21 Action Items to Help Companies Successfully Execute a Digital Transformation

Company leaders feel the urgency to transform their organizations in the face of digital disruption. New rivals are digitizing whatever can be digitized to attack incumbents’ value chains, gaining marketing share, eroding margins, and wreaking havoc on the competitive landscape in virtually every industry.

For large and midsized companies, the imperative to transform is clear. How to transform is another matter.

In one of the appendices of our book Orchestrating Transformation, we present an “Orchestrator’s Cheat Sheet”. It’s a compendium of all the key actions for transformation practitioners. This cheat sheet provides a handy reference summarizing 21 of our most critical recommendations for executing a digital business transformation.

General Principles

1. When pursuing digital business transformation, embrace the need for a connected approach to change, and operate in the Orchestration Zone, rather than relying on ill-suited change management doctrines.

2. Ensure that the executive team consistently reinforces the direction of the transformation, along with their explicit expectation that managers and individual employees plan, invest, and execute in ways that support this direction.

3. Ensure that the CTO works with other key leaders, particularly the CIO and the assigned transformation leads, to increase the overall level of digital business agility in the company—its foundational capacity to change. This involves creating weak connections among organizational resources that provide new or relevant information, as well as strong connections that create the trust and cohesion needed for a connected approach to change.

Establishing Guiding Objectives 

4. Make the customer the centerpiece of your company’s digital business transformation. Work backward from how you intend to create new or improved value for the end customer.

5. Set guiding objectives that include creating value for customers, delivering and capturing that value through an appropriate business model, and the strategy needed to make it happen. Guiding objectives must be set at the line-of-business level, not for the company as a whole. The leader of a given line of business, and ideally the entire executive team, must be supportive of these guiding objectives— it’s not the job of the CTO to dictate these to the business.

6. Pursue a portfolio of strategies, with different guiding objectives for each line of business.

Articulating A Transformation Ambition 

7. Articulate a transformation ambition—the company’s holistic change goal—that is precise, realistic, inclusive, succinct, and measurable (PRISM). Encourage senior leaders to become ambassadors of the change and stress the transformation ambition in their teams’ communications and planning.

Orchestration Competencies 

8. Document major digital initiatives occurring across the business to create visibility and potential synergies. The orchestrator, however, shouldn’t try to “own” these projects.

9. Create an appropriately sized internal venture fund that can accelerate cross-functional efforts and business outcomes.

10. Engage resources that can model value impacts of transformation programs. This keeps efforts on track and creates support among stakeholders, especially senior management and the board.

Mobilizing Resources and Enabling Connections

11. Create a business architecture map of the company spanning all the instruments of the Transformation Orchestra. Map the people, data, and infrastructure that exist, as well as their relationships and the workflows between them.

12. Determine which instruments—and the organizational resources they represent—are most relevant to the transformation challenges presented by the company’s guiding objectives.

13. Create transformation networks consisting of multiple instruments to address transformation challenges. Keep each transformation network small, agile, and focused on a highly specific transformation challenge. This makes measuring the progress and impacts of the change easier.

Organizing For Orchestration 

14. Appoint a chief transformation officer. Hire someone who is humble, adaptable, visionary, and engaged.

15. Make the chief transformation officer responsible for orchestrating the company’s digital business transformation, mobilizing organizational resources and enabling connections among them, but create shared accountabilities and joint KPIs with the business for results. The rest of the business should focus on implementing digital capabilities and driving change in their respective areas.

16. Invest the CTO with a high level of seniority—not as a middle manager or one of the coordinators, but as a member of the executive team that holds sway in the organization.

17. Build a transformation office under the CTO. Keep the team small and remember it should orchestrate most of the work associated with transformation, rather than performing it.

18. Prioritize hiring skill sets in the transformation office that reflect orchestration competencies like design thinking or business architecture. Look to an ecosystem approach to fill skills gaps, and be agile in your approach to engaging talent (i.e., develop a “talent cloud” for skills that are scarce, expensive, or just occasionally needed).

19. Encourage the CTO to build a strong rapport with division and functional leaders; rather than competing with the business, the transformation office should be seen as a source of innovation, agility, and speed.

20. Appoint “transformation leads” from other teams who can help thread execution across groups. Rather than creating a transformation unit that is a silo unto itself, weave an “organizational fabric” of connected execution on top of the existing org structure.

21. Keep the transformation office focused on incubating new processes and better capabilities. Transition ongoing management of these processes and capabilities when they reach maturity to the business. The transformation office should remain engaged to adjust the outputs over time.


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