Don't fail at agile: Common mistakes companies make

Published on May 17, 2021

Don't fall into agile traps: Common practices that wreck organizations

Would you rather be a slice of bread in a loaf or a pancake in a stack? Before you answer, let me give you some insight on what bread and pancakes have to do with agile team management for digital-first businesses.

As an agility coach, I use the loaf of bread as an analogy for the traditional workflows where information passes from slice to slice or team to team. If you’ve ever played a game of telephone, you know how information gets lost or misconstrued each time the conversation is repeated. People naturally accentuate some information and downplay other parts of the conversation until the final person, or team, is left with vague directions that lack context. In business this leads to a lot of back and forth that slows work down.

The stack of pancakes shows an agile approach. Each pancake represents a micro unit or team that is end-to-end capable. This means they can go from concept to cash indepently. Think of them as tiny startups within the company. These units can take a problem directly from the customer, solve it, run the solution and be accountable for the results. This reduces the distance from the customer and cuts out all the back and forth by giving each unit the skills and authority it needs to get the work done.

Companies have multiple pancakes in the stack so that failures by one team are offset by successes on other teams. In practice it works like a diversified investment portfolio, yielding higher returns over time. The key is to understand agile well enough that you avoid short-term missteps that can undermine the long-term gains and ruin your stack of pancakes.

Why digital-first businesses are adopting agile team management practices 


“... agile methodologies — which involve new values, principles, practices, and benefits and are a radical alternative to command-and-control-style management — are spreading across a broad range of industries and functions and even into the C-suite.”  — Harvard Business Review, “Embracing Agile” 

People and processes are two key components of the new playbook for the digital-first era. The people businesses need embody what we call the builder ethos — that drive to take good ideas and run with them all the way to production. These are developers, content creators, marketers, project managers and others driven to learn and innovate. Agile processes help businesses maximize the value of these digital builders. 

Agile team management is about removing outdated processes that get in the way of highly-skilled workers. It’s about supporting the talent you have and empowering them to learn and innovate faster than the competition. When done right, agile team management increases team productivity, improves employee satisfaction and results in higher-value products and solutions that give businesses a competitive edge. 

Learn how to increase sales with agile ecommerce software solutions

Is your company ready to adopt an agile team management approach?

For companies transitioning from a traditional team management model to agile practices, it can be helpful to start with areas of the business that have favorable conditions for an agile approach

How to assess change aversion and agile readiness

The biggest challenges to agile are usually associated with leadership and culture. The C suite has fears that they hide behind a strong face and people can advocate for agile without fully understanding what that will look like in practice. As agile changes the status quo, leaders and builders can become averse to change as a coping mechanism. Try these quick readiness checks to assess change aversion and agile readiness:

Are you willing to change performance reviews to align with the principles of agile? Your definition of performance should change when you 'go agile' — and thus your performance review process should change. This is a great readiness test because it touches so many parts of the organization: people, finances, managers, etc. 

For agile to succeed you need to change the incentive that governs behavior. Legacy organizations define performance by cost and output. Agile organizations work with fixed budgets (each 'sprint' or 'team' is an upfront cost) and focus on maximizing outcomes.

When you walk into a room does everyone have eerily similar job titles?  If every title starts with marketing something, then it's a silo. Agile takes people out of functional silos and creates customer-focused, multidisciplinary teams that take a problem, develop a solution and execute it end-to-end. This is a big shift for companies that have little practice with cross-functional teams.

Do you understand the different flavors of agile? Agile is not one size fits all. Before you get started, teams and business leaders should learn about the different agile tools and methods. This article from Harvard Business Review includes a helpful chart of how the advantages and challenges of different agile methods suit different work conditions and cultures. 

Five common practices that undermine agile team management

Even when conditions are favorable, as they were when I joined Contentful as their first agility coach, it takes dedication to implement agile practices without slipping back to the more familiar status quo. Be on the lookout for these five common agile traps:

Leadership is not ready to embrace agile

  • Warning signs: Leaders who are resistant or don’t fully understand agile, can start to micromanage agile teams, which undermines the benefits of agile and takes senior leaders away from higher-value work. These behaviors include second-guessing team decisions, adding layers of control, setting deadlines instead of priorities and pulling people out of agile work to attend meetings. Watch our fireside chat featuring Dion Hinchcliffe, VP and principal analyst at Constellation Research, for insight on leading high-performing by example.

  • How to course correct: Getting leadership on board starts with education and one of the best ways to learn is by doing. Encourage the C suite to take an agile approach to some of their own work. C-suite leaders can form agile teams around strategy and organizational challenges or opportunities. This can help break managers out of silos and build an appreciation for the language and principles of agile team management. Leaders who practice agile can better understand what behaviors will help or hinder their agile teams.

