Blue Sky Insights

04-Aug-2026: AI Agents may have an important second-order effect: accelerating democratized workflow automation by getting organizations to rethink work that has remained unchanged for years.

28-Jul-2026: The bigger AI opportunity may be moving from personal AI that improves individual productivity to structural AI that redesigns how teams work together.

09-Jun-2026: AI makes building easier than ever, but judgment has not become easier with it. Are we sometimes confusing reduced friction with reduced complexity?

12-May-2026: At SaaSiest, the AI conversation had shifted from why AI matters to how leading SaaS companies are redesigning their operating models - but the gap is widening.

03-Mar-2026: My take: AI is changing the build-vs-buy equation, but building software isn’t the same as building enduring SaaS. The bar for SaaS isn’t disappearing - it is getting higher.

03-Feb-2026: Most organizations are good at evolutionary change. But realizing AI’s bigger potential requires something more revolutionary - redesigning work, not just optimizing it.

21-Oct-2025: Forget the magic prompt and the perfect incantation. Working well with AI is more science than wizardry - experiment, adjust, learn, and build the right system around it.

09-Sep-2025: AI is evolving so fast that the “middle of the pack” may not be a safe place to be. With a technology this transformative, average adoption could quietly become falling behind.

28-Aug-2025: AI is changing what “lean” can mean for startups - compressing the cost and speed of experimentation, and challenging old assumptions about how we build, fund and govern innovation.

01-Sep-2026: AI may be changing more than how we build software. It may be changing the very assumptions that shaped today's product organizations in the first place.

23-Jun-2026: AI may do more than make individual roles more productive. As disciplinary boundaries become easier to cross, it could enable smaller, broader teams organized around outcomes rather than specialist handoffs.

15-May-2026: As AI accelerates execution, leadership needs to shift from directing work to shaping the context, systems and judgment that keep teams focused on the right outcomes.

07-Oct-2025: AI can amplify product decision-making - but only if there is something solid to amplify. Opinion-driven workflows accelerate noise; data-driven ones accelerate learning.

16-Sep-2025: What if AI could take more of the routine complexity out of software development - and leave engineers more time to do the epic sh.t that actually needs them?

26-Aug-2025: Conversations with leading SaaS teams reinforced what I am seeing: AI may be shrinking the two-pizza team to 3–4 people - requiring broader skills, fewer handoffs and making every seat count.

24-Mar-2026: Early-stage AI products rarely have enough user data. The advantage comes from finding representative real-world scenarios and turning them into learning loops before the data arrives.

17-Mar-2026: Inconsistent LLM outputs are often an architecture problem, not a model problem. Designing instruction and context in layers makes AI features easier to debug, maintain and scale.

25-Nov-2025: How do you build an AI that doesn’t just answer correctly, but feels right? A practical look at the two kinds of evaluation I used when testing Work2gether AI coaching models.

18-Nov-2025: Foundational models are evolving too fast to hardwire your product to one of them. A model-agnostic architecture makes it easier to experiment, switch models and keep pace as the landscape changes.

12-Aug-2025: LLMs aren’t deterministic software, so testing them needs a different playbook. Think acceptable ranges, golden sets, guardrails and iteration - not exact outputs.

08-Sep-2026: An experiment in formalizing discovery, design and build handoffs for multi-specialist teams - and an honest look at where the process held up, and where it didn't.

11-Aug-2026: Before adding agentic AI, most organizations should be asking a different question first - and it's not about the tooling.

19-May-2026: Building an Obsidian AI plugin in a weekend made me realize just how dramatically AI has reduced the distance between curiosity, learning and a working result.

16-Jun-2026: Using AI to turn process discussions into Mermaid diagrams makes them easier to review, refine and share - with a short video showing how.

28-Apr-2026: What happened when we added AI to an existing QA workflow? It reinforced why the best place to start may be deciding what should not be AI at all.

11-Nov-2025: Think it’s too late to start documenting? I experimented with using AI to reconstruct product documentation directly from source code - with surprisingly useful results.

20-Aug-2026: Part two of the FDE thread: the simple test I would apply before scaling it, and why the test only passes if you build for it.

18-Aug-2026: A closer look at where FDE actually diverges from the empowered engineering teams I've spent my career building - and what that reveals about ownership.

02-Jun-2026: The strongest Product, Engineering and GTM organizations don’t just build faster - they operate as one learning system, turning insights into better decisions together.

04-Nov-2025: Balancing today’s core, tomorrow’s growth and the longer-term future is one of product leadership’s hardest trade-offs. I find that The Three Horizons model helps make those choices visible.

07-Apr-2026: Good product principles are often simple. Executing them in a real SaaS business means navigating customers, revenue, incentives and timing - and where the hard work really begins.

28-Oct-2025: Scaling SaaS can feel a lot like flying an airplane: takeoff, turbulence, then hopefully cruising altitude. The trick is knowing which stage you are in - before someone starts serving snacks during takeoff.

30-Sep-2025: When Product, Engineering and GTM pull in different directions, chaos compounds. Shared strategy, ruthless prioritization and a clear operating rhythm can make growth compound instead.

02-Sep-2025: Scaling B2B SaaS is not just about adding people and moving faster. It is about building the right disciplines to turn fragile growth - bigger teams, roadmaps and burn - into resilient growth.

19-Aug-2025: As SaaS companies scale, the founder can shift from greatest asset to biggest bottleneck. The challenge is moving from founder-led to founder-inspired - without losing the vision that got you there.

23-Sep-2025: Agile was never an excuse for poor documentation. Done right, documentation helps decisions and knowledge scale - and becomes even more valuable when AI can act on it.

15-Sep-2026: A reflection inspired by Microsoft's Scott Hanselman's analogy between AI coding agents and open source collaboration - and what it might mean for collaborative product & engineering teams.

14-Oct-2025: What if resilient organizations should look more like Olympic rings than dominoes? A simple metaphor for why overlapping skills and responsibilities may matter more than ever in the age of AI.

21-Apr-2026: Execution Debt builds quietly as friction accumulates in decisions, ownership and alignment. What looks like a normal scaling problem may actually be that debt starting to accrue interest.

17-Feb-2026: “Who do I refer to now?” is a common question after a re-org. But the real confusion may not be reporting lines - it is where ownership and decision authority actually live.

27-Jan-2026: Empowered teams don’t just need autonomy and accountability - they need focus. Without clear priorities and trade-offs, ownership can easily turn into diffusion.

17-Jun-2025: Giving teams more freedom is only half the equation. Without clear accountability, autonomy can quickly turn into friction, confusion and eroding trust.

19-Jun-2025: High-performing teams aren’t built by hiring more heroes. They are built by creating the conditions where people can collaborate, perform and succeed together.

27-May-2025: Great collaboration doesn’t happen automatically when teams become distributed. Trust, engagement and performance across locations need to be designed for - and led differently.