It's hard to respond to a statement without examples of how it's not working, but it's crucial to understand that TFVC (in "Server Workspace" mode, which was the mechanism prior to TFS 2012) does not examine the state of your local filesystem. TFVC Server Workspaces are a "checkout-edit-checkin" type of system where this is by-design, an intentional decision made to massively reduce the amount of file I/O required to determine the state of your workspace. Instead, the workspace information is saved on the server.
This allows TFVC Server Workspaces to scale to very large codebases very efficiently. If you are in a multi-gigabyte code base (like Visual Studio or the Windows source tree) then your client does not need to scan your local filesystem, looking for files that may have changed, because the contract you have with TFS is that you will explicitly check a file out when you want to edit it.
You are expected to not mark a file as write-only and change it without explicitly checking it out first. If you go down this route, then the server does not know that you have made changes to your file, and performing a "Get Latest" operation will not update your local workspace, because you haven't told the server that you've made changes.
If you do subvert this mechanism then you can use the tfpt reconcile command to examine your local workspace for changes that you have made locally.
If you find yourself using "Get Specific Version" and selecting the "force" and "overwrite" options, then it is very likely that you are in the habit of bypassing all of the enforcements that TFS has implemented to keep you from hurting yourself, and you should probably consider TFVC Local Workspaces.
TFVC Local Workspaces provide an "edit-merge-commit" type of version control system, which means that you do not need to explicitly check files out before editing them and they are not read-only on-disk. Instead, you simply need to edit the file, and your client will scan the filesystem, notice the change, and present this as a pending change.
TFVC Local Workspaces are recommended for small projects that do not require fine-grained permissions control, since they present a much nicer workflow. You are not required to be online, and you do not have to explicitly check files out before editing them.
TFVC Local Workspaces are the default in TFS 2012, and if they are not enabled for you, then you should ask your server administrator. (Organizations with very large codebases or strict auditing requirements may disable TFVC Local Workspaces.)
Eric Sink's excellent book Version Control By Example outlines the differences between checkout-edit-checkin and edit-merge-commit systems and when one is more appropriate than the other.
The Professional Team Foundation Server 2013 book also provides excellent information about the differences between TFVC Server Workspaces and TFVC Local Workspaces. The MSDN documentation and blogs also provide detailed information: