May 2021

How to be insightful

Sam Knowles

An insight is a profound and useful understanding of a person, thing, situation or issue

Insights live in a context

A point in time

  • Insights are most valuable when they are new, and offer an advantage over competitors
  • The digital world is complex and fast moving, and therefore rich in potential insights

Prevailing assumptions

  • Many ideas are dismissed because they fall foul of an implicit assumption
  • e.g. “People won’t want electric cars because there is nowhere to charge them
Tesla supercharger

“What if we built our own charging network?”

Required scale

Family of related insights

  • One insight is rarely sufficient
  • Insights breed insights
  • Creativity, Inc. explains how DreamWorks strings together thousands of ideas, big and small

Insights can feel obvious in hindsight because our assumptions adapt without us noticing

  • When Drew Houston, the founder of Dropbox, was trying to raise money, he was told in meeting after meeting that the file sharing market was crowded with existing products
  • Investors didn’t understand Drew’s proposition because it was subtle, and it was easier for them to think in terms of their existing, assumed market knowledge
  • Drew eventually overcame this problem by using a video to explain his insight. Today Dropbox is a $10bn company
Thinking Fast and Slow by Daniel Kahneman

The mind is “a machine for jumping to conclusions” –

Thinking, Fast and Slow by Daniel Kahneman

The Lean Startup  by Eric Ries

Story of Dropbox founding –

 The Lean Startup by Eric Ries

Improve your chances of being insightful by nurturing your unconscious mind

In his 1951 book The Art of Clear Thinking, Rudolph Flesch identified half a dozen, unrelated fields in which similar, four-steps models of insightful thinking had been developed spontaneously

1. Sweat – Gather inputs

  • Ongoing, chronic curiosity
  • Talk to people, and take in the widest diversity of inputs from different cultures / perspectives / points of view
  • Immerse yourself in new places & experiences
  • Dig where your interests lie

2. Timeout – Let your unconscious mind work

  • Insight problems demand the focused application of subconscious processing. This means distracting the conscious mind
  • Try exercise, walking or doing boring tasks (like mowing the lawn, washing up, or ironing)
  • Work on something else

3. Eureka – Record ideas when they come to you

  • When insight strikes, it often does so at inconvenient times – during a dream or just when waking, when out running, or in the shower
  • Write down your ideas when they happen – keep pens and pads by the bed, recording apps on your phone, and waterproof crayons in the shower. Try Mem.

4. Prove – Test and iterate your idea

  • While it’s important that you can articulate your insight simply and clearly, don’t spend too much time making it perfect
  • Share your insights with colleagues and clients, and start road-testing as early as you feel happy to
  • The world is so complex that it’s impossible to have perfect insight. Winning companies are able to iterate and learn

Learn more

How To Be Insightful by Sam Knowles

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