What is the most challenging part of being a CIO?

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CIO in Healthcare and Biotecha year ago
Staying on top of the constantly changing landscape. Part of the expectation of the role is that you are the expert in technology in your organization. However, it is impossible to stay on top of all of it. You must learn to delegate and be vulnerable enough to say "I don't know." Staying in tune with your executive leadership and the desired business outcomes will help to narrow where you are focusing and then use your team to bring you new and emerging ideas from other spaces. 
Chief Information Officer in Educationa year ago
Navigating between different stakeholders and being proficient and able to deal with all of them.  Your peers, the executive team, your technical team and business partners all have different needs and modes of operation.  You need to be able to speak the language of all of them, understand how to optimize each layer and stay current from a business, technology and staff management perspective.  
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CIO in Telecommunicationa year ago
I think it's cleaning up the messes left by other CIOS, predecessors, in the role.  Some weren't technically savvy and left a technology mess because they were clueless.  Some lacked people skills, leaving relationship messes, lack of trust, and lack of respect with their colleagues, usually along with shadow IT.  Some lacked business experience and left a disaster in the budget and financials.  Some lacked leadership and left teams that were frustrated and burnt out, unmotivated, and unskilled.

It's hard enough having all the skills and knowledge that other commentor's shared in this discussion, but having to clean up the messes left behind by those without them doubles the challenges because you're starting from behind before you've even begun.
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CTO in Healthcare and Biotecha year ago
Not understanding business as it is. Yes, we have tech knowledge, but we must match it to the business needs, not the tech we want to implement, but rather the one that is fit and will provide the required solutions.
Head of Transformation in Governmenta year ago
I agree with all of the comments above. The most challenging part of being a CIO *are* business leadership, people leadership, legacy technical debt, changing technology landscape, but like the famous EDS Herding Cats superbowl advertisement said at the end... "It ain't an easy job. But when you bring a herd into town and you ain't lost a one of them, ain't a feeling like it in the world."

https://www.youtube.com/watch?v=m_MaJDK3VNE

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