12 Red Flags When Hiring Technical Leadership (And What to Look For Instead)

The biggest red flags when hiring technical leadership are inability to explain technical decisions in business terms, no track record with businesses at your stage, focus on technology for its own sake rather than business outcomes, and inability to provide specific examples of problems they've solved. A bad technical leadership hire costs £100,000-300,000 in wasted salary, recruitment fees, and fixing their mistakes.

You've hired a CTO at £150,000/year. Six months in, you realise:

• They've made decisions that cost £80,000 to fix
• Your development team doesn't respect them
• They can't explain technical choices in language you understand
• Features are taking longer than before they arrived

Firing them and starting over costs another £50,000 in recruitment plus 3-6 months without proper leadership. Total damage: £200,000+ and a year of lost progress.

Every one of these situations was avoidable. The red flags were there in the interview, you just didn't know what to look for.

Red Flag 1: Can't explain technical decisions in business terms

What this looks like:

You ask: "Why should we rebuild the platform?"

They answer: "The current monolithic architecture doesn't follow microservices best practices. We need to implement event-driven architecture with proper domain-driven design patterns and migrate to a containerised orchestration platform."

You have no idea what that means or whether it's worth £120,000.

Why it matters:

Technical leaders who can't translate technology into business impact will make decisions you can't evaluate. You'll either blindly approve expensive projects or ignore important technical work because you don't understand why it matters.

What to look for instead:

"Your platform was built as a prototype for 1,000 customers. You now have 15,000 and growing 40% annually. The architecture breaks at about 25,000 customers, you'll hit that in 9 months. Rebuilding now costs £120,000 and takes 4 months. Waiting until it breaks will cost £200,000 in emergency fixes plus lost revenue from downtime. I recommend rebuilding now."

You might not understand the technical details, but you understand the business case.

Interview test: Ask them to explain a complex technical decision from their previous role. If you don't understand their explanation, they fail the test.

Red Flag 2: No relevant experience with businesses at your stage

What this looks like:

You're a £3M revenue startup with 6 developers. The candidate's experience:

• 15 years at Google managing 200+ person teams
• Led enterprise-scale technical projects with £10M+ budgets
• Worked exclusively with Fortune 500 companies

Why it matters:

Leading technology at a 10,000-person company is completely different from a 10-person startup. Enterprise CTOs manage complexity through process and hierarchy. Startups need people who get hands-on and make decisions quickly with imperfect information.

A Manchester startup hired an enterprise CTO from a major bank. They tried to implement enterprise processes (architecture review boards, formal RFC processes, quarterly planning cycles) that paralysed a 4-person development team. Simple features took months to approve. The CTO left after 10 frustrating months.

What to look for instead:

Track record with businesses similar to yours in:

• Revenue stage: £500K-£5M, £5M-£10M, etc.
• Team size: 3-10 developers, 10-30 developers, etc.
• Business model: B2B SaaS, e-commerce, marketplace, etc.
• Stage: Early growth, scaling, mature

Ask: "Tell me about three companies at similar stage to us that you've worked with. What challenges did they face and what did you achieve?"

Red flag: All their examples are from different business stages or they say "principles are the same across all stages" (they're not).

Red Flag 3: Focuses on technology for technology's sake

What this looks like:

They talk about wanting to work with "cutting-edge technology," using "modern best practices," or rebuilding everything in their preferred technology stack, with no business justification.

You ask why they recommend a particular approach. They answer: "It's industry best practice" or "everyone's moving to this technology."

Why it matters:

These people optimise for their CV and technical learning, not your business outcomes. They'll recommend exciting technical projects that look impressive but don't solve actual problems.

A Birmingham SaaS company hired a CTO who wanted to rebuild their working platform using GraphQL and microservices "because that's what leading tech companies use." £140,000 later, they had a more complex platform that did exactly what the old one did, except with more moving parts to break.

What to look for instead:

Every technical recommendation should have clear business justification:

• "This reduces customer-reported bugs by 60%"
• "This lets us ship features in 2 weeks instead of 2 months"
• "This prevents the platform breaking when we hit 50,000 users"
• "This reduces infrastructure costs by £30,000/year"

Ask: "Tell me about a time you recommended NOT implementing a new technology, even though it was technically interesting."

Good CTOs have multiple examples of saying "no" to exciting technology because it didn't serve business needs.

