All Blog Posts
Below are my current blog posts and a number of years of historical posts. Note: that the older posts are from a variety of sites, social networks, projects and consulting help I have provided over the years. I have leveraged AI to help make them very consistent to read, validate links and add some references and footnotes. I have worked to make sure that those unfamiliar with what we were dealing with at certain period can get a solid understanding of time. I have reread, updated and put a current point of view on as many as possible. I have enjoyed this exercise and having a change to revisit the journey I have been privileged to take.
Browse all my blog posts, organized by year. Click on a year to expand or collapse.
Big Models, Bigger Bills: Why Training LLMs Just Doesn’t Add Up for Most Enterprises
Summary: This August 2025 post unpacks the economic and practical realities behind training large language models (LLMs) inside traditional enterprises. It argues that most organizations lack the data, scale, and sustained value proposition to justify the cost of custom LLMs. Instead, companies are seeing better ROI with fine-tuned small models, hybrid AI stacks, and task-specific agents. The piece uses DeepSeek as a case study of smart trade-offs and introduces the concept of a "boutique AI renaissance" — a move away from size and toward smart, contextual AI.
More Than Words
Summary: July 2025 - This post challenges the LLM-centric view of AI, highlighting high-value, non-language AI systems that have been transforming industries for years. From financial trading algorithms and fraud detection engines to demand forecasting, drug discovery, and shipping optimization, these models prove that execution and accuracy often matter more than conversational prowess. The piece warns against letting hype overshadow practical, results-driven AI.
Feature Flags and the Illusion of Control
Summary: In May 2017, feature flags were all the rage in engineering circles. They promised flexible rollouts, safe experimentation, and faster deployment cycles. But as usage skyrocketed, many teams lost control. Flags multiplied, went undocumented, and stayed long past their usefulness. Bugs emerged that were impossible to trace. This post reflects on how smart teams learned to manage flag sprawl by auditing usage, assigning ownership, and building processes to clean up behind the magic.
18-Month Update: By late 2018, tools like LaunchDarkly and internal flag registries gained popularity. Organizations began treating feature flag management as a product discipline in itself.
2025 Insight: Today, responsible teams treat feature flags as temporary tools with a lifecycle. The rest still risk drowning in flag debt — or worse, shipping bugs only some users ever see.
The Great Reprioritization Spiral
Summary: In April 2017, many product teams found themselves trapped in endless cycles of reprioritization. Stakeholder demands, customer escalations, and market reactions constantly disrupted sprint plans. Agile was misinterpreted as permission to change direction at any time — often without consideration of tradeoffs. This post highlights how leading teams began reclaiming control by creating clear prioritization criteria, pushing back on low-value interruptions, and learning to say “Yes, but not n...
18-Month Update: By late 2018, some teams adopted clearer planning cadences and stronger guardrails against mid-cycle change. However, many still confused agility with responsiveness, undermining long-term progress.
2025 Insight: Today, prioritization discipline is seen as a core product management skill. Teams that treat every new request as urgent still struggle. The rest have learned that flexibility without structure is just chaos in disguise.
When Metrics Became the Mission
Summary: In March 2017, metrics dominated the conversation in product teams — sometimes for the worse. This post looks at how dashboards and KPIs, initially intended to inform better decisions, became the main objective instead. Teams started optimizing for numbers that looked good on paper but didn’t translate to meaningful outcomes. The result was product decisions driven by targets rather than user value. A few teams resisted the trend, balancing data with insight and asking whether metrics reflec...
18-Month Update: By late 2018, some orgs embraced North Star metrics and broader storytelling around KPIs. Others remained stuck in gamified dashboards, failing to connect numbers to actual impact.
2025 Insight: Today, more mature organizations use metrics with context — triangulating quantitative data with customer feedback and qualitative research. But the temptation to optimize for vanity metrics still exists, especially under executive pressure.
Everyone Was a Product Owner… and No One Owned the Product
Summary: In February 2017, companies were eager to embrace Agile roles — but not always the discipline behind them. This post looks at the muddled role of Product Owner during that period. Many teams had multiple people claiming the title, but no one truly owning outcomes. The result? Bloated backlogs, confused priorities, and feature bloat driven by committee decisions. A few teams broke the cycle by trusting a single empowered Product Owner to drive vision, prioritize ruthlessly, and communicate w...
18-Month Update: By mid-2018, some organizations started redefining product roles more clearly, especially those aligning with outcome-based delivery models. But many still clung to shared responsibility models that slowed decision-making.
