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September 30, 2025Decoding the ‘Is it a Blister or is it a DDO’ Dilemma in M&A Technical Due Diligence
September 30, 2025As a CTO, I spend my days connecting tech decisions to business outcomes. But the real skill? Knowing which technical questions actually matter—and which ones are distractions in disguise. Let me show you how a tiny coin anomaly taught me to think differently about ambiguity in tech leadership.
The Hidden Cost of Ambiguity: Why ‘Blister vs. Doubled Die’ Mirrors Real-World Tech Decisions
You’ve been there: your team debates whether an issue is just a surface-level glitch or something deeper. That moment of uncertainty? It’s just like a coin collector arguing over a plating blister versus a doubled die obverse (DDO). What seems minor at first glance can have massive implications.
After 20 years in this role, I see the same pattern everywhere:
- Is this technical debt slowing us down, or is it a dormant strategic opportunity?
- Is this a simple bug, or should we turn it into a feature flag?
- Is our material science issue a plating defect, or are we accidentally onto a breakthrough?
The real cost isn’t the issue itself—it’s the wrong call on how to treat it.
The Blister Mindset: Treating Symptoms, Not Causes
Last quarter, we spent three weeks patching a UI bug that kept reappearing. Classic blister approach—surface fix, fast resolution, minimal analysis. It worked. But it was also a waste of time.
A plating blister is the same: a quick visual check, a temperature adjustment, and you’re done. Safe. Predictable. Boring. Our maintenance flywheel spins the same way:
- Band-aids for recurring bugs
- Throwing bodies at technical debt
- Polishing legacy systems instead of replacing them
Our data showed this consumed nearly 70% of our engineering budget last year. Not because the fixes failed—but because we treated every problem like a blister, never asking: “Wait, what if this is actually trying to tell us something bigger?”
Here’s what changed our approach:
- For every issue, we now ask: Surface (Blister) or Structural (Doubled Die)?
- Surface issues? Hand them to junior engineers with a 40-hour cap.
- Anything structural? That triggers a CTO-level review with product, engineering, and finance—no exceptions.
Now we catch systemic problems early—before they become budget black holes.
The Doubled Die Mindset: Seeing Patterns in Noise
A doubled die isn’t a problem. It’s a story—a rare error that, in the right context, becomes valuable. I learned this the hard way when we spent months troubleshooting a “bug” that turned out to be unexpected user behavior. Instead of fixing it, we built a new feature around it. Launched it the next quarter. It’s now our most-used tool.
This is the innovation flywheel:
- Not just investigating anomalies—asking if they’re opportunities
- Not just fixing things—asking if we should redefine them
- Not just reacting—building processes that capture value from the unexpected
When we find something that looks like a doubled die—like that “material defect” our R&D team reported last month—we don’t just analyze it. We ask:
- What if this isn’t a flaw, but a new property we haven’t seen before?
- Could this change how we think about our product?
- Is there a market for this “error”?
Last year, three issues we initially flagged as “probably just noise” turned into patent filings. That’s the doubled die effect: looking at what others dismiss and asking, “What if we’re wrong about what this is?”
As engineers, we love clear answers. But as leaders, our job isn’t to eliminate ambiguity. It’s to navigate it wisely. Some issues are blisters—fix them fast and move on. Others? They’re doubled dies in disguise. The trick is knowing the difference before you make a call that costs millions.
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