Leonard's corruption route depends on the following key conditions:
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In your first conversation with him at free time, respond negatively.
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During your first sleep scene, ask about what happened to his body rather than his family.
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When Leonard disappears after going to gather food alone, make sure to move around the dungeon as much as possible and trip over a rock. After this, when you find Leonard, his condition will be noticeably different.
If you meet these three conditions, you will successfully enter his corruption route.
To be sure you're on track, check the Management Notes in your notebook from time to time. If you see red "Red Corruption Notes" piling up, that means you're progressing correctly.