Strategic IT Governance

Jayson Hahn

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MANAGEMENT

Most companies spend millions on technology they cannot clearly explain, defend, or govern. Strategic IT Governance delivers decision-grade clarity on IT spend, risk, and ROI for CEOs, CFOs, and operators who own the outcome, not just the budget.

6D AGO

Cloud Didn’t Save You Money. It Duplicated Your Cost.

Send a text Cloud migration was sold as an efficiency play. For many leadership teams, it became a duplication of cost. If your cloud bill went up last quarter and the explanation focused on “usage” instead of economics, this isn’t a spike. It’s an ownership gap. This video is for business leaders who approve technology spend and are expected to explain results when margins tighten. We address the structural reasons cloud spend drifts: The myth of “stable” usage Why data center exit plans fail to reduce fixed cost The data exit tax built into architecture How overprovisioned “safety buffers” become permanent margin erosion The risk isn’t the bill. It’s not knowing why it exists at that level.

10 min
FEB 5

The AI Governance Gap: Why Your Strategy is a Fiduciary Risk

Send us a text Most enterprise AI pilots are "credibility theater" that mask significant model drift and autonomous risk. This briefing exposes the gap between technical spectacle and financial ROI, providing the three mandatory questions boards must ask to protect their personal economic liability.

6 min
JAN 29

The Backup Trap: Why Your Business is Still at Risk

Send us a text Does your executive team have the illusion of protection? If you’ve sat in a post-incident board review, watching your IT lead explain why systems are still dark despite “successful” backups, this is for you. Most leadership teams approve "DR" spend without ever defining "Recovery". In this video, Jayson Hahn (former Global CIO with 18+ years of experience managing $150M+ budgets) exposes the hidden gap between having your data and having a functional business. In this session, we cover: The Lifeboat System: A single governing analogy for BCP layers: Cargo (Backups), Twin-Engines (High Availability), and the Lifeboat (Disaster Recovery). The Laptop Test: A micro-case explaining why "perfect backups" fail when there is no environment left to restore to. Fiduciary Audit: Four board-grade questions you must ask on Monday to expose unpriced risk in your recovery strategy. Executive Summary: Business Continuity Planning (BCP) is not about traditional ROI, it is about the ability of your company to survive an incident.

5 min
JAN 22

Why AI Investments Fail (The Process-First Architecture)

Send us a text The AI Balance Sheet Liability Most AI investments are currently tracked as innovation assets, but without structural "plumbing," they rapidly become balance sheet liabilities. This briefing addresses why 90% of agentic projects failed in 2025 and how to move from "paving over potholes" to rebuilding the road for an AI-native world. The Process-First Architecture To ensure an intelligence layer is defensible, fiduciaries must apply three non-negotiable filters: Redesign over Automation: Fixing the workflow before the tool. Inference Economics: Comparing daily run rates to initial deployment costs. Data Integrity: Ensuring data is normalized and represents a single source of truth. Even a perfect process fails if the board remains skeptical of the ROI numbers. Watch the deep dive on why AI ROI is fake: https://youtu.be/jpILq7Pg5uc Next Briefing: Disaster Recovery (DR) in the realm of ROI. 0:00 – The AI Balance Sheet Liability 0:53 – Authority Flash: 18 Years as a Global CIO 1:22 – Why Automation Fails on Top of Chaos 2:05 – The Process-First Architecture Framework 2:48 – Data Integrity: The Governance Mandate 3:50 – What "Normalized Data" Means for Leadership 4:46 – Making the Intelligence Layer Defensible 5:44 – Chaining the Chain: Why AI ROI is Fake

7 min
JAN 15

Why Boards are Skeptical of AI ROI (And What to Ask Instead)