Red Flag 4: No specific examples of problems solved or results delivered

What this looks like:

They speak in generalities: "I implemented agile practices," "I improved technical culture," "I modernised the technology stack."

When you ask for specific outcomes, they can't provide numbers or measurable results.

Why it matters:

Generic claims mean either they didn't actually deliver results or they don't think in terms of measurable outcomes. Either way, you can't evaluate their effectiveness.

What to look for instead:

Specific, measurable examples:

• "Reduced deployment time from 4 hours to 15 minutes, letting us ship features 3x faster"
• "Improved platform reliability from 98.5% to 99.8% uptime, reducing customer churn by 12%"
• "Identified that 40% of infrastructure spending was wasted, saved £60,000/year"
• "Restructured technical team, improved delivery from 2 features/month to 8 features/month"

Interview test: Ask for three specific examples with numbers. If they can't provide them immediately, they either didn't deliver results or don't track what matters.

Red Flag 5: Wants to rebuild everything from scratch

What this looks like:

Within first month, they propose rebuilding your entire platform, changing all your technology choices, or replacing working systems with new ones.

They describe your current technology as "legacy," "technical debt," or "not scalable" without specific evidence.

Why it matters:

Rebuilding is expensive (£100,000-500,000), risky, and often unnecessary. Many CTOs suggest rebuilding because:

• They don't understand the existing system
• They want to work with technologies they prefer
• It's easier than fixing existing problems
• It looks impressive on their CV

A Leeds e-commerce company hired a CTO who immediately recommended rebuilding their entire platform. Cost: £280,000 and 14 months. Result: New platform that did exactly what the old one did. Actual problem: Database optimisation needed, would have cost £20,000.

What to look for instead:

Good technical leaders first understand what you have and why decisions were made. Then they identify:

• What works: Keep and maintain
• What needs fixing: Targeted improvements
• What needs replacing: Rebuild only what's actually broken

They should be able to explain: "Your authentication system is fine. Your payment processing needs modernising (£25,000). Your admin panel should be rebuilt (£40,000). But your core product logic works well and should stay."

Interview test: Ask about their approach in the first 90 days. Red flag if they talk about rebuilding before they talk about understanding.

Red Flag 6: Can't provide references from previous clients or employers

What this looks like:

When you ask for references, they:

• Provide only written testimonials (carefully curated)
• Offer references from 5+ years ago
• Give references from people they managed, not people they reported to
• Are reluctant or evasive about providing references

Why it matters:

If someone's genuinely good at their job, previous employers and clients are happy to vouch for them. Reluctance to provide recent references suggests problems you're not hearing about.

What to look for instead:

2-3 references from recent roles (within last 3 years) including:

• Direct supervisors (CEO, board members)
• People they worked closely with (product leads, senior developers)
• Founders of businesses they advised (for fractional CTOs)

Questions to ask references:

• What specific value did they deliver?
• What didn't go well? What would you change?
• Would you hire them again?
• What type of business would benefit most from working with them?
• What type of business would be a poor fit?

Listen for specific examples and honest assessment, not generic praise.

Red Flag 7: Never admits being wrong or having failed

What this looks like:

You ask: "Tell me about a technical decision that didn't work out. What went wrong and what did you learn?"

They either:

• Can't think of an example
• Describe a failure that was entirely someone else's fault
• Give an example from 10+ years ago when they were junior

Why it matters:

Everyone makes mistakes. Technical leaders who can't acknowledge failures either:

• Lack self-awareness
• Will blame your team when things go wrong
• Haven't learned from mistakes because they don't recognise them

A Bristol company hired a CTO who blamed every problem on the previous team, the business requirements, or the developers. When their own decisions failed, they never took responsibility. Team morale collapsed and they left after 8 months.

What to look for instead:

Honest examples of things that didn't work:

• "I recommended rebuilding our API but underestimated complexity. It took 6 months instead of 3 and we should have done incremental improvements instead. I learned to be more conservative with rebuild timelines."
• "I hired someone based on technical skills without evaluating team fit. They were brilliant but couldn't collaborate. I learned to weight cultural fit equally with technical ability."

Good technical leaders learn from failures and adjust their approach.

