What are the biggest retention challenges you’re currently facing?

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CIO in Education, 1,001 - 5,000 employees
The biggest challenge that I have been facing is that with everyone reading about the Great Resignation—as it's now called—even if people are not thinking of moving, reading all of these news articles acts as a catalyst. They start to think, "He's leaving. She's leaving. I should think about leaving." So there are all these external contributing factors. How do we deal with that?
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Senior Executive Advisor in Software, 10,001+ employees

It’s like Zillow and Redfin. Even if they're not going to sell their house, there are people who keep checking those platforms to find out the perceived value of their home. When you’re bombarded with all these emails, saying, "This person is leaving," you start questioning whether you’re being paid your market worth.

Senior Executive Advisor in Software, 10,001+ employees
This might be a little ageist, but I had a conversation with some of the millennials. And they said, "I don't want to work in an organization that will support a supply chain that actually targets some X countries because of human rights." I have no win there—how am I going to control that? I'm working with a client who probably makes deals somewhere else. How is that going to impact what you're working on?

I think a lot of those who are new to the workforce are looking through a very utopian and unrealistic lens. This is not “cancel culture” for enterprises—it's impossible for us to cancel our clients. We have to work; we have to make money. If we don't make money, we won't have jobs. So there are some other complications that also come into play.
Vice President for Information Technology in Education, 1,001 - 5,000 employees
The dilemma I have now is that my HR department is stuck in the 1980s. They wanted forms filled out for flexible scheduling, so we sent them in 30 forms, because every one of my team members wants a day or two day at home. But I'm getting all these ridiculous questions like, "How will you know they're working?" Well, it’s the same way I know they're working in the next building over. I'm not in their building. I can't tell you where they're sitting, but I can tell you if they're doing their job.

To me, the issue is trying to get the rest of the organization to buy into this hybrid working model. And then other folks say, "Well, why can't we do that, if IT can?" And even in IT, I can't have everyone work remotely. I have folks whose job it is just to touch technology on people's desks and in classrooms. They may want to work remotely, but they don't have a job they can do remotely. When they complain, "Why can't I do that?" I'll say, "Well, when there's an opening, apply for one of those other jobs. But right now you're not getting woken up at 2:00AM when a system's not working, they are. Should we wake you up too, to be equitable?"
Advisor | Investor | Former CIO in Services (non-Government), Self-employed
The challenge that we're dealing with here is that we have complexities on multiple levels. One challenge is to retain the talent that you actually have. The second challenge is whether the talent that you do have has the ability to blossom and grow.

As an example, there are organizations that are so dependent upon their existing workforce, that it's an inhibitor to moving forward. In one situation, there's an organization that may revert to operating out of data centers because of how much they are struggling to find cloud architects, security personnel, and people that actually understand cloud environments, because there's such a dire shortage. One of the problems is that we encounter people who say, "I'm X years away from retirement. I don't need more complexity in my life. I just want to continue to operate the way that I've been operating."

And then you have the added complexity of whether you’re willing to commit and make some transformative changes in your business when you’re unable to find new talent and you have talent with no interest in changing. One ex-CTO I spoke to said that when he came on board, 85% of his workforce was eligible for retirement within five years, and there was zero appetite for making those changes. This is a real challenge that we're seeing across every industry vertical. It's not unique to one specific vertical. It's major.

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One thing I do is include them in the meetings about the changes that will take place and get their opinion.  I also lay out the pros and cons of the changes and how it will effect us as a team moving forward.

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Very difficult28%

Somewhat difficult69%

Not at all difficult3%

We're not looking for IT staff with cloud skills0%


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