Why Doesn’t My Software Work?

by | Mar 23, 2024 | Change Management, I-O Psychology, Organizational Development, Workplace Culture | 0 comments

Your tech likely functions; you need better OCM

Have you ever implemented a piece of technology and deemed it a failure? If so, the problems may stem from a lack of organizational change management (OCM).

When I came aboard a firm, the CEO proudly stated that the company adopted Salesforce like many larger competitors. He felt this gave the company an advantage. However, much to his chagrin, the sales staff did not use the CRM, and he blamed them for the lack of initiative in adopting the new software. The sales team had grown accustomed to using the old CRM, which, ironically, also ran on a version of Salesforce customized for the industry. 

Knowing a thing or two about Salesforce, having implemented it several times in my career and serving as the administrator for at least three previous companies, I discovered that the agency that installed the system did not customize the system to the needs of the company because the company did not provide requirements. Whereas their previous CRM had Salesforce tailored to have Apps (collections of Objects), Objects (collections of fields), and Fields (data points) for industry-specific data, no such things existed in the current system. They had just a “vanilla” out-of-the-box Salesforce org, which didn’t have the proper data points or sales Opportunity processes to meet the needs of the company.

Furthermore, the agency’s onboarding process did not tie into any of the sales processes required in that industry because of Salesforce’s misconfiguration. Therefore, the company had a serious disconnect between the software and strategic objectives. Moreover, the agency’s training did not make sense to the sales team members because it did not fit with their processes.

Strategic Design and Training to the Rescue

I developed a two-pronged solution to the problem:

  1. I reversed-engineered a top-performing industry-specific version of Salesforce, which offered an integrated marketing solution. We licensed the marketing solution already, so I developed the appropriate Sales Opportunity Processes, Custom Objects, Fields, and Workflows to correlate with the marketing system’s data schema, which followed the setup within the knowledgebase of the CRM. After testing, the Salesforce system was ready for prime time.
  2. I developed a training course for the sales team based on their current sales processes for each type of deal. The course included an overall reintroduction to Salesforce and an eight-part series of section-specific lessons, guided exercises, a custom Trailmix (Salesforce Trailhead Training Modules), and on-the-job coaching. 

Adopting the system took several months because the team needed to unlearn the patchwork processes they used when it wasn’t operational. Moreover, the executives did not wish to learn how to use Salesforce or to embrace the culture. Salesforce has its own jargon and ways of using it (rituals, so to speak). If one does not recognize the vocabulary and how things operate, they can easily get lost in the system, become discouraged, and refuse to adopt the new way of doing things. When primary stakeholders do this, it sends a message to the rest of the staff about the lack of importance of the software.

Ultimately, when one of the executives finally took the online training, worked with me through one-on-one training and coaching, and saw the benefit of having reports and dashboards they could use to make decisions, I had a change champion. This allowed me to communicate the importance better, and the team fully adopted Salesforce as their confidence in the system and its ability to match their processes grew. With some understanding and support from organizational leadership, this project finally gained some legs, leading to full adoption throughout the firm.

Over the course of my career, in nearly every organization for which I’ve worked, I have led change initiatives to install new software. This includes CRMs, marketing automation systems, Microsoft 365, project management software such as Basecamp and Asana, POS systems, SCM technology, and moving from internal servers to cloud-based file solutions. While some systems have “bugs,” in my experience, most problems occur from a few issues:

  1. A lack of proper requirements documentation.
  2. A lack of understanding of the constraints of systems.
  3. Over-customizing software or tech instead of working within the constraints of the system.
  4. Lack of communication of the reason for change.
  5. Lack of engaging the workforce in decision-making.
  6. Not listening to people.
  7. Transactional leadership rather than transformational leadership is used to force conformity.
  8. Not offering sufficient training and development.

Technology-Driven Change

In the ever-evolving landscape of technology, the successful implementation of software systems within organizations stands as a critical determinant of operational efficiency, competitiveness, and innovation. However, despite the meticulous planning and investment, many software implementation projects do not achieve their intended outcomes. One can attribute failures to overlooked aspects of change management and organizational development (OD) (Sittrop & Crosthwaite, 2021). Below, I outline a few key reasons why software implementations may falter from these perspectives, including commonly recognized pitfalls and additional considerations that are crucial for success.

Too Much Customization

The allure of excessive customization to meet what some stakeholders consider important “must-haves” can quickly derail a project’s success. Tailoring a software solution to meet every conceivable need may seem advantageous, but it can lead to significant complexity, increased costs, and extended timelines. Customizations can make the system cumbersome to use and difficult to update, leading to resistance among users and a higher likelihood of project failure. Organizations should strive to strike the right balance between customization and standardization to ensure the software meets key business needs without becoming a source of endless complications.

