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  • You Ask, I Answer: AI as Critical Thinking Crutch?

    August 19, 2026

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    AI, Education, Leadership, Management, Professional Development, Videos

    Summary In today's episode, I unpack why junior employees lean on AI as a crutch and how leaders can stop that pattern from eroding their critical thinking skills. Here's what this means for you. You'll discover that the root causes usually sit in stressful, psychologically unsafe workplaces rather than in individual laziness. You'll also learn…

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  • Agentic AI Chat Trap: Why GPT-5, Claude 5, and Gemini Skip Questions (And How to Fix It)

    August 18, 2026

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    Christopher S Penn

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    AI, Artificial Intelligence, Generative AI, Google, LinkedOut, Marketing automation, Productivity, Public Relations, Technology

    “Ask me up to 20 clarifying questions until you have enough information to succeed at the task.” I have been advising folks for years to tell AI to ask it questions, but I’ve noticed something in the most recent generation of models – any model that’s tuned for agentic AI specifically really needs a kick…

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  • You Ask, I Answer: Does AI Devalue Agency Services?

    August 18, 2026

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    agencies, AI, Client Service, search engine optimization, Strategy, Videos

    Summary In today's episode, I tackle an SEO agency owner's question about whether using AI to automate 78% of their client deliverables devalues their services in the eyes of clients. Here's what this means for you. You'll discover that your clients already know about and likely use AI themselves, meaning your survival depends entirely on…

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  • AI Detectors and the Hidden Cost of False Accusations: Why Students Can’t Risk It

    August 17, 2026

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    Christopher S Penn

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    AI, Artificial Intelligence, Email Marketing, Generative AI, LinkedOut, Marketing, Public Relations, Technology

    Pangram, the AI that powers the new Substack AI validation system, is proud of its 0.02% false positive rate. Let’s frame that appropriately. First, call it what it is: a false accusation rate. In any situation that matters (not Substacks, but things like students being kicked out of school for academic dishonesty, professors losing tenure,…

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  • You Ask, I Answer: AI Tools for Messy Notes to Slides?

    August 17, 2026

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    AI, Generative AI, Presentations, Productivity, Videos

    Summary In today's episode, I answer Rachel's question about the best AI tool for turning messy notes into readable PowerPoint slides. Here's what this means for you. You can accomplish this without buying extra software by using capable agentic AI tools, provided you first establish design standards, information architecture frameworks, and a storytelling structure. You'll…

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  • Almost Timely News: 🗞️ How To Expand and Improve Content with AI, Part 1 (2026-08-16)

    August 16, 2026

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    Christopher S Penn

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    AI, Almost Timely, Artificial Intelligence, Generative AI

    _Almost Timely News: 🗞️ How To Expand and Improve Content with AI, Part 1 (2026-08-16) :: View in Browser_ The Big Plug I’m doing a free Ask Me Anything on August 18 at noon Eastern time – register to tune in live and bring your "I want to pick your brain for a few minutes"…

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  • Hero or Villain: How Positive Messaging Wins Audiences

    August 14, 2026

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    Christopher S Penn

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    AI, Artificial Intelligence, LinkedOut, Public Relations

    Compare these two sets of messages. Positive: You belong You are welcome here You are one of us You are not to blame You are part of the solution You are one of the good guys You are an equal You have a voice Negative: You do not belong here You are not welcome here…

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  • So What? How to Automate Content Transformation

    August 14, 2026

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    AI, Content, Generative AI, Marketing Technology, Podcasting, Videos

    Summary In today's episode, I walk through automating content transformation by cleaning up an old podcast archive with hundreds of broken links and dead sponsors using agentic AI tools. Here's what this means for you. You'll get a repeatable blueprint for turning messy legacy content into clean, monetizable assets without spending your life on manual…

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  • You Ask, I Answer: Drawing the Line on AI Review?

    August 14, 2026

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    AI, Artificial Intelligence, Brand, Marketing, Videos

    Summary In today's episode, I explain how to decide where to draw the line for human review in AI marketing tasks based on risk levels. Here's what this means for you. You'll calibrate your review process to match the consequences of each AI output so you scale low-risk work without exposing your brand to high-risk…

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  • AI Automation Accelerates: How One Year of Breakthroughs Is Reshaping the Future of Work

    August 13, 2026

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    Christopher S Penn

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    AI, Artificial Intelligence, Economy, Generative AI, Google, LinkedOut, Public Relations, Review, Speaking

    What a difference a year makes. I was putting together slides for a private workshop I’m doing today, and for fun I decided to take a snapshot of Humanity’s Last Exam results from a year ago and from today. That was eye-opening. In a year’s time, what was described as one of the most difficult…

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  • So What? What’s New with the LinkedIn Algorithm?October 1, 2026
  • How to Make AI Truly Creative: Leverage Cross-Domain Data for Breakthrough IdeasSeptember 30, 2026

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Christopher S. Penn – Marketing AI Keynote Speaker

Practical, engineering-grade AI strategy for enterprise audiences. No hype, just results.

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