For over 50 years, astronomers have searched the skies for evidence of electromagnetic signals from extraterrestrial (ET) civilizations that have reached or surpassed our level of technological development. Although often overlooked or given as granted, the parallel use of an equivalent communication technology is a necessary prerequisite for establishing contact in both leakage and deliberate messaging strategies. Civilization advancements, especially accelerating change and exponential growth, lessen the perspective for a simultaneous technological status of civilizations thus putting hard constraints on the likelihood of a dialogue. In this paper, we consider the mathematical probability of technological synchronicity of our own and a number of other hypothetical ET civilizations and explore the most likely scenarios for their concurrency. If Search for Extraterrestrial Intelligence (SETI) projects rely on a fortuitous detection of leaked interstellar signals (so-called ‘eavesdropping’) then with minimum prior assumptions N⩾138–4991 Earth-like civilizations have to exist at this moment in the Galaxy for the technological usage synchronicity probability p⩾0.95 in the next 20 years. We also show that since the emergence of complex life, coherent with the hypothesis of the Galactic habitable zone (GHZ), N⩾1497 ET civilizations had to be created in the Galaxy in order to achieve the same estimated probability in the technological possession synchronicity that corresponds to the deliberate signalling scenario.