Many of us dream of spending a month on a sailboat but brush the idea off as pure fantasy. We have too much work to do, our boss will say no, maybe we'll rock the boat too much even by asking. Usually all of these things are true, unless you do your homework first. Headwaters' newest staff member recently made this request and I happily said yes. Is it because I am a kind executive director and will happily take over her workload for a month? Nope. It's because she made it so easy to say yes. Here's what she did:
She got a feel for the organization's culture- We have many staff members that have taken extended vacations. I often rave about what a good job they did preparing the other staff for their time away. She took mental notes and used that as part of her strategy when approaching her own leave.
She didn't surprise me- When she first heard about the opportunity to go on the sailing trip, she let me know that she was thinking about doing this and was concerned about missing an event that we are hosting during that time. I appreciated that she was so concerned about the event and wanted to make sure it was successful but I made sure that she knew that, while there was a lot of work to be done to get ready for the event, her attendance on that day wasn't mandatory.
She made a plan- She wrote up a list of all of the activities that needed to take place during that month, figured out who could be alternatively responsible, got their buy-in, and also listed all of the things that she could do in advance to either finish that activity or to make it easier for the person taking over.
She always does a good job- It is much easier as a supervisor to say yes to someone who consistently keeps up with their responsibilities. She does her job well everyday and so that made it really easy for me to trust that she would properly prepare for this leave and be ready to get back to work when she returns.
Do don't give up on your dream of going on a safari, a mission trip to Honduras, or backpacking in Australia. Just make it easy for them to say yes.