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Heavy Strategy

Latest episodes

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Jun 17, 2025 • 28min

HS106: Planning for the Epochalypse

IT teams deal with technology lifecycle issues all the time–including Y2K, which enterprises across the world grappled with for years. The Epochalypse, or Year 2038 Problem, is similar. Specifically, some Linux systems’ date-time counters will go from positive to negative at a specific date in 2038, potentially wreaking havoc on embedded systems and any other... Read more »
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Jun 3, 2025 • 27min

HS105: How to Train Your Unicorn: Thoughts on Ops Architects

You need someone to design your operations processes–or perhaps redesign them. That’s an Ops Architect. Should you take an ops person and train them up in architecture? Or an architect and train them up in operations? Do you even have that ops/engineer/architect organizational structure – and should you? Johna and John dive into this discussion... Read more »
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May 20, 2025 • 29min

HS104: How Long Should Your Planning Horizon Be?

How far ahead should you plan, and what things belong in your strategic plan? Conventional wisdom holds that a 3-year planning horizon is “about right”–but in a period of rapid technical and geopolitical change (such as we’re arguably in right now) does that go too far out, particularly when agile methodologies recommend shorter action plans... Read more »
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May 6, 2025 • 26min

HS103: Why IT Is Like Ultimate Frisbee

It’s all well and good to develop a technology strategy, articulate and document the strategy, and agree (supposedly) on that strategy. But what do you do when one or more of the tech teams act in apparent opposition to the strategy? John and Johna discuss why this happens and what questions you need to ask... Read more »
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Apr 29, 2025 • 41min

HS102: IT’s Role In AI (Sponsored)

AI can impact an enterprise in several ways: making individuals more productive, making products and services more effective, and making it easier for customers and partners to do business. IT plays a critical role in enabling AI to have these impacts. On today’s sponsored Heavy Strategy, Cisco CIO Fletcher Previn explains how to locate AI use... Read more »
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Apr 22, 2025 • 32min

HS101: Time for a Cybersecurity Spring Cleaning?

Most organizations have a long list of security holes in the form of unpatched systems and other known but unresolved vulnerabilities. Is it time to hit the big PAUSE button and fix, patch, or mitigate all of that before we resume deploying new systems (and their accompanying risks)? Join us as we tear into whether... Read more »
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Apr 8, 2025 • 42min

HS100: Lead Without Lying: The (Radical) Strategy of Honesty

Is it actually possible to run a team without lying? Steven Gaffney, author of the book, “Just Be Honest”, joins Johna and John to talk about why being honest is harder than it sounds–and how (and why) to do it anyway. Steven spends his career advising science and technology leaders about how to be more... Read more »
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Apr 1, 2025 • 35min

HS099: From CLI to CFO: Translating Complex Network Data into Clear Strategic and Financial Insights (Sponsored)

IT and network leaders need more than uptime—they need to know what their networks cost, what they deliver, and how future changes will impact the business. That’s where Netos comes in. CEO and founder Richard Foster joins Johna and John in a lively discussion to explore how Netos turns complex operational data into clear financial... Read more »
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Mar 25, 2025 • 34min

HS098: Just Following Orders?

What do you do when your colleagues or senior leaders ask you to do something illegal? It’s hardly hypothetical; recent years have seen high-profile firings and convictions of CIOs and CISOs who’ve been ordered to break the law. John and Johna discuss steps that tech leaders can take if they’re put on the spot. Episode... Read more »
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Mar 11, 2025 • 30min

HS097: Build A Strategy, Not Just A Project Plan

IT teams too often wrap a strategy statement around a basket of projects already in progress or known to be coming, rather than defining a strategy and then letting it spawn, guide, or absorb projects. On today’s Heavy Strategy we discuss whether IT teams have any alternative to this approach, given how much gets “thrown... Read more »

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