Gabriel Weinberg: Using Mental Models To Make Better Decisions – The Learning Leader Show With Ryan Hawk

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Key Takeaways

  • Great leaders share these 3 traits:
    • They’re open to growing and learning
    • They help everyone around them succeed in their role
    • They make sure their team is working on great ideas/projects
  • Advice for the workplace:
    • When beginning a new project, first answer the following questions:
      • What is the objective of the project?
      • What is the success criteria?
      • What are we trying to solve?
    • Create a post-mortem report for every project (ones that fail AND ones that succeed) – ask your team:
      • What went well?
      • What didn’t go well?
      • Given those things, what can we do better next time?
  • Be careful about trusting your intuition – very often you have have a few biases you’re not immediately aware of
  • Career advice:
    • Either go really deep into a single discipline that’s in demand or combine two different disciplines (i.e., become someone who’s really knowledgeable about finance and also really good at public speaking)
    • If you have a particular set of skills that the market really desires, you can demand a better salary or more benefits

Intro

  • Gabriel Weinberg (@yegg) is the CEO & Founder of DuckDuckGo, an internet privacy company that empowers you to seamlessly take control of your personal information online, without any tradeoffs
    • Check out the Podcast Notes from Gabriel’s appearance on The Knowledge Project

Books Mentioned

Commonalities of Excellent Leaders

  • Great leaders share these 3 traits:
    • They’re open to growing and learning
    • They help everyone around them succeed in their role
    • They make sure their team is working on great ideas/projects
  • Gabriel follows “The North Star” model
    • It’s a metaphor for the DuckDuckGo’s mission statement
      • Everything you do in your company should be moving you towards your North Star

About DuckDuckGo

  • Gabriel is the CEO of DuckDuckGo – an internet privacy company that provides traffic blockers, encryption, and private search
    • Gabriel started the company in 2008 as private search engine
      • Search engines are one of the most personal services on the internet – people frequently type in their financial, medical, and life problems

Gabriel’s Book: Super Thinking

  • Mental models are concepts used for general decision making
    • They’re essentially shortcuts for higher-level thinking
  • Mid to higher tier managers need to be good decision makers, so Gabriel created a list of mental models and shared them internally with DuckDuckGo employees
    • This list eventually turned into the book
  • Gabriel co-wrote the book with his wife
    • It took about 2 years of intense writing to get done
  • One popular mental model – thinking in first principles
    • Break things down to the most basic assumptions and then build up a train of thought from the fundamentals
      • Elon Musk is a big proponent of this one

Advice For the Workplace

  • On Projects:
    • When working on a project, Gabriel has his team write down/answer:
      • What is the objective of the project?
      • What is the success criteria?
      • What are we trying to solve?
    • Everyone should agree with the above before moving forward
  • Instead of making a pro/con list, make a cost/benefit list
    • Write down all the costs and benefits for the activity – this allows you to easily see the profit or loss over time
  • Create a post-mortem report for every project (ones that fail AND ones that succeed)
    • This creates a feedback loop of critical thinking – ask your team:
      • What went well?
      • What didn’t go well?
      • Given those things, what can we do better next time?
    • Why is it rare to do a “success autopsy?”
      • No one wants extra meetings, especially after things went well – you have to build the autopsy process into the culture

The Hiring Process at DuckDuckGo

  • Since DuckDuckGo is very distributed and gives its workers lots of autonomy, the company looks for people who are self-starters
    • Employees must also:
      • Question assumptions
      • Communicate well
      • Give people the benefit of the doubt
        • As an example, some text messages may be interpreted in a negative tone – assume it’s a neutral or positive tone
      • Have an experimental mindset and validate direction
        • Run experiments if you have a hunch and then analyze your findings
      • Build trust
        • DuckDuckGo is very transparent and widespread, trust is a must when working remotely
    • To test if applicants have these traits, Gabriel gives them a paid project to complete, allowing him to get a feel for how they work and the way they think through problems

Can you trust your gut?

  • You can’t always trust your gut intuition
    • Why? – People have biases that they might not be aware of. This includes:
      • The availability bias (you may not remember all the options you have)
      • The confirmation bias (If you’ve already made a decision in a certain direction, you’re much more likely to make decisions that push you towards that same direction)
  • Instead – use your intuition as a hypothesis generator (don’t fully commit to any decision)
    • Gabriel calls this “thinking gray” – Delay decisions until they absolutely must be made
    • Jeff Bezos thinks of decisions as doors
      • Go through the door you think is right, but if it turns out to be wrong – just reverse course, head back, and go through another door

Additional Notes

  • Flex your market power muscles
    • If you have a particular set of skills that the market really desires, you can demand a better salary or more benefits
  • Either go really deep into a single discipline that’s in demand or combine two different disciplines (i.e., become someone who’s really knowledgeable about finance and also really good at public speaking)
  • The fastest way to build trust is through vulnerability
    • Being vulnerable and honest speeds up the process of building a trusting environment
  • To get better at a skill, you need deliberate practice. Here’s how to accelerate your learning:
    • Work at the edge of your comfort zone
    • Hire a coach who can give you feedback
    • Create a board of advisors
    • Check your thinking and explain it (by talking or through writing)
  • Writing is the best form of thinking critically
    • You can easily see if your argument is logical or full of holes
  • Find the highest leverage points in life – where the least amount of work is doing the most positive impact
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