Agile Transformation Challenges

Ruth Hadari
Ruth Hadari
Agile Advocate, Engineering Ops Expert
Posted on
Sep 20, 2022
Updated on
Sep 22, 2022
Table of Content

6 Missteps That Slow Down Change and How to Overcome Them


In case you haven't heard, Agile is all the rage these days. In theory, Agile transformation should be simple: start with a pilot project, show some success, and then scale that success across the enterprise. But in practice, it's not always that easy.

Several challenges can trip an Agile transformation, resulting in a slower-than-expected rollout or even complete failure. Teams can fall into old habits, managers can be resistant to change, and company culture can keep things from moving forward.

If you are considering embarking on an Agile journey, there's good reason to be aware of these challenges and to have a plan for overcoming them. Without experience, it can be difficult to know where to start or what might lie in front of you.

Below, we will examine:

  • What Agile is
  • What an Agile transformation looks like
  • Why teams go through Agile transformations
  • Common mistakes and how to fix them

Ready? Let's dive in.

What is Agile?

In software development, Agile is an iterative, incremental approach to project management and software delivery that emphasises flexibility, collaboration, customer feedback, and rapid responses to change.

In simple terms: with Agile, instead of trying to do everything all at once (which can lead to scope creep and budget overruns), you break projects down into smaller pieces. This way you can deliver value more quickly and easily make changes along the way based on customer feedback.

Agile Key terms

There are a few key terms you should know before we dive into the challenges of Agile transformation.

  • Scrum: A specific framework for Agile that includes roles, events, and artifacts.
  • Scrum Master: The individual responsible for helping the development team adhere to Scrum values, practices, and rules.
  • Sprint: A time-boxed period (usually two weeks) during which a development team works to complete a set of deliverables.
  • Product backlog: A list of all the features, functions, and tasks that need to be completed to launch a minimum viable product (MVP).
  • Kanban: A lean approach to Agile that emphasizes continuous delivery and visualization of work.
  • Extreme programming (XP): A software development methodology that includes practices such as test-driven development, pair programming, and continuous integration.
  • User story: A description of a specific functionality from the user's perspective. User stories are typically written in the format "As a [type of user], I want [some goal] so that [some reason]."
  • Acceptance criteria: The specific criteria that a user story must meet for it to be considered done.

These are the most common Agile frameworks and methodologies, but there are many others. The important thing to remember is that Agile is not a one-size-fits-all solution. Teams should tailor their approach to fit their specific needs and goals.

What is an Agile transformation?

An Agile transformation is a process of adapting an organization's culture, processes, and structure to support Agile values and principles.

This can be a daunting task. Agile transformations often require changes at every level of the organization, from the individual contributor up to the C-suite. That can make it difficult to accomplish without buy-in and support from the top.

But when done correctly, an Agile transformation can lead to increased efficiency, better quality products, and happier employees.

Why do teams go through Agile transformation?

The most common reason teams embark on an Agile transformation is to improve their speed and quality of delivery.

In today's business environment, customers expect faster turnaround times and more frequent updates. They also expect higher quality products with fewer bugs. To meet these expectations, organizations need to be able to deliver value quickly and iterate based on feedback.

Agile transformations can also help organizations become more efficient and save money. By breaking projects down into smaller pieces, teams can avoid the sunk cost fallacy and waste associated with traditional, waterfall approaches.

Finally, Agile can help create a more positive work environment. When done correctly, it gives employees more autonomy and ownership over their work. This can lead to increased job satisfaction and engagement.

How can a team fix a bad Agile transformation?

There are several mistakes that teams can make during an Agile transformation. Here are six of the most common ones, along with advice on how to avoid them:

Teams, leaders, and management not communicating

One of the most common mistakes is not having a clear plan or roadmap for the transformation. Teams, leaders, and management need to be on the same page from the start.

There should be a shared understanding of what Agile is and why the transformation is happening. This will help ensure that everyone is working towards the same goal.

It's also important to communicate regularly throughout the process. As team members begin to adopt new Agile practices, they will likely have questions or feedback. Leaders should be open to listening and making changes where necessary.

Remember these three things:

  • Have a clear plan and roadmap from the start
  • Communicate regularly throughout the process
  • Be open to feedback and making changes

If you can do these things, you'll be much more likely to have a successful Agile transformation.

Having no shared vision/goals

Another mistake teams make is not having a shared vision or goal for the transformation. Without a clear destination, it can be difficult to stay on track.

It's important to set concrete goals for the transformation and ensure that everyone is aware of them. These goals should be specific, measurable, achievable, relevant, and time-bound (SMART).