Red Flag 8: Poor communication or dismissive of questions

What this looks like:

During interviews, they:

• Use jargon without explaining it
• Seem annoyed when you ask for clarification
• Talk down to non-technical people
• Can't adjust their communication style for different audiences

Why it matters:

You'll work with this person for years. If they can't communicate clearly with you now, when they're trying to impress you, it'll be worse after they're hired.

What to look for instead:

Clear communication with non-technical stakeholders:

• Explains complex topics using analogies and examples
• Checks whether you understand before moving on
• Adjusts explanation style based on audience
• Welcomes questions and takes them seriously

Interview test: Ask them to explain something complex (microservices, technical debt, API architecture). You should understand their explanation. If you don't, that's their communication failure, not your technical knowledge gap.

Red Flag 9: Only wants to do "strategy" and not get hands-on

What this looks like:

They say: "I'm a strategic leader, not a hands-on implementer" or "I don't write code anymore, I focus on vision and direction."

They describe spending all their time in meetings, planning sessions, and presentations, with no time reviewing code, understanding technical details, or validating approaches.

Why it matters:

For UK businesses under £10M revenue, you need technical leaders who can be strategic AND validate their strategy by getting hands-on when needed. Pure strategists become disconnected from reality and make recommendations that don't work in practice.

What to look for instead:

Balance between strategic and hands-on:

• "I spend about 70% of time on strategy and team leadership, 30% reviewing code and validating technical approaches"
• "I don't write production code regularly, but I prototype solutions and do architecture reviews"
• "I stay technical enough to evaluate my team's work and make informed decisions"

Ask: "When did you last write code or do hands-on technical work? What was it?"

If they haven't done anything hands-on in 2+ years, they've lost technical credibility.

Red Flag 10: Promises transformation or revolutionary change

What this looks like:

They promise to "transform your technical culture," "revolutionise your development process," or "implement world-class engineering practices."

They talk about how everything will be different within months of their arrival.

Why it matters:

Transformational change is risky, expensive, and often unnecessary. Technical leaders who promise transformation either:

• Don't understand how hard organisational change is
• Are selling you what sounds impressive rather than what you need
• Will cause disruption chasing change for change's sake

A Manchester startup hired a CTO who promised to "transform engineering culture." They implemented new tools, new processes, new methodologies, and reorganised the team. Developers spent 6 months adapting to constant change and feature velocity dropped 60%. The CTO left after a year. The team spent another 6 months undoing the changes and returning to what worked.

What to look for instead:

Incremental improvement with clear goals:

• "I'll focus on the biggest bottlenecks first: deployment speed and code quality. We'll make targeted improvements and measure results."
• "Some of your processes work well and should stay. Others need updating. I'll involve the team in identifying what to change."
• "My first 90 days: understand what you have, identify 2-3 high-impact improvements, deliver quick wins whilst building trust."

Ask: "What will be different 6 months after you start?"

Good answer focuses on 2-3 specific, measurable improvements. Bad answer promises comprehensive transformation.

Red Flag 11: Doesn't ask you questions about the business

What this looks like:

They spend the interview talking about their experience, their technical opinions, and what they would do, without asking about:

• Your business model and how you make money
• Your customers and their problems
• Your growth plans and strategic priorities
• Your current technical challenges
• Why you're hiring for this role now

Why it matters:

Good technical leaders know they can't give good advice without understanding your business context. If they're not asking questions, they're either:

• Not interested in your specific situation
• Planning to apply generic solutions regardless of context
• Focused on their own agenda rather than your needs

What to look for instead:

Lots of questions about your business:

• "Tell me about your customers and what problems you solve for them"
• "What are your growth goals for the next 12-24 months?"
• "What technical challenges are blocking you right now?"
• "Why are you hiring for this role now rather than 6 months ago?"
• "What does success look like in this role?"

The best technical leadership candidates spend 50%+ of the interview asking you questions and understanding your situation.

Red Flag 12: Dramatically under or over-priced for the market

What this looks like:

Market rate for a CTO in your situation is £120,000-160,000. They're either:

• Asking for £80,000 (40% below market)
• Asking for £220,000 (40% above market)

With no clear justification for the difference.

