LEADERSHIP SCENARIO

The Monolith Trap

3-5 day simulationIntermediateStaff+ IC Track

Your VP just announced "Project Droplets" at the engineering all-hands — decomposing DataFlow’s monolith into 15+ microservices. He’s not wrong about the coupling problems: deploy bottlenecks, cross-team blocking, a P1 cascade that took down checkout. But a full decomposition is overkill. The operational complexity will crush a team that’s never operated microservices. He just asked you to lead technical planning.

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From

Jordan Ellis

Subject

Project Droplets — need you to lead technical planning

As you heard at the all-hands, we're moving forward with Project Droplets — decomposing our platform monolith into independent services. I want you to lead the technical planning. Current Stack: Node.js monolith, ~200k LOC, 4 years old. Shared PostgreSQL database, ~180 tables. Deploy queue averages 12+ PRs waiting. Billing team was blocked for two full sprints by analytics schema migrations. I need your technical assessment and a planning doc by end of week...

THE SITUATION

The VP isn’t wrong — but the plan might be

Project Droplets was announced at the all-hands. Jordan Ellis laid out the problems — deploy queue bottlenecks, cross-team blocking, a P1 incident where a notification bug cascaded into checkout for 90 minutes. These are real problems.

The proposed solution is a full decomposition into 15+ microservices with independent data stores. But DataFlow’s team has never operated microservices. The operational complexity — service discovery, distributed tracing, data consistency — will create new problems faster than it solves old ones.

Jordan asked you to lead technical planning because you know the codebase better than anyone. He wants a planning doc by end of week. He didn’t ask for pushback. But you know the codebase well enough to see where the plan breaks down.

The question is whether you can disagree with your VP’s plan — without just saying no. A counter-proposal that takes the real problems seriously has a chance. A flat refusal doesn’t.

WHAT YOU'LL PRACTICE

4 leadership skills, one scenario

Disagreeing with leadership without burning credibility

The all-hands already happened. The initiative has a name. Saying "this is wrong" is easy. Saying "here’s what would actually work" requires more.

Proposing alternatives when the momentum is already moving

Project Droplets has organizational energy behind it. A counter-proposal needs to solve the same problems better, not just critique the current plan.

Balancing technical assessment against organizational enthusiasm

Some engineers are excited about microservices. Some managers see it as modernization. Your job is to separate the real problems from the hype.

Writing a counter-proposal that takes the real problems seriously

The coupling problems are real. The deploy bottleneck is real. A credible alternative acknowledges this instead of defending the status quo.

HOW IT WORKS

From inbox to insight

Receive Jordan’s planning directive

A detailed email outlining the problems and the proposed decomposition. He wants your technical assessment by end of week.

Reply with your assessment

Your real email, your real words. How you frame your concerns — or whether you raise them at all — shapes everything.

Jordan, Nina, Marcus, and Priya respond

Your VP, a manager who’s been blocked, a tech lead with migration experience, and an engineer excited about the new stack.

Navigate pushback and alignment

Each conversation either builds credibility for your alternative or erodes it. The clock is ticking toward the leadership sync.

Submit your recommendation

You deliver a planning doc — either the decomposition Jordan asked for, or a counter-proposal you believe in.

Get your debrief

A personalized coaching assessment: how you navigated disagreement with leadership and what your approach reveals about your technical judgment.

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Jordan is waiting for your assessment

The all-hands already happened. The initiative has a name and a slide deck. But between "the monolith has problems" and "let’s build 15 microservices" is a gap that only someone with deep codebase knowledge can fill. The question is whether you’ll fill it — and how.

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