Digital disruption is no longer a passing trend. It has become part of the landscape, and businesses must decide how they intend to move through it. As a result. innovation becomes a critical skill. In a thoughtful piece for Harvard Business Review titled “Why Playing It Safe Is the Riskiest Strategic Choice“, Steve Dennis offers a sober warning. The familiar corporate instinct to plan carefully and adjust in small steps now carries its own danger. When the ground shifts at such speed, slow responses can leave even established firms stranded.
A Renewed Innovator’s Dilemma
Dennis returns to Clayton Christensen’s well-known idea of the “Innovator’s Dilemma“. Christensen described how strong companies can falter when new technologies appear, not because they lack skill or resources, but because their strengths tie them to the familiar. The dilemma has become sharper. Organisations must now keep pace not only with new technology but also with the tempo at which it changes. McKinsey reported in 2021 that most executives view innovation as essential, yet only a minority feel their organisations are doing it well. The gap between intention and outcome has widened.
The Cost of Caution
Some of the most striking examples come from consumer-facing industries. Companies such as Airbnb and Netflix did not simply refine existing models. They chose to reimagine them. Their success lies not in reckless risk-taking but in recognising that modest adjustments would never match the scale of change around them. Businesses that rely on small, carefully measured steps often find that the world moves faster than they do.
Retail as a Mirror
Dennis draws heavily on the retail sector, which has seen decades of disruption compressed into a few years. Traditional department stores once dominated by virtue of size and reach. Many hesitated to challenge their own assumptions and paid dearly for that hesitation. By contrast, companies like Ulta and TJX have flourished by focusing on clear offerings and by treating agility as a core strength rather than a passing tactic. Their progress shows how clarity of purpose and timely action can reshape an entire field.
What We Have Learnt in Our Own Work
Our experience at Gislen Software echoes these themes. We have worked with organisations across a wide span of maturity, from new ventures still exploring their identity to long-established bodies with intricate operational histories. The variety of projects has taught us that digital transformation succeeds when technology serves a clear purpose and when change is allowed to happen in steady, practical steps.
For Clarendo, we built a platform that helps organisations maintain and deepen their ISO work. Instead of offering a generic tool, we designed a system that supports the discipline of continuous improvement and guides companies through the rhythm of audits, reviews, and corrective actions. The value lay not in novelty but in clarity and fit.
Our long collaboration with EACTS involved creating a system that brings together membership management, training activities, and conferences. Their annual congress is large and complex, and the software had to support everything from registration to on-site logistics. The work has evolved over many years, reflecting new expectations in the medical community and the organisation’s own growth. It is an example of how transformation happens not in a single leap but through a sequence of well-judged changes.
For Skin & Tonic, we developed a streamlined e-commerce solution under tight time pressure. Their business needed a platform that could grow with them, without carrying the weight of an oversized system. The project showed how a focused solution, delivered quickly, can unlock momentum for a young company.
Across these engagements, the pattern is the same. Success comes when courage and practicality meet: a willingness to aim high paired with a steady, manageable path towards that aim.
A Culture That Allows Ideas to Move
While fostering a culture of innovation is hard, it is crucial for the long-term success of any organisation. Innovation is often spoken of in grand terms, yet its practice is usually modest. It begins with a culture that encourages people to test ideas without fear of rebuke. Large ambitions become workable when divided into smaller, well-defined steps. This “shrink the change” approach helps organisations adjust their course as they learn, rather than waiting for perfect conditions that never arrive.
Such a culture does not emerge overnight. It grows through leadership that rewards curiosity, through routines that allow time for reflection, and through technology that supports rather than constrains. The companies that adapt best are often those that give their teams room to explore, while keeping a gentle but firm eye on purpose.
Looking Ahead
If there is one lesson to take from recent years, it is that the old comfort of caution can no longer be relied upon. Organisations must decide how they relate to risk. They can continue to move carefully while the world changes around them, or they can engage with change on their own terms.
Generative AI and other emerging technologies will reshape industries in ways we cannot yet fully see. The choices leaders make today will influence whether their organisations are swept along or help to set the direction. Boldness, in this context, does not mean rash action. It means thoughtful decisions made in time.
