What are the best practices for ensuring IT outsourcing fits your organization's culture and values?

Defining the expectations and setting them up in an efficient manner is crucial in any outsourcing partnership. I found that 99% of the time, if the know-how does not start from and stays within the organization that is looking to outsource, it's hard to achieve success. Without understanding the project/product, the current situation and where you would like to end up in the long term, it's pretty much impossible to just rely on an outsourcing provider to do that for you. Even if in theory the would be able to do it by themselves :)

Defining expectations for IT outsourcing is crucial, but I've observed that involving the actual end-users – the employees – is often overlooked. IT serves the business, and hence, understanding and incorporating employee needs and preferences is vital. Successful outsourcing initiatives often result from serious consideration of employee feedback, making them feel a part of the project and helping them understand and accept the changes. More importantly, outsourcing should not be viewed merely as a cost-cutting measure; it must offer tangible benefits to the employees, enhancing their work experience and contributing positively to the organization

Cultural compatibility is an overused term these days, but in an outsourcing partnership it's a crucial part of success. I would go so far to say that technical ability is less important than common ground for communication and good collaboration. If companies manage to treat the outsourced team as an integral part of its own structure and see them as work colleagues, rather than "throwing" to them things they do not want to do themselves, or do not understand, they are already set up for success. Very important part, that should not be underestimated.

No/low stakeholder involvement is one of the main reasons why outsourcing partnerships never get off the ground. The need is there, the right partner is there, the projects are there, but if nobody is in charge of managing this ecosystem, it's hard to make it work. In my experience, when companies decide to have a dedicated person to oversee the outsourcing relationship by not only understanding and creating a good relationship with the outsourcing provider, but also acting as an internal promoter of the provider's capabilities, being aware of different areas where they could come in and help, while having the backing up of the management team, the results were immediate and plain for everyone to see.

In the context of IT outsourcing, it’s important to view the initiative as part of a long-term strategic plan, rather than a short-term solution. This involves looking beyond the internal needs of the company to consider how outsourcing will impact relationships with external partners like suppliers and customers. IT outsourcing is an excellent opportunity to break free from legacy systems and move towards a more modern, digitalized business model. A phased approach is advisable, starting with the overhaul of internal processes and then progressively moving to external services. This careful, step-by-step planning is key to a successful transformation that benefits all stakeholders.