It’s no longer a mystery that agile was created as a response to the various concerns that the traditional waterfall methodology brought to both project managers and teams of an organization.

There isn’t any doubt that agile focuses on helping teams to deliver faster and better products and services. 

But it does come with a lot of challenges that need to be well handled by the organizations adopting an agile approach. 

Let’s today look at some of the challenges of agile transformation and get ourselves ready to fight back. 

To maintain a proper alignment on the objective and value of an agile transformation

What do you understand about agile? Well, it can be considered fundamentally as a redesign of the operating model of an organization. 

It is often observed that organizations mindlessly begin agile transformations without even first prioritizing alignment among the leaders on the objective and value of such transformations. This is one of the biggest challenges a company faces while adopting an agile transformation. 

Let’s say sometimes even if there is an alignment, it is found that different leaders adopt different approaches within the organization for executing agile which leads to messing up the entire transformation process. 

Agile transformation necessitates proper alignment on a high level regarding the ambition, the value it wants to deliver, and a logical plan in order to successfully accomplish the process. 

Once the value drivers are being recognized, then they are appropriately used throughout the transformation process, starting from guiding the operating model design to offering value delivery, to creating metrics to keep an eye on value capture in the time of rollout.

For better clarity, here is an example. A large global company actively adopted agile transformation without first aligning on the end-state ambition and the value the transformation process would possibly create. 

The transformation resulted in limited impact since different teams of the company applied agile principles to different degrees and in various flavors, which led to an important increase in the overhead of managing over teams. 

Also, the unavailability of alignment on the value of the transformation proves that the teams happen to spend very little time thinking through and keeping a track of the value their efforts and endeavors would offer. 

To consider agile transformation as a strategic priority 

Very often it is observed that organizations fail to consider agile transformation as a strategic priority and restrict agile to pilots within a small part of the company, with a limited set of leaders. 

Although the pilot is often successful, its impact is limited to a few technologists or a few teams of the organization. 

This restricted nature of the pilot time and again stops the executive team and CEO from attaining the far-reaching influence or impact and strategic value a wider agile transformation could have. 

Well, it won’t be wrong to start the agile transformation within let’s say a small part of the organization, but you are not supposed to stop there and simply treat it as a strategic priority for the company. 

If you are able to take agile beyond little experiments, that’s where you find the real benefits. 

For instance, a big North American company tried to execute agile in its technology organization that includes more than 1,000 people. 

Whenever the business executives were asked about agile, they said that they had very limited knowledge and the project upon which the technical team is trying to execute agile is not known to them. 

So, the impact remained very limited till 18 months into implementation, and then surprisingly, one of the senior vice presidents began to take an interest, adopt, understand, and make some significant changes to his business practices in order to correspond to the more agile technology organization. 

Therefore, this resulted in an organization-wide transformation, while recognizing agile as one of the top five organization priorities. To know more, read the business impact of agile transformation.

To prioritize culture first over anything else

One of the toughest challenges of an agile transformation is to emphasize culture first over everything else. 

Let me tell you that successful transformation needs not only top-down change in the process of working at the team level but also requires a change in the process the executive level operates since it has an unfair impact or influence on the culture of the enterprise. 

Culture can be considered as the king, as expressed by a senior executive while mentioning the formula of success for an agile transformation. 

On the contrary, an agile transformation can allow driving important cultural changes that were wanted, enabling an increase in customer-centricity, learning, collaboration, and many more. 

These gains can be attained by giving up some of the preexisting manners of working. 

For instance, a big North American company began an agile transformation and actively hired various agile coaches in order to support teams. But in one of the businesses, leadership continued working within the patterns of the old culture. 

This led to an ignorance of empowering teams and a requirement of complete designs of the end product and project-management-office-style status reports every week. 

Within the same enterprise, leadership in another business adopted a different approach and emphasized changing the culture. Also, the leaders were seen empowering product owners and minimizing bureaucracy. 

After the completion of a one-year effort, the former business witnessed minimum progress, while the latter could successfully release several minimum viable products.

To smartly invest in the right talent  

Sometimes it becomes very challenging to find the right talent for your organization to successfully accomplish the agile transformation. Since talent can be regarded as the fuel which powers the agile machine. 

But unfortunately, you will find that in many traditional companies, talent strategy isn’t prioritized and is rather considered as an afterthought of an agile transformation process. 

For instance, a midsize global company looked for prioritizing customer centricity as part of the agile enterprise. 
To accomplish this particular goal, the client planned to build a “design function” from 0 to more than 25 designers in several roles over various customer journeys. 

Such an ambition needed talent and recruiting strategy, interviews, and a perfect approach to find the right talent. 