Conversely, out-of-the-box solutions will likely also fail to hit the mark regarding stakeholder requirements. Organizations should expect some level of configuration. However, configuration does not mean customization per se. Setting up fields, collections of fields, branding, processes, and automation likely fall within the constraints of the system and allow the technology to do what it must to meet objectives. Change leaders then must help people to adapt their normative behaviors from previous system iterations to meet the new ways of doing things.

Lack of Clear Vision

A clear, coherent vision forms the foundation for successful software implementation projects (Landers, 2023). Without a well-articulated vision, stakeholders may find it difficult to understand the new system’s purpose and benefits. This lack of clarity can result in misaligned expectations, diminished stakeholder buy-in, and, ultimately, a failure to leverage the software’s full potential. A compelling vision outlines the end goal and inspires and motivates the entire organization to embark on the journey toward digital transformation.

Inadequate Coalition of Support

Implementing new software does not merely pose a technical challenge. It creates a significant change event that affects the entire organizational culture. After all, the language people use to describe function within the system, how workflows operate, and how people share and retrieve information fundamentally transform with new technology. A change leader must build a coalition of support to overcome resistance and foster an environment of collaboration and engagement (Kotter, 1996). This coalition should include top management and influential figures at various levels who can champion the change, address concerns, and advocate for the benefits of the new system. Failure to cultivate such support can lead to the isolation of the project team members and a lack of momentum in the implementation process.

Ignoring Stakeholder Feedback

Failure to listen to the people ranks at the top of the list of the cardinal sins of software implementation. Stakeholder feedback, including complaints, suggestions, and concerns, provides invaluable insights into how the software impacts daily operations and user satisfaction. Neglecting this feedback can lead to a disconnect between the system’s functionalities and its users’ actual needs, fostering frustration and resistance. Engaging with stakeholders throughout the process ensures user-friendly software that meets the organization’s needs.

Inadequate Training and Support

The importance of comprehensive training and support in software implementation cannot be overstated. Using Kirkpatrick’s Model for Training Evaluation can provide a structured approach to assessing training programs’ effectiveness across four levels: Reaction, Learning, Behavior, and Results (Kirkpatrick & Kirkpatrick, 2021). Often, organizations fail to invest adequately in training, focusing solely on the technical aspects of the software without fostering the necessary skills and confidence among users. This oversight can lead to underutilization of the system, errors, and a slow adaptation process. Effective training programs are tailored to the diverse needs of users, providing them with the knowledge and support needed to transition smoothly to the new system. Moreover, managers should receive training with ongoing performance evaluations and on-the-job coaching to reinforce learning.

Additional Considerations

Beyond the common pitfalls outlined above, several other factors can influence the success of software implementation from change management and OD perspectives:

  • Effective Communication: Consistent, clear, and transparent communication about the implementation process’s progress, challenges, and successes keeps stakeholders informed and engaged.
  • Cultural Alignment: The new software should align with the organization’s culture and values. Any dissonance between the system and the organizational culture can lead to resistance and reduced efficacy. New normative processes, a common vernacular, and artifacts such as signs, posters, slogans, and documentation can bring the new tech into workers’ everyday lives.
  • Post-Implementation Support: After the software goes live, ongoing support, monitoring, and optimization make the technology part of the fabric of the organization. Continuous improvement based on user feedback and performance metrics ensures the system remains effective and relevant.


Software implementations pose complex, multifaceted projects that extend beyond the mere technical deployment of a new system. Leveraging change management and organizational development interventions beyond the nuts and bolts of the technology can foster adoption. Organizations can significantly increase their chances of successful software adoption by recognizing and addressing the potential pitfalls discussed herein—including the balance between customization and usability, the clarity of vision, building a supportive coalition, listening to stakeholder feedback, and ensuring adequate training. Moreover, incorporating additional considerations such as effective communication, cultural alignment, and ongoing support further solidifies the foundation for achieving the transformative potential of new software systems. In navigating these challenges, organizations enhance their technological capabilities and foster a culture of continuous improvement and innovation.

For more information on how organizational change management and organizational development can help your organization, contact WorkBalance Consulting.


Kirkpatrick, J. & Kirkpatrick, W.K. (2021). An introduction to the New World Kirkpatrick Model. Kirkpatrick Partners, LLC.

Kotter, J. P. (1996). Leading change. Boston, Mass: Harvard Business School Press.

Landers, A. (2023). The Modern Practitioner’s Field Guide to OD and Change Leadership. Landers Consulting Group.

Sittrop, D., & Crosthwaite, C. (2021). Minimising Risk—The Application of Kotter’s Change Management Model on Customer Relationship Management Systems: A Case Study. Journal of Risk and Financial Management. https://doi.org/10.3390/jrfm14100496.

Join Our Newsletter

Share This