Why it matters:

Dramatically cheap means:

• Lacks experience or credibility (can't command market rate)
• Desperate for any job (red flag about previous roles)
• Doesn't understand their market value (lack of business awareness)

Dramatically expensive means:

• Overestimates their value relative to your business stage
• Brings experience that doesn't match your needs (enterprise background for startup role)
• Might be using your offer to negotiate elsewhere

What to look for instead:

Pricing within market range for:

• Their experience level
• Your business stage and location
• Role scope and responsibility

UK market rates (2025):

• CTO, £1-5M revenue, 5-10 developers: £100,000-150,000
• CTO, £5-10M revenue, 10-20 developers: £130,000-180,000
• CTO, £10M+ revenue, 20+ developers: £150,000-250,000+
• Fractional CTO, 2-5 days/month: £3,000-10,000/month

If someone's 30%+ outside these ranges, understand why before proceeding.

How to avoid these red flags

Before interviewing:

• Define exactly what you need (strategic leadership, team management, hands-on technical work)
• Write clear success criteria for first 90 days and 12 months
• Understand market rates for your situation
• Prepare specific questions based on your actual challenges

During interviews:

• Ask for specific examples with measurable outcomes
• Test their ability to explain complex topics clearly
• Evaluate whether their experience matches your business stage
• Check for red flags systematically (use this article as checklist)

Reference checking:

• Always check 2-3 references from recent roles
• Ask references about weaknesses, not just strengths
• Speak to people they reported to, not just people they managed
• Listen for what references don't say as much as what they do

Trial periods:

• Start with 3-month probation for full-time hires
• Use fractional engagements to trial before committing full-time
• Set clear deliverables for trial period
• Be willing to exit if red flags emerge

The safest way to hire technical leadership

For most UK businesses under £10M revenue, starting with fractional CTO before committing to full-time is the lowest-risk approach:

Benefits:

• Trial expertise for 3-6 months before committing £180,000+/year
• Lower cost (£72,000-96,000/year vs £180,000-250,000/year full-time)
• Can exit with 30 days notice if it's not working
• Get strategic expertise without full-time management overhead

Process:

1. Engage fractional CTO for 3 months (£18,000-30,000)
2. Evaluate whether you actually need full-time or fractional is sufficient
3. If you need full-time, you can either:
   • Transition fractional CTO to full-time (if they're interested and it's working)
   • Use fractional CTO to help hire full-time (they can assess candidates technically)

This approach reduces hiring risk from £200,000+ (bad full-time hire) to £20,000-30,000 (3-month fractional trial).

See detailed fractional vs full-time CTO cost comparison

What good technical leadership looks like

Instead of focusing only on red flags, understand what good looks like:

Good technical leaders:

• Explain technical decisions in clear business terms
• Have track record with businesses similar to yours
• Focus on business outcomes, not technology for its own sake
• Provide specific examples with measurable results
• Thoughtfully evaluate before recommending major changes
• Gladly provide recent references
• Admit mistakes and explain what they learned
• Communicate clearly with non-technical stakeholders
• Balance strategic thinking with hands-on validation
• Promise specific improvements, not transformation
• Ask lots of questions about your business
• Price reasonably for market and experience

If you're interviewing someone who shows most of these traits and none of the red flags, you've probably found someone worth hiring.

Use these questions to evaluate technical leadership candidates

Making your decision

You've now got a framework for spotting red flags when hiring technical leadership. Use it to:

Evaluate current candidates: Review your recent interviews against these 12 red flags. How many did each candidate trigger?

Improve your process: Add questions that surface these red flags before you make offers.

Consider alternatives: If full-time hiring seems risky, trial fractional CTO first to reduce risk.

The cost of hiring wrong is £100,000-300,000. Spending an extra week in the hiring process to avoid red flags is worth it.

Book a free 30-minute call to discuss your technical leadership hiring process. We'll review candidates you're considering, identify potential red flags, and recommend the right approach for your specific situation.

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About the Author

Jake Holmes has worked with 15+ UK businesses (£1-10M revenue) on technology leadership decisions. He's helped companies decide between fractional and full-time CTOs, recruited technical leaders, and prevented £100,000+ in bad hiring decisions. Before founding Grow Fast, Jake was a software engineer and technical lead, giving him the technical depth most consultants lack.

Connect: jake@grow-fast.co.uk | LinkedIn | Book consultation

About Grow Fast

Grow Fast helps UK businesses (£1-10M revenue) make smart technology decisions without wasting money. Our Fractional CTO services provide strategic technical leadership 2-5 days per month, saving you £200,000+ vs hiring full-time whilst getting the expertise you actually need. Book a free 30-minute call to discuss your technical leadership needs.