But due to the absence of such thorough planning via these discussed steps, seven months through the transformation, the client not just struggled in recruiting new potential designers to the function but even went through attrition among the present designers due to the absence of role clarity. 

To think through the speed and strategy to successfully expand beyond pilots

One can pilot agile in small parts of an enterprise, where resources can be deployed over the enterprise in order to support the pilot and make it a huge success. 

Although, scaling over a wide cross-section is a whole different story that needs planning in advance. 

It is important that one must give a thought to the readiness of the enterprise, leadership bandwidth, resource restrictions, and the speed of the transformation, among other things. 

All these plans are required to be adjusted depending on learnings via execution. Companies at times fail to follow such an ideal approach and end up struggling within the transformation process.

For instance, a midsize global company had planned its agile transformation around five waves. 

But it didn’t spend sufficient time thinking about the scale of leadership bandwidth that would be needed and the effort required in recruiting for the new agile enterprise. 

So, after completion of the first two waves, the enterprise was bound to reconsider the speed of its agile transformation and to extend it to seven waves.

To prioritize supporting tools and core management processes 

It is seen that agile is taken as an approach for managing projects. 

Also, it is very essential to identify that in order to operate using agile methodology, the teams need changes to core management processes and the supporting tools to which a team has access, among all other things. 

But this sometimes proves to be a challenge for some organizations as they fail to do so. 

For instance, iterative development also needs iterative funding. Well, this is a concept that can be difficult to understand for many traditional businesses. 

A large North American company required estimates of each project in respect of the investment needed and benefits anticipated when the project came to an end. 

Although the early and initial estimates are advantageous, a dogmatic approach brought fear among the product owners, also resulting in fights among the teams over some hypothetical financials, and causing huge organization-wide confusion. 

To infuse iteration and experimentation into the organizational culture 

Iterative development can be considered as one of the characteristics of an agile transformation. 

Well, for the start-up this comes very naturally, which doesn’t have an established product and requires testing and learning to build one, but it is more complicated to grasp for a company that has more than one product line which holds a good reputation in the market. 

This can also be applicable to something beyond product development. Let’s say, how your company prepares, for instance, product launch strategies, business strategies, and suggestions to the leadership team. 

You will see that very often efforts are simply spoiled by teams who are operating in a vacuum, then assuming what stakeholders may want to see, or even implementing the wrong plan instead of actively engaging stakeholders throughout the procedure to attain regular input and make sure that the team is focusing well on the right things. Read product mindset vs project mindset to know more.  

One another aspect that often restricts experimentation can be the rigid application of the scaled agile framework. 

Very often organizations tend to shift the focus of an agile transformation away from minimizing procedures and changing behaviors and mindsets to allow innovation, and placing the perfect framework. 

In fact, frameworks prove to be beneficial in offering a proper structure to the transformation, it is also essential to not be rigid in their adoption and to ponder upon how well they can be adapted in order to suit the requirements of the company. 

Therefore, iteration and experimentation are very important for successfully conducting the agile transformation which the companies find difficult to grasp and end up struggling really hard during the process.

To give up the practice of servant leadership

It is observed that conventional leadership styles often dictate people about what to do and what not to. But when it comes to an agile environment, such leadership styles do not go well and instead cause harm to the transformation process. 

In fact, it is advisable that leaders remove every sort of obstacle and enable the team to focus well on agile best practices and approaches. This can be challenging for the organizations but they need to prioritize it and make it work. 

Learn more:

• Understanding technical leadership
• What business leaders should know for a successful legacy modernisation
• Choosing transactional analysis for great leadership

To provide the necessary training upon implementing agile transformation

Supposedly, if your team is not well experienced with Agile practices, then it can be really challenging. 

It will be unfair to have expectations from people to suddenly change their behaviors and habits, come out of their comforts and become Agile specialists without any formal training. 

Therefore, it will be the company's utmost responsibility to provide proper training to its employees and make them capable of successfully implementing the agile transformation.

To normalize change after successfully conducting agile transformation

People usually are hesitant to change and at times change can cause stress, fear, and anxiety. 

Agile needs buy-in from everyone, however with such a large-scale and deep change, many employees of your company might be hesitant to make the change. 

It’s very normal to see such kinds of discomforts among people but in situations like that, you will have to give them a sufficient amount of space for adapting to the new way of doing things. 

You need to give time to your company in order to adjust while emphasizing the advantages of agile, how it will enhance the way they work, and how business owners and leadership will provide support to the team. 

Just keep in mind that the success of your agile transformation mainly depends on every single person embracing agile adoption irrespective of their role. 

I agree that agile transformation in any organization can be time-consuming and one has to pass through various challenges to successfully execute the process. But amidst the challenges, the organizations that are willing to learn, unlearn and relearn new procedures and approaches can fully embrace the transformation.