If a non-democratic country wants to change into a democratic set up, then which kind of challenge would it face?

A non-democratic country wanting to change into a democratic country would face the foundational challenge.

NOTE - Democracy is a form of government which represents the will of the people and works for the betterment and well-being of the people. In contrast to the non-democratic governments such as dictatorship (formed without the will of the people and oppressive in nature), democracy is a transparent government which is very much sensitive to the needs of the people.