Technical Leadership

Year-End Tech Audit: 5 Questions Every CEO Should Ask Their CTO

By Jeff Wray •

It's December. You're planning next year's roadmap, setting budgets, making promises to investors and customers. But before you commit to building 10 new features, there's something you need to know: What's the actual state of your technology?

Most CEOs assume things are fine until they're very much not fine. By then, it's expensive to fix. Here are five questions to ask before the year ends—while you still have time to course-correct.

Question 1: "If Our Lead Developer Quit Tomorrow, What Happens?"

Why This Matters:

This question reveals whether you have a system or just a talented person holding things together with duct tape and hope.

Good Answers:

  • ✓ "We have documentation for all critical systems."
  • ✓ "Multiple people understand each part of the architecture."
  • ✓ "We could onboard a replacement in 2-3 weeks."
  • ✓ "Everything is in our repos with clear README files."

Bad Answers:

  • ✗ "That would be... really bad."
  • ✗ "Only Sarah knows how the payment system works."
  • ✗ "Some of the configuration is in his head."
  • ✗ "We'd have to reverse-engineer parts of it."

This is called the "Bus Factor." If one person getting hit by a bus tanks your company, you don't have infrastructure—you have a single point of failure.

What to Do About It:

Allocate January sprint capacity for documentation. No new features until critical systems are documented. This is insurance, not overhead.

Question 2: "What Security Vulnerabilities Do We Currently Have?"

Why This Matters:

You can't fix what you don't know about. Most breaches happen through known vulnerabilities that nobody bothered to patch.

The Answer You DON'T Want to Hear:

"None. We're totally secure."

This answer means they either haven't looked, or they're lying. Every system has vulnerabilities. The question is: Do we know what they are and how serious they are?

Good Answers:

  • ✓ "We have 3 high-priority issues we're addressing in Q1."
  • ✓ "We run automated security scans weekly and fix critical issues within 48 hours."
  • ✓ "Our dependencies are monitored for CVEs, we're current except for X which requires a migration."
  • ✓ "Here's our prioritized list of known issues with timelines."

Follow-Up Questions:

  • • "When was our last security audit?" (If the answer is "never," budget for one)
  • • "Do we have automated scanning?" (Should be yes)
  • • "Who's responsible for security patches?" (Should have a clear owner)
  • • "What's our incident response plan?" (If they pause, you don't have one)

Question 3: "What Technical Debt Are We Carrying, and What's It Going to Cost Us?"

Why This Matters:

Technical debt is like credit card debt—some is manageable, but if you only make minimum payments, eventually the interest crushes you.

Every development team has technical debt. The question is: Is it documented, prioritized, and under control? Or is it a growing tumor nobody wants to talk about?

What You're Listening For:

Healthy Technical Debt Management:

  • • They can list the top 3-5 items
  • • Each item has an estimated cost to fix
  • • There's a plan to address them incrementally
  • • They can explain the impact if left unaddressed
  • • 15-20% of each sprint goes toward paying it down

Warning Signs:

  • ✗ "We'll deal with it later" (it's already later)
  • ✗ They can't quantify it
  • ✗ "Everything is technical debt" (lost control)
  • ✗ Zero time allocated to address it
  • ✗ "The whole thing needs to be rewritten" (red flag)

If the answer is "we need to rebuild everything," get a second opinion. That's either panic or a developer who wants to work on something more interesting.

Question 4: "What Happened to Our Development Velocity? Why Are We Shipping Slower?"

Why This Matters:

If it used to take 2 weeks to ship a feature and now takes 6 weeks, something's wrong. Understanding what is the first step to fixing it.

Possible Honest Answers:

  • 1.
    "Technical debt is slowing us down." Every change now touches brittle, poorly-understood code. Time to pay down debt.
  • 2.
    "We're spending 40% of our time firefighting." Too many production issues. Need to invest in stability and monitoring.
  • 3.
    "The architecture has gotten complex." What used to be 1 file is now 8 services. Maybe the complexity isn't justified yet.
  • 4.
    "We lost key people and knowledge transfer was poor." See Question 1 about documentation.
  • 5.
    "Features are legitimately more complex now." Early features were simple. Later features build on top of everything, require more integration work.

All of these are addressable problems. The worst answer is: "I don't know" or "We just need more developers." Adding people to a broken process makes it slower, not faster.

Red Flag:

If velocity is declining quarter over quarter with no clear explanation or plan to address it, you've lost control of your development process.

Question 5: "If We Got Acquired Tomorrow, What Would Due Diligence Find?"

Why This Matters:

Technical due diligence can kill deals or slash valuations. You want to know the skeletons in your closet before a buyer's auditors do.

What Acquirers Look For:

Code Ownership & Access

Do you actually own all your code? Is it in your repos? Can you grant access without your current vendor?

Infrastructure Control

Is everything running in your AWS/Azure account, or your vendor's? Can you deploy without them?

Security Posture

Recent audit? Known vulnerabilities? Compliance with relevant standards? Encrypted data at rest and in transit?

Documentation

Can a new team understand and maintain the system? Or is it all in people's heads?

Scalability & Technical Debt

Can the current architecture handle 10x growth? What needs to be rebuilt? What's the cost?

Dependencies & Licensing

Any GPL violations? Unlicensed software? Vendor lock-in that creates ongoing costs?

You don't need perfect answers to all of these. But you should know where the problems are and how much they'd cost to fix. Surprises in due diligence are expensive.

What to Do With the Answers

The point of these questions isn't to create panic. It's to surface reality before it becomes a crisis.

Action Items for January:

  1. 1. Document critical systems - Fix the Bus Factor problem before it's urgent
  2. 2. Run security audit - If you haven't done one, budget for it
  3. 3. Quantify technical debt - Turn vague concerns into concrete items with costs
  4. 4. Allocate debt paydown time - Reserve 15-20% of sprint capacity for technical health
  5. 5. Address velocity blockers - Whatever's slowing you down won't fix itself

The Question You SHOULD Ask But Probably Won't

"On a scale of 1-10, how confident are you in the technical foundation we've built?"

If your technical leader hesitates or gives you a number below 7, dig deeper. That pause tells you everything.

Technical leaders want to protect you from worry. They'll minimize problems until they can't anymore. Push for honesty. You can't fix what you don't know about.

The Bottom Line

You wouldn't plan next year's revenue goals without understanding your current financial position. Don't plan next year's product roadmap without understanding your technical position.

These five questions give you the technical health snapshot you need to make informed decisions. Ask them now, while there's still time to address problems before they become crises.

The answers might not be comfortable. But uncomfortable truths in December are better than disasters in March.

Need Help Assessing Your Technical Foundation?

A fractional CTO can conduct a year-end technical audit, translate technical jargon into business impact, and help you build a realistic plan for technical health in 2026.

Schedule Your Year-End Technical Review