Don't Repeat Yourself (Leadership)

Encode your feedback, taste, and standards into prompts so AI can push your judgment to the edges

Dan Shipper
The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code.

Don't Repeat Yourself (Leadership)

"It's really stunning how much of your job is just repeating yourself. And that is one of the best things about this AI revolution—you don't have to repeat yourself." - Dan Shipper

What It Is

Don't Repeat Yourself (DRY) for Leadership is the practice of encoding your recurring feedback, standards, and taste into AI prompts so that others can access your judgment without needing to speak with you directly. It's the leadership version of the programming principle—but instead of avoiding duplicated code, you're avoiding duplicated explanations.

Leaders, especially founders and CEOs, spend enormous amounts of time giving the same feedback repeatedly: "Here's how to write a good headline," "Here's what our brand voice sounds like," "Here's how I think about this type of decision." By capturing this feedback in prompts that others can use, you push your taste and judgment to the edges of the organization without being the bottleneck.

How It Works

The framework operates in a continuous cycle:

1. Notice the repetition Every time you catch yourself saying the same thing in different contexts, flag it. These repetitive explanations are candidates for encoding.

2. Record and codify Work with someone (an AI Ops person, or do it yourself) to turn that feedback into a prompt. The prompt should replicate what you would say if someone asked you to review their work.

3. Deploy to the team Make the prompt accessible—in a shared repository, a slash command, a custom GPT, wherever your team works. Train people to use it before coming to you.

4. Iterate based on output The prompt won't be perfect initially. Review outputs, identify gaps, and refine the prompt to better capture your standards.

At Every, Dan set a quarterly goal: "I don't want to ever say the same thing in a meeting twice." The editorial team now uses prompts that encode his feedback on headlines, intros, and story structure. Writers "talk to" a simulation of Dan's taste before their work ever reaches him.

How to Apply It

  1. Set the goal explicitly - Tell your team (and yourself) that you want to stop repeating yourself. Make it a conscious objective.

  2. Start with high-leverage repetition - What do you say most often? Brand voice? Quality standards? Strategic frameworks? Start there.

  3. Use recordings - When you give feedback, record it. Have someone transcribe and turn it into a prompt. Dan's team member made a year of progress in two months by recording every feedback session.

  4. Deploy through existing workflows - The prompt should meet people where they work. A Claude Code slash command, a custom GPT in the tools they already use.

  5. Accept approximation - The prompt won't perfectly mimic you. It doesn't need to. It just needs to get 80% of the feedback done so you can focus on the 20% that truly needs your attention.

When to Use It

  • When you notice yourself giving the same feedback repeatedly
  • When you're a bottleneck for quality reviews
  • When scaling a team but wanting to maintain standards
  • When onboarding new people who need to learn your preferences
  • When you want to create leverage without hiring more people

Source

  • Guest: Dan Shipper
  • Episode: "The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code."
  • Key Discussion: (00:24:26) - Dan discusses setting "don't repeat yourself" as a quarterly goal
  • YouTube: Watch on YouTube

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