In an ideal world, we'd never have to question or decide against any of our superiors' decisions. But that's not always the case.
When we find ourselves in disagreement with our superiors, we're often forced to choose between two difficult decisions: Safeguard our careers by keeping our mouths shut or risk ostracism by going over their heads.
Willink, who hosts the podcast, hesitated only briefly before doling out some sage wisdom on the topic.
Situations like this "can be very, very problematic. Going over your immediate superior's head can cause irreparable damage and it should be your very last resort," he said.
When you skip the chain of command, "you're breaking the trust and damaging the relationship you've been building," Willink explains. "Sometimes, it's unsalvageable and you'll never be able to recover."
On the other hand, if your boss is doing something illegal, immoral or unethical, only then is it "your duty" to take action, he says.
If that's the case, Willink suggests speaking to them directly sooner rather than later. If integrity is indeed your goal — and it should be — don't be afraid to speak and act with confidence.
"It's going to be a very hard conversation, so be careful with how you approach it," Willink warns. "You want to raise the situation in a non-threatening way." He emphasizes using the word "we," as opposed to "I."
He offers an example of how to initiate the conversation: "You could say, 'I was thinking about what we were doing [...]' — and then lay out the plan, the costs and the benefits. Then suggest, 'Would you mind if we bring this up to the [superior's] boss to see what he thinks?'"
The nature of the conversation will depend on your boss' personality. If you have a defensive and insecure boss, for example, Willink suggests massaging their egos to let them know you respect them.
It's critical that you don't make yourself out to be someone who feels above them, Willink said a previous interview with CNBC Make It about how to communicate with a defensive boss. You'll build a better relationship with them by proving that "you're actually there to make them look good."
If that doesn't work, then it's time to go over your boss' head and speak to their direct superior.
"You could say something like, 'I'm on so and so's team. We're working on a tough mission, but I was thinking of another way to do it,'" he says. "You want to try to get them to say, 'that sounds like a good idea.'"
The most important thing is to make it clear that you're only acting on principle. Of course, it helps if you've already established your principles from the very start.
"When you work for someone, or someone works for you, you need to lay it right out of the gate, like, 'Hey, this is where I stand,'" says Willink, adding that it's the only way to ensure your actions don't take anyone by surprise.
Tom Popomaronis is a commerce expert and proud Baltimore native. Currently, he is the Senior Director of Product Innovation at the Hawkins Group. His work has been featured in Forbes, Fast Company and The Washington Post. In 2014, he was named a "40 Under 40" by the Baltimore Business Journal.
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