Free Technology Readiness Assessment

How mature is your organisation's technology setup?

Evaluate your business across four critical dimensions and get an instant readiness score — with a clear picture of where the gaps are.

3 minutes Instant results No payment required

This assessment evaluates your organisation across four dimensions:

  • Technology Leadership & Governance — strategic direction and decision-making
  • Infrastructure & Security — technology foundation and risk management
  • Team & Capabilities — skills, capacity, and organisational readiness
  • Strategic Planning — future initiatives and alignment with business goals

About Your Organisation

1. What's your company size?
Under 20 employees
20–50 employees
50–100 employees
100–200 employees
200+ employees
2. Which best describes your industry?
Financial Services / Fintech
Healthcare / Life Sciences
Professional Services
Manufacturing / Logistics
E-commerce / Retail
SaaS / Technology
Other

Technology Leadership & Governance

3. Do you have a CTO or Head of Technology?
Yes — full-time CTO with deep technical expertise
Yes — part-time or fractional CTO
No — CEO or founder handles technology decisions
No — outsourced to external provider
No senior technology leadership
4. How often is technology discussed at board or leadership level?
Weekly — technology is core to strategy
Monthly — regular strategic reviews
Quarterly — periodic check-ins
Annually — budget cycle only
Rarely — only when problems arise
5. Do you have a documented IT strategy aligned with business goals?
Yes — reviewed and updated quarterly
Yes, but outdated (1+ years old)
In progress — being developed now
No, but we plan to create one
No plans for one
6. Who makes major technology purchasing decisions?
CTO with board oversight
Technology leadership with executive approval
CEO or founder directly
Finance or operations team
Ad-hoc — no clear process

Infrastructure & Security

7. Where is your primary infrastructure hosted?
Fully cloud (AWS/Azure/GCP) with modern architecture
Hybrid cloud with a strategic migration plan
Primarily on-premise with some cloud services
Fully on-premise legacy systems
Don't know / multiple disconnected providers
8. When was your last comprehensive security audit?
Within the last 6 months
6–12 months ago
1–2 years ago
2+ years ago
Never had one, or I don't know
9. Are you confident you're compliant with relevant data protection regulations — PDPA, GDPR, or similar?
Yes — fully compliant with documented evidence
Mostly compliant — minor gaps being addressed
Not sure — haven't done a full assessment
Known gaps we're working to address
Not currently compliant
10. Do you have a tested disaster recovery plan?
Yes — tested successfully in the last 6 months
Yes, but not tested in over a year
Plan exists but never tested
No formal plan — just backups
No plan or backups, or I don't know

Team & Capabilities

11. Size of your internal IT or technology team?
No internal team — fully outsourced
1–2 people
3–5 people with diverse skills
6–10 people with specialised roles
10+ people with clear departments
12. What's your biggest technology team challenge right now?
Finding and retaining talent
Significant skill gaps in current team
No team at all
Team overwhelmed with day-to-day work
Lack of leadership or direction
No major challenges — team is performing well
13. How do you handle after-hours IT issues?
24/7 internal coverage or dedicated NOC
Structured on-call rotation
Outsourced to MSP or managed services
Best effort — team responds when available
No coverage — wait until next business day
14. Do you have documented processes for critical IT operations?
Yes — comprehensive and regularly updated
Yes, but outdated or incomplete
Some documentation exists — very basic
Mostly tribal knowledge
No documentation

Strategic Planning

15. Are you planning any major technology initiatives in the next 12 months?
Yes — clearly defined with budget and timeline
Yes — in planning phase
Considering but not committed
No major initiatives planned
Don't know / no planning process
16. What's your biggest technology challenge right now?
Lack of strategic technology direction
Security and compliance concerns
Outdated infrastructure holding us back
Scaling technology to support growth
Cost management and optimisation
Team capability and skill gaps

Get Your Results

Your details
Your Technology Readiness Score
0
/ 100
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Your Top Priorities

Want a deeper diagnosis?
Your score shows where you stand.
The ClearPath Diagnostic shows what to do about it.
A 15-question diagnostic built for C-suite leaders and founders — with four scored dimensions, a hidden cost estimate, a risk exposure summary, and a 90-day action plan delivered instantly.
  • Technology Spend Clarity — what overlapping tools are costing you
  • Risk Exposure Summary — what your IT team may not have flagged
  • IT Leadership Gap Analysis — is your setup fit for your growth stage
  • 90-Day Action Plan — three concrete steps with named owners
Get the Full ClearPath Diagnostic — $97 →

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