What are some of the biggest challenges in a transformation journey?

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CIO in Finance (non-banking), 51 - 200 employees
It's critical to have buy-in from not only management, but across the organization. You need buy-in for why this transformation is needed, so people feel comfortable about the change. The biggest hurdle to a transformation journey is establishing why it needs to happen. People will wonder, "Why are we changing; am I going to lose my job? Or will I be doing something different? Will it be more challenging?" It's important to manage those expectations or provide as much clarity as possible.

These days, technology is very smart, affordable and quick thanks to all these companies who build cloud technologies. That makes technology simpler because it's just a matter of understanding which product is going to solve your problem and then getting an expert to implement it. That's what most organizations do, but they're missing change management, which is what you need to exploit the full potential in the value chain. There could be a system you have already built that is not being used, maybe due to lack of awareness. If people are hesitant to use it, it has not been fully embraced, and that's why buy-in at every level is required.
CTO in Healthcare and Biotech, 11 - 50 employees
The most important of all it would be to change the mindset of those who will benefit from the transformation itself. People aren't very fond of changes, they will reject the changes immediately if something affects them directly. This is a task that has to be continuously talked to all involved parties ( Before, during and after the journey has started ).
VP, Information Technology in Consumer Goods, 10,001+ employees
People... Most people don't like change, and unless they feel they are part of the journey and understand it, they will push back to various degrees. As Apurva mentioned below, technology these days is smart, affordable, and easy to implement (in most cases), however the challenge then becomes bringing the users on the journey of using new tech and helping them embrace any change to their daily work processes.
Director ERP Management in Travel and Hospitality, 1,001 - 5,000 employees
Legacy applications..... There is a new solution/tool available which looks beneficial for your business but your existing application architecture doesn't support it!!

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