Agile or Waterfall? Most Companies Are Somewhere in the Messy Middle
By Incountr
Organizations have been debating the advantages of Agile and Waterfall for years, frequently viewing them as mutually exclusive choices. While many project managers continue to cling to the predictability and structure of classic Waterfall approaches, business leaders are under pressure to "go Agile" in the name of innovation.
However, most organizations operate somewhere in the middle, which is a fact that few people want to acknowledge. Not quite Agile. Not just Waterfall. Simply put, messy.
And if you know how to control it purposefully, that's fine.
This essay examines why the majority of businesses end up in this "messy middle," the dangers it poses, and how to transform a haphazard hybrid approach into a potent, deliberate strategy that actually brings about change.
Agile and Waterfall: A Quick Refresher
Before we explore the middle ground, let’s ground ourselves in the basics.
🌀 Agile Methodology
Agile is an iterative, flexible approach to project delivery, emphasizing:
Customer collaboration over contract negotiation
Working solutions over comprehensive documentation
Responding to change over following a fixed plan
It thrives in environments where innovation, speed, and responsiveness are key—especially in software development and digital transformation.
🧱 Waterfall Methodology
Waterfall is a linear, sequential approach with defined phases: requirements, design, implementation, verification, and maintenance. It emphasizes:
Upfront planning
Clear documentation
Predictable timelines and deliverables
Waterfall works well for regulated environments or projects with fixed scopes and low change tolerance (e.g., infrastructure upgrades or compliance-heavy systems).
Why Most Organizations Are in the Messy Middle
If Agile and Waterfall each have clear use cases, why do so many organizations end up blending the two?
Because business today isn’t binary. It’s complex.
1. Legacy Meets Agility
While aiming to create customer-centric, digital-first services that require speed and flexibility (an Agile need), many businesses continue to rely on old systems that require stability and long-term planning (a Waterfall strength).
2. Mixed Maturity Levels
While your finance team continues to work on yearly funding cycles, your DevOps team might work in sprints like clockwork. While your engineers monitor user stories and velocity, your PMO can insist on stage gates and Gantt charts.
3. Compliance and Governance
Agile's lightweight procedures are in conflict with regulatory environments' frequent requirements for traceability, sign-offs, and documentation. You cannot "iterate" your way around data privacy controls or financial audits.
4. Cross-Functional Dependencies
Collaboration amongst several departments, including IT, operations, HR, and marketing, is necessary for modern transformation. Since each may have its own language, tools, and delivery cadence, a pure-play Agile or Waterfall paradigm is not feasible.
The outcome? Hybrid deliveries are becoming more and more prevalent, yet they are frequently inadvertent and chaotic.
The Risks of an Unintentional Hybrid Approach
Blending Agile and Waterfall without clear intent can create more problems than it solves. Here’s what to watch out for:
🚫 Mismatched Expectations
Agile teams may prioritize customer value and speed, while leadership expects milestone tracking and fixed deadlines. This misalignment breeds frustration and mistrust.
⚠️ Bottlenecks and Delays
When Agile teams wait for approvals from Waterfall-governed departments (like risk or legal), velocity stalls. Meanwhile, Waterfall teams struggle to plan against constantly shifting Agile backlogs.
🔄 Endless Replanning
Without a shared delivery model, stakeholders spend more time reconciling reports, redoing forecasts, and navigating conflicting processes than delivering value.
❌ Transformation Fatigue
When no one understands “how things get done,” employees disengage. Change initiatives stall. Innovation slows. And your transformation efforts risk failure.
Making Hybrid Work: Principles for Navigating the Middle
A hybrid approach doesn’t have to be dysfunctional. In fact, when done right, it can offer the best of both worlds.
Here’s how to make the messy middle work for you:
✅ 1. Define Your Hybrid Delivery Model
Don't let your model evolve by accident. Be explicit about:
Which types of projects follow which approach
How decision-making works across teams
What "done" looks like for Agile vs Waterfall efforts
Use frameworks like Disciplined Agile or SAFe (Scaled Agile Framework) to guide hybrid governance.
