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One Simple Question That Keeps You From Falling on Your Sword

Clarifying moments that help you better evaluate a situation

Ricardo Cruz / Unsplash

Mike Figliuolo
Tue, 07/08/2025 - 12:02
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I love passionate people—people who throw themselves into their work with every last bit of energy they have. To them, everything about their work is important. It’s serious business, and they drive hard to form the world in an image they’re proud of.

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However, with passion comes peril. If everything is important, you tend to get worked up over every issue, no matter how large or small. You feel it necessary to stand up for what’s right in every instance. You might even seek to transform situations by injecting yourself into them, even if you don’t really have a say in the matter.

This often results in falling on your sword for many issues, or sticking your beak where it doesn’t belong and getting involved in problems that are larger than you.

As usual, I’m going to give you a helpful little tool to help you avoid all those nasty sword gashes. All you have to do is ask and answer one simple little question:

“What’s the upside?”

That’s it. That simple. That single question will keep you out of more trouble than you can imagine. It provides what I call “clarifying moments” that help you better evaluate a situation and the possible range of impacts and implications of the actions you’re considering. If there’s no upside, it’s not worth fighting for or taking the risk. If the upside is clear, dive on in.

For example, I’ve jumped into several conversations knowing a decision had already been made and offered a contrary opinion (vociferously, in some cases). The decision was made. The conversation was over. Yet I failed to ask if there was any upside to my additional “contribution” to the conversation. Clearly there wasn’t, and in several cases I paid for it.

Had I simply assessed whether there was an upside to my participation, I would have seen there wasn’t any and could have more appropriately chosen not to argue the point. I’m not saying you should back down from a scrap. Not in the least. All I’m advocating is that you clearly understand what the upside is to your participation.

If the upside is large (avoiding a huge mistake, saving an associate’s career when they’re unjustly treated, exploiting a large market opportunity), you should absolutely fight for your beliefs. Before doing so, make sure you know what outcome you’re trying to achieve and that it’s worth the risk you’re taking.

The question also works in broader business situations. If you’re making a business decision and wondering whether to commit your resources, just ask, “What’s the upside?” You should be able to quantify it. The outcome should be something compelling that the organization will be excited to achieve.

If the upside isn’t “all that,” then stop. It’s not worth pursuing. Seems simple, I know, and many of you are probably sitting there nodding saying, “I already do that.”

OK, I believe you. Let’s just conduct a little test. Go look at all the things you’re working on right now and ask, “What’s the upside?” I’ll bet a few things you’re working on drop off the list. We’re all guilty of it. Work creeps onto the plate without an articulated upside. The only way to eliminate said work is to show it has no upside and stop doing it.

It’s a great question to ask in many situations. It will save you personal and professional pain as well as help you prioritize what you do and don’t do. And to be clear—the upside of reading The thoughtLEADERS Brief is you get neat little tools like asking, “What’s the upside?”

Published May 14, 2025, in The thoughtLEADERS Brief on LinkedIn.

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