Can I give an asset to a Beneficiary and put in instructions for him/her to follow?

Sometimes we get questions such as “ Can I give my house to my parents and after they pass away, for the house to be sold off with the proceeds pass on to my husband?” or "Can I give my house to my sister but she has to keep it and let my wife stay in it?"

In a trust, a nominal owner (the trustee) holds the asset for the benefit of the trust beneficiary allowing the trustee (within the trustee powers allocated to him/her) to apply the asset accordingly. However, assets directly distributed to a beneficiary through a Will are considered his/hers which generally will be up to him/her to do what he/she wants with it. Regardless, beneficiaries might still follow the testator's wishes out of goodwill.

Think of it as giving your spouse a car so she doesn’t have to take public transport anymore (i.e. transfer the car to his/her name). Since the car is now under your spouse's name and the car also belongs to her, what she do to it is entirely up to her even if she decides to sell the car to invest the sales proceed or to buy a branded bag.

Specific to the housing examples above, while you still can pen down your wishes under “Additional Instructions”, it might not be legally binding since technically the beneficiary will now own the asset once he/she inherits it.

This leaves you with a few possible options:

You might be better off speaking with your financial adviser to take up another plan so you will have more assets (e.g. you can allocate a sum of money to provide housing or rental or outright give a payout to the relevant beneficiaries).
Put the asset into a living/standby/testamentary trust (please note that approval is required to put HDBs into a trust). However, this brings out another set of problems (stamp duties, taxes, finding trustees, etc.)
Try to appeal to the beneficiary's moral sense by having a chat with him/her and pen down your wishes in the Will, so long as you are aware the possibility that it might not be legally binding since technically the beneficiary will now own the asset once he/she inherits it.
Try getting a separate signed contract* with the beneficiary stating that he/she will follow your instructions accordingly after receiving the inheritance.

*getArrange.com platform currently does not provide such contracts/templates as it goes beyond the scope of a Will / Trust. Additionally, the effectiveness of such a contract is subjective.