First, let’s figure out whether your CEO is insane. Listen carefully to the actual request. If your CEO is standing in front of the engineering team asking you to transform lead into gold, you should grin, nod, and start mentally editing your resumé, but don’t bolt from the room just yet. Now, if he’s asking you to reduce your release cycle from 90 days to 10, you can let yourself be shocked, but be relieved by the fact that you’re not being asked to perform matter transmutation.

There’s a subtle difference between insane and impossible.

You should respect your gut when that internal “he’s insane” flag starts waving, but that doesn’t mean you should stop listening. There’s more data to gather, and there are times where an insane approach might be the right thing.

Our next assessment has to do with legwork. Has your CEO done any preliminary work to actually figure out whether the impossible idea is achievable? What is his strategic intuition about this crazy idea? Is he able to articulate, however vaguely, why this idea is a good idea for the company and how you might pull this off? You’re not looking for a definite plan, more the strategic broad strokes, a point from which the managers can begin sketching in the details.

A word of warning: there are managers and executives out there who can pitch the impossible on confidence alone. They need no intuition or evidence regarding feasibility to get their teams’ buy-in, and while these chutzpah-laden individuals sure are inspiring, you should trust that nagging feeling that shows up later when you’re driving home, the high fades, and you’re left with a strategic emptiness. That emptiness is the practical result of the CEO’s request lacking everything but confidence. The absence of some thread of an idea about how you’re going to do the impossible means you might be screwed.

The lack of a glimpse of a plan beyond the charisma translates to a lack of hope.

Next, you want to figure out how much skin your CEO has in the game. How much of the company is he betting on this request? If this is a bet-the-company decision, I’m comforted by the fact that he’s backing this impossible request up with his job. He knows that failure means everyone is looking for a new gig. That’s motivation.

If the request is smaller, if this is a bet-the-department request, well, the risk is more localized. The cost of failure will likely be born by the senior guys and gals running the show. I’m not suggesting the CEO thinks any less of the importance of this impossible request, but trust me, he knows that it’s not necessarily his job on the line if the team blows it.

What you’re assessing here are two things: size of the request and level of executive commitment. Having a gut feel for these two things is often a moot point. Depending on your seat on the org chart, you might not even have a chance to choose whether you’re saddled with the impossible. However, developing this swag out of the gate means when the impossible hits the fan, you can be one of the first to act.

The glimpse of a plan and confidence. These two fuzzy mental assessments are in play when deciding to ask the impossible, but there is one more that needs to be considered.

Remember, this is an impossible request. This isn’t, “Hey, can you fix these 10 bugs by Friday?” It’s, “Hey, can you rewrite this major component in half the time it took you to write it the first time?” Forget whether it’s remotely feasible. Forget whether the confidence is oozing out of every pore of your CEO. You’re not going to be convinced, and more importantly, you’re not going to engage if you don’t respect the person who is asking you to do something.

Financial rewards, promotions, IPOs, promises of future interesting projects. All of these incentives matter and can be used to light a fire under a team, but an individual’s decision to engage in the impossible starts with the question, “Do I respect this person enough to tackle the impossible?”

There’s a book to be written about how to build respect in an organization. My brief advice is, when you are asked the impossible, carefully consider every hard request already made of you. Does he ask the impossible every month? Every Monday? Does he follow up on his impossible requests, or does he expect you to run with them? Have we ever successfully completed an impossible request? Is he there at 3 a.m. on Sunday morning with everyone else, looking like he hasn’t shaved in a week?

I don’t know how many impossible requests you get, but I do know that frequent impossible requests result in an erosion of respect and a decaying of credibility. And that means when the CEO is standing up in front of the troops asking them to perform magic, all they’re thinking is, “This crap again?”

Nothing I’ve described is concrete. Nothing I’ve described is going to placate your initial intense, negative engineer reaction when your CEO asks you to do something utterly absurd and irrational.

It gets worse...I mean better.

There are times when your leadership should be unencumbered by your version of reality. There are times when it’s important that your CEO isn’t intimately familiar with a product space or lifecycle. Day to day, doing business requires reasonable expectations and an adherence to plans, but those things actually prevent the extraordinary from occurring. The extraordinary requires a catalyst like an impossible request.

What’s important when the CEO asks for the impossible is that he’s pushing the definition of possibility for what the team can accomplish. Maybe your CEO only has an idea and can only feel the possibility in what he’s asking, but it’s not his job to make it all happen. That’s where you come in. You’re the person responsible for transforming the feel, the intuition, the glimpse of a plan, and the confidence into knowing and doing.

You’re the one who is actually responsible for delivering the impossible, and all I’m asking is that you consider the request because agreeing to engage in the impossible shatters normality and ignores fears, and I love that.