2025 Insight: Today, the importance of having a clear, empowered product owner is well understood in high-performing teams. Organizations that still dilute the role often suffer from misalignment, delays, and poor customer outcomes.
The Roadmap Is Not the Strategy
Summary: In January 2017, product teams were full-speed ahead on building roadmaps — and mistaking them for actual strategy. This post explores how teams often substituted feature timelines for true prioritization. Strategy was frequently hidden behind vague corporate slides or buried in documents no one read. Some teams began pushing back, tying roadmap items to customer outcomes and framing tradeoffs instead of pretending they could do everything. It wasn’t always well-received — but it shifted the co...
18-Month Update: More teams started using OKRs and hypothesis-driven planning, tying roadmaps to outcome goals. Still, many large enterprises clung to fixed delivery models that favored predictability over learning.
2025 Insight: By now, the distinction between roadmap and strategy is more widely recognized — but not universally practiced. High-performing teams treat roadmaps as flexible expressions of strategic intent. The rest still confuse activity with impact.
Agile Theater: When the Ceremonies Replaced the Substance
Summary: In December 2016, Agile was everywhere in form but fading in spirit. This post explored how teams had turned agile ceremonies into a hollow performance: standups were status updates, retros were complaints, and planning focused more on estimation than user outcomes. Agile had become a checklist, not a mindset. A few brave teams stripped away the noise and focused on what really helped them deliver value — often at odds with the corporate definition of “doing Agile right.”
18-Month Update: By mid-2018, many teams began trimming or redefining rituals to suit their actual workflows. Async standups and outcome-driven planning became more common, though resistance persisted in compliance-heavy or rigidly scaled environments.
2025 Insight: Today, teams that succeed with agile often deviate significantly from textbook frameworks. They adapt ceremonies to their context, challenge bureaucracy, and measure success by outcomes — not adherence. Agile is no longer a theater script; it’s an evolving culture of learning and delivery.
Why “Outcomes Over Outputs” Was Harder Than It Sounded
Summary: By November 2016, “Outcomes over outputs” had become a corporate favorite. The phrase was everywhere — but rarely lived. This post explored why the shift was so difficult: output was easy to measure, outcomes weren’t. Teams were shipping features that didn’t solve problems, and metrics often focused on delivery speed rather than impact. A few bold teams began experimenting with user-centric KPIs and hypothesis-driven development, but most organizations struggled to balance impact with legacy fundi...
18-Month Update: Some progress emerged, especially in teams adopting OKRs tied to customer or business signals. But in most enterprises, output remained the default success metric — especially where funding and staffing were project-based.
2025 Insight: Today, outcome-driven product development is better understood, with teams aligning to customer behaviors and long-term goals. The best orgs track fewer metrics, but with more meaning. Still, many lag behind, using “outcomes” as theater while continuing to reward output.
The PMO Didn’t Die — It Just Changed Its Name
Summary: In October 2016, the PMO was undergoing a quiet identity crisis. Across organizations, “project” had become a dirty word, prompting rebrands to Delivery Office, Transformation Hub, and other euphemisms. But the traditional behaviors — stage gates, fixed budgets, top-down oversight — persisted beneath the surface. This post explored how some PMOs leaned into the shift by embracing agility, focusing on outcomes, and supporting teams as coaches rather than controllers.
18-Month Update: A growing number of organizations restructured their PMOs into Agile Portfolio Management functions. Some success was found, but many were still clinging to legacy funding models and rigid KPIs that undermined flexibility.
2025 Insight: Today’s strategic PMOs play a very different role: enabling flow, aligning investment to customer outcomes, and supporting decentralized decision-making. Those that failed to evolve have been replaced by Product Operations or embedded strategy teams within product lines.
When We All Became Product Owners (Sort Of)
Summary: In September 2016, teams across enterprises were grappling with unclear product ownership. The post described how, in the absence of a clear Product Owner, roles blurred and confusion reigned. Engineers, designers, and even Scrum Masters took on product decisions without the context, authority, or alignment needed to do so effectively. The piece argued that without one accountable voice, product leadership became a negotiation, not a direction. It made the case for explicit roles, transparent prioritization, and decision boundaries that enable real collaboration instead of chaos.
18-Month Update: By 2018, some organizations began restoring clarity to product roles by embracing dedicated triads — PM, Design, and Engineering leads — with clear responsibility splits. Proxy roles faded, and focus returned to having a single accountable owner for prioritization.