At Gislen Software, we continue to support clients who choose to move forward with purpose. Whether their ambitions are wide in scope or focused on a single process, we help them build systems that match their aims and give them the confidence to navigate what comes next.
If you are considering your own next steps in the digital world, we welcome a conversation.
This article was originally written in December 2024 and updated on 8/12/2025.
What does “digital disruption” mean for established businesses today?
Digital disruption means rapid, ongoing change in markets and customer expectations, where familiar advantages can lose value quickly. It pushes leaders to decide how to respond rather than assume stability will return. In practice, it turns innovation into a capability: learning faster, acting in time, and avoiding slow responses that leave even strong organisations stranded.
What is the “renewed Innovator’s Dilemma” in the digital age?
The renewed Innovator’s Dilemma is that successful organisations can struggle with new technology not due to lack of talent, but because their strengths keep them tied to what already works. The dilemma is sharper now because it’s not only about adopting new technology—it’s also about matching the pace of change and closing the gap between wanting innovation and delivering it.
Why can “playing it safe” become the riskiest strategy?
When the environment changes quickly, cautious, incremental moves can be too slow to matter. Planning carefully is not automatically safer if the market shifts before plans can deliver value. The risk is timing: slow responses can strand established firms because modest adjustments cannot match the scale and speed of disruption around them.
What does the article suggest is the real cost of excessive caution?
Excessive caution can lock organisations into small adjustments while competitors reimagine the model. The cost is falling behind the tempo of change. The article contrasts companies that rethink the approach with those that rely on measured steps and discover the world has moved faster than they did.
What can retail disruption teach leaders about innovation?
Retail shows how disruption can compress decades of change into a few years, exposing companies that hesitate to challenge assumptions. The lesson is that clarity and timely action matter: firms that treat agility as a core strength and focus on clear offerings can reshape outcomes, while delayed decisions can be costly.
How can bold innovation be “thoughtful” rather than reckless?
Boldness doesn’t mean rash action—it means making thoughtful decisions in time. The idea is to aim high while choosing a manageable path. Instead of chasing novelty, leaders can pair ambition with practical steps that support learning and adjustment, so the organisation moves with purpose as conditions evolve.
What does “shrink the change” mean, and why does it help?
“Shrink the change” means turning big ambitions into smaller, well-defined steps so progress is workable and learning can happen sooner. It helps because organisations can test ideas, adjust course as they learn, and avoid waiting for perfect conditions that rarely arrive—making innovation more practical and less fragile.
What does an innovation-friendly culture look like in practice?
An innovation-friendly culture encourages testing ideas without fear of rebuke and gives teams room to explore while staying anchored to purpose. It grows through leadership that rewards curiosity, routines that allow reflection, and technology that supports rather than constrains. The goal is steady movement—exploration with a gentle but firm eye on why the work matters.
How does Gislen Software describe successful digital transformation?
Digital transformation succeeds when technology serves a clear purpose and change happens in steady, practical steps rather than a single leap. The emphasis is fit and clarity: building systems that match real aims, support continuous improvement, and evolve through well-judged changes as organisations mature and expectations shift.
What do the Clarendo, EACTS, and Skin & Tonic examples have in common?
They show that progress comes from solutions designed for purpose and context—discipline and fit for ISO work, integrated support for complex membership and events, and a focused platform that can grow without unnecessary weight. Across these projects, the shared pattern is courage paired with practicality: aiming high while delivering change through manageable steps.
How should leaders think about Generative AI and emerging technologies in innovation planning?
Generative AI and other emerging technologies will reshape industries in ways that are not fully visible yet, so leaders’ choices now matter. The article frames it as direction-setting: organisations can be swept along or help shape outcomes by making thoughtful decisions in time, aligning technology choices with purpose rather than relying on comfort or delay.
What are sensible “next steps” for an organisation deciding how to move forward?
A sensible next step is to decide how the organisation relates to risk—continue cautious movement while the world changes, or engage change on its own terms. The article points toward purposeful action: clarify ambition, break it into manageable steps, support teams with culture and enabling technology, and seek guidance when planning the next stage of digital work.