Is it possible to combine information from two blocks from a matrix to an if function?
The question is a little unclear, is this what you are looking for?

{% set requiredProgram = false %}
{% for block in entry.workshopInstructor %}
   {% if block.requiredPrograms.contains('Photoshop')%}
      {% set requiredProgram = true %}
   {% endif %}
{% endfor %}

{% if requiredProgram %}
  Photoshop is enabled on one of this entry's blocks field.
{% endif %}