Send us a text Most leadership teams are told that if they don’t invest millions in AI immediately, they will be left behind. But for many organizations, "AI" is currently nothing more than a marketing term—a "Google search on steroids" wrapped in urgency. In this briefing, I break down the collision between technical reality and financial accountability. I explain why over 90% of AI initiatives fail to reach sustained production and provide the exact two-question decision filter that can save your organization hundreds of thousands in undisciplined spend. What this briefing delivers: The Authority Arc: Why leadership intelligence requires more than just technical hype. Category Confusion: Defining LLMs vs. Agentic AI in boardroom terms. The Trillion-Dollar Failure: A look at the 2025 data showing why trillions in spend are failing. The Interrogation: The specific follow-up questions to ask your CIO to expose undisciplined thinking. Fiduciary Discipline: How to let strategy lead technology to restore financial leverage. Featured Resource: For a deeper dive into these frameworks, my book "AI Clarity: A Straightforward Guide for Business Leaders" is available on Amazon (Link Below). It provides the full interrogation scripts for LLMs, AI agents, and agentic systems. Next in the Series: Stay tuned for the next briefing on Disaster Recovery (BCP), where we reveal why most organizations are not nearly as protected as they believe. 0:00 Why AI Assumptions are Wrong 1:30 The Authority Arc: From Helpdesk to Global CIO 3:45 Defining Artificial Intelligence in the Boardroom 5:10 What AI Actually Is: LLMs vs. Agents 6:30 The "Marketing Term" Trap: A Monitoring Case Study 8:15 The Gemini Ad and the Inevitability Narrative 9:25 The Trillion-Dollar Failure: Why AI Data Matters 10:45 The Truth About AI Job Losses 12:20 The Two-Question Decision Filter 14:00 The Interrogation: How to Challenge AI Proposals 15:05 AI Clarity: Mental Models for Executives 16:15 How Strategy Leads Technology 17:35 Next Briefing: The Disaster Recovery Gap

19 min
JAN 13

Why Boards Reject Confident Executives

Send us a text Boards don't reward confidence; they reward comprehension. Most executives believe authority comes from a strong delivery or polished presence, but that belief collapses the moment a board member asks a question you didn't prepare for. In this briefing, I explain why boards are evaluating whether you understand a decision well enough to own the risk, not just defend it when things go right. I share the exact moment a $22 million ERP transformation failed—not because of the technology, but because of a lack of boardroom clarity. What you will learn in this briefing: Confidence vs. Clarity: Why "prepared confidence" breaks under pressure and how to build logic-based clarity. The "Category without Content" Trap: Why vague answers like "strong change management" erode trust with audit committees. The One-Slide Framework: How to condense $150M+ decisions into three clear sections: Decisions Enabled, Options Evaluated, and Success Metrics. The Thinking Constraint: Why the inability to fit a proposal on one slide is a signal that you don't understand the decision well enough to lead it. Chapters: 0:00 Boards Buy Comprehension, Not Confidence 1:11 The Mistake Executives Keep Repeating 2:31 Case Study: The $22M ERP Failure 4:09 Rebuilding Authority: Decisions vs. Systems 5:14 Why Boards Distrust Unexplained Uncertainty 6:34 How to Present Evaluated Options 7:35 Defining Success Metrics Before Approval 8:25 The One-Slide Boardroom Framework 9:35 How to Use This in Your Next Meeting 10:10 Phase 1 Conclusion & New Briefing Schedule 11:01 Preview: The Truth About AI in the Boardroom About this Series: This briefing concludes Phase 1 of our IT ROI and Boardroom Clarity series. Starting next Thursday at 9:00 AM, we pivot to explaining current technology trends (starting with AI) using the language of executive leadership—no technical jargon. Next Briefing: What AI actually is, what it is not, and why those two things are being blurred on purpose in your boardroom. Subscribe to stay equipped to challenge IT leadership and protect your capital.

13 min
JAN 10

Why CIO and CFO Alignment Breaks (And How to Fix It)

