An Exclusive Sneak Peek: The Part of Digital Transformation Nobody Plans for (But Everyone Suffers Through)


Hi Reader,

I hope this email finds you well! This week’s excerpt is one I’m particularly eager to get your reaction to, because in my experience it’s the area where the gap between what leaders say they’ll do and what actually happens is widest.

A quick update first. I’ve been working through feedback from several of you on earlier excerpts, and it has been genuinely useful. A few of you pushed back on how I frame the executive sponsor’s role in change management — specifically whether non-technical sponsors are truly equipped to lead it. That’s a fair challenge and one I’m addressing directly in this chapter. More on that in a future email.

This week’s excerpt is from Chapter 5, covering Organizational Change Management — what it is, why it matters more than most leaders realize, and what a real change management strategy actually includes. I’ll be honest: in my experience, OCM is highly accepted and seldom executed. I’m hoping this section changes that.


Excerpt from The Digital Transformation Guidebook

Chapter 5: Building Your Itinerary

The Part of Digital Transformation Nobody Plans for (But Everyone Suffers Through)

Organizational Change Management — OCM — involves structured methodologies and practices designed to transition individuals, teams, and organizations from a current state to a desired future state. This process places a significant emphasis on the human element, ensuring that stakeholders at all levels understand, commit to, and effectively adopt the changes.

OCM is a relatively new discipline in project management. However, it has always been a factor for successful transformation. The organizations that intuitively implemented the principles of OCM found greater success than those who didn’t.

In my experience, OCM is highly accepted and seldom executed. I rarely see substantive action taken to adopt the principles of OCM. You will need to adopt those principles if you want to have the best chance for successful transformation.

Why Change Management Matters More Than You Think

Without change management best practices, DX projects may experience limited effectiveness and even failure to meet their objectives. Prioritizing change management can result in:

  • Higher adoption rates: By actively engaging and training employees, you ensure they are equipped and ready to embrace new technologies and processes.
  • Smoother transition: A well-crafted change management strategy reduces disruptions in workflow and maintains productivity throughout the transition.
  • Less change resistance: Proactively managing and addressing specific concerns reduces pushback and fosters a positive attitude towards change.
  • Quicker realization of benefits: Streamlined change adoption means that the organization can start reaping the benefits sooner.
  • Bigger ROI: Effective change management ensures that investments in new technologies and processes deliver maximum returns.
  • Sustainable change: Embedding change management practices ensures long-term success and the ability to adapt to future changes efficiently.

What a Change Management Strategy Actually Is

A Change Management Strategy is a high-level plan outlining a tailored approach to managing the proposed transformation within your organization. Beyond simply outlining generic change management best practices, your Change Management Strategy uses information from previous assessments — like the Organizational Risk Assessment — and specifies the involvement needed to support your change initiative.

Here are some of the things you will want to consider when crafting your strategy:

  • Relative Complexity: If the DX initiative seems small compared to previous projects by the same team, it may suggest less need for extensive change management. On the other hand, that same small DX initiative may be relatively large in the context of a different organization with fewer implementations under their belt.
  • Previous Project Track Record: Maybe there is a high level of trust between business units due to a good track record of delivering previous projects on time and on budget. Or, conversely, perhaps past DX initiatives had several go-live date shifts, causing a breakdown in trust when current deadlines are set.
  • History of Engagement: Evaluate the engagement of previous initiatives. Did they experience poor user adoption? Are there specific key players who have a track record for being positive — or negative — change agents?
  • Misaligned Priorities: Even though an executive is championing the initiative, other stakeholders might not view it with the same level of priority or urgency.

An effective Change Strategy factors in your organization’s unique culture, needs, abilities, and available resources. This ensures your team is equipped to successfully adopt the proposed changes and that the changes will be sustained long after the implementation is finished.

What to Include in Your Change Management Strategy

There are many different facets that should be addressed in your Change Management Strategy.

Leadership Alignment

The first step in implementing a successful change strategy is to secure consensus among organizational leaders that the initiative is a priority. This alignment — or misalignment — with the initiative can set the tone for the entire organization and ultimately affect its success. The level of consensus will determine the level of involvement needed for a successful implementation.

Communication Plan

A communication plan outlines the necessary level of communication throughout the DX initiative. It aims to bridge gaps between the project team and the broader organizational community. This may involve creating plans for specific groups — executives, managers, and front-line employees — to effectively communicate the changes to the relevant members.

Stakeholder Engagement

Active and engaged stakeholders throughout the DX initiative are paramount to its success. This section of the change strategy should outline who the stakeholders are and how they will be utilized throughout the DX initiative to drive positive change. Identifying and leveraging effective change agents can facilitate smoother transitions and mitigate resistance.

Organizational Culture

The existing organizational culture plays a significant role in the approach to change management. A history of positive or negative experiences with DX projects will influence the level of change management efforts required. Understanding team dynamics and cultural nuances enables a more effective engagement strategy.

Organizational Alignment

Identifying discrepancies in how various teams or divisions perceive the DX initiative helps in tailoring the change management efforts to address these differences and bring about alignment. As the saying goes, “A house divided cannot stand.” Some teams or divisions may not be aligned on this initiative or have a history of resistance. It’s important to identify this and strategize ways to address it through additional change management measures.

Training

Adapting training programs to fit the company, team, or individual roles is essential for ensuring everyone is equipped with the necessary knowledge and skills for the transformation. At this stage, provide preliminary recommendations on the type and level of training required during change management.

Using a Change Management Strategy

The goal of the Change Management Strategy is to ensure that the change management efforts contribute to the realization of the benefits associated with the DX initiative. By aligning change management strategies with organizational objectives and creating an approach tailored to the organization's specific needs, culture, and resources, companies can maximize the impact of their transformation efforts.

Properly executed, Change Management ensures that digital transformations are not only technologically successful but also have the full support and engagement of the entire organization, leading to sustained improvements and a competitive advantage.


This is one of the areas where I’d really like your real-world input. Have you worked with an organization where OCM was planned but never truly executed? Or have you seen it done well? Either story would be genuinely useful to me. Please hit reply and let me know.

I hope you found this email useful. I'd love to hear your feedback. You can send me an email with your thoughts or if you would like to talk to me you can use the button below to schedule a time on my calendar.

Kind regards,

Tory Bjorklund

The Digital Transformation Guidebook

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