Focusing on small drivers instead of agile’s bigger benefits 

  • Warning signs: When leaders fixate on cost reduction, quality, productivity or any single metric they can miss the bigger value that agile delivers to the organization. Teams might be adopting agile in pockets, but unless the organization leverages those healthy teams, all they get are small gains. The biggest benefit of agile happens at the organization level: Agile changes the way companies respond to stress. Instead of crumbling under pressure, agile teams learn, respond and thrive. We call these antifragile organizations. This is hard to measure with traditional KPIs, but it’s easy to see in practice. They’re the companies that easily shifted to remote during the pandemic. They’re the companies that explore and thrive in uncertain markets. They have the resiliency to fail, learn and grow back stronger.

  • How to course correct: First, teams need to understand that the value of agile isn’t realized by checking off a list of requirements, meeting due dates, or doing all the things. The value comes from the insights and learnings that happen as you practice agile. It's following new ideas, experimenting and learning faster. Measures such as speed of innovation, time to production and stickiness or success of the end product can more closely tie agile to business outcomes. Be prepared to experiment with different measures and let them evolve with your business.  Learn how Contentful identified four key metrics for software development.

Starting with big disruptive change  

“Large companies typically launch change programs as massive efforts. But the most successful introductions of agile usually start small.” — Harvard Business Review, “Embracing Agile” 

  • Warning signs: Most change programs identify a desired change or end state, apply those standards company-wide and then try to stabilize the resulting disruption. For example, a company might undertake a reorg*, implement enterprise-wide agile tools or mandate changes in workflows as a first step to adopting agile. Don’t do this. Forcing agile onto the entire organization is likely to create resistance to change and misses the agile principles of experimenting and iterating to see what works for your company. 

  • How to course correct: Use agile practices to become agile. Start where you are and look for places within your organization where agile is most likely to grow. Implement pilot programs and safe-to-fail experiments to see how your organization behaves. Start small with teams who are willing to pilot agile practices. Contentful started with a pilot to compare approaches. As the teams involved became proficient with agile practices they served as evangelists within the company. By sharing their experience and success they helped advocate for agile and drive culture change in a more organic, less disruptive way. 

*A word of caution: While changing the organizational structure shouldn't be your first step, companies should expect and encourage the organizational structure to evolve. By far the most common mistake is keeping the old reporting structures in place. Rigidly sticking to a marketing department, a product department, an engineering department and a support department will get in the way of building teams that can independently market, manage, deliver and operate solutions. 

Applying agile too broadly or too narrowly

  • Warning signs: Agile isn’t the best approach for every aspect of a business. For example, you probably don’t want your legal or accounting teams to embrace failure too tightly. On the flip side, applying agile to just one team or project can curtail the business benefits. Imagine a car manufacturer that optimizes windshield production. This won’t impact business outcomes if the rest of the process is still going at the same pace.

  • How to course correct: Aim for the right level of agility at the right time. Companies need to balance their ambition with their capabilities to avoid overspending or underspending on agile. Agile requires investment in transition so choose places where it is easier to implement and likely to add value to the business as a whole. Think about aspects of the business where creativity can help solve complex problems and where it is safe to make and learn from mistakes. Don’t force agile into routine processes and operations that typically operate well in a command-and-control model. 

Rigidly adhering to a specific agile approach

  • Warning signs: Trying to implement agile “by the book”  misses the point of agility. Agile is a set of principles that can be supported by a number of different agile tools and techniques. No one approach is going to be right for every company or even for every team within a company. Initially, companies will want to experiment with proven agile methods and might guide teams in applying specific practices, but being too strict in controlling how these methods evolve can stifle the innovation that agile fosters.

  • How to course correct: Agile lends itself to an approach in which you seek to understand the how and why behind the principles so that you can experiment and make it your own. As teams develop proficiency with agile, encourage them to use agile principles to develop their own agile style, even if that means agile looks different from team to team. It's those differences and diverse capabilities that make companies stronger and more resilient. 

Tips for successfully implementing agile team management

2021-05 Agile Traps that Wreck teams Infographic-A
  • Learn about agile. Get training from leadership on down.

  • Invest in expertise. Contentful started with a consultant and has in-house agile coaches.

  • Measure outcomes. Align success metrics and performance measures with agile principles.

  • Adapt the principles of agile to your business and teams. Keep changes consistent with the principles and measure impact to make sure they are improving not hindering outcomes.

Contentful is the content platform of choice for businesses making the pivot to become agile, digital-first businesses. Measure your digital maturity and learn how to move further along the digital continuum. Download The digital transformation maturity model

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Garbrand Molen

Garbrand Molen

Organizational Agility Coach, Contentful

Organizational agility coach at Contentful

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