The Challenges with Agile

Recently I got asked by Knowledge Train what I consider the most common challenges with Agile projects. These are projects that have such a high rate of uncertainty and complexity on how and what to build, an Agile approach is necessary. Together with 5 other authors we answered this question and merged it into an ebook. You can download this ebook for free via the website of Knowledge Train or my personal website.

In this blog post I’ll share some of our insights and lessons learned with Agile projects. Want to know all of them? Check out the ebook with articles from Emanuele Passere, Andrea Fryrear, Martin Wickman, Mario Lucero, Tanner Wortham, and myself.

Emanuele Passera

The organisation isn’t ready for Agile

The most common challenge I usually face during a transition to agile is when the organisation isn’t ready for the application of agile. The second challenge is that it is not always easy for the business side of a company to engage. Agile project management simply cannot fit every organisation. They already need to have the correct enterprise environmental factors in place to apply an agile approach successfully. Alternatively, you must receive strong commitment from senior management.

Andrea Fryrear

“We can’t mess up or the Scrum Police will come and take us away.”

I think with Scrum in particular there’s a fear of doing it “wrong,” especially among marketers. We have a sense that it’s a sacred way of working that we can’t mess up or the Scrum Police will come and take us away. But really every team — dev, IT, or marketing — makes adjustments as they go along. That’s the whole point of continuous improvement.

Martin Wickman

“Too trusting of early estimates.”

It’s hard to accurately estimate software tasks. Really hard. Organisations often request estimates that span months or even longer. In my experience, new development teams can estimate a couple of days’ work with precision, a week with some luck and maybe two weeks with some dignity still intact. More than that, and we’re entering unknown territory and are pretty much guaranteed to be wrong. That’s just how it is and we need to accept that. Unfortunately, estimates are often given as deadlines to the customer which then expects the team to deliver on the mark.

But the nice thing here is that self-organizing teams do become better with time and practice. Give them two-three sprints, allow them to fail, allow them to grow and allow them to learn. After a while, estimates will get better and the team’s velocity becomes stable enough to make more educated projections.

Note the word projection here. The idea is to be able to say something like: ”We’re confident that we can finish these 20 stories, and we’re 60% certain that we can complete 25 stories, but it’s near impossible to finish all 40 stories”. Now the organization can make real business decisions based on reasonable projections.

Mario Lucero

“Lack of agile culture.”

If a company wants to adopt agile they must build a culture to support the agile principles. Everybody has to pursue one common and big goal – the company goal.

I have come to realise that, in many companies, each business unit is concerned only in achieving his targets. Most of the time, the employees achieved their goals, but as they did not work as a team, the goal of the business wasn’t reached. To avoid each employee being concerned only about business unit metrics, you have to adopt the mantra: Collaborate, Collaborate and Collaborate.

To adopt agile successfully, it is also necessary to have a culture of transparency that improves the morale of employees. For instance, there are companies (unfortunately not many) in which employees know how much their coworkers earn or salaries are listed publicly.

Agile is about mindset, but it is being corrupted by approaches which put more emphasis on tools and processes. The key to the mindset is the ability and willingness to learn. In a complex world, your only chance for survival is learning.

Tanner Wortham

“Scrum is a problem-finding, not a problem-solving framework”

When Scrum is first introduced to an organisation, it exposes a great deal of dysfunction. This is intentional. People solve problems, new processes and new tools don’t. When’s the last time you’ve seen a hammer swing itself? I think you see my point. Often, this dysfunction is attributed to the organisation’s Scrum adoption. After all, we didn’t see all these problems until we adopted Scrum so Scrum is obviously the problem. If we do away with it, these problems will go away. Nothing could be further from the truth.

Barry Overeem

“Truly embracing the values and principles of the Agile manifesto.”

Every organisation wants to be agile. Every organisation wants the necessary agility to deal with the increasing rate of volatility, uncertainty, complexity, and ambiguity. The Agile Manifesto offers 4 values and 12 principles to support organisations build software/products in such a complex environment. Many organisations acknowledge these values and principles. However, ensuring the right side of the Agile Manifesto truly enables and strengthens the left side is the #1 challenge with agile projects. It’s a challenge organisations must deal with, otherwise projects with a high rate of complexity and unpredictability are bound to fail!


In this blog post I’ve shared some of the challenges that often occur with Agile projects. A more comprehensive description can be found in the ebook “The Challenges with Agile”. Consider this article therefore as a teaser and trigger to download the free ebook. I hope you enjoy it and offers you some useful insights.

What do you consider the most common challenge with Agile projects?

One thought to “The Challenges with Agile”

  1. This is quite an interesting look at the current challenges that we face when it comes to the Agile Methodology. We agree with the points made here such as that some organizations are not yet ready for using agile. Thank you for sharing this useful article.

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