What is your biggest pain point when outsourcing IT/software jobs?

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VP of Global IT and Cybersecurity in Manufacturing5 years ago
Time zone and language challenges between the teams.
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Group Chief Information Officer in Construction5 years ago
To fined the Right partner who care about the project not only finishing the contract with as less efforts as possible, someone who understand what strategic partner means, and long term relationship, and believe it could be Win-Win rather than "Hit and Run".
I'm sorry to say that it is very difficult to find such partner
Chief Techical Officer in Software5 years ago
Quality, skills and Timezone. Timezone wouldn't have been an issue if the quality had been there but it became a daily chore to correct all the work that was being done.
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Chief Techical Officer in Software5 years ago

Also, ethics. I found cases of existing copy written code submitted sans copy write information as the authors own work. I was OK with open source code and libraries as long as you provide the license and don't try to pass it off as something else.

Plus unrealistic promises that obviously couldn't be met and weren't.

Chief Customer Engagement | Enterprise Architecture | Provide The Technology That Fits You in Software5 years ago
I would say the following:
1. time difference
2. sometimes lack commitment to the project
3. cultural difference
4. lack of trust
5. lack on-site strong leadership

It also varies if one does really off-shore or has an own team. We do very often over-communicate and share a lot more than others may do. This helps to minimize the miscommunication risks. Despite all challenges I still love international development. It has definitely enriched my life.
1
Director of Information Technology - Ag Valley Coop in Retail5 years ago
Our biggest challenge when outsourcing IT is either setting proper expectations or communications. When outsourcing skilled work, my expectations are often out of sync with what the customers capabilities were sold as.
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