The paper evaluates the attempt to launch a National Dialogue process in Ukraine backed by the Organization for Security and Cooperation in Europe (osce) from the perspective of its teleology, design and impact in the context of the aggravating internal divisions, problematic legitimacy of the post-Maidan leadership, Russia actively backing the forces in opposition to the interim government in Kiev and subversive of the integrity of the Ukrainian state, and peaked geopolitical tensions in the broader region. in the run up to the extraordinary presidential election in Ukraine scheduled for 25 May 2014, the osce backed the launching of a National Dialogue to prevent further escalation of the destructive and increasingly violent internal conflict. The efforts aimed at the consolidation of the Ukrainian political elite from across the country, including in the rebellious East and South regions, and across the political spectrum, also involving the party of the fugitive President Yanukovych. This endeavor, by the osce Swiss Chairmanship, provides insight into the opportunities and limitations of the top-down and elite-based approach to the National Dialogue in Ukraine, particularly in comparison with the local grassroots dialogue initiatives in the divided communities as well as the center-region dialogue formats, on the one hand, and with the extra-national formats of talks involving Ukraine and Russia, on the other. Besides, lack of the strategic sequencing and embeddedness of short-term objectives of the stakeholders to either keep or challenge the political status quo and long-term accommodation of political differences by the reformed political and administrative arrangements and national reconciliation prevented the National Dialogue from gaining the momentum, was prohibitive of its continuity and did not get traction with the population irrespective of the political preferences. There were objective reasons that prevented proper design and implementation of the dialogue, such as urgency, extreme polarisation and strong pressure on the post-Maidan leadership at the time from opposing constituents that ardently rejected dialogue, a factor that could not be ignored against the backdrop of the upcoming series of elections. However the osce political imperative had prevailed over the professional approach to the design and facilitation of the National Dialogue. In particular, no clear agenda that resonated with the diverse constituencies’ actual needs and grievances was developed, no broad consultations had been held prior to the dialogue, disagreements between the stakeholders regarding the participation were not resolved, and the very design of the events, including media presence, was not conducive of the genuine deliberation and joint search for the mutually acceptable short-term and long-term trajectory of the country.