This chapter presents pilot study with aim to characterise the potential connections and synergies between statistics and modelling education. By developing a methodological approach of applying the software NVivo and grounded theory, we analysed the 17 ICTMA books published to date and the books from ICME-6 and the 14th ICMI study. The results show synergies in terms of the identified themes: teach and learn statistics/modelling; ICT; curriculum; and theory. The context units analysed frequently provide suggestions for how to teach statistics using modelling approach, but seldom is the relationship between mathematical and statistical modelling from a theoretical point of view discussed. The discussion brings forward some limitations of the methodological approach applied and suggestions for how to overcome these to develop a more robust methodology.