✅ 2. Align Governance with Delivery
Match oversight to the nature of the work. For example:
Agile teams may still report on progress via value-based KPIs, but not on rigid timelines.
Waterfall efforts might follow a phased-gate model, but integrate Agile input for change handling.
The key: govern for outcomes, not just compliance.
✅ 3. Invest in Change Leadership
Support teams through coaching, training, and role clarity. Equip leaders to:
Facilitate cross-method collaboration
Translate between Agile and traditional models
Foster a shared transformation mindset
✅ 4. Drive Value Alignment Across Functions
Create a shared north star—customer value, not just process efficiency. Whether a team delivers via Kanban or stage gates, they should all measure progress by impact, not output.
Key Roles in a Hybrid World
To manage the hybrid reality effectively, certain roles and responsibilities become critical:
🔗 Bridge Roles
Product Managers: Connect business needs to delivery teams
Business Analysts: Translate across functional lines
Portfolio Managers: Ensure strategic alignment across delivery types
🌍 Change Agents
Transformation Leads: Orchestrate change across teams
Agile Coaches / PMO Leads: Provide tailored support to both Agile and Waterfall efforts
💼 Executive Sponsors
Champion cultural and structural shifts
Remove organizational barriers
Sponsor tooling, governance, and upskilling efforts
Tools and Techniques That Support Hybrid Delivery
Blended approaches require integrated tools and frameworks that speak both languages. Look for tools that support:
🛠️ Tool Flexibility
Jira, Azure DevOps: Great for Agile tracking, with plugin support for Waterfall reporting
MS Project, Smartsheet: Traditional planning tools that now support Agile templates
🔧 Integration Frameworks
SAFe: Combines Agile principles with portfolio-level governance
Wagile (Waterfall + Agile): A lighter-weight, pragmatic mix of the two
📊 Metrics and Reporting
Use dashboards that bridge both worlds—combining sprint metrics (velocity, burn-down) with delivery milestones and financial tracking.
Metrics That Matter in a Hybrid Model
You can’t improve what you don’t measure—but hybrid models demand nuanced metrics.
📈 Agile Metrics
Sprint velocity
Lead time and cycle time
Customer satisfaction (NPS, CSAT)
📊 Waterfall Metrics
Schedule variance
Cost performance index
Milestone completion rate
🔄 Hybrid KPIs
Business value delivered per cycle
Time to market
Dependency resolution time
The goal? Measure value, not just activity.
A Real-World Scenario: The Unintentional Hybrid
Recently, a big financial services company started a digital transformation project. Because the CIO wanted to "go Agile," engineering teams started using Jira boards, sprints, and stand-ups.
However, monthly milestone reports and stage-gated approvals were still necessary for the enterprise PMO. The procurement process followed annual cycles. Documentation up front was required by compliance.
The result?
Agile teams delivered fast—but had to stop every few weeks to explain why there were no Gantt charts
Projects slowed down due to delays in approvals and sign-offs
Executives lost trust in timelines because reporting didn’t reflect real progress
Eventually, the organization paused and re-evaluated. They adopted a hybrid delivery model:
Agile teams continued sprints, with quarterly business reviews
Governance shifted to outcome-based checkpoints
PMO leaders became transformation partners, not just gatekeepers
In six months, delivery velocity improved by 35%. Stakeholder satisfaction increased. Teams were more aligned and less burned out.
Conclusion: Don’t Fear the Middle—Master It
The Agile vs Waterfall debate is outdated. In today’s complex enterprise environment, most organizations live in the messy middle. The key is to stop pretending it's a problem—and start managing it as a strength.
You don’t have to choose one over the other. But you do have to be intentional.
Define your delivery model
Align governance to work types
Equip your teams to collaborate across boundaries
Focus on value, not just velocity
Because at the end of the day, transformation isn’t about methods—it’s about outcomes.