I’ll be honest. Some weeks, I feel like I’m keeping up with AI. Most weeks, I feel like AI is keeping up with me — and winning. AI actually stresses me out that I need to walk away… many times. 😂 

These past few months have been a lot. I launched my Inc. column, updated both books for 2026, and have been deep in Copilot training with enterprise teams who bought all the licenses and are now wondering why nobody is actually using them. 

I’ve also experienced the tokenomics problem firsthand. The more we automate, the more we spend. The more we spend, the more we have to think about which AI does what, at what cost, and whether the ROI actually closes. It’s a full-time job on top of the full-time job. Ugh!

The lesson I keep coming back to: AI doesn’t simplify your work until you do the hard thinking and planning first. The tools are the easy part. The strategy, the workflows, the measurement — that’s where most teams are still stuck., me included. 

That’s what this issue is about. Grab your coffee.

Everything in here is built around one idea: helping you stay ahead without having to figure it all out on your own. Copilot ROI, AI tools worth your time, what’s changing with costs, and what I’m seeing work with real teams right now. Read it, save it, share it with your team.

There’s something useful here for wherever you are in your AI journey.

If you still have questions, just hit reply. Let’s talk!

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Copilot in the Real World: What to Use, What to Measure, and How to Prove It

 

You Already Pay for Copilot. Here Is When Claude Is Worth Adding

Copilot vs. Claude — or both? Most sales and marketing teams don’t need a second AI subscription on top of the one they’re already paying for. But there are specific situations where Claude earns its place. In this post, I break down the key architectural difference between the two tools and exactly when adding Claude makes sense — including a token limitation most reviews skip entirely.

Read more here.

How to Measure ROI from Microsoft Copilot Training (And What to Track in the First 90 Days)

Most organizations measure Copilot ROI by looking at seat activation rates and calling it adoption. That number tells you almost nothing. In this post, I lay out a 90-day measurement framework — starting before training begins — that tracks time savings by role, output quality, and active usage, and shows you how to present the results to finance in a way that actually lands.

Read more here.

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I’m Now Writing for Inc. Magazine

I recently joined Inc. as a columnist, and my first ten pieces are live.

The topics are ones I care about deeply and talk about constantly — why most executives are still AI-curious instead of AI-fluent, what companies get wrong when they cut headcount for AI and then scramble to rehire, why your AI bill is quietly becoming an unmanaged operating cost, and what the FIFA World Cup of all things, can teach us about marketing that actually works.

I’m also writing about the bigger picture — the pressure marketing leaders are under right now, and why the most important AI skill of the next five years has nothing to do with prompting.

These are the conversations I’m having with clients every week. Now I’m having them in a bigger room.

Follow my column on Inc. here.

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Copilot Cowork Is Live. Here’s What Your Team Needs to Know.

Copilot finally got skills. Now I’m complaining about the price tag. 😂

For months, I told clients that Copilot had nothing like Claude’s skill features. Then Copilot Cowork went GA in mid-June — and now you can set up projects and build skill.md files the same way you would in Claude.

I should be thrilled. Instead, I have a new complaint.

• Setup is not a solo project. 
• And usage is not free. Cowork runs on Copilot Credits at $0.01 per credit.
• My honest take: if you’re a light user, pay-as-you-go is fine. If you’re running medium and heavy tasks constantly, do the math before assuming Copilot is cheaper than a flat-rate plan like Claude Max.

Read the full breakdown on LinkedIn.

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The Modern AI Marketer Series — 3rd Edition Is Live

Two years ago, AI for marketers meant getting better at prompting. Today it means something bigger — workflows, automation, rethinking how your entire team operates. I’ve lived that shift, and these books reflect everything I’ve learned along the way, including what didn’t work.

The two books are designed as a pair. One gives you the strategy and the thinking framework — how AI has matured, where it fits in your org, and how to scale it without chaos. The other is pure execution — 95+ tested B2B prompt templates ready to use today, with dedicated chapters on Claude and Microsoft Copilot.

Think of it this way: one book is the map. The other is the toolkit you keep open while you work.

Whether you’re trying to get more out of the tools you already have, or just finding your footing with AI — there’s something here for you.

Learn more about both books here.

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Copilot Tips and Tricks

Most enterprise teams barely use their Microsoft Copilot licenses despite the investment. The problem isn’t the technology — it’s a lack of proper training on practical application. Here are three tips to get more out of it:

1. Practice Prompts During Training, Not After

Watching a Copilot demo is not the same as learning to use it. The single biggest predictor of 90-day adoption is whether employees actually wrote and iterated on prompts during training — not just watched someone else do it. If your team is doing self-directed learning, build in hands-on practice time. Passive learning doesn’t stick.

2. Start Your ROI Measurement Before Training Begins

Most teams try to measure Copilot ROI after the fact — and end up with nothing to show for it. Pick two to three high-frequency tasks per role, track how long they take before training, and repeat the measurement at 30, 60, and 90 days after. A simple spreadsheet is enough. No baseline means no proof.

3. Know When Copilot Ends, and Claude Begins

If you need cell-level citations on financial models, airtight PowerPoint template compliance, or live data from platforms like PitchBook or FactSet — that’s Claude’s territory, not Copilot’s. Most teams don’t need both. But knowing exactly where Copilot hits its ceiling saves you from blaming the wrong tool.

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4 AI Tools to Boost Your Productivity This Month

The AI tool landscape moves fast, and I test many tools so you don’t have to. Here’s what’s actually earning its place in my stack right now.

Fireflies.ai — Joins your Zoom, Teams, and Google Meet calls automatically, transcribes everything, and pulls out action items, decisions, and key moments. If you’re still taking manual notes in meetings, this one will change your week immediately.

Runway — An AI video generation and editing suite that produces professional-quality short-form video from text prompts and image inputs. Client demand for video is relentless; Runway lets small teams deliver it without adding headcount or budget.

Perplexity — An AI-powered search engine that gives you direct, sourced answers instead of a list of links to sort through. For competitive research, market trends, and fast background checks before a client meeting, it beats traditional search hands down.

ElevenLabs — Generates realistic AI voiceovers in minutes, with 300+ voices and support for multiple languages and accents. Perfect for marketers producing video content, product demos, or localized campaigns without the time or budget for voice actors.

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Where I’ll Be in 2026 (So Far)

If I’m in your city, let’s connect!

• 10/5 SMASH, Las Vegas, NC – End of Sales and Marketing Tug of War
• 10/6-10/7 Content Marketing World, Denver, CO – Building an Actionable Marketing Plan and Content Marketing GTM Workshop
• 10/8 NexThink Global Field Marketing, Orlando, FL – AI Workshop
• 10/28 -10/29 ShowPro 2026, Chicago, IL – Practical AEO Strategies for Modern Marketers
• 11/4 B2B Forum, Boston, MA – Marketing Planning & Strategy
• 9/16/27 MarketingProfs Webinar – Messaging and Positioning Know-How

If you’re planning an event, workshop, or training session, let’s talk:

📩 hello@pamdidner.com

What AI workflows are you trying to build right now? Hit reply and let me know – I’d love to hear what you’re working on!

Until next time, keep experimenting, stay authentic… and have FUN!