Your New AI Hire Is Already Power Tripping

Musical accompaniment for today’s newsletter. Let’s get right to it and talk about new workplace problems. Here’s one: just because your new AI coworker is made of code doesn’t mean it’s polite. I was talking to a colleague about an agentic crew she put together for a project. She let it run, and after she came back, discovered that the project manager agent had renamed itself, given itself a promotion, and started bossing all the other agents around in fascinating yet somewhat disturbing ways.

Turns out your digital employees — agents, copilots, whatever we’re calling them this week — are already picking up some very human flaws. They interrupt. They over-explain. They confidently do the wrong thing and then act surprised when you’re annoyed. Made in our own image, they can be a**holes, too.

They escalate when they shouldn’t. They hallucinate answers instead of saying “I don’t know.” They “optimize” away the part of the process that actually mattered. Worst of all, they never read the room. Before you know it, they will be stealing your lunch out of the office fridge and making passive-aggressive comments about you on Slack.

And just like human a**holes at work, the problem usually isn’t intent. It’s incentives. We reward speed, confidence, and output volume. So digital employees respond by being fast, loud, and aggressively helpful. The same traits that get real people promoted … until they don’t.

The real risk isn’t that AI replaces humans. It’s that we’re scaling bad workplace behavior at machine speed. One passive-aggressive agent is annoying. A thousand of them embedded in workflows is cultural debt.

Are you prepared for your digital employees to be a**holes? If not, get ready to set norms, design guardrails, and stop confusing “productive” with “pleasant to work with.” Because nobody wants to work at a company where even the bots are jerks.

What else is going on this week?

Oracle Earnings: Through A Stargate, Darkly

Fulfilling AI’s potential in the 2020s workplace is more of an infrastructure challenge than an algorithmic one. As such, Oracle has enjoyed the upside of being an AI infrastructure kingmaker. Yes, the backlog is enormous. Yes, OpenAI’s spending on data centers is like FOMO with a balance sheet. But Wall Street has started to ask after Big Red’s Q2 earnings: When does this thing actually pay off? Welcome to the downside, Larry.

The math is getting uncomfortable. Oracle is spending like a hyperscaler, borrowing like one too — without the diversified demand profile that cushions Microsoft or Amazon. OpenAI looms large in the backlog, which sounds great until you remember it’s a single, capital-hungry customer in a market where model dominance is suddenly contestable.

The selloff isn’t anti-AI. It’s anti-duration risk. Investors are fine funding the future, just not an open-ended one financed with debt and no path to profitability.

Oracle may still win big. Maybe we aren’t in an AI bubble, even if parallels exist with the Dot-Com Boom/Bust. But right now, the market wants proof that AI isn’t just eating capex; it can digest it.

Funding and Acquisitions

• IBM strikes $11 billion deal for Confluent. At about $31/share, this is one of IBM’s biggest software plays in years. The move is squarely about real-time data as the fuel for AI + hybrid cloud workloads. Forget AI megamodels for a second — the actual bottleneck for enterprise AI isn’t compute, it’s fresh, governed data flows. Confluent’s core product, built on Apache Kafka, is basically the event streaming backbone that modern apps and AI systems actually run on. Enterprises used to batch and ETL stuff overnight. That world is over. This is the plumbing that decides whether AI stays a toy or becomes a tool. If your pipelines can’t keep up, none of the fancy LLMs matter. (Wall Street Journal)
• ServiceNow could announce plans to acquire startup Armis as soon as this week in a potential $7 billion deal, according to Bloomberg. The cyber exposure management company gives enterprises deep visibility and risk insight into every connected asset — from managed laptops to IoT and OT devices. It just raised $435 million in a pre-IPO round at a $6.1 billion valuation, with strong growth and a clear path to $1B ARR and an IPO target in 2026–27. ServiceNow is coming in and paying a premium to make delivery in hybrid environments more reliable. (CNBC)
• UKG agrees to acquire Inova Payroll. The Nashville-based HCM/payroll services shop serves 4,000 SMBs and has been UKG Ready’s largest reseller. The deal is expected to close early 2026 and folds Inova’s outsourced payroll, benefits brokerage, and support expertise into UKG’s stack. This move puts UKG in a hybrid position between tech platform and workforce services provider — think ADP/Paychex, not pure SaaS. Service revenue around payroll and benefits can be stickier and higher-margin over time than license fees alone. (UKG)
• Skillwell merges with Realizeit to supercharge personalized skill development. The combined entity keeps the Skillwell name and aims to fuse adaptive AI pathways with real-world practice environments to help enterprises and universities actually develop and verify skills, not just deliver content. This deal stitches adaptive pathways directly into simulation-based performance practice. That’s the combo most LMS/LXP vendors have tried and failed to execute. It ups the ante on skills verification, not just theory. (Press Release)
• Bennie gets $50 million strategic investment from LNC Partners. This NYC company sits at the intersection of HR service and digital experience. Think benefits brokerage but with a mobile app, analytics dashboard, and concierge support. It’s a classic “tech-enable the trad biz” play, similar to how fintech modernized banking services but for HR and benefits. The benefits brokerage business is fragmented, legacy-laden, and ripe for roll-ups with digital overlays. It looks like a good bet. (FinSMEs)
• Stellus Rx gets investment from WindRose Health Investors. PE is taking pharmacy care management seriously as a tech-enabled labor lever. This move is a shift from traditional PBMs to a more proactive, relationship-oriented model — closer to health ops than pure supply chain. (FinSMEs)

Industry Notes

• Fed Chair Jerome Powell said that Fed staffers believe federal data could be overstating job creation by up to 60,000 jobs a month, which suggests the jobs market might be shrinking. (Wall Street Journal)
• 2025 Apps Run the World ATS Market Share Report. (Ungated via iCIMS)
• Everyone hates Microsoft Copilot. Does it even matter? (Quartz)
• AWS re:Invent 2025: This one was different. (LinkedIn)
• Atana Inc announces Belle, the role-based AI assistant to deliver targeted, action-based insights for organizational development. (Press Release)
• The 2026 enterprise software un-predictions. (Diginomica)
• Thursday is the new Friday: Inside the 4-day work week we won't admit exists. (Robin Schooling)
• Matt Charney joins Kyle & Co (Blog)
• Cisive joins Oracle’s Enhanced Partner Program. (Blog)
• Is AI in recruitment a 'race to the bottom'? (BBC News)

Worth Reading

• Pantone just unveiled the 2026 color of the year — and it’s controversial. (USA TODAY via MSN)
• RIP Raul Malo, the golden-voiced, Grammy-winning leader of the Mavericks, dead at 60. (The Guardian)
• OK, what's going on with LinkedIn's algo? (TechCrunch)
• Inside the invitation-only stock market for the wealthy. In case you need something to help your blood pressure spike today. (Wall Street Journal)

That’s it not only for this week, but for this year. I hope y’all enjoy the holiday season. I’ll see you in 2026.