Want to get digital transformation right? Address what’s left behind

Neil Raden
7 min readSep 3, 2023

Summary: Digital transformation is sure to run into obstacles. One under-recognized pitfall? The fear of leaving something behind. A vital field lesson revealed the problem — and ways to address it.

Consider this real-life scenario: an innovative furniture manufacturer developed a compelling application that allowed potential customers to design their own furniture. Traffic on the site was heavy, but very few “designers” appeared to have confirmed their purchase over time.

Clearly, the company was disappointed by the outcome, and they dispatched a “tiger team” to understand why the conversion rate was so low. The first choice was that their product was too expensive, so they lowered prices and offered various discounts and incentives. Nothing changed.

Their next action (which should resonate with enterprise software vendors) was to enhance the offering with features and benefits such as more options in colors, materials and design patterns, which only complicated the design effort. Design completions fell.

Finally, Marketing got into the mix and claimed that more people needed to hear about their product and boosted marketing spend 20%. All to no avail.

A member of the Board had an acquaintance with an academic anthropologist who specialized in doing ethnographic studies for businesses that desired to better understand the market from a cultural perspective. Anthropologists observe and analyze these dynamics within societies, examining how fear and resistance to change manifest at the individual, group, and societal levels. They explore how cultural narratives, social institutions, and collective memory shape people’s perceptions of change. By understanding these complexities, anthropologists can contribute to a deeper comprehension of the barriers to change and devise strategies to facilitate a more adaptive and inclusive approach to societal transformation.

The anthropologist was engaged to study the problem and offer solutions. The results were startling.

The study revealed that ninety percent of the “designers” were millennials, and finalizing the purchase of their design was often their first substantial purchase of a piece of furniture. A significant factor in their reluctance was that they needed to figure out what to do with the item they’d replace. Some had an emotional attachment to it; others didn’t know how to get rid of it. The solution was to offer to deliver the new piece and carry away the old one, either to donate it to a worthy charity or to dispose of it.

Conversion rates soared.

What does this have to do with transformation in the enterprise? In addition to desiring something new, the reluctant designers were concerned about what they’d leave behind — none of the previous attempts to improve sales addressed this problem. From an anthropologist’s perspective, the fear of leaving something behind can be a significant barrier to organizational change. The fear of leaving behind familiar routines, relationships, and esteem of well-honed skills can impede progress and hinder the acceptance of change.

People develop a sense of identity and belonging within their workplace framework, which is deeply intertwined with their tools, practices and process. These cultural elements serve as anchors that provide stability, security, and a sense of continuity. Therefore, when confronted with the prospect of change, individuals may experience anxiety, uncertainty, and a fear of losing their identity. Often, they manifest these fears as passive resistance, creating obstacles and delaying or derailing progress. The fear of leaving something behind can be rooted in resistance to relinquishing power dynamics or social hierarchies. Change may challenge existing power structures, redistributing resources, authority, or privileges.

It is common for digital initiatives to be subject to delays, cost overruns, failure to gain acceptance, only achieving a portion of their initial objectives, or to fail altogether. Those in charge of the initiative usually point to “culture” as the primary reason, but to them, culture is a euphemism for everyone else. They are partially correct; culture plays a large part.

Digital transformation involves adopting new technologies, processes, and ways to enhance efficiency, productivity, and innovation within organizations or societies. Digital transformation can be attenuated by overlooking individuals’ fear of leaving behind familiar practices, systems, or technologies. However, people’s fear of leaving behind what they are comfortable with can pose a significant obstacle to successful digital transformation initiatives.

When organizations embark on digital transformation journeys, it is crucial to consider the human aspect of change. People have established routines, skills, and expertise within traditional systems, and they may resist or feel threatened by introducing new technologies or digital processes. They might need help to avoid being left behind, becoming obsolete, or losing their jobs or positions of authority.

Furthermore, individuals may also experience anxiety and uncertainty about their ability to adapt to new digital tools or systems. Technology can be perceived as complex, alienating, or inaccessible, especially for those unfamiliar with digital devices or platforms. The fear of being unable to navigate the digital landscape effectively can hinder individuals from embracing the transformation and fully participating in the digital age.

