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Digital Transformation Game Plan- Book Review

1 December 2022
Dr. Moria Levy
book cover

The book "Digital Transformation Game Plan: 34 tenets for masterfully merging technology and business" was written in 2020 by Gary O'brian, Guo Xiao & Mike Mason (published by O'Reilly). The book discusses, as its name implies, the implementation of digital transformation in organizations to obtain:

Value for the customer

An organization built in a way that allows maximum service and flexibility to deal with new needs.

Building the next generation of technologies as a core and in a way that creates differentiation.

Although the book was written first and foremost for IT professionals, it is, in fact, highly relevant to any knowledge management professional - both as a business entity that works with them, both thanks to the mentioned emphasis on knowledge preservation and sharing required for every organization, and also while projecting parallel transformations that we can and want to carry out based on the knowledge assets.

Background - The need

The digital transformation

The digital transformation is much more than a fashion or a trend, business or computing. It redefines both the business organization and its computing, while making technology the core of the activity.

The business environment and the market are changing:

  1. Customer expectations are rising

  2. The speed of changes and uncertainty are increasing.

  3. There are plenty of technologies that can create a competitive advantage.

We as an organization need to change, and also change. To know how to learn faster, to know new things, to adopt innovative concepts, and to have the organizational courage to change and implement.

Not once, but continuously and continuously. Because there is no desired end point where one stops and rests. There is always more.

The Solution

Professional perception


Value to the customer


  • Understanding that value to the customer includes, aside from the cost and functional benefits, is also an emotional benefit

  • An example of emotional value: is the ability to make decisions yourself as a customer

  • The formulation of the strategy, the implementation concept, and the organizational structure will all be around the customer and the value he receives

  • Speaking in the customer's language

  • Looking from the customer's point of view

  • Thinking and doing in terms of outputs (outcomes) and not around capabilities (features)

  • Measuring customer value instead of input metrics

  • Re-adjustment of the work packages to those defined around bringing value

  • Thinking and doing guided products (products) and not projects (projects).

Exercise flexibility


  • Gradual learning of the correct answers - while doing; Decisions are ranked accordingly

  • Lean approach to implementation - small and focused pilots (at least 3) before wide deployment; planning-implementation-measurement

  • Planning of work teams around the defined narrow piece of work

  • Implementing AGILE (Principles and Practices)

  • Frequent repositioning (once a year)

Illustration (visualization) and transparency


  • Use of language, images and graphs/indicators

  • Multiple physical and virtual presence for elements that illustrate the organization and activities

  • A common physical work environment for each executive team

  • If possible - a designated room dedicated to illustration (meeting room?)

  • Emphasis on progress towards the value and not on performance reports and detailed excel sheets

Data Based

For what?

  • As a source of information and knowledge

  • As a basis for a true understanding of the customer's needs (where possible) and what gives him value

  • As a basis for understanding the progress towards the desired value and making decisions (by a person or a machine)

  • As a personalization tool

  • As a basis for new value propositions and the creation of a smart organization

How? methodologies

  • Analytics

  • Machine learning

Value-based measurement


  • As to the outputs and value desired by the client

  • As to the desired result

  • Measuring progress and improvement (in quality, provocativeness, supply, predictability, financial,...)

  • Also in financial business KPI’s (don't give up)

  • Personal KPI's as a tool for driving and creating renewed energy (and not for measuring and comparing performance).

The process of promoting transformation

The development process will be iterative, and will include:

  • Team formation to think about how to simplify the existing business model.

  • Forming a business strategy focused on customer value.

  • Identifying the abstract model of the organization's customer: understanding the specific value for the organization's typical customer and formulating the strategy in the customer's language, around outputs that the customer receives (value for the customer).

  • Choosing the first output to focus on. One must choose an output that will be real enough to reveal through it the core limitations and constraints of the organization as it is today, which hinder its natural development.

  • Establishing the first production team. Identifying the appropriate staff members in a cross-organizational way, in a way that will produce maximum learning and allow the first proposed hypothesis to be selected for examination and application experience in the context of digital transformation.

