The 4 Biggest Execution Mistakes Founders Make

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Oct 20, 2025

Discover the four execution mistakes that could be sabotaging your startup. Learn how oversimplifying complex problems can lead to costly errors and why overcomplicating processes can kill momentum. Uncover the importance of categorizing issues correctly and the concept of 'necessary and sufficient' work. Explore how mistimed priorities can cause chaos, making it seem like you're doing everything but finishing nothing. Gain insights into developing the judgment and discipline needed to achieve effective execution.

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INSIGHT

Nuances Hide In Seemingly Similar Use Cases

Oversimplifying hides meaningful differences between similar use cases and leads to wrong features and models.
Dig into details to reveal distinctions and avoid conflating distinct customer needs.

ADVICE

Pick The Right Abstraction Level

Choose the right abstraction level so you neither treat every user as unique nor blob everything together.
Use taste and judgment to find a specific, generalizable category worth solving first.

ANECDOTE

The 'Going Out' Backlog Example

Chris uses the 'going out' backlog example to show how tasks differ by destination and goal.
He shows stepping from simple errands to fancy events creates easier adjacencies over time.

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Think you’re executing well? Think again. Chances are you’re making one of these four common mistakes.

Drawing from Chris’s latest essay and real-world advisory experience, Chris and Yaniv spend this episode breaking down the four biggest execution mistakes you're probably making right now. They explore how to recognize these patterns early, how to apply taste and judgment when scaling, and how to develop the discipline needed to execute with precision.

In this episode, you will:

Identify when you’re oversimplifying, and mistaking nuanced, unique use cases for the same problem
Understand how overcomplicating your product or process can destroy focus and momentum
Learn to categorize problems correctly using the principle of mutually exclusive, collectively exhaustive thinking
Apply the concept of “necessary and sufficient” work — doing everything that’s needed and nothing that’s not
Recognize that mistiming priorities ends in attempting to do everything at once, but finishing nothing
Develop the taste, judgment, and rigor to strike the perfect balance between simplicity and depth
Avoid falling into domain dogma; naming, structuring, and communicating ideas clearly for your team and customers

Read Chris’s original LinkedIn post: https://www.linkedin.com/posts/chrissaad_the-big-4-execution-mistakes-youre-probably-activity-7379681603847049216-ApcV

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