2025 Insight: Today, high-performing product teams balance shared ownership with clear decision rights. The product owner role is now better defined and rarely overlaps with delivery or design leadership. Teams that still distribute prioritization without structure tend to ship slower and miss customer signals.
Why So Many Standups Felt Like Sitdowns
Summary: This August 2016 post explored how daily standups became hollow rituals in many Agile teams. Updates were scripted, blockers were buried, and real conversations happened only after the meeting ended. The post explained how fear, not apathy, drove the silence — and how a lack of psychological safety turned valuable ceremonies into checklists. It celebrated teams that reimagined their standups as moments of honesty and collaboration, and it warned against confusing motion with meaning.
18-Month Update: By early 2018, some teams had started experimenting with alternative formats: async standups, walking meetings, and open-ended prompts. But many organizations still struggled to create environments where truth-telling felt safe, especially in cross-functional or high-pressure settings.
2025 Insight: In 2025, teams that thrive treat rituals like standups as flexible moments of connection, not fixed processes. Status updates have largely moved to async tools, freeing real-time conversations for what matters — surfacing friction, celebrating small wins, and asking better questions.
When Agile Was Just Theater
Summary: In July 2016, this post called out the performative Agile practices spreading across large enterprises. Teams were going through the motions — standups, retros, velocity tracking — but without the psychological safety, autonomy, or trust that true Agile requires. The piece explored how middle management, stuck between executive pressure and team reality, often undermined transformation efforts. It ended with a call to return to authenticity, user connection, and real cultural change.
18-Month Update: By early 2018, some organizations began to abandon surface-level Agile for deeper change: outcome-based roadmaps, dual-track discovery, and embedded research. The shift toward real cross-functional teams gained traction, though many still struggled to let go of waterfall metrics.
2025 Insight: In 2025, most mature enterprises acknowledge that Agile is about mindset and culture, not rituals. Top-performing teams prioritize user outcomes and adaptability over velocity charts. But in many organizations, a shadow Agile still lingers — all sprint, no soul.
When the Roadmaps Lied
Summary: This June 2016 post examined the widespread use of fixed, feature-driven roadmaps that promised certainty but delivered confusion and burnout. Teams were pressured into creating polished plans for executive approval, even when dependencies were unresolved and user needs unvalidated. The piece explored how some teams began shifting toward outcome-oriented roadmaps that prioritized learning, adaptability, and honest conversations over theater.
18-Month Update: By late 2017, the concept of outcome roadmaps gained traction. More product organizations embraced rolling planning models, roadmaps tied to user problems, and transparent updates. Leadership began accepting — even expecting — flexibility over fixed commitments.
2025 Insight: In 2025, outcome roadmaps are now common in mature product teams. Agile planning frameworks accommodate learning and change, and product leaders are rewarded for transparency rather than false predictability. But some lagging orgs still cling to the illusion of certainty — often at great cost.
The Outsourcing Hangover
Summary: This May 2016 post reflected on the moment enterprises realized the true cost of outsourcing wasn’t just in vendor invoices, but in lost capability and customer understanding. It described how over-reliance on external vendors led to slow delivery, opaque systems, and disengaged internal teams. The piece highlighted how some companies began reversing course — rebuilding internal teams and treating vendors as partners, not proxies.
18-Month Update: By late 2017, more enterprises embraced hybrid models, bringing strategic engineering functions in-house while shifting vendors toward commodity work. Product thinking began to shift from “who does it cheapest” to “who understands the user.”
2025 Insight: In 2025, leading organizations balance outsourcing with core ownership. Engineering, design, and data capabilities are viewed as differentiators — not overhead. Strategic vendors are embedded in teams, but internal talent sets the direction and owns the outcome.
The Innovation Antibodies Strike Again
Summary: This April 2016 post explored how large enterprises often suppress internal innovation through excessive governance, risk aversion, and entrenched processes. It told the story of a promising mobile app that was killed not by failure, but by an immune-system response of architecture reviews, compliance fears, and misaligned incentives — a pattern all too familiar in risk-averse organizations.
18-Month Update: By late 2017, forward-thinking companies began introducing innovation sandboxes and fast-track governance lanes to protect early-stage ideas. Embedding risk and compliance partners within teams became a recognized best practice to avoid blind-side rejections.
2025 Insight: Today, innovation in enterprise settings is treated as a collaborative process. Guardrails remain, but are adaptive, and support for change is built into the system. High-performing organizations structure themselves to learn quickly, not just operate safely.
