To evaluate a web filtering solution, an organization should: 1) Understand its internet policy and enforceability needs, 2) Determine stakeholder roles and privileges, 3) Decide where to implement the filter on the network for optimal performance, and 4) Evaluate solutions hands-on to assess criteria like ease of use, integration, and total cost of ownership. Choosing a solution that installs easily, requires no extra hardware/software, seamlessly integrates, and minimizes administration will save money while providing comprehensive protection.