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Last updated: Mar 30, 2023

How to ensure smooth sailing on your waterfall-to-agile transition

Author: Jack Foraker
Last updated: Mar 30, 2023
What's inside

When you picture a waterfall, what comes to mind? The roaring curtain of Niagara Falls? The lone, sheer drop of Yosemite Falls? The brook tumbling over rocks on that last great hike you took?

Or the prospect of tearing your hair out with never-ending requests for changes and chronic deadline creep?

If a slow-but-thorough development lifecycle is slowing down business a little too much, then read on for suggestions on how to make the leap from traditional, sequential software development methodology — “waterfall” — to its alternative: agile software development, which has traction with both startups and fast-growing companies for short development cycles, speed, flexibility, and its, well, agility.

The difference between waterfall and agile development

First, a little history: There are good reasons why waterfall, which breaks projects down into distinct phases, was the go-to methodology for decades, despite it being a bit plodding and rigid.

“Looking back twenty or thirty years, building, testing, and releasing software was a much more tedious process,” says Vention West Coast CTO Dave Hecker, “Software was a special, expensive undertaking, mostly done by governments, big companies, and the military.”

Without rapid prototyping and with costs high, the best way to manage risk was planning excessively and completely — every step of the way. Distinct phases are the hallmark of waterfall development, and each phase needs to be completed before moving on to the next.

That works well enough in slow-moving environments where delays might be the norm anyway and punishing documentation requirements are de rigueur, but with the explosion in software development and startups, the snail’s pace of waterfall’s methodical approach became the antithesis of what companies needed in order to get to market fast and build out a custom feature. Adaptability, short development cycles, regular feedback loops, speed, and continuous integration and delivery: As web-based applications took off, those were imperatives for companies to be competitive and successful.

Enter history’s only game-changing après ski, where the Agile Manifesto was drafted by a group of veteran developers. It was a declaration that celebrated twelve principles that upended the waterfall — as well as a shot heard round the software world.

Agile development, they posited, is iterative and incremental, involving regular feedback loops that help teams respond to change quickly and easily. Importantly, it also involves stakeholders — including people from the business and operations side of the house — in every step of the project lifecycle, rather than at the beginning and end, as in waterfall methodologies. Stakeholders can provide regular feedback and guidance to the engineering team at every step of development, reducing inefficiencies and streamlining the entire process.

In other words, it’s designed for the way software development happens today.

At its core, agile development is all about being flexible and adjusting as you go. There are lots of good reasons for using agile methodology: It infuses a team (or an entire organization) with an ethos of operating smarter and faster, it cultivates a mindset of ongoing improvement, and it often results in happier team members. All of that adds up to a better product.

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Best practices for a smooth transition

With agile development, changes can occur very quickly, with much tighter collaboration among teams. But to make the waterfall-to-agile transformation a success, some tools are essential:

  • agile workflow tools
  • version control
  • continuous integration and delivery tools


Beyond these tools, workflows like sprint planning, daily stand-up meetings, sprint reviews, and retrospectives can also help ensure a smooth transition to agile development.

Effective communication is key during the transition, so make sure everyone on the team is on the same page and understands their roles and responsibilities. Training is also essential to ensure that everyone understands the new processes and tools. Add in strong project planning and your team will be even better prepared to stay on track and deliver projects on time and within budget.

One important aspect of transitioning to agile development is the need to adjust team roles and responsibilities. In a waterfall development process, team members are often specialized in their roles. There’s not much elbow room. In contrast, in an agile development process, team members are expected to be more cross-functional, working collaboratively on all aspects of the project, rather than siloed.

Another critical piece of successful agile development? “The concept of ownership,” notes Dave. “Agile requires rapid decision-making in a group environment.”

With waterfall development more common in bigger organizations, decisions can end up watered down, and teams can resist owning any one decision. But with an agile process, there’s more of a sense of collective responsibility. “Everyone needs to have skin in the game and a team approach to make decisions together, quickly,” Dave says.

Common challenges and pitfalls to avoid

Transitioning to agile development requires a culture of continuous improvement. Such is the norm in startups and other smaller, nimble companies — less so in established and legacy businesses. In an agile development process, with the emphasis on regular feedback loops and continuous improvement, teams must be open to feedback, willing to experiment and try new approaches, and committed to learning and growth. Indeed, a so-called “growth mindset” is a fundamental ingredient.

The most common challenges during the waterfall-to-agile transition include resistance to change, lack of buy-in from team members, and difficulty adapting to the new processes and workflows. In other words, everything that might already be slowing down your development lifecycles.

To avoid these pitfalls, involve everyone on the team in the transition process, provide training and support, and be open to feedback and suggestions as the transformation unfolds.

Stay clear-eyed as the process unfolds

Scope creep is another challenge during the transition. Because agile development allows for greater flexibility, it's vital to establish clear project goals and scope to prevent projects from becoming too large and unwieldy during the iterative process. Having a clear understanding of how agile development will impact project timelines and budgets is a good way to manage scope creep and ensure developments don’t balloon into processes too ambitious to succeed in a timely manner.

“Because there are no guardrails in agile, and because anything can be changed as each sprint is planned, it’s easy to wind up in a development death march,” according to Dave. (Fortunately, the classic SCRUM/agile approach controls for this when executed properly, as all stakeholders and team members should be aware of and in agreement about any changes to the plan.)

He says that it’s important to avoid stuffing each sprint with new features at the expense of refactoring, testing, release, and refinement. “Normally a product owner will be the main voice when it comes to staying on track, but it’s a collaborative process.”

Transitioning from waterfall to agile development can be a challenging process, but with the right tools, workflows, and best practices, it can also be incredibly rewarding. By following best practices and avoiding common pitfalls, engineering leaders and CTOs can ensure a smooth transition to agile development, resulting in more efficient teams, better project outcomes, and a happier, more satisfied workforce.

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