The Calculus of IT
The Calculus of IT

Calculus of IT - Season 3 Episode 11 - Shadow AI vs Shadow IT

25 February 2026 1:57:00 Nathan McBride & Michael Crispin

Listen to episode

About this episode

Newsflash: Shadow AI is just Shadow IT with better branding and worse consequences.

We set out to compare Shadow AI (people using ChatGPT at home because you won't give them tools at work) versus Shadow IT (people using Smartsheet because your approved system doesn't meet their low quality standards), and discovered they're pretty much the exact same problem. BLUF: if you don't have governance, training, and approved options, you've already lost. Your employees are prompting away on personal accounts and there's nothing you can do about it except train them properly and give them legitimate alternatives. Nate revealed his company trains 100% of employees on GenAI within their first week, runs daily tests to see if Claude's LLM has been "whitewashed", and has a nine-level certification program where personas don't unlock until level six. We discussed the high probability that 80-90% of employees at most companies probably use personal AI accounts, suggested the solution is "lightweight guardrails" and multiple approved options. We also learned that Mike cooks frozen burritos (aka shit logs) in an air fryer and we agreed that TestiCoin might be our best option for a retirement plan. Beard Watch officially launched: Mike's two-week beard progress is "barely visible" and resembles dirt splashed on his face. Next week we're diving into CWP (Cakewalk Pro? Build-first culture? Both?) and why low-code/no-code is the newest (and lamest) Shadow IT.

Listen at thecalculusofit.com • Join our Slack board at thecoit.us • Leave five stars • Invest in TestaCoin • Stop dry shaving while driving.

—Nate & Mike


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
Slack - Invite Link
Email - [email protected]
Email - [email protected]

Want to find AI jobs?

Join thousands of AI professionals finding their next opportunity

We respect your inbox. Unsubscribe at any time.

© 2026 The Calculus of IT. All rights reserved.

Common Questions

Frequently asked questions

Quick answers about how DevFound's AI matching, resumes, and referrals work.

DevFound's AI Copilot ingests your profile, goals, and live job data to deliver curated matches in seconds. Every match includes a resume variant, suggested referrals, and interview prep so you can act immediately. The more feedback you provide, the sharper the Copilot becomes.

AI-led job searches shrink the hours spent sifting through boards and formatting resumes. DevFound pairs automation with your personal outreach, so you reserve energy for interviews and negotiation. Traditional networking still matters, but AI gives you a lift before you even send a message.

Modern AI roles expect comfort with production-grade code, data fluency, and practical ML tooling. The strongest candidates pair deep technical chops with storytelling—translating model impact to product, GTM, and exec partners. Continuous learning keeps you ahead as stacks evolve.

DevFound rewards active seekers. Keep your profile fresh, respond to match quality prompts, and enable alerts so you never miss a role. The AI prioritizes companies and teams that align with your feedback, accelerating both introductions and interview invites.

High-density tech hubs continue to host the deepest AI talent pools, yet distributed teams are catching up fast. Use DevFound filters to hone in on onsite, hybrid, or fully remote roles and watch openings expand across time zones.

DevFound aggregates thousands of remote AI openings and flags the nuances—core hours, async culture, and visa needs—up front. The Copilot also recommends how to position your distributed work experience so hiring managers know you can thrive on a remote team.