  • Redefining metrics in the organization

Re-planning of the existing indicators in the organization against what they serve (where we are leading; value).

Training in the first programs in value measurement.

  • Defining the work you want to promote as a derivative of the indices.


Includes creating a model illustrating how the work definition, through the indicators, reflects the strategy.

Evaluating the work that already exists, and how it aligns with the new concept, and with bringing value.

It should be taken into account not to create too many gaps and "completion obligations" due to dealing with the new.

  • Prioritization:

    Someone responsible on behalf of the organization for the value to the client will confirm that, indeed, progress in the aspect in question will be valuable to the client and will prioritize between different possible jobs. The prioritization itself will not consume too many resources, will be based on data, and will also take into account parameters of level of risk/opportunity; the size of the work; the value to the customer; the cost of rejection. The cloud has this priority from time to time.

  • Gradual implementation through iterations of experiences, feedback, learning, and progress.

  • Establishing a supportive visual environment

Anchoring the desired future and the concept in the heads of the employees in different visual ways

Establishing a system of indicators that will allow flexibility and adjustments: a comparison between what is required and the situation, as a basis for discussions on shortcuts, compromises and adjustments.

  • Managing cultural change

Identification of inhibiting factors.

A joint discussion of how the culture can develop in the desired direction (see chapter below).

Change management.

  • Functional change management

Examining options for providing maximum value by the various functions.

Identifying the personnel that can support, upgrading skills and external complements (ML) to address gaps.

Identifying and implementing upgrade patterns by experience.

Making the functional unit's new methods the new norm.

  • Adjusting the wrapping system. Adapting the functions that support the organization (finances, human resources, etc.) to guide, report, measure and support the new concepts.



The leadership must know and be able to:

  • Present a vision of digital transformation and take responsibility for leading it.

  • Connect the middle managers:

The key to success, according to the authors, is in the middle managers.

The senior leadership must connect them to the changes, give them a sense of security and the possibility of learning so that they can grow and grow the entire organization.

  • Demonstrate technological wisdom combined with business:

How to adopt technologies to create a strategic added advantage

Which new technologies and technology combinations are most relevant to your organization's success

Understand the meaning of technological excellence, new development methodologies

Form a good technological team that will succeed in realizing the transformation

Help position technology as a differentiator, focusing on value and quality (and not just cost)

Know how to create new business opportunities based on technology

Know how to fight and succeed in the war by recruiting the appropriate employees.

  • Develop a culture of experiences:

Safe space

A celebration of victories and a celebration of learning events

for the promotion of manpower so that he can realize

Know how to ask questions

Experiment; be a role model

  • Shaping the face of the future:

How the work will be done: experiment-learning oriented; data based etc.

Where the work will be performed: partner bodies within the organization; partners from other organizations; whether and how work spaces will look; and more

Who will do the work: human-machine integration (artificial intelligence, robotics, etc.)

How to create an endless transformation process, constantly advancing to new goals.

But beyond all of these, leaders will be required to have the same qualities that leaders are required to have today - authentic leadership skills, setting a clear mission, decentralizing implementation powers in a way that everyone maximizes their abilities, removing obstacles from the way, recognizing and rewarding the work teams, and empathy and emotional intelligence to lead the people through the process the whole.

Executive teams

The execution teams of the various activities will be cross-functional and focused on customer value. The authors warn against the tendency to look for existing units and transfer the responsibility for doing the work to them.

The team leader will be responsible for setting a positive example and creating a safe space for the team to try, test, and progress.


  • Focus on work and not on employees

  • Share decision-making processes and parameters

  • Demonstrate vulnerability.

Team members will avoid job titles as much as possible, and instead will have job holders who cooperate together to achieve the value.

The execution teams will be as stable as possible around a product and value for the client (and not around a project), while giving maximum independence to the team and delineating its operational relations required on a daily basis with the others in the organization.

Work drivers:

  • The decisions for the ways of carrying out the work: will be open to discussion and joint thinking; Independence for employees.

  • Planning: will be defined, but it will be easy to update, depending on the development.

