For seasoned PMs
Levelling Up in the AI Era
You've shipped products, managed roadmaps, and navigated org politics. These insights are for the next level — leading with strategy, staying relevant as AI reshapes the craft, and making decisions that actually move the business.
“ Ask yourself: if you were the CEO of this company, would you fully fund your own team? Frankly, most people I ask that question to don't know the answer right away.
Why it matters: The low-impact PM death spiral starts innocuously — small features, cosmetic improvements — until the next round of layoffs. Aligning every team goal to no more than one step from company goals is the antidote.
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Matt LeMay
Author, Product Management in Practice · Impact First Product Teams
The one question that saves product careers
“ There are three levels of product work: impact, execution, and optics. Most team conflict comes from people operating at different levels without realising it.
Why it matters: When a PM is optimizing for optics (looking good in reviews) and an engineer is optimizing for execution (shipping cleanly), they'll clash — not because they're wrong, but because they're playing different games. Naming the level changes everything.
strategy team dynamics leadership
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Shreyas Doshi
Former PM Leader, Stripe · Twitter · Google
4 questions Shreyas Doshi wishes he'd asked himself sooner
“ Most execution problems are really strategy problems in disguise. When teams can't ship, look upstream — the strategy probably isn't clear enough to make decisions from.
Why it matters: It's tempting to fix execution with more process. But if people don't understand *why* they're building what they're building, no amount of standup cadence or project management tooling will save you.
strategy execution diagnosis
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Shreyas Doshi
Former PM Leader, Stripe · Twitter · Google
4 questions Shreyas Doshi wishes he'd asked himself sooner
“ There was a perception that some people were intrinsically good at strategy and others weren't — as if there was a strategy gene. The answer is: anyone can build great product strategy through a clear, repeatable process.
Why it matters: Strategy isn't a talent, it's a skill. Chandra's process — starting with why people don't understand what you're building, then working backwards to a written strategy — turned Headspace's product around and led to his promotion to CPO.
strategy leadership frameworks
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Chandra Janakiraman
CPO, VRChat · ex-Meta, Headspace, Zynga, Amazon
An operator's guide to product strategy
“ The AI models you're using today are the worst AI models you will ever use for the rest of your life. If you're building something that barely works right now, keep going — in two months, the models will make it sing.
Why it matters: The biggest mistake experienced PMs make with AI is evaluating product ideas against current model capabilities. The right question is: will this be magical when models improve? If yes, build it now.
AI product strategy building
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Kevin Weil
CPO, OpenAI · ex-Instagram, Twitter
OpenAI's CPO on how AI changes must-have skills, moats, and startup playbooks
“ Product strategy should delight customers in hard-to-copy, margin-enhancing ways. If your strategy could be copied by a well-funded competitor next quarter, it's not a strategy — it's a feature.
Why it matters: Gibson Biddle's DHM framework from Netflix cuts through strategic vagueness. A good strategy has all three: customer delight, a competitive moat, and a business model that gets stronger over time.
strategy frameworks moat
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Gibson Biddle
Former VP Product, Netflix · Chegg
DHM product strategy framework and 5 Netflix case studies
“ If you aren't prototyping with AI to build the thing you want to build, you're doing it wrong. NLX — natural language experience — is the new UX.
Why it matters: The CPO of Microsoft's productivity suite argues that PMs who aren't personally building with AI tools are losing the ability to shape what they're asking engineers to build. Taste requires hands-on experience.
AI prototyping product craft
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Aparna Chennapragada
CPO, Microsoft · ex-Robinhood, Google
Microsoft CPO: If you aren't prototyping with AI, you're doing it wrong
“ Influence is the skill AI can't replace. If you don't have the buy-in and backing of your key stakeholders, you can't build great products — no matter how good the idea.
Why it matters: As AI handles more of the tactical PM work, the uniquely human edge becomes the ability to build trust, align organizations, and move people. The PMs who invest in influence now will be the ones who thrive.
influence AI era leadership
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Jessica Fain
VP Product, Webflow · ex-Slack
The art of influence: The single most important skill AI can't replace