The new episode is live. As usual, we were topical af.

The question: In an industry flooded with analysts, vendors, and LinkedIn thought leaders, who actually speaks for IT versus speaking to IT?

Short answer: Gartner speaks TO IT (specifically to CIOs with budgets). The Register speaks FOR IT (with appropriate cynicism). Your Discord/Slack communities speak WITH IT (peer-to-peer, no bullshit).

Longer answer: IT spent decades being invisible. Now everyone’s asking what to do about AI, and suddenly we need spokespeople. Problem is, most IT people weren’t trained to articulate value or push back on bad ideas. We were trained to keep things running quietly.

The shift from order-taker to value generator requires having a voice. And your voice is directly connected to your autonomy. If you can’t explain what you do, you won’t get authority to make decisions.

Our Hot Takes

Nate: “If you put all your chips in the Microsoft basket, you’re in for a rude awakening. Diversify or enjoy your web-only future.”

Mike: “AI won’t kill all jobs. Companies will invest heavily, realize they need humans to verify everything, and create a whole verification economy. It’s regulatory job creation all over again.”

Also Nate: “99% of enterprise data is garbage. Stop putting ‘confidential’ in document titles, you’re literally giving attackers the bread crumbs trail.”

What We Actually Covered

• Why analyst firms talk to budget holders, not practitioners
• How IT communities (like our Slack board) are the REAL peer support network
• The uncomfortable truth that nobody QCs anything anymore
• Why younger IT professionals will push transparency and voice further
• Mike’s unused Vision Pro (eBay value: $2,500, bids: 0)
• Nate’s fantasy honeypot containing 200,000 PowerPoint decks with a hidden cipher

Next week: Slack as an Operating System (e.g., when did your chat tool become your company’s nervous system?)

Join our Slack board (vendor-free, occasionally unhinged): links in the footer.

Leave five stars. We said we don’t care but we definitely care.

And remember: 99% of your data is garbage. Focus on the 1%.

—Nate & Mike

P.S. We’re better than Gartner and we’ll let you in our Slack for free.

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In part two, we tackle who actually does all this verifying, what it costs, and the uncomfortable questions nobody's asking yet.

IT is becoming the verification department whether you signed up for it or not. You're verifying employee identities, contractor credentials, AI agent authority, data provenance...basically everything, constantly.

We explore the shift from proactive governance to reactive verification, the impossible tension between privacy and verification, and scenarios that keep you up at night: locked-out executives, disputed transactions, and verification systems that might be wrong.

Big questions we couldn't fully answer: How do you verify AI agents? What gets verified - person, device, behavior, or all three? Can verification be continuous without becoming surveillance?

Mike predicts 2-3 years before verification pressure really hits IT departments. New job titles emerging: Chief Truth Officer, Model Auditor, Verification Vigilante.

We also accidentally invented a post-apocalyptic western about the last verification expert alive. It involves tape backup accidents and Mandalorian trust buoys. Don't ask.

Next week: Who Speaks for IT Anymore?

Support the show

The Calculus of IT website - https://www.thecoit.us
"The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library
"The New IT Leader's Survival Guide" Book - https://www.longwalk.consulting/library
"The Calculus of IT" Book - https://www.longwalk.consulting/library
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In Episode 4 of The Calculus of IT, Mike Crispin and I dive deep into what happens when "proof of X" becomes the fundamental currency of digital interaction. We're entering an era where verification matters more than the technology itself and IT leaders are on the front lines whether we're ready or not.

We explore the five pillars that need verification:

• Identity (are you who you say you are?)
• Humanity (are you even human?)
• Authority (are you authorized to do this?)
• Provenance (did you actually create this?)
• Expertise (do you actually know what the fuck you're talking about?)

From deepfakes and social engineering at industrial scale to the coming wave of AI agents that need their own credentials, we break down why your company's verification gap is probably bigger than you think and what you need to do about it.

Fair warning: This is Part 1 of a two-part episode. We got so deep into the weeds (in the best way) that we had to split it. Next week, we'll tackle IT's specific role in all this chaos, the impossible balance between friction and security, and whether continuous verification is our future or our nightmare.

Mike drops his latest prediction: We're moving from a governance economy to a verification economy. Instead of asking permission upfront, we'll increasingly ask forgiveness afterward with an army of human verifiers cleaning up the mess. He even coins two new roles you'll see in 2028: Chief Truth Officer and Model Auditor (complete with an otter mascot, obviously).

