head to head
Neither is simply harder - they are hard in different places. Heroes of Might & Magic: Olden Era demands more variance; Portal demands more execution.

Optimization · Pure Optimization
A turn-based strategy game built on hero development and army optimization.

Optimization · Pure Optimization
The portal-gun puzzle game whose solutions are everything.
Heroes of Might & Magic: Olden Era leans Optimization (Pure Optimization); Portal leans Optimization (Pure Optimization).
Portal leans clearly harder on execution.
Heroes of Might & Magic: Olden Era
no reflex demand, turn-based strategy
Portal
Portal placement timing modest.
Heroes of Might & Magic: Olden Era leans clearly harder on reads.
Heroes of Might & Magic: Olden Era
human multiplayer opponents adapt strategy
Portal
No adversary modeling player.
Heroes of Might & Magic: Olden Era leans clearly harder on variance.
Heroes of Might & Magic: Olden Era
combat rolls and map randomness
Portal
Deterministic chambers; no randomness.
Heroes of Might & Magic: Olden Era leans a little harder on optimization, though the gap is small.
Heroes of Might & Magic: Olden Era
hero builds, economy, army composition
Portal
Pure puzzle-solving optimization.
A matching score does not mean a matching test. Two games can both sit at 10 on execution and demand completely different things of you - which is why the reasoning above matters more than the number beside it.