What is the biggest problem you have in work

Bean counters trying to drive product and in turn, engineering.

Hm, how does this typically manifest itself? Is it in having overly tight budgets or more so in having unrealistic expectations?

I wonder if there's a more seamless way to facilitate vertical communication when the chain of command is long.

Outdated Tools

Any specific area? Is it more an issue of the company not updating to newer releases or is it more a lack of up-to-date software offerings.

Do you have any examples of outdated tools and why they're no longer well-equipped?

users

Getting users? Or maintaining them (eg. resolving complaints, etc.)?