Abstract At the moment worldwide some organizations are losing valuable knowledge due to a potential increase in retirement rates. Others are though underutilizing the capacity of older employees and the potential of younger generations. Both situations have very high costs. An intergenerational intelligent approach may help aging organizations find solutions for an optimizing learning as a bridge between generations helping societies deal with this societal challenge. The aim of this paper is to discuss the potential of intergenerational conversations on professions to help organizations become intergenerational intelligent. We will base our discussion in a short pilot experience we conducted in Portugal by creating two ten minutes videos each of them with two professionals with a difference of 30/40 years of professional experience. Keywords: intergenerational conversations professions organizations intergenerational intelligence generations societal challenge