being the seasoned/experienced listener in column (C), and asking a few more questions to understand the claim/pitch/assertion better.

Defining what a Spoonful of Healthy Skepticism means

For the seasoned/experienced listener in column (C) a spoonful of healthy skepticism means:

  • Humble curiosity, which leads to asking more questions because of a desire to learn more.
  • Detail orientation, which leads to seeking the details, even if it is complex and challenging.
  • Execution focused, which means thinking ahead to how to implement the pitch/claim/assertion, rather than hoping for the best and punting the problem to later. It means getting clarity on timelines, so as to ensure it’s baked into the execution.

I’ve anecdotally observed that the best (and usually more experienced, seasoned, thoughtful) product and engineering folks I’ve worked with listen supportively, BUT also dig deep (like with the questions provided in the table above) to understand and pressure test claims.

Caveat: what a Spoonful of Healthy Skepticism does NOT mean

  • Cynicism and despair: It does not assume every claim is false.
  • Personal: It is not directed to make the speaker feel small. It’s focused on the content, not person.
  • Pedantic: It is not so overly detailed, that it overwhelms the conversation, asks for irrelevant data, and fails to grasp the big picture.

That’s why I recommend a SPOONFUL of healthy skepticism at claims, not utter disbelief in everything, and an excessive focus on the detail.

Explaining the costs

In the context of finding the right partner to develop a product, the primary cost of not having a “Spoonful of Healthy Skepticism” is that one will fail to deliver on the best product for your customers. In the yellow section if the table, you’ll see some potential negative consequences.

Hypothetical examples

It sounds harsh, but energy and enthusiasm cannot compensate for missing features, inflated metrics, or caveats discovered late in a pitch/claim/assertion. All the energy in the world cannot make a product pitch that does not exist come to life.

A spoonful of skepticism is needed in all of life, listening to ALL claims (news, google search results, chatgpt answers, church sermons, politician speeches...the list goes on). Stay energetic, and be a listener with a spoonful of skepticism. It’ll lead to more delightful outcomes.

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Celine Wee
Celine Wee

Written by Celine Wee

Opinions are my own: a collection of Go To Market, Payments, Biz Ops learnings across Stripe, Coinbase, Twitter. I also write @celinewee.substack.com

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