This paper presents authors’ experiences gathered from several large infrastructure projects on Macedonian road network. The results of the slope stability assessment using mainly limit equilibrium and empirical methods are presented for over 80 deep cuts composed of Paleozoic schists metamorphic complex or in Eocene flysch sedimentary deposits. The rock masses are usually highly weathered, tectonically disturbed, and often folded with low rock mass quality. They are prone to local or global instabilities deformations expressed as wedge, planar, or rotational mode of failure, depending on local joint set combinations and slope elements. Results are mainly presented in a form of partially modified diagrams from known Q-slope method, where in parallel, values from calculations of Factor of Safety are added. Some elements related to new Eurocode 7 Design Approaches are also analyzed. The key finding is that uncertainties in a final definition of slope geometry comes not only from input parameters, but also from chosen design approach. The best way to assess the stability condition is with a combination of different tools and methodologies, especially when we face highly weathered and weak rock mass formations. Some recommendations for further development of the methodology are also presented, and they are mainly related to possibilities to estimate decreasing of strength properties as important elements for long-term rock slope stability for such rock slopes.