Why Many Transformations Never Cross The Finish Line

Ryan den Rooijen
Ryan den Rooijen

In recent years, many organisations have embarked on ambitious digital transformation programmes. Whether driven by a desire to promote agility, increase profitability, or harness AI, in practice these initiatives often do not move as quickly or yield the benefits expected. While various reasons underlie this, one overarching principle tends to determine programme success or failure.

Primarily, there needs to be an organisation-wide drive to achieve programme goals. Like in any race, if participants lack the desire to cross the finish line, what is the point? No amount of coaching, nutrition, or footwear will propel someone through a marathon if they do not care about finishing the race. Similarly, many transformation programmes are instituted as bureaucratic exercises where the average employee seems indifferent to both the journey and the outcome.

This hunger is arguably the single biggest reason why startups can disrupt the dominance of established enterprise players. The latter might have billions in resources, but their employees often lack the will to fight. You might have all the data and engineering talent in the world, but if employees are content with the status quo, you will eventually fail. So, how do you cultivate this hunger?

Firstly, align your transformation goals with company values and clearly articulate the so what. If everyone understands that "crossing the finish line" will result in positive environmental impact, more enjoyable work, or significantly happier customers, they will be far more invested than if the goal is simply a reduction in "total cost of ownership" of technology assets. Except for the CFO, perhaps.

You can judge a digital transformation by employees' body language. Image by DALL·E.

Secondly, instead of trying to convince everyone – a folly, particularly in organisations with 10,000+ employees – select and engage champions early on. As with any trend, people tend to follow influencers. Identifying these figures across different parts of the organisation is critical when it comes to getting buy-in and building momentum. They can also provide an important feedback mechanism to understand the mood music during a digital transformation.

Thirdly, while it is important to give people time to adjust to the new reality, secure unwavering commitment from all key players. Particularly in large technology transformations, there are so many complexities and dependencies that one stroppy stakeholder can delay or derail an entire programme. Once a course has been set, people should either commit or choose to step aside.

Finally, in the words of ultra runner Dean Karnazes: "Run when you can, walk if you have to, crawl if you must; just never give up." For example, if one of your transformation goals is to improve customer experience, then the work is not done until you have upgraded your customer touch points, empowered your customer service teams, and seen measurable improvement in your target metrics. Investments matter little if they do not result in tangible impact.

True digital transformation demands far more than tools and technology; it requires an organisation-wide desire for something better. The status quo, no matter how comfortable, is unsustainable in a world of constant innovation. Leaders who are able to instill hunger, secure commitment, and embrace change will position their organisations for long-term success. Those who fail to do so will be forgotten over time, having wasted both money and opportunity.

– Ryan

Cover image by DALL·E.

Digital Transformation

Ryan den Rooijen

Former Chief Strategy, Chief Ecommerce, & Chief Data Officer. Currently consultant to private equity.