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.