Key moments you won't want to miss:

• The safe word strategy we implemented at Xilio (and why you need one too)
• Why 60% of LinkedIn accounts are now fake—and what that means for professional networking
• The uncomfortable question: If an employee uses AI to create 90% of their deliverable, did they create it? And do you care if it's good?
• Why verification fatigue is about to become your biggest user experience problem
• Sam Altman's ben-wah ball crypto solution to solve the world's identity

This episode will make you question everything about how you onboard employees, verify identities, and trust the content flowing through your systems. Because whether you're ready or not, we're building systems where proving you're real is becoming harder than faking it.

Listen now, and join us next week for Part 2 where we tackle the really hard questions about IT's role in making verification work without turning your organization into a surveillance state.

Support the show

The Calculus of IT website - https://www.thecoit.us
"The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library
"The New IT Leader's Survival Guide" Book - https://www.longwalk.consulting/library
"The Calculus of IT" Book - https://www.longwalk.consulting/library
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Two years ago, we spent 4 hours and 27 minutes hours dissecting decentralized IT models. Now, AI has changed everything or has it?

In this episode, Mike and Nate return to one of Season 1's most epic deep dives to ask a critical question: Has the AI revolution fundamentally altered how we should think about IT organizational models? (Hint: Maybe?)

The uncomfortable truth? AI simultaneously pushes companies in BOTH directions. It makes decentralization technically feasible (business units can now code, troubleshoot, and build without IT) while making centralization organizationally necessary (governance nightmares, cost explosions, and compliance chaos).

We explore:

• Why the four classic models (centralized, matrixed, decentralized, federated) still matter
• How AI is turning "shadow IT" into "shadow AI", and why it's worse
• The case for (and against) pulling cybersecurity, governance, and employee experience OUT of IT entirely
• Whether every employee should have Claude as their personal IT department
• Why 2028 might require a "verification economy" instead of traditional governance
• The prediction: Most companies will land on a federated model with centralized AI governance and distributed execution

The fundamentals haven't changed, but what HAS changed is our understanding that IT doesn't need to own everything (as if it ever did). The healthiest organizations will recognize what to control, what to influence, and what to let go.

Plus: Why Gemini 3.0 matters (or doesn't), the 5,000-calorie Shake Shack challenge, and whether we're all just one well-crafted prompt away from knowing as much as our bosses.

Episode runtime: 2+ hours of unfiltered IT leadership reality

Support the show

The Calculus of IT website - https://www.thecoit.us
"The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library
"The New IT Leader's Survival Guide" Book - https://www.longwalk.consulting/library
"The Calculus of IT" Book - https://www.longwalk.consulting/library
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Identity...I mean...super easy topic right? 

Wrong.

Season 3 is largely devoted to looking at "capital-I Identity" from all available viewpoints.  Tonight, we just started to try and figure out what the hell it actually means.  We will come back to this idea many times this season so let this be the baseline to our discussion.

We also spent some time talking about idealizing tech stacks for small businesses and why Bob Barker's microphone was so long.

Dare I say it...yet another smash hit episode.

Support the show

The Calculus of IT website - https://www.thecoit.us
"The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library
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"The Calculus of IT" Book - https://www.longwalk.consulting/library
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aaaaand we're back!!

Season 3 of The Calculus of IT is here, and we're coming in hot with 40 episodes that go way beyond the AI silliness. Sure, we'll talk about GenAI when it matters - but from angles nobody else is touching. This season is about identity, autonomy, the death of IT as we know it, and why your infrastructure is probably lying to you right now.

We kicked off with a recap of Season 2's autonomy deep-dive and laid out the roadmap for what's coming. Spoiler: it's gonna kick ass.

Here's what you can expect:

What Is Identity? (Really?)
Distributed vs Centralized IT: The Eternal Battle
The Verification Economy (Because Nothing Is Real Anymore)
PowerPoint Inc.: Why We're Still Using the Cave Drawing Method
The OpenAI Walled Garden Paradox
The 99% vs 1% Data Problem (Why are we protecting all of the garbage?)
Creative Business Slop vs AI Slop
Edge + AI + Governance: The New Frontier
The Viewer/Editor Paradox (hint: not everyone deserves creator rights)
The COVID Retrospective: What changed forever for no particular reason
Building a Website in 2026: Who still does this and why?
The Death of the Password (For real this time - we mean it)
...and 28 more topics that'll make you rethink everything

Join us every Wednesday (unless we change it, because...you know...autonomy). 

