Why "Bigger Questions"

Elevating strategic advantage by reading about smarter questions, not just newsletter answers

Apr 27, 2025 - 21:40
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Why "Bigger Questions"

In my new Product Coalition series, I surface under-explored strategic challenges, enlist advanced AI to generate multi-angle responses, and then expose both the questions and the answers to rigorous, public critique.

In a market where AI can replicate conventional “how-to” content in seconds, advantage now belongs to those who frame the sharpest questions. The outcome is a disciplined framework for second-order thinking—exactly the level of analysis the board expects but seldom receives.

I recognise that collective intelligence reliably outperforms individual expertise. By fusing AI breadth with the diverse experience of our global membership, I minimise blind spots, uncover hidden risks, and spotlight opportunities earlier in the decision cycle. Each edition becomes a living, auditable record of how senior product leaders refine their strategic enquiry.

Subscribe for direct access to this iterative process, benchmark your own assumptions, and keep your organisation ahead of fast-moving market dynamics.

Newsletters alone are not enough

  • Broader pattern-recognition. AI canvasses vast datasets and current research in seconds, so you see signals emerging across industries, not just one person’s niche.

  • Bias buffering. My public critique plus community feedback exposes blind spots early. You get a “cleaned” insight stream instead of one writer’s mental model.

  • Question-first framing. Each edition starts with a hard, under-asked question. That upstream focus clarifies strategy and avoids the rabbit holes of tactics-only content.

  • Transparent thinking trail. Every step; the prompt, the AI output, the critique—is visible. You can audit the logic, reuse the prompts, and adapt the framework inside your own organisation.

  • Faster learning loop. Collective input turns weekly issues into living documents that improve with each iteration, so insight compounds rather than expiring after one read.

  • Actionable artefacts. You leave each issue with refined questions, ready-to-use prompts, and a checklist of pitfalls—all immediately deployable in road-mapping sessions or board decks.

  • Time leverage. Instead of trawling half a dozen newsletters for viewpoints, you get a curated synthesis—saving hours while raising the quality of decision-making fodder.

Why it’s worth a paid subscription

  • Strategic ROI, not storytelling. You’re buying the questions that unlock new revenue levers and de-risk million-pound bets. Far cheaper than a consulting sprint or a missed quarter.

  • My track record, your shortcut. Twenty years steering nine-figure e-commerce P&Ls means I know which questions move the margin needle and which are board-meeting noise. I do the filtering; you keep the upside.

  • Numbers over noise. Each edition includes metrics, prompts, and ready-to-use checklists you can drop straight into roadmap reviews—saving your team hours and sharpening executive confidence.

  • Collective intelligence, expertly curated. I harness AI breadth and a 700k-strong product community, then stress-test the output with commercial rigour. You get bias-buffered insights without drowning in chatter.

  • Ongoing advantage. Subscription funds the deep work that some generic newsletters skip. The questions improve every cycle, compounding value well beyond the cover price.

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