In a study with 450 IT decision-makers in Western Europe, the database company Couchbase identified several challenges in digital transformation projects. 

A vast majority of organisations declared they have had significant or even revolutionary transformations to their end-user experience (an impressive 95%!). However, despite this increasing positive outlook, yet 86% of companies are deterred from pursuing digital transformation projects as several challenges get in the way.

Among the causes, while a significant amount as a technical original, organisational- and people-driven challenges are often quoted - especially, since 52% of digital transformation projects still come from IT, with rare involvement by other verticals or the C-suite.

The risks of not foreseeing and preparing for these challenges fall in a broad gamut of gravity; delays on the implementation, scaling back in scope, falling short of being transformational and the most definitive of all, failing. And in staggering numbers: the same study points to organisations showing these negative outcomes in a 55% to 86% of the cases.

Grouping the challenges you might face as a team leader depending on their nature will help to overcome them quickly and effectively.

Technical

Reliance on legacy technology, over-specification, complexity implementation: these are the most cited causes for technical challenges on digital transformation projects. It is understandable, given that the same Crunchbase study cites the major motivator of digital projects as reactions: to competition advances, to customer demands, to legislations and even to C-level pressure without a proper strategic plan in place. 

Aligning the business objectives with these of IT and closing the gap between these verticals from the very start of the strategy definition is an essential move, acknowledged by CEOs like John Mullen for Capgemini.

Organisational

SMEs typically suffer little in this arena, as their scale favours flatness, flexible decision-making and operational flows. However, large-scale organisations lack agility, as functional silos, strict operational processes and shareholder short-termism strategies are in place.
Organisational change is hard, broad in scope and people involved and takes a significant amount of time, so you might not be able to cover it all. However, a deep understanding of where the potential roadblocks for your project might help anticipate the obstacles and let you work granularly to mitigate them.

People

Cultural and organisational legacy tend to produce complacent teams lacking the skills, agility and motivation required by digital projects. 

Posing several questions as a team leader - have we anticipated and won the buy-in of all stakeholders? Do we have the necessary skills in place, and if not, can we nurture or source them on the way? Does our culture empower people to work in uncertainty and find a purpose? Do we have the right profiles at the right times and tasks? - will help create a top team of motivated, accountable and highly performing people.

Resources

Last but not least: proper resource planning is behind every successful project. Digital transformation projects tend not to be planned strategically - that is to say, involving all functions, with sufficient time ahead and proactively instead of reactively. 

This causes under-planning of financial resources - lack of budget is an often-cited source of challenges for all company sizes - but also other resources as skills, time for roll-out, etc.

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