Ecclesiastes and the Byrds together remind us that there’s a time to laugh, a time to cry, and a time for everything under the sun. There’s also a time to be a yes-man and a time to be a no-man—and you need to be twice as careful not to mix-up these two.

By default, it definitely makes sense to be a yes-man. To the person who hired you, you’ll always be subordinate and, thus, you need to help him figure out his objectives and achieve them—two goals that are impossible in an environment of primarily constant vetoes and negativity. Think about your friends, do you want to be with the person who stops all action in your life or with the person who propels action forward?

But being a no-man also has its time and place. What happens when the ship is headed towards a cliff, to mix metaphors? Someone needs to be the truth-teller, a role traditionally fulfilled by the jester but in your enterprise, too important to be left to the jokester. The No-Man or No-Woman, the Dream of Every Narcissist, and the Enemy of Every Child of a Narcissist!

So, given that the two extremes of always-yes and always-no are just, well, problematic, how do you balance the two?

Here are some rules of thumb that may be useful to keep in mind.

First, ask yourself: if things go wrong, how severe would it be? The more severe the answer you come to, the more important it is for you to speak up.

Second, ask yourself: do you have a solution that your client or boss could reasonably implement (and “reasonably” includes his willingness to be open to solutions such as the ones you have in mind)? If you don’t know what should be done, then you should be a bit more cautious before arguing against a proposal.

Third, how much in your wheelhouse is the issue at hand? The more of an expert you are on the topic, or the more under your authority it is, the more confident you should be in speaking up.

If you are like a younger version of me (Ba’al help you), you may be reading this and wondering: why not just say “no, no, no” constantly. I argued above why not to, but it gets deeper.

Years ago, I studied comedy. Most of what I learned was not useful, but the most important thing I learned was one technique that was profoundly helpful in, well, life. It is a trick to make any situation more fun or funny. The trick, the simple way to make any situation fun is to respond to anything by saying, “Yes, but…” This works because saying “no” stops all the action. “No” is a conversation ender. “Do you want to go to this cafe for a drink?” “No.” What more is there to say? Nothing! Now compare, “Do you want to go to this cafe for a drink?” “Yes, but only if you speak in Pig Latin while pretending you’re German when we’re in there.” Do you see how much fun this is?

I did this for years and became funnier in person and in writing—more accurately, I tried to—before I realized the same principle applies in business as well. When someone, in a business context, suggests an idea in a brainstorm, and you just veto it the action stops. The company stops moving forward. But imagine you adopt this humor technique in conjunction with the rules of thumb listed above about saying “no.”

“Our next landing page, should we do it in 1998 Flash?” “Well, I think that one of the requirements of the site should be that it works on the browsers that 95+% of our target market is using. So, if we’re targeting my parents, still on AOL, and their browsers still have flash, then that makes sense. But if we’re targeting anyone else… maybe we should have a no-flash policy?”

“Yes, but” is the shortcut to problem-solving (including the problem of boredom) in work and in real life alike.