The best engineering managers don’t make big decisions through perfect analysis—they build conviction through strategic experimentation.

The Problem with Big Decisions

When facing major technical or organizational choices (microservices vs. monolith, new programming language, team restructuring), most EMs fall into analysis paralysis. They gather more data, schedule more meetings, and delay until the “right answer” emerges. It rarely does.

The Small Bets Approach

Instead of betting the farm on unproven ideas, run tiny, time-boxed experiments that build real conviction.

How It Works

1. Identify the core assumption - What must be true for this approach to succeed?
2. Design the smallest possible test - Can you validate this with one team, one sprint, one feature?
3. Set clear success criteria upfront - What would prove or disprove your hypothesis?
4. Time-box ruthlessly - 2 weeks max for most experiments
5. Extract learnings, not perfection - You’re buying information, not building production systems

Real Examples

Considering a new framework? Build one internal tool with it first. You’ll learn about developer experience, hiring implications, and operational complexity without risking customer-facing systems.

Thinking about team topology changes? Pilot the new structure with one squad for a quarter. Measure velocity, morale, and cross-team dependencies before rolling out organization-wide.

Evaluating a major architectural shift? Extract one bounded context and migrate it. You’ll discover hidden integration challenges and true migration costs.

Why This Matters

Small bets give you three critical advantages:

• Organizational buy-in - Teams trust leaders who validate before mandating
• Reduced risk - Failed experiments are learning, not disasters
• Faster decisions - Real data beats theoretical analysis every time

Start Tomorrow

Pick one “big decision” you’ve been agonizing over. Ask yourself: What’s the smallest experiment that would increase my conviction by 30%?

Then run it.

The goal isn’t to eliminate uncertainty—it’s to build enough conviction to act decisively while maintaining the ability to course-correct based on reality.

Great engineering leaders don’t wait for certainty. They manufacture it through disciplined experimentation.