When Projects Masqueraded as Products
Summary: This March 2016 post exposed the disconnect between product language and project behavior. While many teams rebranded their work as “products,” they retained fixed-scope, deadline-driven delivery models. It explored how the superficial shift failed to bring durable teams, outcome-based funding, or long-term accountability — and how only true structural change enabled real product value.
18-Month Update: By late 2017, leading organizations began to institutionalize product funding, long-lived cross-functional teams, and outcome-oriented metrics. Project management remained, but served product goals instead of controlling scope.
2025 Insight: Today, the product model has matured in many enterprises, with permanent teams tied to value streams and customer outcomes. While the language shift began in 2016, the cultural and structural transformation took years — and remains incomplete in lagging organizations.
When Architecture Became Accidental
Summary: This February 2016 post examined how many enterprises unknowingly fell into accidental architecture — systems that evolved through isolated decisions, firefighting, and lack of ownership. It highlighted the risk of local optimization without global coordination and made the case for reintroducing intentional, collaborative architectural practices within engineering and product teams.
18-Month Update: By 2017, architecture guilds and engineering councils began appearing in agile organizations to balance autonomy with coherence. Technical strategy reviews, tech radars, and platform KPIs gained traction as lightweight but effective architectural governance models.
2025 Insight: Today, in 2025, architecture is widely treated as a product. The best organizations invest in it continuously, with embedded architectural leadership and cross-team visibility. Accidental complexity is a known risk — and avoided with intent, documentation, and shared responsibility.
The Fallacy of One-Size-Fits-All Metrics
Summary: This January 2016 post explored the flawed practice of applying uniform metrics across all product teams in an enterprise. It showed how one-size-fits-all dashboards distorted performance evaluation, encouraged gaming, and discouraged mission-aligned goals. The piece advocated for outcome-driven, context-specific measurement tied to each team’s purpose and users.
18-Month Update: By mid-2017, more companies adopted outcome-based OKRs and moved away from velocity-based comparisons. Dashboards became more narrative-driven, and product leaders gained more autonomy in defining success with business partners.
2025 Insight: Today, in 2025, smart organizations embrace flexible performance frameworks. Teams define their own KPIs within a structured governance model, ensuring alignment without rigidity. Storytelling through data is prioritized over numeric comparisons, and context is non-negotiable.
Digital Isn’t a Department
Summary: This December 2015 post explored how many companies treated 'Digital' as a new department or lab instead of a business-wide mindset. Innovation teams were isolated, under-integrated, and often ignored by core functions. The post emphasized that real transformation only occurs when digital capabilities are embedded across the enterprise.
18-Month Update: By late 2016, organizations began dismantling digital silos, embedding product and digital leaders into business units, and aligning IT, UX, and business outcomes. Change management emerged as a critical success factor for digital efforts.
2025 Insight: In 2025, companies no longer isolate digital — they cultivate it. Digital fluency is expected across leadership, and successful transformations are measured by cultural adoption, not lab output. It's no longer about a digital team — it's about a digital company.
Agile Theater and the Death of Delivery
Summary: In November 2015, this post called out the rise of Agile Theater — a performative version of Agile where teams followed rituals without delivering value. Standups, velocity tracking, and story points became checkboxes, but real outcomes lagged. The post argued for a return to principle-driven delivery focused on actual user impact.
18-Month Update: By 2017, many companies introduced agile maturity models, shifted focus from velocity to business outcomes, and integrated product management practices to recenter delivery on value. Coaches became more outcome-oriented and less process-policing.
2025 Insight: In 2025, most organizations understand that agility is a mindset, not a set of ceremonies. Empowered teams, outcome-driven metrics, and continuous value delivery have replaced cargo-cult Agile — at least in the best-run companies.
Stop Calling Everything a Platform
Summary: This October 2015 post critiqued the overuse of the word 'platform' in enterprise tech. Many teams mislabeled basic services as platforms, leading to confusion, misaligned investments, and disappointing outcomes. The piece offered clear definitions and accountability models for true platform work.
18-Month Update: By late 2016, enterprise architecture teams began formalizing platform taxonomies and separating shared services from extensible platforms. Funding models began to reflect usage, adoption, and enablement metrics.
2025 Insight: By 2025, platform teams are held to higher standards: measurable internal adoption, clear APIs, and responsibility for enablement. Mislabeling is still common, but far more frequently challenged by informed leadership.
Why Compliance Doesn’t Have to Kill Agility
Summary: September 2015 called out the false dichotomy between regulatory compliance and agile development. The post made the case for automated controls, in-line documentation, and integrating compliance into the development process rather than treating it as an afterthought.
