“That won't work” tells you the proposed arrangement has been declined. It does not always tell you why. The deadline might be fixed, the request might be unclear, or the other person might need something different.
If the conversation is appropriate to continue, ask a simple question about the obstacle.
Ask for the practical constraint
“What needs to be ready for tomorrow's meeting?” may be more useful than “Why are you being unreasonable?” It helps identify what the other person is trying to accomplish.
For a shared household plan, ask which day would be possible. For a project, ask which parts are essential and which can wait. Keep the question open enough to receive information, rather than disguising an accusation as curiosity.
Offer an option you can fulfil
Perhaps the figures can arrive tomorrow and the commentary on Friday. Perhaps a meeting can be shorter or a task can be assigned elsewhere. Check the effect on your own commitments before agreeing.
The Program on Negotiation's material on alternatives to agreement provides background for thinking about your other options. An alternative should be realistic, and the other person is still free to decline your proposal.
Confirm what has changed
If you reach agreement, repeat who will do what and by when. A short written summary may help where several details matter. Distinguish an actual agreement from an option that still needs approval.
If no workable option emerges, close the conversation with a clear next step. You might need to gather information, consult an appropriate person or accept that this request will not be granted.
Four useful questions
- Which part of the proposal is difficult?
- What must happen by the fixed deadline?
- Would this smaller or differently timed option work?
- What have we actually agreed, and what remains open?
Do not respond to every refusal by offering unlimited extra effort. A revised arrangement should address the original problem as well as the other person's needs.


