Learning from Mistakes That Cost Digital Transformation Project Managers Their Jobs [Career Advice]

Written By: Eric Kimberling
Date: July 3, 2023

"You're fired." Those are two words that no project manager hopes to hear. However, one of the frequently asked questions from our clients is why project managers get fired, why their job is so challenging, and what are the common reasons behind their termination.

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One of the roles we frequently work with among our clients is project managers. Our primary focus is advising project managers, along with other individuals, to ensure their success in digital transformations.

However, project manager turnover is significant in complex and challenging digital transformations. Today, I aim to discuss the common reasons why project managers often struggle and fail in their roles. My goal is to provide guidance, input, and career advice to help you avoid the pitfalls and mistakes frequently made by project managers.

Why Project Managers Are Under Pressure

The project management role in digital transformations is known for its challenges, necessitating an understanding of the underlying factors. Project managers find themselves in the center of a perfect storm, facing high expectations and accountability from executives. They often become the scapegoat for any issues that arise during the transformation, intensifying the pressure they experience.

Furthermore, project managers must navigate diverse project teams, where alignment on the transformation's direction may vary. This creates additional pressure from the bottom up. Additionally, employees throughout the organization often struggle with change and tend to attribute their day-to-day job challenges to the project manager, further holding them accountable.

The complexity of digital transformations, with numerous moving parts, adds to the demanding nature of the project management discipline in this context. Recognizing these difficulties and the lofty expectations placed upon project managers is crucial.

Now, let us explore strategies that can help you overcome these complexities, difficulties, and challenges to ensure your ultimate success in your project management role.

Poor Project Management

One of the primary reasons for project managers' failure in their role is poor project management. By poor project management, I mean inadequate management of the project's scope and budget, neglecting the fundamental aspects of project management.

These projects are significant and complex endeavors with various interrelated components. They encompass a wide range of work streams, including technological aspects such as software deployment, data migration, and integration. Additionally, there is a focus on managing business processes and ensuring alignment between software and processes. Another critical aspect is managing organizational change, which is arguably the most crucial part. This entails ensuring people are onboard, providing adequate training for new processes and systems, and clarifying changes and new roles.

The digital transformation process involves significant unpredictability and complexity, encompassing various moving parts, dependencies, milestones, and resource needs. Managing all these aspects can be overwhelming for any individual. Consequently, poor project management, the inability to maintain a comprehensive understanding and control over the project, becomes a core reason for project managers' failure.

While having certifications such as PMP and formal project management training can be beneficial, effective digital transformation project management requires both an art and a science. Many project managers fall short in mastering this balance, which we will discuss in detail shortly.

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Art vs. Science of Project Management

Digital transformations differ from other types of projects due to the combination of art and science involved in project management. Merely following a Gantt chart and ticking off milestones is not sufficient. There exists a qualitative aspect that requires extensive experience. It is not just about completing tasks but understanding whether they were completed in line with industry standards and with the potential for success.

As a project manager, it is possible to check off tasks that were completed poorly, without comprehending the nuances of success and the actual fulfillment of a task. To succeed in project management, one must grasp the distinction between the art and science of the discipline. Unfortunately, organizations often prioritize the science of project management, providing training only to improve technical capabilities, while neglecting the artistic aspects required for success.

Understanding the art of a digital transformation, comprehending its requirements for success, and managing the diverse and complex components of people, processes, and technology is challenging for project managers. To achieve success, it is essential to integrate the scientific, fact-based understanding of project management with the experiential and artistic aspects unique to digital transformations.

Lack of Change Management

Another reason for the frequent failure of project managers is their excessive focus on the technological components of a transformation while neglecting the people aspects. They often fail to invest sufficient time, effort, methodologies, and tools in organizational change management, which is crucial for ensuring the organization itself undergoes a transformation, rather than solely deploying new technologies.

Even if a project impeccably designs, deploys, builds, tests, and goes live with new technology, it will not be well received by the organization if the organizational change management side is not addressed. The organization may reject anything external or any changes that could impact it if the people and organizational change components of the transformation are overlooked. Hence, having a comprehensive understanding of organizational change management becomes essential, reinforcing the earlier point about the art versus science of digital transformation.

It is vital to educate yourself and grasp the concepts of change management and its implementation in your organization. This understanding is crucial for your success as a digital transformation project manager.

Poor Vendor Management

One common challenge faced by project managers is their inadequate management of third-party vendors. This issue often stems from a lack of understanding of how digital transformations should be handled. While they may be experienced and qualified project managers in other project types, they may lack sufficient experience in managing digital transformations specifically. Due to this knowledge gap, project managers may struggle to grasp and oversee the activities of their third-party vendors.

Consequently, organizations can find themselves facing hefty bills and invoices from software vendors, system integrators, and software consultants, without the corresponding value delivered. To address this, effective vendor management is crucial. Project managers must be willing to ask probing questions, delve into the details, and, to some extent, engage in micromanagement. While micromanagement is not considered favorable in today's management practices, selectively implementing it is necessary when dealing with third-party vendors. By holding them accountable and avoiding a blank check scenario, project managers ensure that they receive the desired outcomes and do not bear the consequences of unsatisfactory results alone.

Managing software vendors should be approached as part of an overarching program within a broader set of work streams. Learning how to effectively manage these vendors is essential for the success of the project, the team, and the organization.

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Lack of Risk Management

Finally, one of the most significant reasons why project managers often fail is their failure to recognize and mitigate risks. They lack an understanding of the business risks involved, the necessary trade-offs, and the fact that mitigating one risk may give rise to new risks that require attention. Moreover, many project managers struggle to identify and manage risks effectively.

This problem is exacerbated by the unintentional incentives or compensation structures in place for software vendors and system integrators. These entities are often motivated to downplay risks and emphasize the strengths of their software solutions and associated services. This is not necessarily due to malicious intent but rather a desire to ensure that you, as the project manager, perceive the positive aspects of their offerings. However, it is crucial for you to grasp the potential drawbacks and risks associated with their solutions.

This combination of factors makes it challenging to objectively identify and overcome risks. Therefore, engaging independent, third-party, and technology-agnostic providers, such as Third Stage Consulting, who specialize in risk identification and mitigation, can be highly beneficial. They can assist in identifying and addressing risks as they arise, preventing them from becoming insurmountable obstacles.

These are some of the common reasons why project managers may face dismissal. By performing your job effectively and possessing the right support, tools, and skills, you can achieve success. While there have been project managers who have been fired over the years, there are even more who have achieved and can achieve success. By following these initial steps, you can increase your chances of success in your role as a project manager in a digital transformation project.

I would enjoy brainstorming ideas with you if you are looking to strategize an upcoming transformation or are looking at selecting an ERP system, so please feel free to contact me at eric.kimberling@thirdstage-consulting.com. I am happy to be a sounding board as you continue your digital transformation journey.

Be sure to download the newly released 2023 Digital Transformation Report to garner additional industry insight and project best practices.

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Eric Kimberling

Eric is known globally as a thought leader in the ERP consulting space. He has helped hundreds of high-profile enterprises worldwide with their technology initiatives, including Nucor Steel, Fisher and Paykel Healthcare, Kodak, Coors, Boeing, and Duke Energy. He has helped manage ERP implementations and reengineer global supply chains across the world.

Eric Kimberling
Eric is known globally as a thought leader in the ERP consulting space. He has helped hundreds of high-profile enterprises worldwide with their technology initiatives, including Nucor Steel, Fisher and Paykel Healthcare, Kodak, Coors, Boeing, and Duke Energy. He has helped manage ERP implementations and reengineer global supply chains across the world.
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