18-Month Update: By 2016, DevSecOps practices emerged that baked auditability into CI/CD workflows. Regulatory bodies began to accept modern documentation formats, provided traceability and accountability were maintained.
2025 Insight: In 2025, many regulated industries have fully embraced agile-compliant delivery. FDA and SOx audits regularly pass with CI/CD evidence, and real-time compliance dashboards are standard in enterprise platforms.
SaaS Sprawl and the Illusion of Simplicity
Summary: This August 2015 post examined how decentralized SaaS adoption created fragmentation, security risks, and operational overhead. The illusion of simplicity from plug-and-play SaaS quickly turned into complex integration and governance challenges.
18-Month Update: By late 2016, SaaS management platforms emerged to help consolidate billing, access, and risk oversight. Central IT began working with teams to curate approved tools without stifling innovation.
2025 Insight: By 2025, most enterprises maintain a hybrid SaaS model — combining freedom of choice with platform guardrails and data architecture governance. Tool sprawl is now measured and managed instead of ignored or banned.
When Governance Becomes a Cage
Summary: This post from June 2015 explored how well-intentioned governance models had become bureaucratic obstacles. Rules were followed without purpose, approvals were opaque, and innovation was stifled. Forward-thinking teams began to rethink governance as a tool for enablement, emphasizing principles, transparency, and risk-based thinking.
18-Month Update: By late 2016, several large organizations adopted agile governance models, leveraging automation and embedding compliance into development pipelines. Guardrails replaced gates, empowering teams to move faster while staying aligned with risk appetite.
2025 Insight: In 2025, the best enterprises treat governance as an enabler of innovation. Legacy structures that slow teams down are being phased out. Real-time observability, audit automation, and adaptive controls have become the new norm.
The Rise of Feature Teams (and the Fall of Accountability)
Summary: In May 2015, enterprises continued their shift to Agile feature teams — but often misunderstood what ownership really meant. While velocity increased, accountability fractured. This post explored how slicing teams by feature, rather than by problem ownership, led to poor UX, conflicting priorities, and low accountability.
18-Month Update: By 2016, some companies restructured into true product teams with full-stack ownership and autonomy. Others stuck with delivery-focused features teams and struggled with alignment.
2025 Insight: By 2025, most leading companies operate through durable product teams that own outcomes, not just stories. Feature teams, where they remain, are typically legacy patterns being phased out.
Why Everyone Misunderstood DevOps (and Still Might)
Summary: This post dissected the 2015 wave of DevOps adoption, where companies invested heavily in automation and CI/CD, but failed to shift the cultural behaviors that DevOps actually required. Teams adopted tools but not shared ownership, leading to friction, risk, and disappointment.
18-Month Update: By 2016, some enterprises began investing in DevOps coaching and SRE practices to bridge the cultural gap. Security was increasingly embedded earlier in the lifecycle, evolving into DevSecOps.
2025 Insight: In 2025, DevOps is no longer considered a special role or movement. It’s embedded into how high-functioning teams work — with shared accountability, automation, and collaboration as table stakes.
The Rise of Product Thinking in IT
Summary: In early 2013, a few forward-thinking IT teams began quietly abandoning the traditional project model. They weren’t following trends—they were reacting to real frustration: long timelines, brittle releases, and business teams who had stopped engaging. This post explored the early signs of “product thinking” in enterprise IT: stable teams, customer empathy, value delivery over requirements documentation, and roadmaps that were actually useful.
18-Month Update: By mid-2014, product roles were emerging in titles—Product Owner, Technical Product Manager—and the early wins were tangible. Teams aligned to outcomes, not output, and business partners reengaged.
2025 Insight: This shift is now foundational. Every modern IT team that delivers real business value uses product thinking. But in 2013, it was still a quiet rebellion.
The Year IT Finally Gets Out of Its Own Way
Summary: In early 2012, IT teams were still seen as the department of “no.” Long project queues, outdated architectures, and rigid processes left business teams frustrated and led to costly delays. This post made the case for transforming IT’s operating model from service provider to business partner — one that aligns to product thinking, accelerates value delivery, and gets out of the way of innovation.
18-Month Update: By mid-2013, some companies had begun experimenting with Agile and product teams. The tide was slowly turning, but traditional governance still dominated in most enterprises.
2025 Insight: This was the inflection point. Most Fortune 500 IT departments now operate in product-centric models, with agile principles and value stream alignment. But back in 2012, even saying “IT needs to get out of the way” felt radical.