Support the show

The Calculus of IT website - https://www.thecoit.us
"The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library
"The New IT Leader's Survival Guide" Book - https://www.longwalk.consulting/library
"The Calculus of IT" Book - https://www.longwalk.consulting/library
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Oddly enough, the bots don't seem to be too emotionally affected by their future rise to becoming our overlords.

Support the show

The Calculus of IT website - https://www.thecoit.us
"The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library
"The New IT Leader's Survival Guide" Book - https://www.longwalk.consulting/library
"The Calculus of IT" Book - https://www.longwalk.consulting/library
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.....aaaand that's a wrap folks.  It’s the end of the season, the end of an era, and maybe the last human-hosted podcast you’ll ever hear. In our Season 2 finale, Nate, Mike, and Kevin take everything we’ve learned about autonomy and decision-making power—and push it into the future with a deep-dive into Industry 5.0.

What’s after digital transformation? What happens when the data giants own 80% of the world’s information? And how do you lead when technology is evolving at ludicrous speed?

In this finale:

• Demystifying Industry 5.0: Why it’s not just “4.0 with extra steps”—and why it’s about human-centricity, sustainability, and resilience
• Real talk on the data economy: What happens when autonomy and purpose collide, and what IT leaders can do to keep their teams, their values, and their sanity
• Surviving the next wave: Practical advice for IT leaders on strategy, people, and using your independence for something meaningful
• Hope for the future: Building organizations that thrive—even as technology, data, and society change faster than ever

We wrap it up with our biggest question yet: What’s the point of autonomy if you’re not using it for something bigger?

Thanks for listening, for joining the conversation, for the Slack debates, the five-star reviews, the merch, and the beer. We’ll see you after a well-earned break for Season 3 - with new topics, new rants, and maybe a whole episode on why PowerPoint is the most insidious tool ever invented.

Until then: Be nice. Stay purposeful. And keep fighting for autonomy - one decision, one team, and one bold move at a time.

Support the show

The Calculus of IT website - https://www.thecoit.us
"The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library
"The New IT Leader's Survival Guide" Book - https://www.longwalk.consulting/library
"The Calculus of IT" Book - https://www.longwalk.consulting/library
The COIT Merchandise Store - https://thecoit.myspreadshop.com
Donate to Wikimedia - https://donate.wikimedia.org/wiki/Ways_to_Give
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The bots will have their way.  So get out of their way.  

Support the show

The Calculus of IT website - https://www.thecoit.us
"The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library
"The New IT Leader's Survival Guide" Book - https://www.longwalk.consulting/library
"The Calculus of IT" Book - https://www.longwalk.consulting/library
The COIT Merchandise Store - https://thecoit.myspreadshop.com
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We’ve talked resilience, compliance, AI, and risk - but what does it really take to become the architect of your organization’s technology future?

In this penultimate episode of Season 2, Nate and Mike step back to connect the big picture. It’s not just about weathering trends or keeping up with the latest tech - it’s about building systematic autonomy into every layer of IT leadership.

This episode covers:
- The Standardization Paradox: how to create innovation zones without losing operational control
- Matrix leadership and decision rights: thriving in the age of distributed authority
- The rise of composable enterprise architecture—and why optionality > efficiency
- Rethinking IT talent: why tomorrow’s teams need both deep specialists and versatile generalists
- Building adaptive learning and knowledge transfer into your org’s DNA

And, as always, we tie everything back to the original four pillars - Risk, Productivity, Automation, and Innovation - showing how true autonomy is the thread that connects them all.

Wrap up with our final IT leader archetype: The Autonomy Architect - the leader who builds for adaptability, modularity, and future strategic choice.

Next week: our grand finale, as we take everything we’ve learned into the future of Industry 5.0.

Keep fighting for autonomy, one decision, one architecture, and one team at a time.

Support the show

The Calculus of IT website - https://www.thecoit.us
"The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library
"The New IT Leader's Survival Guide" Book - https://www.longwalk.consulting/library
"The Calculus of IT" Book - https://www.longwalk.consulting/library
The COIT Merchandise Store - https://thecoit.myspreadshop.com
Donate to Wikimedia - https://donate.wikimedia.org/wiki/Ways_to_Give
Buy us a Beer!! - https://www.buymeacoffee.com/thecalculusofit
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Email - [email protected]
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