Assessing Digital Transformation, Agile, DevOps, and DevEx Maturity: A Practical Guide

In a prior post, we help readers understand how digital transformation, Agile, DevOps and DevEx frameworks and practices connect together to build the fabric of high performing engineering organisations.

In this post, we want to help you dive deeper into strengthening these pillars of your engineering organisation by assessing the maturity levels of each so you can define strategies that act to focus effort and investment on where you need it most to achieve sustained levels of high performing productivity and engagement.

Using these quick frameworks below, we're offering a more structured approach to understanding the maturity of each, and suggest indicators that can be scored on a scale (e.g. 1-5: Initial → Optimising).

1. Digital Transformation Maturity Assessment

Key Areas to Evaluate:
✔ Strategy & Leadership: Is there an executive-driven digital strategy?
✔ Technology Adoption: Are you leveraging cloud, AI, automation, and data analytics?
✔ Business Model Innovation: Are you evolving your services or just digitizing existing processes?
✔ Customer Experience: Are you using digital tools to enhance customer engagement?
✔ Change Management: How well do teams adapt to new tools and workflows?

📊 Maturity Levels:

• 1 - Initial: No clear digital strategy, reliance on legacy systems.
• 2 - Emerging: Digital projects exist but are siloed.
• 3 - Defined: Clear digital roadmap, investments in cloud/automation.
• 4 - Managed: Measurable outcomes, AI/data-driven decision-making.
• 5 - Optimized: Fully digital-first, leveraging advanced tech at scale.

How to assess?

• Interviews with leadership
• Reviewing tech stack and processes
• Benchmarking against competitors

2. Agile Maturity Assessment

Key Areas to Evaluate:
✔ Mindset & Culture: Do teams embrace Agile principles, or is it just a process?
✔ Ways of Working: Are teams using Scrum/Kanban effectively?
✔ Cross-functional Collaboration: Are business and IT teams aligned?
✔ Delivery Cadence: Are teams delivering iteratively with frequent feedback loops?
✔ Measurement & Adaptation: Are they tracking and improving Agile adoption?

📊 Maturity Levels:

• 1 - Ad hoc: Waterfall-dominated, Agile adoption is superficial.
• 2 - Piloting: Some Agile teams exist but lack standardization.
• 3 - Scaling: Agile is used widely but with inconsistencies.
• 4 - Managed: Well-defined Agile practices, measurable improvements.
• 5 - Optimized: Agile mindset is embedded in company culture.

How to assess?

• Team surveys & Agile retrospectives
• Reviewing sprint cadences & workflows
• Observing Agile ceremonies (standups, retros, etc.)
• Agile metric ratings

3. DevOps Maturity Assessment

Key Areas to Evaluate:
✔ Automation: Are CI/CD pipelines in place? How automated is the deployment process?
✔ Collaboration: Are Dev and Ops teams working as one, or are they still siloed?
✔ Infrastructure & Cloud Adoption: Are they leveraging Infrastructure as Code (IaC), cloud-native architectures?
✔ Security & Compliance: Is security integrated into the pipeline (DevSecOps)?
✔ Monitoring & Incident Response: Do they have real-time observability and fast recovery processes?

📊 Maturity Levels:

• 1 - Manual & Siloed: No automation, long deployment cycles.
• 2 - Basic Automation: Some CI/CD, but deployments are risky and manual.
• 3 - Standardized Pipelines: CI/CD used broadly, some IaC, basic observability.
• 4 - Self-service & Cloud-first: Full automation, frequent deployments, strong observability.
• 5 - Elite: Everything is automated, infrastructure is fully cloud-native, fast recovery.

How to assess?

• Reviewing deployment frequency & lead time metrics
• Checking CI/CD pipeline usage & automation levels
• Evaluating incident response and monitoring setups
• DORA metric ratings

4. DevEx (Developer Experience) Maturity Assessment

Key Areas to Evaluate:
✔ Tooling & Developer Efficiency: Are developers using modern, well-integrated tools?
✔ Onboarding & Training: How long does it take for a new developer to be productive?
✔ Cognitive Load: Are developers overloaded with context-switching and unnecessary processes?
✔ Self-service & Automation: Can developers provision environments and deploy code easily?
✔ Feedback Loops: Do developers get rapid feedback from tests, monitoring, metrics and users?

📊 Maturity Levels:

• 1 - Frustrating & Slow: Poor tooling, long onboarding, lots of manual work.
• 2 - Fragmented: Some good tools but disjointed workflows.
• 3 - Improving: Efforts to reduce friction, better automation in place.
• 4 - High Efficiency: Streamlined tooling, self-service infrastructure, low friction.
• 5 - Developer-centric: Developers have everything they need to focus on coding, minimal distractions.

How to assess?

• Developer surveys & feedback sessions
• Analyzing onboarding times & productivity blockers
• Reviewing tool integration & automation capabilities

Final Step: Building a Roadmap

Once you have undertaken your maturity assessment, don't lose the opportunity to evolve.  Take action to:
✅ Prioritize gaps (e.g., if DevOps is weak, focus on automation).
✅ Align initiatives with business goals (e.g., improve Agile if teams struggle with adaptability).
✅ Set measurable targets (e.g., reduce deployment lead time from weeks to days).
✅ Track progress with key metrics (e.g., sprint velocity, deployment frequency).