For companies determined to remain 100% remote, what are the top obstacles they will have to overcome?

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Innovation Technologist in Finance (non-banking), 1,001 - 5,000 employees
There will be companies that say, "You know what? We're just completely off of this. You don't need to come up. We're going to give up our real estate. You guys can work from wherever you want. And in fact, we're going to hire all over the world." Those companies will learn what works for them in their ecosystems. They will start to answer questions: What are the policies that we need to put into place? How do we measure productivity? How do we ensure that training happens? How do you manage knowledge management in the company? How do we ensure culture is maintained? So for a company that is fully remote, those things become very important.
CTO, 10,001+ employees
I can speak to the security aspect.  So there's security in multiple ways. You may need to change your group policies to say your device cannot be left unlocked because anybody can access it. A guest or friend may need a device to do something and they can just go on and the screen is on. At work, we used to put a screen protector so that people cannot see it. So are you going to have a screen protector at home? Your laptop is going to come with a screen protector. The security is at all levels, from software to network to device to print..... We have to completely rethink the whole security. That's the one thing we didn’t have the time to think about. We just went home. In our company, we have now put in an initiative where we do a security assessment in all the executives' houses to make their things are all secure.
CIO in Education, 1,001 - 5,000 employees
There's still an element of organic conversation that occurs during the in-person experience that is just impossible to replicate in a 100% remote environment.
CIO in Services (non-Government), 501 - 1,000 employees
If you peel the onion just one layer beyond "collaboration," you find the need is closer to Knowledge Management. Getting information out of people's heads and up for discussion is a more specific way to discuss what collaboration lacks during work-from-home.

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CTO in Software, 201 - 500 employees
Without a doubt - Technical Debt! It's a ball and chain that creates an ever increasing drag on any organization, stifles innovation, and prevents transformation.
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