Additionally, digital transformation may disrupt established social structures and organizational power dynamics. Certain individuals or groups may resist change because they fear a loss of control, status, or influence that the new digital landscape may bring. The fear of relinquishing established hierarchies or ways of doing things can create resistance and slow down the pace of transformation.

Proactively addressing people’s concerns and fears is crucial to mitigate these challenges. Education and awareness campaigns can help individuals understand the benefits and opportunities that digital transformation can bring, alleviating fears and resistance. Organizations and societies need to provide proper training, support, and resources to facilitate the transition to digital technologies.

Inclusive decision-making processes, where individuals have a voice and can contribute to shaping the digital transformation, can also foster a sense of ownership and reduce fears. Open communication, transparency, and clear explanations about the objectives and benefits of digital transformation initiatives can help individuals understand the need for change and alleviate anxieties.

Overall, recognizing and addressing the fear of leaving something behind is essential for successful digital transformation. By acknowledging and empathizing with individuals’ concerns, organizations and societies can implement strategies that facilitate a smoother transition, empower people to embrace new technologies, and unlock the full potential of digital transformation.

What we hear most about digital transformation is how essential it is, how the business will benefit and certain gee-whiz factors about keeping up. Precious little is devoted to overcoming resistance.

To ease the fear of leaving behind during digital transformations, planners can take several steps to address individuals’ concerns and facilitate a smoother transition. The first step is to acknowledge people’s reservations about leaving behind. Some strategies to employ may sound familiar, and they are:

1. Communication and Transparency: Planners should communicate clearly and openly about digital transformation plans. They should articulate the objectives, benefits, and anticipated changes, addressing fears or uncertainties. Transparent communication helps individuals understand the purpose of the transformation, reducing anxiety and resistance.

2. Education and Training: Providing comprehensive education and training programs is crucial to equip individuals with the necessary skills and knowledge to navigate the digital landscape. Offering workshops, seminars, and hands-on training sessions can help individuals gain confidence in using new technologies and systems. This empowers them to embrace the change rather than fear it.

3. Gradual Transition: Planners can consider implementing a gradual rather than a sudden and abrupt change. This allows individuals to adapt to new technologies and processes comfortably, reducing the fear of being overwhelmed or left behind. Piloting new digital initiatives in specific areas or departments before scaling up can be a practical approach.

4. Inclusivity and Collaboration: Involving individuals in the planning and decision-making process can foster a sense of ownership and reduce resistance. Planners should actively seek input from employees or stakeholders, considering their perspectives, concerns, and suggestions. By involving people in shaping the transformation, they feel valued and are more likely to embrace the changes.

5. Support and Resources: Planners should provide adequate support and resources to facilitate digital transformation. This includes technical support, access to training materials, troubleshooting guides, and helpdesk services. Ensuring individuals have the necessary tools, resources, and support systems helps alleviate their fears and boost confidence.

6. Recognition and Rewards: Recognizing and rewarding individuals actively engaging in digital transformation can motivate others and alleviate fears. Celebrating small wins, acknowledging individual contributions, and showcasing success stories can create a positive atmosphere and encourage others to embrace change.

7. Continuous Evaluation and Improvement: Planners should establish ongoing evaluation and feedback mechanisms to identify challenges or areas of concern during the transformation process. This allows for timely adjustments and improvements based on feedback from individuals. Regular communication channels should be maintained to address emerging issues and provide reassurance.

8. Addressing Job Security: One of the significant fears during digital transformations is the concern about job security. Planners should address these concerns by clarifying how roles and responsibilities may evolve and emphasizing how digital transformation can create new growth and skill development opportunities. Transparent communication about potential impacts on jobs and proactive measures to support individuals in transitioning to new roles or acquiring new skills can help alleviate this fear.

My take

Following these guidelines can improve your chances of success, but more is needed. The yawning gap in every playbook, framework or methodology for digital transformation I’ve ever seen is the need for more rigor about the fear of leaving behind. Promoting the benefits is insufficient, and it took an anthropologist to open my eyes to this. That fear is just that powerful but can be overcome, just like the furniture company did.

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Neil Raden

Consultant, Mathematician, Author; focused on iAnalytics Applied AI Ethics and Data Architecture