5 Questions You Need to Ask Your Boss Today

5 Questions You Need to Ask Your Boss Today
By Catherine Conlan
Monster Contributing Writer
Have you asked your boss any good questions lately? Your boss can be an excellent source of useful information -- insights into the company’s goals and culture, for example -- or an inspiration for you and your career. You have to ask the right questions, though. Here are five questions you should ask your boss soon.
1. “Is that the best use of my time?”

Andy Bailey, CEO and head entrepreneur coach at Petra Coach, says that this question takes guts, but it’s worth it. “It’s absolutely brilliant,” he says. “I coach every team I work with to think that question for themselves when their leader asks them to do something.” It may be the toughest thing for a manager or leader to hear, he says, but managers should value employees who can think on their own and ask questions.

2. “What keeps you awake at night?”

Andrea Ballard, owner of Expecting Change, says this question came to her after attending a presentation titled “The 5 Things That Keep Your CEO Up At Night.” “When I got back to my office, I mentioned it to my CEO, and he said, ‘Wow, I could sure add a few.’ I said, ‘Really? Like what?’ And he opened up and shared some things that were complete revelations to me.” 

Ballard says the question can provide a new perspective for both of you, and that answers will vary widely, depending on the manager. “My boss was nervous about speaking in front of a group of CEOs at an upcoming event,” Ballard says. “I offered to be a mock audience for him and view his presentation and provide feedback.”

3. “What is expected of me?”

“Very, very few businesses do a good job of defining specifically what is expected of their team members,” says Bailey. “They may give an outcome -- like ‘sell 40 million’ or ‘get the work done by five.’” Instead, Bailey says, ask for a specific set of expectations for both production and culture. “If you know what is expected, you can do it. If not, you’re shooting in the dark,” Bailey says.

4. “How am I doing?”

Employees crave feedback from their managers, and some managers are more forthcoming with performance assessments than others. To get an idea of how you’re doing, you might just have to ask. “A business cannot grow if the team members don’t grow too,” Bailey says. “You go ask, then ask again and again and again. You’ll quickly be the rock star of the team -- that is, if you do the work needed to actually make the improvements.”
5. “Want to grab lunch?”

This is a question few employees think of asking their bosses, but Ballard recommends it for team-building and connections. “I think going to lunch or drinks after work with the boss once a quarter is reasonable,” she says. “You could try and ask a few times and see how it is received. Some bosses don't want to socialize outside of work, for fear of looking like they are playing favorites.” If your boss is up to it, Ballard recommends sticking to neutral, non-work topics. “Only bring up work if the boss does,” she says.

Knowing the right questions to ask can keep you in the know or even help you grow your career. Ask and see what you receive.