So you’ve cut the connectivity cord and managed to transport yourself to a tropical resort where days seem endless and your time is nearly always free. You make a morning pass by the concierge desk, where the attractive and earnest personnel make eye contact with you, smile and ask “what may I do for you, sir?” The open-ended question allows you to consider all the options you have in front of you. Will it be a pool-side massage or the snorkeling tour this morning? This spoil-of-riches that the concierge desk has just allowed you to consider reinforces the good feeling of being away from the office pressure cooker. You feel your muscles relax, you breathe in the ocean air and think to yourself “Yes, I’m finally on vacation.”

Back in the office the following week, though, the same question evokes the opposite response. When your “executive” assistant asks “How can I help you today” in that same earnest tone, your anger rises. It’s a question that’s meant to make you stop in your tracks and prioritize your assistant’s day for her. Effectively answering the question would force a busy executive to think about everything he has to get done and prioritize it, as well as decide how to delegate whatever he decides to hand over. That can be a real time suck.

The most effective personal assistants understand that asking open-ended questions only creates more work for the very people they are seeking to help. A successful assistant should be familiar enough with the context and contacts in their executive’s email, schedule and CRM to prioritize for him. Having the background and understanding allows these assistant to take a strong point-of-view on the executive’s day, and on the work that they themselves should take on.

Instead of asking how they can help, these assistants say things like “I’ve noticed you have a hole in your schedule tomorrow, and that you will be near the office of important client ABC. Would you like me to see if that client can meet with you or do you want to keep the downtime to get caught up on some work?” Or, the assistant will be familiar with upcoming deadlines and remind or prepare their executive to meet those deadlines.

Having an assistant who asks you how she can help every morning is nearly the same as doing the work yourself. Having an assistant who expresses a strong point-of-view on what you can delegate and how to delegate it can create a lot of value, reduce your stress and maybe even make those tropical exertions less needed.