We hired a new VP named Michael Lee. Unfortunately we already have a Michael Lee. He works in the warehouse. He's been here 11 years. New VP gets: michael.lee2@company.com He immediately messages IT. “Can you move the other Michael to michael.lee2 and give me michael.lee?” No. He asks HR. HR asks me if we can “prioritize seniority.” I explain that the warehouse Michael has eleven years of email history tied to that address and changing it because someone with a nicer title arrived would be insane. VP reluctantly keeps the 2. Warehouse Michael finds out. Changes his Teams display name to: Michael Lee (Original) By Friday the VP is being referred to as Sequel Mike. He has asked IT to intervene. Unfortunately nickname management is outside our support scope.

I was cleaning up DNS and found a record called: OLD-PAYROLL-PROD It pointed to a server named: DO-NOT-DELETE No owner. No documentation. No tickets mentioning it since 2019. I asked three senior engineers what it did. Nobody knew. So naturally I deleted it. Four minutes later every hourly employee disappeared from the timeclock system. I restored the record. Everyone came back. We still don't know what the server does. We don't know where it physically lives. We don't know who pays for it. We don't know why DNS controls payroll. We only know that if it disappears, 600 people stop getting paid. I renamed the record: DO-NOT-DELETE-SERIOUSLY Audit asked me to document the dependency. I listed the system owner as: “Ancient forces beyond our understanding.”

At 2:07 AM our shared support inbox sent an automatic reply to a vendor. “Thanks, we've received your message.” The vendor's ticketing system automatically replied: “Thanks, we've received your message.” Our inbox thanked them for receiving our message. Their system thanked us for receiving their message. This continued until 6:18 AM. 11,438 emails. Security woke me up because they thought we were under attack. I checked the logs. No attack. Just two enterprise systems being extremely polite to each other for four straight hours. I killed the loop. The vendor's support ticket now contains 5,700 updates and is too large for their portal to open. Their account manager called the incident “concerning.” I disagree. We just completed the world's first fully automated vendor relationship. No humans. No decisions. Thousands of emails. Enterprise software has finally achieved its final form.

Our identity provider went down this morning. Which meant nobody could access: Slack. Email. VPN. The help desk. Our incident-management system. Or the company status page. The status page was also behind SSO. So we had successfully centralized authentication to the point where an authentication outage removed every method we had for telling employees there was an authentication outage. I spent 20 minutes walking around the office carrying a whiteboard that said: SSO IS DOWN STOP REBOOTING YOUR LAPTOP The CTO asked why we didn't have an external status page. Security reminded him they made us put the external status page behind SSO last year. We're designing a new emergency communications plan now. Current leading technology: a bigger whiteboard.

Legal asked who owns the admin account for the software that provisions every new employee. Good question. Not IT. Not HR. Not Security. I traced the account back to 2019. It was created by an intern named Brittany using her personal Gmail. Brittany left the company five years ago. We have 900 employees now. Every new employee still gets their accounts because somewhere, somehow, Brittany's Gmail is holding the entire onboarding process together. We called her. She answered from a brewery. She still remembered the password. Legal asked why we never migrated it. I said because until today none of us knew Brittany existed. HR is now discussing a consulting agreement with her. Our most critical identity administrator hasn't worked here since before COVID. She also wants us to stop emailing her every time someone gets promoted. Reasonable request.

Every department has purchased its own AI meeting bot. Sales has one. HR has two. Marketing somehow has four. Monday's standup had 9 employees and 11 bots. Half the meeting was robots announcing that they were recording the meeting. So I scheduled an “AI Governance Alignment” call and invited only the bots. They all joined. One bot summarized another bot's introduction. Another generated action items based on that summary. A third bot assigned those action items to two bots that weren't invited. After 30 minutes I received seven different meeting summaries, none of which agreed on what happened. One of the bots automatically scheduled a follow-up for Thursday. The follow-up also has no humans invited. I was going to shut the whole thing down. But this is the first time we've achieved fully autonomous middle management. I'm letting them cook.

Finance told IT to cut software spending by 15%. Done. I pulled the license report and removed every paid license from anyone who hadn’t opened the software in 30 days. Annual savings: $184,000. At 2 PM the CFO called because his PDF editor disappeared. He hadn’t opened it in 63 days. He demanded I restore it immediately. I told him that would add $240 back to the software budget and asked which savings target he wanted me to revise. Long silence. Then: “Can’t I just open PDFs in the browser?” I said yes. He said never mind. We hit the quarterly savings target before lunch. Turns out cost optimization becomes much easier when executives are personally introduced to the free tier.

A manager messaged me: “Can you give my new hire the exact same access I have?” Absolutely. I ran a permissions comparison. Turns out this guy has been at the company for 9 years and accumulated access to 47 different groups through promotions, reorganizations, and people forgetting to remove things. Marketing. Finance. Old project folders. A folder literally called: BOARD - CONFIDENTIAL Security policy says access must match your current role. So instead of giving the new hire 47 permissions, I removed 39 from the manager. Ten minutes later: “Why can’t I access half my folders anymore?” I told him his request triggered a least-privilege review. He said that wasn’t what he meant. I told him security isn’t about what we mean. It’s about what we discover. The new hire got access to one folder. The manager lost access to eight departments. Security posture improved dramatically.

I accidentally rebooted the network switch for the entire third floor. Internet disappeared. Phones dropped. About 70 employees immediately stood up from their desks like prairie dogs. I had two choices: Admit I clicked the wrong switch. Become proactive. I sent this message: “Unannounced infrastructure resilience exercise currently in progress. Please continue normal operations.” Then I waited five minutes and turned everything back on. Service restored. No data loss. Nobody died. The CTO replied: “Love that we’re testing this stuff proactively.” So I wrote a post-exercise report. Objective: Validate employee response to unexpected connectivity loss. Result: Successful. Finding: Employees become extremely loud after approximately 12 seconds without internet. Recommendation: Continue resilience testing quarterly. My mistake now has a budget.

HR asked IT for Wi-Fi login data to measure who is actually coming into the office on time. Small problem. According to the logs, I arrive at 10:43 AM almost every day. So I explained that Wi-Fi authentication timestamps do not represent physical arrival because laptops can remain asleep, roam between access points, renew DHCP leases, or delay “meaningful network presence.” Most of that is technically true. Then I built them an attendance dashboard. Any device connecting before 11:00 AM is classified as: MORNING ARRIVAL 11:00–1:00: MIDDAY ARRIVAL After 1:00: ANOMALOUS PRESENCE EVENT HR loved it. Last month our dashboard showed 96% morning attendance. Leadership presented it as proof the return-to-office policy is working. I still get in at 10:43. Never argue with bad data. Give it categories.