Our internal IT person is not keeping up. Do we replace them or add to them?

The person who was the right hire at twenty employees is often underwater at eighty, through no fault of their own. One person cannot cover a help desk, security, servers, network, vendor management, projects, and multiple locations. What that looks like from your chair is someone who has stopped being responsive, and it is genuinely hard to tell apart from someone who has checked out.

If it is capacity, co-managed usually works well. Your person keeps the things that benefit from being in the building and knowing your business, and we take the specialized and after hours load off them. Most people in that position are relieved rather than threatened, because they have been drowning quietly.

If it is capability or engagement, that is a management decision, not a technology one. We can take over fully, and we can do it in a way that does not depend on that person's cooperation.

What usually settles it is the assessment: whether the undone work is the specialized kind nobody could reasonably cover alone, or the basic kind that should have been happening all along.