How do I make decisions that hurt someone no matter what?

You lead an HR team now, caught in the middle, holding both your people and the business, making decisions that hurt someone no matter which way you turn. That position is genuinely hard, and the discomfort you feel is not a sign you are doing it wrong. It is a sign you can see both sides clearly, which is exactly why you are in the seat. There is rarely a clean answer in that chair. Protect the person and the business suffers; serve the business and a person gets hurt. You cannot make that tension disappear, and pretending a perfect choice exists only leaves you feeling like a failure for not finding it. Accept, instead, that your job is often to choose the least harmful path, not a painless one. So aim for that honestly. Make the hard call with as much fairness and humanity as the situation allows, tell people the truth plainly, and treat those affected with dignity even when you cannot give them what they want. That is the real work, and you can do it well. And carry your own version of the weight to someone, a peer, a mentor, so it does not sit alone in you. When a decision will hurt either way, choose the one you can stand behind, do it kindly, and let that be enough. It is.