Comparing LLM Outputs

Sander Schulhoff is the OG prompt engineer. He created the very first prompt engineering guide on the internet (two months before ChatGPT’s release) and recently wrote the most comprehensive study of prompt engineering ever conducted (co-authored with OpenAI, Microsoft, Google, Princeton, and Stanford), analyzing over 1,500 academic papers and covering more than 200 prompting techniques. He also partners with OpenAI to run what was the first and is the largest AI red teaming competition, HackAPrompt, which helps discover the most state-of-the-art prompt injection techniques (i.e. ways to get LLMS to do things it shouldn’t). Sander teaches AI red teaming on Maven, advises AI companies on security, and has educated millions of people on the most state-of-the-art prompt engineering techniques.

In this episode, you’ll learn:

1. The 5 most effective prompt engineering techniques

2. Why “role prompting” and threatening the AI no longer works—and what to do instead

3. The two types of prompt engineering: conversational and product/system prompts

4. A primer on prompt injection and AI red teaming—including real jailbreak tactics that are still fooling top models

5. Why AI agents and robots will be the next major security threat

6. How to get started in AI red teaming and prompt engineering

7. Practical defense to put in place for your AI products

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Brought to you by:

Eppo—Run reliable, impactful experiments

Stripe—Helping companies of all sizes grow revenue

Vanta—Automate compliance. Simplify security

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Where to find Sander Schulhoff:

• X: https://x.com/sanderschulhoff

• LinkedIn: https://www.linkedin.com/in/sander-schulhoff/

• Website: https://sanderschulhoff.com/

• AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC

• Free Lightning Lesson “How to Secure Your AI System” on 6/24: https://bit.ly/4ld9vZL

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Introduction to Sander Schulhoff

(04:29) The importance of prompt engineering

(06:30) Real-world applications and examples

(10:54) Basic prompt engineering techniques

(23:46) Advanced prompt engineering techniques

(29:00) The role of context and additional information

(39:24) Ensembling techniques and thought generation

(49:48) Conversational techniques for better results

(50:46) Introduction to prompt injection

(52:27) AI red teaming and competitions

(54:23) The growing importance of AI security

(01:02:45) Techniques to bypass AI safeguards

(01:05:21) Challenges in AI security and future outlook

(01:18:33) Misalignment and AI's potential risks

(01:25:03) Final thoughts and lightning round

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Referenced:

• Reid Hoffman’s tweet about using AI agents: https://x.com/reidhoffman/status/1930416063616884822

• AI Engineer World’s Fair: https://www.ai.engineer/

• What Is Artificial Social Intelligence?: https://learnprompting.org/blog/asi

• Devin: https://devin.ai/

• Cursor: https://www.cursor.com/

• Inside Devin: The world’s first autonomous AI engineer that’s set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• Granola: https://www.granola.ai/

• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika

• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons

• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad

• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch

• Technique #3: Examples in Prompts: From Zero-Shot to Few-Shot: https://learnprompting.org/docs/basics/few_shot?srsltid=AfmBOor2owyGXtzJZ8n0fJVCctM7UPZgZmH-mBuxRW4t9-kkaMd3LJVv

• The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0

• State-of-the-Art Prompting for AI Agents | Y Combinator: https://www.youtube.com/watch?v=DL82mGde6wo

• Use XML tags to structure your prompts: https://docs.anthropic.com/en/docs/build-with-claude/prompt-engineering/use-xml-tags

• Role Prompting: https://learnprompting.org/docs/basics/roles?srsltid=AfmBOor2jcxJQvWBZyFa030Qt0fIIov3hSiWvI9VFyjO-Qp478EPJIU7

• Is Role Prompting Effective?: https://learnprompting.org/blog/role_prompting?srsltid=AfmBOooiiyLD-0CsCYZ4m3SDhYOmtTyaTzeDo0FvK_i1x1gLM8MJS-Sn

• Introduction to Decomposition Prompting Techniques: https://learnprompting.org/docs/advanced/decomposition/introduction?srsltid=AfmBOoojJmTQgBlmSlGYQ8kl-JPpVUlLKkL4YcFGS5u54JyeumUwlcBI

• LLM Self-Evaluation: https://learnprompting.org/docs/reliability/lm_self_eval

• Philip Resnik on X: https://x.com/psresnik

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• Introduction to Ensembling Prompting: https://learnprompting.org/docs/advanced/ensembling/introduction?srsltid=AfmBOooGSyqsrjnEbXSYoKpG0ZlpT278NHQA6Fd8gMvNTJlWu7-qEYzh

• Random forest: https://en.wikipedia.org/wiki/Random_forest

• Chain-of-Thought Prompting: https://learnprompting.org/docs/intermediate/chain_of_thought?srsltid=AfmBOoqwE7SXlluy2sx_QY_VOKduyBplWtIWKEJaD6FkJW3TqeKPSJfx

• Prompt Injecting: https://learnprompting.org/docs/prompt_hacking/injection?srsltid=AfmBOoqGgqbfXStrD6vlw5jy8HhEaESgGo2e57jyWL8lkZKktt_P6Zvn

• Announcing HackAPrompt 2.0: The World’s Largest AI Red-Teaming Hackathon: https://learnprompting.org/blog/announce-hackaprompt-2?srsltid=AfmBOopXKsHxy4aUtsvPCUtEu7x74NCAEnlTIdNzo7nfMDVwZ9ilTlkp

• Infant with rare, incurable disease is first to successfully receive personalized gene therapy treatment: https://www.nih.gov/news-events/news-releases/infant-rare-incurable-disease-first-successfully-receive-personalized-gene-therapy-treatment

• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan

• Copilot: https://copilot.microsoft.com/chats/rcxhzvKgZvz8ajUrKdBtX

• GitHub Copilot: https://github.com/features/copilot

• Defensive Measures: https://learnprompting.org/docs/prompt_hacking/defensive_measures/introduction

• Sam Altman on X: https://x.com/sama

• Three Laws of Robotics: https://en.wikipedia.org/wiki/Three_Laws_of_Robotics

• Anthropic’s new AI model turns to blackmail when engineers try to take it offline: https://techcrunch.com/2025/05/22/anthropics-new-ai-model-turns-to-blackmail-when-engineers-try-to-take-it-offline/

• Palisade Research: https://palisaderesearch.org/

• When AI Thinks It Will Lose, It Sometimes Cheats, Study Finds: https://time.com/7259395/ai-chess-cheating-palisade-research/

• A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html

• 1883 on Paramount+: https://www.paramountplus.com/shows/1883/

• Black Mirror on Netflix: https://www.netflix.com/title/70264888

• Daylight Computer: https://daylightcomputer.com/

• Theodore Roosevelt’s quote: https://www.goodreads.com/quotes/622252-i-wish-to-preach-not-the-doctrine-of-ignoble-ease

• HackAPrompt 2.0: https://www.hackaprompt.com/

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Recommended books:

• Ender’s Game: https://www.amazon.com/Enders-Ender-Quintet-Orson-Scott/dp/0812550706

• The River of Doubt: Theodore Roosevelt’s Darkest Journey: https://www.amazon.com/River-Doubt-Theodore-Roosevelts-Darkest/dp/0767913736

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

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