There are so many changes happening in our current times that are linked to the introduction of ever more powerful digital tools and machines. Our focus is often technical and there is not so much attention devoted to the human and cultural side of digitalisation. Research evidence from our consulting practice reveals that leaders and managers find themselves up against a number of key dilemmas when seeking to digitize. By confronting these dilemmas and seeking effective reconciliations between their competing demands, organizations can embed new solutions that synergize older traditional business with the new worlds of IT. The more we go digital, the more we need analogue.