When asking for flexibility at work, the most important thing is to focus on the needs of your company. By positioning your alternate work arrangement as a good business decision that saves your company money or benefits your customers, you are more likely going to get your request granted.
However, the first response of many company managers is "No." The no is not always because the manager is not open to something different. It is usually because the idea of flexible work is something new, and the manager is not sure about how it will work. When change is feared, it is just easier to say no.
The next step in the negotiation process after a no response is to ask questions to try to figure out what additional information you need to provide to convince your manager that your arrangement will work. And the most simple question you can ask is, "why not? "
If you challenge your manager to see beyond their immediate resistance to change by asking him and her why your arrangement won't work, you will either find that there is no reason it won't work, or you will get more information to restructure your proposal.
The hardest part is asking. Many fear that their manager will think less of them if they ask for flexibility. But, if you approach your request conveying your interest in helping the company succeed, you will more likely impress your boss.