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Fractional CTO Decision Framework

10 Critical Questions Every Founder Must Answer

All Decision Frameworks • Offshore Dev Team Framework

Discover if you need fractional CTO support before technical mistakes cost you your runway.

Your Red Flags

0/10

Answer the questions below to see your assessment

1. The Investor Reality Check

Are investors asking technical questions you can't confidently answer?

  • Do you fumble when asked about your tech stack choices?
  • Can you explain your scaling strategy in technical terms?
  • Do you know your unit economics around infrastructure costs?

Red flag: If you're deflecting technical questions or speaking in vague terms, investors notice.

2. The Hiring Blindspot

How are you evaluating technical talent right now?

  • Can you tell a senior developer from a junior one in an interview?
  • Do you know what "good code" looks like?
  • Are you relying purely on gut feel or referrals?

Red flag: Hiring the wrong technical team early can set you back 6-12 months and cost you your runway.

3. The Architecture Gamble

Is your current tech stack a strategic choice or just what your first developer knew?

  • Will it handle 10x your current user base?
  • Are you building on legacy technology that will be expensive to maintain?
  • Do you have a clear migration path as you scale?

Red flag: If you can't answer these questions, you're building on quicksand.

4. The Burnrate Reality

What's your monthly technical spend vs. your total runway?

  • Developer salaries + tools + infrastructure = ?
  • Are you getting ROI on every technical dollar?
  • Could you extend runway 3-6 months with better technical decisions?

Red flag: Technical inefficiency is often the silent killer of startups. Most founders don't realize they're overspending until it's too late.

5. The Feature Trap

Who's deciding what gets built and what gets cut?

  • Are you building features customers asked for or features they need?
  • Do you have a technical roadmap that aligns with business goals?
  • Can someone tell your team "stop building that"?

Red flag: Building the wrong things is worse than building nothing. You need someone who can say no.

6. The Security & Compliance Question

Are you handling user data, payments, or operating in a regulated space?

  • Do you know your security vulnerabilities?
  • Are you compliant with GDPR, SOC 2, HIPAA (if applicable)?
  • Could a breach or audit tank your business?

Red flag: One security incident or compliance failure can kill a startup overnight.

7. The Technical Debt Meter

How much "we'll fix it later" is piling up?

  • Are bugs taking longer to fix?
  • Is new feature development slowing down?
  • Are your developers frustrated with the codebase?

Red flag: Technical debt compounds like financial debt. The longer you wait, the more expensive it becomes.

8. The Communication Gap

Can you translate between business needs and technical execution?

  • Do your developers understand the business priorities?
  • Can you explain technical constraints to your board?
  • Are estimates constantly wrong?

Red flag: Misalignment between business and tech is expensive. You need a translator.

9. The Scale Horizon

When will you need to 10x your infrastructure?

  • 6 months? 12 months? 24 months?
  • Do you know what breaks first as you scale?
  • Are you architecting for where you're going or where you are?

Red flag: Rebuilding your entire tech stack mid-growth is the most expensive mistake startups make.

10. The Honest Assessment

Can you afford NOT to have technical leadership?

  • What would one major technical mistake cost you? (Hint: Usually 3-6 months of runway)
  • What's your confidence level (1-10) in your current technical decisions?
  • If you had to pitch your tech strategy to a technical investor tomorrow, would you be comfortable?

Red flag: If your confidence is below 7/10, you need help now, not later.

© 2024 Shawn Mayzes. All rights reserved.
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