Improving compliance with labor legislation in Colombia requires long-term transformative processes and the participation of many actors. Short-term projects that intend to improve compliance with labor laws and relevant standards by focusing only on strengthening workers’ capacities are not likely to generate a significant systemic impact, since an improved compliance requires long-term processes as well as the joint participation of workers, employers, and the Ministry of Labor. Ensuring full compliance in the five priority sectors would reasonably require more time than the limited project lifespan. It would also require systemic transformations at all levels in/related to each of the prioritized sectors, and, crucially, further engagement by, and increased capacity of, the Ministry of Labor and relevant institutions to create an enabling environment that is conducive to the labor law, regulations and their respective enforcement. In addition, it would require promoting and strengthening constructive tripartite social dialogue and eventually collective bargaining processes at the local, regional, and national levels. This, in turn, requires the participation of strong unions and employers’ organizations that are open to such dialogue, where serious challenges exist. Increased success in government-led dialogue would also be required. These factors should have been given greater weight in the project’s design phase.