AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt)
AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt)How to get better answers from AI, avoid common prompt-engineering myths, and keep your AI tools safe from bad actors
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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:
Some takeaways:
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 In this episode, we cover: (00:00) Introduction to Sander Schulhoff (04:56) The importance of prompt engineering (09:01) Two modes for thinking about prompt engineering (12:02) Few-shot prompting (17:30) Prompting techniques to avoid (24:52) Decomposition (28:26) Self-criticism and context (40:29) Ensembling (45:59) Thought generation (48:23) Conversational vs. product-focused prompt engineering (51:56) Introduction to prompt injection and red teaming (53:37) AI red teaming competitions (55:23) The growing importance of AI security (01:03:39) Techniques to bypass AI safeguards (01:06:17) Challenges in AI security and future outlook (01:09:31) Common defenses to prompt injection that don't actually work (01:13:18) Defenses that do work (01:16:33) Misalignment and AI's potential risks (01:19:29) Are LLMs behaving maliciously? (01:26:05) Final thoughts and lightning round 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/ 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 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed. You're currently a free subscriber to Lenny's Newsletter. 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