3 Questions Your Boss Wishes You Would Ask

According to Inc. Magazine, three out of every four employees report that their boss is the worst and most stressful part of their job. And sixty-five percent of employees would rather have a new boss than a pay raise. Even more concerning, employees who have a “bad boss” have significantly higher rates of heart disease than those who don’t.

In my twenty years of leadership development and communication consulting, I have had the unique opportunity to work with both staff and management. It’s fascinating to hear two sides of the exact same issue. Most people don’t intentionally communicate poorly, so it’s safe to assume that most people believe they are doing or saying the right thing.

Unfortunately, this can make communicating a challenge. The stakes are high with your manager because if you’re not able to communicate effectively, you are more likely to be unhappy at work.

Well, comedian Craig Ferguson may have just revolutionized communication without even knowing it. With his raw humor and uncanny wit, he explains that it took him three marriages to figure out three questions that would have made his life a whole lot easier. As it turns out, the same questions can also improve your relationship with your boss (and just about everyone else).

Here are three questions your boss will thank you for asking:

1. Does it need to be said?

Is this issue important? If it is, communicate assertively and focus on being solution-oriented. If the issue isn’t that important in the grand scheme of things, let it go.

2. Does it need to be said by me?

Are you better off waiting for the message to come from someone else, or should it come from you? Your cranky co-worker has come in late for the fifth time this month. Is it really your responsibility to point it out? If it’s directly impacting your work, it might be. But if it doesn’t, let it go.

3. Does it need to be said by me right now?

Timing is everything. Sometimes the exact same message may be received very differently depending on when it’s delivered. Next time you’re in a meeting and have the urge to disagree with your boss in front of the entire team, is it the right time to vocalize it? It might be worth the risk, depending on the issue. Or, it might make more sense to bring it up at a different time.

While the questions are simple, it’s actually quite difficult to catch yourself in the moment to ask them.

Given that we spend the large majority of our waking hours at work, it stands to reason that anything you can do to make that experience easier is a no brainer.

So before you say something you may regret, before you challenge the issue, voice your opinion, or put your foot in your mouth, take a moment to ask yourself these questions.