Upgrade Your Managers’ Toolkit

Sai Prakash
Aug 8
3 min read

WorkOS + Sprint Rhythm for High-Velocity Teams

When I ask CEOs what keeps them up at night, they rarely mention competitors. They mention velocity—and the invisible sludge that slows it. The sludge has a name: work about work.

Microsoft’s 2025 Work Trend Index shows nearly half of employees (48%) and 52% of leaders call their day “chaotic and fragmented.” Dig into the ledger and you find the draw: 117 average emails and 152 Teams messages received each workday with barely 2 mins between these disruptions throughout the day. That’s hours spent describing work instead of doing it. Every hour carries a double cost—salary paid, opportunity missed.

Meanwhile, the managerial safety net has thinned from pre-pandemic levels. Those extra heads generate more updates, which spawn more meetings, which steal more focus. It’s a flywheel of friction that even the hardest-working manager can’t outrun.

July 2024 handed us a painful case study. A faulty CrowdStrike update bricked 8.5 million Windows devices and left Delta Air Lines clawing back $500 million in five days. Supervisors were everywhere—gates, crew rooms, control towers—but no live re-routing engine linked them. The outage proved a brutal law: supervision breaks under real-time pressure; only systems scale.

So if your managers still ask, “What’s the status?” it means you don’t yet have an execution system only a managerial middleware. It works for 20 people. But try scaling that to 200. Or 2,000.

You’ll end up with:

More managers than makers
A hierarchy of follow-up
Execution delays hidden behind communication noise

The manager’s role has changed. But the playbook hasn’t.

Let’s rewind.

In the industrial era, managers existed to ensure repeatability. Tasks were repetitive. Teams were co-located. Visibility was built into the physical world.So managers optimized for compliance, efficiency, and coordination.

Then came the knowledge era. Suddenly, work became invisible. Distributed. Cross-functional. Messy. Yet we kept applying the same supervisory model:

“Check if they’re working.”“Collect their updates.”“Escalate when things slip.”

It’s exactly why teams today feel micromanaged, over-measured, and underpowered.

Supervision scales poorly; systems scale naturally

Two structural shifts have broken the old supervision model.First, teams have grown while ladders have shrunk. At small and mid-size firms, the average manager now oversees almost six people, up from slightly over three in 2019—a “Great Flattening” driven by cost cuts and AI adoption. Span of control doubled, but the rituals of check-ins and status decks stayed the same.Second, generative AI is automating the very chores that once justified those rituals. McKinsey notes that more than half of administrative tasks in a manager’s portfolio are technically automatable today. Strip out the reminders and report prep, and many managers are left without a clear charter.

We worked with a 100-person tech firm where every team had a manager running weekly standups, pushing people for updates, and building dashboards manually. Delivery was slipping. Morale was dropping. Everyone was tired. We made one change:We turned every manager into a Sprint Owner. Their role was no longer to chase tasks. It was to:

Define the sprint goal
Set the flow of the work
Build the workflow stages
Assign clear ownership
Facilitate the sprint review
Flag systemic blockers—not individual delays

Within 6 weeks, meetings dropped, sprint throughput improved and employee satisfaction jumped. Because no one was being micromanaged anymore

Old Habit	Flow-First Habit
Ask “What’s the status?”	Build boards that self-report
Host marathon updates	Facilitate ten-minute reviews
React to slips	Design cadence that prevents them
Assign tasks by name	Create role-based hand-offs
Track hours	Shape capacity and flow