Articles
Long-form, in depth
Deeper reads on the problems I help companies work through, organized by the problem each one speaks to.
When should I hire a fractional CIO or CTO?
A fractional CIO or CTO is a part-time executive who owns the technology agenda when a full-time hire is more than the role needs. The signals it is time, which seat you actually need, and how the engagement runs.
Read the article →Why Your Engineering Team Is Underperforming and How to Fix It
When engineering delivery is slow or inconsistent, the problem is rarely the engineers. Here is how to diagnose what is actually happening and what to do about it.
Read the article →How to Prepare for a SOC 2 Audit Without Losing Six Months of Productivity
SOC 2 preparation does not have to derail your organization. Here is a practical approach to getting audit-ready without treating compliance as a full-time job.
Read the article →How to Build a Technology Roadmap That Actually Gets Used
Most technology roadmaps end up in a shared drive and never get referenced again. Here is what makes the difference between a roadmap that drives decisions and one that does not.
Read the article →Is Your Company Ready for AI: What to Check Before You Invest
Most companies are using AI before they are ready for it. Here is a practical framework for understanding where your organization actually stands and what needs to be in place before AI investment delivers real returns.
Read the article →The CEO Who Came Back from the Conference
Why AI strategy built without technology at the table produces expensive pilots that never reach production.
Read the article →Most AI projects do not fail for technical reasons
A large share of AI and data spending is being written off, and the reason is almost never the technology. Why the failures are leadership and organizational, and what a seasoned technology leader changes.
Read the article →How to Do a Technology Assessment for Your Business
A technology assessment gives your leadership team a clear, honest picture of your current technology environment. Here is what the process involves and what you should walk away with.
Read the article →Why systems go down, and what keeps them up
Most outages are not exotic failures. They are ordinary, preventable process problems. The engineering practices and business-continuity discipline that keep systems up.
Read the article →Why your technology spend is a black box, and whether you are overpaying
Large technology invoices that rise every year, with no clear answer on value. Most of what is hiding in there is technical debt, and how to get the black box open.
Read the article →When legacy systems hold the business back
The technology that got you here starts working against you at scale. Why big replacement programs fail and what incremental modernization that works looks like.
Read the article →Perspectives
Shorter takes, grouped by problem
Short, practical takes grouped by the problems they speak to. Each one links to a full page with the relevant outside reading.
Engineering delivery
Most engineering teams are not as productive as leadership thinks
One of the most consistent findings when I assess an organization is the gap between what an engineering team appears to deliver and what it is actually...
Read the perspective →Engineering culture is a leadership responsibility, not an HR one
The quality of an engineering culture, how decisions get made, how disagreement is handled, how failure is treated, how people are developed, is set by...
Read the perspective →Agile in name is not agile in practice
Most technology teams have adopted the vocabulary of agile.
Read the perspective →The engineering talent problem is also a retention problem
More than half of CIOs cite staffing and skills shortages as a primary obstacle to delivering on strategic priorities.
Read the perspective →DevOps maturity affects more than deployment speed
Organizations at the lower end of DevOps maturity spend a disproportionate amount of engineering time on manual processes, incident response, and coordi...
Read the perspective →Visibility and trust
The technology inventory most companies do not have
Ask most leadership teams what technology systems their organization runs and they will give you a partial answer.
Read the perspective →Technology due diligence is not just for acquirers
Companies that are preparing for a transaction, whether as a buyer or a seller, benefit from understanding their technology environment before anyone el...
Read the perspective →Legacy and modernization
What happens to your technology environment after an acquisition
The technology integration work after an acquisition is almost always underestimated.
Read the perspective →The systems that look fine from outside need the most attention
In my experience, the technology risks that cause the most damage are not the ones leadership is already worried about.
Read the perspective →Reliability and resilience
Reliability is a design problem, not bad luck
When systems keep going down, the natural instinct is to treat each outage as bad luck.
Read the perspective →What downtime actually costs
Reliability gets underfunded for a simple reason.
