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Context Costs

The Steady Beat, Issue #90: human context windows, storytelling for technical leaders, AI token economics, and redirecting difficult colleagues

March 20th, 2026

by Henry Poydar

in Newsletter

You’re reading The Steady Beat, a weekly pulse of must-reads for anyone orchestrating teams, people, and work across the modern digital workplace – whether you’re managing sprints, driving roadmaps, leading departments, or just making sure the right work gets done. Curated by the team at Steady.

The Token Tab

You finally got your team using AI. Congratulations! Now comes the part nobody warned you about: the bill. As companies move past the “just get people to use it” phase, a new management challenge is emerging: tracking and making sense of token consumption. Zapier now monitors per-employee token use the way companies once watched cloud spend, trying to distinguish golden patterns from expensive anti-patterns. The math gets interesting though: a Vercel engineer spent $10,000 in a single day deploying AI agents to build a critical infrastructure service – work that would’ve taken humans weeks. The CEO estimates it saved millions. Meanwhile, Exceeds AI founder Mark Hull rolled out Claude Code to his 15-person team and watched costs spike within 48 hours, forcing immediate guardrails. As University of Chicago researcher Brian Jabarian points out, “everyone thought you just use AI tokens and you have an increase in productivity, and we call it a day.” But token spend without outcome tracking is just a new flavor of waste. Someone burning five times more tokens than their peers might be your most valuable engineer or your most expensive time-waster. You simply can’t tell which without measuring what came out the other end. For managers, this means AI governance is quickly becoming as essential as headcount planning.

Editors note: at Steady, we’re working on a fix to the agent rework (and resulting wasteful token spend) problem.

The Wall Street Journal, 7m, #ai, #productivity, #management

The Human Context Window

AI tools can now generate virtually anything, which means the ability to make stuff is no longer a competitive advantage. Peter Benei and Torsten Sandor argue that the real differentiator is what they call your “human context window”: everything you bring to an AI collaboration that the machine can’t generate on its own: your judgment, taste, accumulated experience, and point of view. It’s a compelling reframe for anyone leading teams through the AI transition. While everyone’s obsessing over prompt engineering and tool selection, the actual moat is the decades of context you’ve built through doing the work. The authors use their own newsletter as proof. They could let AI generate competent marketing content solo, but the publication’s value comes from their combined 40+ years of experience, shared professional history, and cross-disciplinary interests that no model can replicate. They advise developing judgment by saying no to most things, treating every AI correction as a deepening of your own expertise, and investing in depth over variety.

AI-Ready CMO, 6m, #ai, #leadership, #strategy

Tell Less, Land More

Technical leaders are terrible storytellers, and it’s not because they lack interesting things to say, it’s because they can’t stop explaining. Wes Kao identifies four mistakes that turn compelling insights into forgettable presentations, and they all stem from the same root: prioritizing completeness over connection. First, drowning your audience in technical caveats when a simplified hook would get them leaning in. Think J.Crew’s merchandising strategy: put the eye-catching piece in the window, sell the basics from the stockroom. Second, clutching a mental checklist of storytelling tactics instead of actually being present. Rehearse the frameworks beforehand, then let go and focus on making eyes light up. Third, burying the lead under mountains of backstory when you should be starting at the moment of maximum tension – “right before you get eaten by a bear,” as Kao puts it. And fourth, attempting sprawling hero’s journey narratives when a punchy 15-second anecdote would hit harder with a fraction of the risk. Your technical brilliance is worthless if nobody remembers what you said.

Wes Kao’s Newsletter, 5m, #leadership, #communication, #storytelling

Redirect, Don’t Resist

Every team has one: the colleague who treats meetings like debate tournaments, steamrolls alternative viewpoints, and somehow still has senior leadership’s ear. Your instinct is to push back with facts and logic, which is the exactly the wrong move. Yue Zhao’s tactical playbook borrows from martial arts: instead of meeting force with force, use their momentum against them. Ground yourself first – a few deep breaths before you respond keeps frustration from hijacking your strategy. Then redirect rather than oppose: “That’s a great idea for the future. And in the short term…” validates their position while creating space for yours. The real magic is in the reframing. When someone states opinions as facts, anchoring the discussion in belief language – “That’s very possible. What I’ve seen in past situations…” – strips their certainty without triggering defensiveness. You’re not telling them they’re wrong; you’re expanding the frame to include other options. The catch? This only works with relentless consistency. One conversation won’t change a pattern that’s been rewarded by the organization for years. But practiced across weeks and months, it shifts the dynamic from combat to collaboration. The loudest voice in the room isn’t the problem, it’s the culture that confuses volume with authority.

The Uncommon Executive, 5m, #leadership, #communication, #management

Echo of the Week

Echoes are AI agents in Steady that automatically gather and deliver work context to teams on a schedule—answering recurring questions about progress, capacity, and coordination so you stop burning hours assembling the same information manually.

Progress presentation – Stop spending your Sunday nights pulling together status slides. This Echo automatically generates presentation-ready content for two PowerPoint slides every two weeks, summarizing your team’s accomplishments so you can walk into that stakeholder meeting prepared without the manual toil.

Run this Echo in Steady


The lightweight teamwork OS

Teams rely on two coordination loops to function: a big-picture loop connecting plans to progress, and a ground-level loop keeping teammates in sync.

Problem is, status quo approaches to running those loops are an incomplete, inconsistent, and inefficient tangle of meetings, emails, chat threads, dashboards, and manual toil.

Steady is the teamwork OS that runs both loops for you. Purpose-built agents continuously distill updates and activity into personalized intelligence that keeps everyone aligned and informed automatically.

The outcome: high-performing teams that deliver better work, 3X faster.

Learn more at runsteady.com.

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A weekly pulse of must-reads for anyone orchestrating teams, people, and work across the modern digital workplace — whether you're managing sprints, driving roadmaps, leading departments, or just making sure the right work gets done. Curated by the team at Steady.