How are you finding ways to update employee skills while balancing existing workloads?

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Head of IT Operations in Finance (non-banking), 201 - 500 employees
Hi Tobey - Thanks for the question. We are a small shop so when someone is out it definitely affects the workload. I do encourage training and conferences and make sure we have budget for it and put it in people's goals. We also do sprint sessions in IT which helps. We are able to plan two week sprints for our project and incident/request backlog. When someone is going to be out for training, we plan for that in the sprint. That way the work to be accomplished during that period is set ahead of time and the team is still able to meet expectations of that sprint. So in short, we have to plan ahead when we know people will be out for any reason, including training. Another thing that helps is having a primary and secondary for every application and system formally identified. So if something comes up and the primary person is out, it does not just sit until they get back. It can still be worked.

Hope that helps, and good luck!
CIO in Real Estate, 11 - 50 employees
Invest in people, the return is multiple times the time invested, for everyone.  Find the win-win by focusing each employee on a technology skill improvement path that matches your organization's needs and his or her career path and future aspirations.  It may not be a perfect match all the time, but get as close as possible.  In the cases where I've found a good match, individuals excelled far beyond my expectations in speed of learning and gaining expertise - and the time invested paid back in multiples towards improved operations.
Director of IT in Transportation, 5,001 - 10,000 employees
We have cross generational interaction between departments and of course online access to skill improvement through our cloud.  Planned training to test skill understanding and work flow systems to seek out weak points and apply mentors to personally assist anyone who has questions.
ISSO and Director of the IRU in Healthcare and Biotech, 10,001+ employees
I allow my staff to let me know what they want to develop and train in and then we find the best course of action to make that happen.
Senior Security and Compliance Auditor in Software, 1,001 - 5,000 employees
I find real world issues in InfoSec and IT and then challenge staff to address those same issues in our shop.  Leads to great discussions, side research and is energizing for all of us.  I also ask that staff take 15 minutes per day to read their various industry news feeds including the comments sections.  

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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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