It can also be helpful to create a vision statement that articulates what the team wants to achieve. This will provide a North Star to guide decision-making throughout the process. 

If you are a small business, there's a good chance your organization hasn't used a vision statement in the past, so let's look at a few examples.

  • Microsoft: "To help people and businesses throughout the world realize their full potential."
  • Apple: "We believe that we are on the face of the earth to make great products and that’s not changing."
  • Tesla: "To create the most compelling car company of the 21st century by driving the world’s transition to electric vehicles."
  • Amazon: "To be Earth’s most customer-centric company, where customers can find and discover anything they might want to buy online."

No management/senior buy-in

Not getting buy-in from management or senior leaders can be devastating for any proposed transformation. Without their support, it will be difficult to implement Agile successfully.

Management needs to be on board from the start. They should understand the benefits of Agile and be willing to make changes to how they operate. This might include things like giving teams more autonomy or changing budgeting processes.

Senior leaders also need to be supportive. They should provide resources and funding for the transformation. They should also be willing to make changes to company culture if necessary.

To achieve this, you have to be able to make your business case for the process. When building it, focus on:

  • What the Agile transformation will accomplish. List achievable and realistic goals. For example, "We want to decrease our average time to market by 30%."
  • What the Agile transformation will cost. Include both the monetary and opportunity costs. Make sure to address any concerns about potential risks.
  • How you will measure success. Define what success looks like for your organization. Be as specific as possible. For example, "We will know we are successful when our average time to market decreases by 30%."

If you don't get buy-in at the start, it might not be possible to implement Agile successfully.

Not understanding the true principles of Agile

Many teams think they are being Agile when in reality they are only following a few of the principles. To be successful, it is important to understand what Agile is and how it can benefit your team.

Four main values underpin the agile manifesto: 

  • Individuals and interactions over processes and tools
  • Working software over comprehensive documentation
  • Customer collaboration over contract negotiation
  • Responding to change over following a plan

If your team is not adhering to these values—regardless of what other measures you are implementing—you are not being truly Agile.

To fix this, start by reading the manifesto and discussing it with your team. Once you have a shared understanding of what Agile is, you can begin to implement the principles in your daily work.

Not trusting your teams to self-organize and self-manage

This means giving them the autonomy to decide how best to complete their work, without micromanagement from management.

However, many managers find it difficult to let go of control and trust their teams to do their job. This can lead to tension and conflict within the team, as well as a feeling of being stifled creatively.

To fix this, start by discussing with your team why you are going through an Agile transformation. Explain that part of this is giving them the freedom to self-organize and self-manage.

Once they understand the reasoning, it will be easier for them to buy into the change. You can also put processes in place to help them transition, such as Scrum or Kanban.

Rushing the transformation

Another common mistake is to try and implement Agile too quickly, without taking the time to understand it properly or plan for the change.

This can lead to a lot of confusion and frustration, as well as a feeling that the transformation is being forced on them. It can also make it difficult to sustain the transformation in the long term.

To fix this, take the time to educate yourself and your team about what Agile is and how it works. This will help everyone to be on the same page and buy into the change.

It's also important to create a realistic plan for the transformation, with milestones and timelines. This will help to avoid any surprises along the way and keep everyone on track.

By the time you start implementing changes, you should have:

  • A clear understanding of Agile
  • Buy-in from everyone on the team
  • A realistic plan in place
  • Milestones and timelines for the transformation
  • A way to measure progress
  • A clear understanding of what success looks like
  • A plan for sustaining the transformation

Without even just one of these in place, you're likely to run into trouble.

Final thoughts

Agile transformation can be a daunting task, but it's important to remember that you don't have to do it alone. There are several tools and resources available to help you along the way.

One such tool is GoRetro, which helps teams retrospect and learn from their mistakes. GoRetro provides a safe space for team members to share honest post-Sprint feedback about what isn’t working well. This feedback can then be used to improve the Agile transformation process.

Make sure to check out GoRetro's resources for more information or sign up for free today. 

About the author

Ruth Hadari
Agile Advocate, Engineering Ops Expert

Highly experienced in leading multi-organizational teams, groups, in-shore as well as off-shore. The go-to person who is able to simplify the complex. An agile advocate, experienced in all common methodologies. Responsible for the entire software development lifecycle process from development, QA, DevOps, Automation to delivery including overall planning, direction, coordination, execution, implementation, control and completion. Drives execution, and communicates on status, risks, metrics, risk-mitigation and processes across R&D.

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