Organizational infrastructure

Organizational Structure:

  • Functional units will continue to exist in places where dedicated expertise is required.

  • It is not recommended to run and change the organizational structure following the implementation teams, at least a year from the beginning of the implementation. Organizational infrastructure and organizational structure are stable, and must be thought about over time and with the appropriate caution.

  • Openness to mobility according to needs (stability is helpful, but definitely not always appropriate).

  • Be careful of layoffs related to the changes taking place. can create tension and concerns, and this certainly during the entire period of the first year and more, in which they are not yet completely sure of the direction of progress.


  • Flexibility for updates regarding the allocation of the budget and the way decisions are made about the budget.

  • making small decisions on a scale; Stopping points for examination and decision on continued budgeting.

  • Budgeting against an activity that produces value for the customer.

Workers management:

  • The flexibility of changing the existing drivers, until finding a way to adapt them to the new era.

  • The promotion of the employees by emphasizing 1) their independence 2) the professional specialization 3) the meaning.

  • Strengthening the technological capabilities of the employees.

  • Providing supporting digital technologies to strengthen engagement.

  • Measuring employee progress in a way adapted to the new concept and not in traditional KPIs.

Evolving Culture:

  • It is not easy to change a culture, all the more to change it in a continuous and changing manner. Desired directions of development:

  • Common intention and common meaning (and not just looking through the prism of profitability)

  • Openness and trust

  • Collaborations and teams (rather than individual workers considered "successful")

  • The concept of managing experiments under the understanding that experiments are not risks, but a way to deal with the risk

  • Learning through feedback loops; The understanding that when you develop you can't be perfect all the time

  • Combining a top-down view with a bottom-up way gives a lot of independence to the area.

Law and regulation:

  • Policies and procedures: Examining the suitability of the existing one for the evolving digital age.

  • Flexibility, as much as possible, for action in the interim period (also in relation to the standards). Flexibility in the content of the procedures and guidance documents developed to reflect continuous development.


There is no doubt that computing is the core of digital transformation, but it is only one component, while in the process, business and organizational perspectives are adjusted to 1) customer value 2) constant change and development.

Management, responsibility and authority:

  • Joint leadership of the business side and the computing side are required for the promotion and success of the digital transformation.

  • The main role of a VP of IT and IT as a whole is to lead the change

  • An overall strategy for IT management that takes into account the frequent changes and increasing complexity

  • Business organization and access to all computing activities

  • Business product and customer value based units, not management/project-based units

  • Continuous responsibility of those employees from the development phase to the operation and maintenance phases (Devop)

  • Task management so that there are not too many "musts to complete".

Principles and work processes:

  • A high technical level of the employees' abilities (details below) - continuously and continuously

  • Continuous contact and close working interfaces with the business entities

  • AGILE work for all activities and stages

  • Development quality (internal) is significant - clean code and a high level of quality

  • Automation as much as possible in the development and testing processes

  • Encouraging the detection of failures quickly and early

Digital platforms:

  • Progress and excellence in the technological tools they use

  • Reinventing old core themes and reference. to them as part of the key factors for business success in the field (in an evolutionary way)

  • Modular tools, and an architecture that enables connectivity (APIs); Promoting the concept of microservices

  • Possibility of self-access to data

  • An infrastructure (architecture) that allows flexibility for the delivery of changing solutions; When appropriate and possible - implementation of solutions based on cloud infrastructure

IT teams:

  • Learning

Feedback - developing a culture of giving and receiving feedback

Mistakes - creating a safe space for mistakes and failures (while learning from them)

A nice training budget for technological advancement and enrichment

Cultivating technological excellence

  • Empowerment

Communication and information sharing

Decentralization of decision-making authority downwards

Cultivating a sense of responsibility for promoting success

Encouragement for collaborations:

  • The source of manpower

Mainly based on internal personnel and their development.


Hiring new personnel with potential (regardless of their current knowledge - more will always be required)

Completion of missing digital knowledge with the help of external providers while learning from each other.

What does it take to get started?

All whats described above. And: a lot of passion.

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