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Compounding Leverage
Most organizations overestimate the value of big transformations and underestimate the power of compounding decisions. Large transformation programs are visible. They create momentum, urgency, and the sense that something meaningful is happening. But visibility isn’t the same as leverage. In practice, I’ve seen lasting advantage come from a series of smaller, deliberate decisions—how ownership is defined, how platforms are simplified, how people are included, how teams are a
Leecox Omollo
Jan 181 min read


Digital transformation through strategic abandonment.
For organizations burdened by brittle, unsupported, and unstable legacy systems, abandonment can be a legitimate digital transformation strategy. Rather than attempting to modernize, refactor, or incrementally repair technology that no longer serves the business, leadership may choose to deliberately replace it with modern platforms designed for current operating realities. While compelling in theory, abandonment is also one of the most failure-prone transformation approache
Leecox Omollo
Oct 27, 20234 min read


From Agile Teams To Agile Organizations.
Over the years, I’ve helped many technology organizations improve speed, resilience, and customer orientation—often through what were labeled “Agile transformations.” When done well, these efforts unlocked real business value and were deeply rewarding to lead. What has been far less successful, however, is how narrowly agility has been defined. In many organizations, Agile became synonymous with how teams execute projects , rather than how the organization itself senses, deci
Leecox Omollo
Oct 16, 20233 min read


Choosing the Right Level of Digital Sophistication.
One organization is on a quest to enable customers to place an order without completing a paper-based purchase order. Another one is toiling to predict when a customer is within 2 days of running out of a product in order to proactively prompt them to re-order with 1 click. Yet another one is creating unattended stores, where customers simply walk in, grab what they need and march straight out, their payment fully processed. These organizations are all on digital transformati
Leecox Omollo
Oct 16, 20233 min read


Choosing Where Transformation Actually Matters.
Most organizations agree that digital transformation matters. What is far less clear is where to focus limited time, capital, and leadership attention to produce meaningful results. The challenge is not a shortage of opportunities. It is abundance. Nearly every part of the organization can be digitized, automated, or modernized in some way. Without clear choices, transformation efforts tend to spread thin—creating activity without corresponding impact. Effective transformati
Leecox Omollo
Oct 16, 20233 min read


Defining the value behind digital transformation.
Digital transformation is ultimately about using technology to create value for customers—reducing effort, saving time, increasing confidence, or enabling outcomes that were previously difficult or impossible. Yet many transformation efforts fall short not because the technology is wrong, but because the value being pursued is poorly defined . Organizations often anchor on business objectives, technology choices, or delivery milestones without sufficient clarity about what wi
Leecox Omollo
Oct 16, 20233 min read


Strategic tradeoffs in digital transformation
There are many paths to any digital transformation objective. This is both a blessing and a curse to those responsible. The blessing is that we have plenty of choices and options for elevating our organizations and improving the lives of our customers. But this is also the curse. Choosing broadly fragments limited resources and minimizes your impact. Choosing too narrowly may lead to missed opportunities. Choosing one thing may keep you open to future possibilities when resou
Leecox Omollo
Oct 16, 20231 min read


Agility Is Built, Not Purchased.
To become better dancers, we don’t buy more elaborate outfits—we improve our steps. Yet many organizations continue to pursue agility by repeatedly acquiring new technologies, while leaving flawed processes, brittle architectures, and inconsistent operating models largely untouched. The result is predictable. Despite significant investment, agility remains elusive—and the business sees little return for the effort. In today’s environment, agility is no longer optional. It is
Leecox Omollo
Oct 14, 20233 min read


Content As An Enterprise Capability.
Modern digital experiences are built on impressive surface layers—mobile applications, sophisticated websites, conversational interfaces, analytics platforms, and AI-powered engagement tools. Yet without a strong content foundation beneath them, these investments rarely deliver their full potential. Content is not an output of digital transformation; it is a prerequisite. Organizations committed to delivering meaningful digital experiences must treat content as a core enterpr
Leecox Omollo
Oct 14, 20233 min read
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