Higher education systems in Denmark and Poland are interesting not only due to their distinct stages of historical development, but mainly due to their size and complexity resulting in a particular policy. The main challenges faced by higher education and their corresponding policy directions have been grouped into the following categories: (1) steering tertiary education: setting the right course; (2) matching funding strategies with national priorities; (3) assuring and improving quality; (4) achieving equity; (5) enhancing the role of tertiary education in research and innovation; (6) academic career: adapting to change; (7) strengthening ties with the labour market; (8) shaping internationalisation strategies in the national context; and (9) implementing tertiary education policy. Earlier research by the authors on comparing public policies between Scandinavia and Poland (Dziedziczak-Foltyn and Musial 2009, 2010 and 2015), as well as their hands-on experience with regard to their higher education systems, allows us to narrow down the broad scope of possible comparative analyses and focus on the most striking challenges: steering, quality and internationalisation. In the domain of steering the challenge of finding proper balance between governmental steering and institutional autonomy appears particularly interesting. In the domain of quality we have concentrated on developing quality assurance mechanisms for accountability and improvement. In the domain of internationalisation we found quality across borders particularly worthy of investigation. The article pursues also a more universal goal to signal out a great analytical potential of comparative higher education research even if only two countries are taken into account (Kosmützky 2016; Välimaa 2008).