Telementoring, also referred to as e-mentoring or online mentoring, has been carried out in a wide range of K-12 environments and continues to grow in popularity. Through a review of several studies, we argue that the potential for telementoring to support deeper and more authentic school learning will not be fully realized unless researchers pay more conscious attention to the developmental character of telementoring relationships. We discuss the flaws of up-front training as an approach to improving program outcomes, and compare three other strategies (iteration, facilitation, and open access to models) that can be used in combination to supplement training.