THERE’S a phrase in the corporate world that became popular in one of Scott Belsky’s books, referring to the challenging phase of projects or organisational growth and change as the “messy middle”. The middle is the stage of a company’s development that typically has the most challenging hurdles. It is also the stage where success or failure is inevitable. For companies, whether large or small, there comes the point where there is progression to the middle. It is the challenge we’re facing as a region when it comes to digital transformation.

It is an uncomfortable journey for many and avoided by many others because of this certainty of discomfort. Everyone wants to hear about the success stories of transformation because of the valid desire to leapfrog the middle. But suppose we accept this phase of the journey as a natural part of our digital evolution? In that case, we may save ourselves years of resistance and suffering and ultimately avoid multiple failed transformation initiatives.

Let’s first examine where the mess usually occurs. The process is generally defined in a series of five or six stages. Firstly, most companies are in the stagnation or resistance stage where change is at the doorstep. Still, there’s either dabbling with siloed projects and no commitment to a formalised process, primarily because of the estimated magnitude of the initiative. Once they take the transformation leap, the journey’s stage requires a formalised strategy, organisational realignment, commitment to spend and, most importantly, a culture shift. You’ll notice that none of these things has anything to do with the actual technology. And that’s the key. Transformation, especially the messy middle, is predominantly about people, the people who are leading the change and the people going through it. Now that this is known, we can understand the critical elements of success in surviving and thriving beyond the messy middle. Here are three of the factors that are also practical, low-hanging fruit.

Intangible, it seems, but the hurdles that usually create frustration in the process require a spirit of perseverance in order to get over them. Being patient, strategic and creative through the transformation process is key to success. The process gets more complex as challenges surface, uncertainty rises, and results are slow to manifest. Incorporating recognition and rewards, gamification and strong communication across teams, and cascading from leadership are some tactics that can boost team enrolment and engagement, resulting in greater resilience.

Many Jamaican companies experienced a push vs a leap towards digitisation due to the pandemic. This created a deficit in the planning department for many leadership teams. We’ve now had enough time to acclimatise to the characteristics of the pandemic. Let’s get back to the core discipline of road maps with clear milestones and an execution plan to support them. Structure wins when transformational change is at hand.

According to McKinsey, the role that leads the digital transformation effort is key to its success. Albeit a temporary role, the responsibility of ensuring the appropriate technology and skills are in place, deciding the sequence of the transformation, monitoring progress against targets, and ensuring that day-to-day tactical priorities get the attention they need, is priceless. This leadership role must be paired with like-minded and skilled execution team members who manage the outcomes and delivery of the transformation.

We will explore the journey of navigating the messy middle and relevant tools at the upcoming BizTech Conference, hosted from Nov 10-12 by the Jamaica Technology & Digital Alliance. Join us for idea-sharing and thought leadership that could benefit your organisation.