Send us a text CIO and CFO alignment does not break because of personalities or communication styles. It breaks because your governance structure never forces the real trade-offs to be defined. When one leader optimizes for capability and the other for capital, "alignment" becomes nothing more than expensive theater. In this briefing, I explain why alignment is not agreement—it is a structure. I break down the three questions that must be forced before any material technology spend to restore capital discipline and board confidence. What this briefing delivers: The Translation Problem: Why the CIO must learn the language of business economics instead of expecting the business to learn technical jargon. The Shadow IT Vacuum: How leadership delays of 6 months force the business to stop waiting and start signing unauthorized SAS contracts. The Three-Question Framework: What are we optimizing? What downside are we accepting? And who owns the outcome financially? Case Study: How a financial services firm cleared an 18-month backlog in 90 days by shifting from "business cases" to "explicit trade-offs". Chapters: 0:00 A Governance Failure, Not a Personality Problem 1:12 Authority Flash: 18 Years in the Boardroom 1:53 Why Alignment Fails 4:08 The Real Cost of "Alignment Theater" 5:10 The CIO Translation Problem 7:09 Alignment is a Structure, Not an Agreement 8:52 Case Study: Reframing the Backlog 11:02 How Governance Restores Clarity 11:37 Next: Why Board Confidence Collapses Next in the Series: Stay tuned for the final briefing in this ROI series, where I explain why board confidence collapses even when every function is performing well.

12 min
JAN 9

Why Boards Never Trust IT Numbers

Send us a text Boards are not confused by IT metrics. They are unconvinced by what those metrics fail to explain. In this briefing, I break down why clean dashboards, green uptime, and precise financial tracking still fail to earn trust, and why pushback from directors is not skepticism but a signal that the numbers are disconnected from how the business actually operates. This is not an IT execution problem. It is a governance and translation failure between IT activity, financial cost, and business impact. What this video covers • Why boards reject accurate numbers that lack business causality • The disconnect between IT dashboards, financial statements, and board decisions • The three traits trusted board-level numbers always share • Why more data increases internal confidence but reduces board confidence • A real manufacturing board case where trust returned without improving performance The core insight Boards do not fund platforms or reports. They fund decisions, predictability, and accountable outcomes. When numbers fail to explain what changed in the business, credibility erodes quietly, meeting by meeting. Who this is for CEOs, CFOs, COOs, private equity operating partners, and business leaders who are tired of defending technology spend that looks right on paper but fails in the boardroom. 01uOFlHxd8XsKkZF7Z6T

6 min
JAN 9

Why IT ROI Collapses in the Boardroom

Send us a text Most companies approve technology investments that look sound on paper, track cleanly in finance, and deliver exactly what was promised, yet still fail when the board asks a single question. What did we get for the money. This is not an execution problem. It is an IT governance failure. In this briefing, former Global CIO Jayson Hahn explains why IT ROI collapses in the boardroom, even when projects are delivered on time and on budget. You will see how misaligned definitions of success between executives quietly break the capital story, and why CFOs are left defending value that was never economically defined. This episode covers: • Why IT ROI fails in translation, not execution • The difference between delivery metrics and economic outcomes • Why ROI must be agreed before capital moves, not after • The three questions boards expect answered, and why most organizations cannot answer them • How governance restores capital discipline and board confidence This is for business leaders who are tired of approving technology spend they cannot clearly defend in a board meeting, an audit, or a strategic review.

8 min
JAN 5

Why IT Governance Fails CFOs

Send us a text Most CFOs approve technology investments that look sound on paper, align with leadership expectations, and receive board approval, only to find themselves defending outcomes they never controlled. When strategy decks and financial results diverge, boards do not blame systems or process. They look to finance. This is not an execution failure. It is an IT governance failure. What the Podcast delivers In this briefing, former Global CIO Jayson Hahn explains why IT governance consistently fails CFOs, how misaligned definitions of success between CEOs, CIOs, and finance create hidden exposure, and why boards uncover these gaps months after capital is committed. You will hear: Why alignment is not governance How capital moves before economic logic is agreed The three questions boards expect CFOs to answer, and why most governance models fail to provide them A practical framework CFOs can use to regain control, credibility, and board confidence This Podcast introduces the Command, Control, Confidence governance framework, designed to ensure capital decisions are tied to business outcomes, ownership, and board-level metrics before dollars move. If you want clarity before your next board conversation, subscribe for the next briefing, where we break down how boards evaluate IT return, and the three numbers CFOs must have ready.

9 min

10 Episodes

Most companies spend millions on technology they cannot clearly explain, defend, or govern. Strategic IT Governance delivers decision-grade clarity on IT spend, risk, and ROI for CEOs, CFOs, and operators who own the outcome, not just the budget.

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Jayson Hahn
Years Active

2K
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10
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