Read the perspective →If customers find your outages first, you have a detection gap
If you are finding out about your outages from customers, you have a detection problem sitting in front of your reliability problem.
Read the perspective →Security and compliance
Vendor risk is now your risk
Third-party breaches account for roughly 30 percent of all incidents, and the number is rising.
Read the perspective →HIPAA is not a one-time project
Organizations that treat HIPAA as a project with a start and end date tend to find themselves out of compliance within 18 months.
Read the perspective →Security is a business conversation, not an IT conversation
The companies that build strong security postures are the ones where security is treated as a business risk, not a technical concern.
Read the perspective →SOC 2 is becoming a sales requirement
Enterprise buyers and mid-market procurement teams increasingly require a current SOC 2 Type II report as part of vendor onboarding.
Read the perspective →The NIST framework is useful even if it is not required
NIST is often associated with federal contractors and regulated industries, but the framework is useful for any organization trying to build a structure...
Read the perspective →AI governance
The AI regulatory gap most companies have not noticed
State-level AI laws are moving faster than most small and mid-size companies realize.
Read the perspective →AI agents are coming whether you plan for them or not
Agentic AI, where software acts independently across systems without human supervision on each step, is arriving in enterprise environments faster than...
Read the perspective →Most small businesses are winging AI adoption
Most small businesses now use AI in some form, around 60 percent by the US Chamber's 2025 survey, but most are still in an exploration phase.
Read the perspective →Your data environment may not be ready for AI
The most common reason AI initiatives stall is not the tool and not the budget.
Read the perspective →The AI ROI conversation, and why CFOs are driving it
The window for AI experimentation without accountability is closing.
Read the perspective →Technology leadership
Leadership and org design
The first technology leadership hire is the most consequential
When a company hires its first CTO or senior technology leader, it is making a decision that will shape its technology organization for years.
Read the perspective →CIO versus CTO is a question of organizational need, not title
Many companies spend time debating whether they need a CIO or a CTO without a clear framework for the distinction.
Read the perspective →Promoting your best engineer into management is not always right
The best individual contributor on a technical team is not automatically the right person to lead it.
Read the perspective →The org chart and the actual decision-making structure differ
In most technology organizations, the formal reporting structure does not fully describe how decisions actually get made, where information flows, or wh...
Read the perspective →The structure that worked at 50 rarely works at 150
Technology organizations need to be redesigned as companies grow, not just expanded.
Read the perspective →Fractional leadership
An interim CIO is not the same as a fractional CIO
These two arrangements get used as if they mean the same thing, and they do not.
Read the perspective →When a fractional arrangement fails, it is usually a scope problem
When a fractional leadership engagement does not work out, the postmortem usually points at fit or chemistry.
Read the perspective →Mid-market is the right fit for fractional leadership
The fractional model is not a fit for every company, and pretending otherwise is how engagements go wrong.
Read the perspective →The board perspective on fractional leadership is changing
For a long time, a technology gap at the executive level was treated as an operational inconvenience, something IT would sort out.
Read the perspective →A fractional arrangement can reduce the cost of a permanent hire
A fractional CIO or CTO is usually framed as a way to defer the cost of a full-time hire.
Read the perspective →Technology roadmap and strategy
Technology strategy and business strategy are not the same
One of the most persistent problems in technology leadership is the disconnect between what the technology team is building toward and what the business...
Read the perspective →The roadmap is not the strategy
A technology roadmap is a tool for communicating and executing strategy, not the strategy itself.
Read the perspective →Stakeholder buy-in is a delivery risk
Roadmaps fail in execution more often than they fail in design.
Read the perspective →Shorter horizons outperform long-range plans
The organizations that execute technology roadmaps most reliably are not the ones with the most detailed long-range plans.
Read the perspective →The hardest roadmap question is what you are not going to do
Most technology roadmaps are too long.
Read the perspective →Follow for more
Short takes on technology leadership posted regularly on LinkedIn.