Tech Life A Hint of an Insane Plan


Right now, there’s a CEO standing in front of his 85-person start-up at an all-hands meeting and he’s saying, “In the next 90 days, we need to do the impossible”.

The particular version of impossible doesn’t matter. What matters is that everyone in the room is shocked when he says it. You can tell by the intensity of the silence.

“We’re going to what in the what?”

What gives this guy the right to ask the impossible? Sure, he’s the CEO, but does that mean he gets to stand in front of the room and ask the team to build a levitation machine?

Yeah, it does.

However, this does not mean the CEO isn’t screwing up.

Asking for the impossible is an advanced management technique and it’s one that is particularly abhorrent to engineers. They are very clear on what is and isn’t possible because they’re responsible for building and measuring all the possible. When you ask an engineer to do the impossible, they often laugh in your face not only because they think it’s an absurd, irrational request, they also have the data to prove it.

Yet, given this irrefutable data, I still want you to consider this request. There is an upside to pulling off the impossible. Not only is it a great morale booster, it can also be incredibly profitable, because all your competition thinks the impossible is, well, impossible. Better yet, WHO DOESN’T WANT A FLUX CAPACITOR?

There are three measurements to take with regard to your CEO and his request when the team has been asked to do the impossible. These measurements aren’t going to help you pull off the miracle, but they will help you size the impossibleness.

A Hint of an Insane Plan

First, let’s figure out if 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 resume, 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, and you might be screwed.

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

Skin in the Game

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 Importance of Respect

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 3am 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?”

What He Really Wants

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.

17 Responses

  1. Why wasn’t the CEO standing in front of his team 90 days later, saying “In the past 90 days, you have done the impossible.” instead?

    Why wasn’t the CEO, and the team, convinced because of their grasp on the situation and the mutual respect for every team member’s capability and ability that they could pull it off in the first place?

    Good “impossible” work is best seen in retrospect, when it is obvious that it shouldn’t have worked, or that very few could have pulled it off, but by gum we managed. It is part of the CEO’s mission to be frank with her troops, and this involves calling impossible things out, but it can act as a de-motivator just as well.

    Even if you’re not phased by working on something supposedly “impossible”, what are the odds that it removes some of that drive from one of the 85 people, that she gives a little less than everything she has and then concludes at the first (or last) opportunity that “oh well, we did agree this was impossible, so I suppose we’d just need more time”?

  2. Thank you for describing my weekend. We’re torn between process and results right now. The past few days were like a foreskin full of zipper.

  3. iphone with a 7 megapixel camera 🙂

  4. “Nothing is impossible for the man who doesn’t have to do it himself.”

    – Somebody Smarter than Me

  5. They aren’t exactly the same thing, but there is a high correlation between please-do-the-impossible and yet-another-plan-to-save-the-company. When I was at SGI in the late 90s, there was a lot of both. I figured out after awhile that my own BS-meter was well tuned, and if it seemed like the execs were high, they probably were.

    So my advice to new engineers: by all means, try to do the impossible. But if they keep asking you to do it, and you can’t even figure out why it will matter if you succeed… there are probably better jobs out there.

  6. irspariah 16 years ago

    The motherfucker should be given a blanket party!

  7. Johan 16 years ago

    In my company the “imposible” results in more profit for the shareholders and 90% of the time no rewards for the staff. Quite frankly this has made me feel like cheap labour because it happens too often. If the work is too much on this regular basis, hire more staff or go practice your managerial maths “in your free time”!

  8. I once worked for a man who asked for the impossible – huge new features, total re-architectures – about 4 times a year. And then he’d disappear, showing up at about 9pm for dinner once a week or so. At the end of the last one I went home surprised that the bar I passed was still open – for the first time in a month I was home before 2am last call! The really stunning part is how many of us did it for two or three years.

    On the other hand, I learned more about shipping software in those three years than I have in any other place. I think there’s value in attempting the impossible for a while, at least, even if it’s nuts (which is sort of is by definition). As long as you’re surrounded by effective peers, it’s an amazing environment to watch and learn what good people can do when they’re under extreme pressure to be the best they’ve ever been.

    There’s something very powerful about the battle cry. The resulting focus and intensity make good people great. Even if it’s just for a while, being surrounded by people doing great things gives you a confidence and an ability that will stick with you throughout your career.

    Long story short, even if it’s crazy, fling aside all the rationality you’ve ingrained and try the impossible… even just once.

  9. Travis Jensen 16 years ago

    When the CEO asks the impossible, I always take a close look at what is going on in and around the company. Engineers can become out-of-touch with the realities of the business situation, which can only hurt them.

    Based on what is happening in the business, that impossible request can be one of two flavors: One is business is good, but we got seriously surprised by something (new competitor, new technology, etc). The other is that the business is in the slow spiral of death.

    Never kid yourself: engineering heroics will never save a business that is tanking. If you see that, get the resume out.


  10. upchuckie_cheezits 16 years ago

    Here’s a novel thought for CEOs and managers who like to challenge and inspire. Let’s save the posturing and bullshit, and the motivational histrionics, and ask instead for the possible. Do the possible, do it well, and deliver it on time.

    If it’s necessary to do the impossible, it’s more than likely the result of a management error, and you need your ass covered. I’ll give it a try, but only if I’m compensated for it. I’m too old and too cynical to be impressed by this nonsense.

    I don’t need to be inspired, I’m a professional and I’m good at what I do. Just pay me properly for my work, and stay out of my way.

  11. Boudewijn 16 years ago

    Impossible is good. Impossible gets the creative juikces going. In fact, companies not trying the impossible are doomed, I think, either from business or from a creative point of view.

    Too often, the CEO will ask you to do something that would have been easy had they picked up the right signals 6 months ago, or given the right resources, or whatever. That will definitely make engineers shrug and think: I’d better start editing my resume.

    It should however be the kind of impossible that makes you think “YES”, that’s what we need, if we could do that, that would be so cool, yes, I’m willing to sacrifice the next 6 months of sleep and social life, because if we make it, we really achieved something memorable.

    Many engineers are very much motivated by impossible stuff. Space travel, Large Hadron Colliders, iPhones. It’s wat makes us tick.

  12. raveman 16 years ago

    I think all of you guys are funny, why would you work for company that ask you to do impossible? even if you have no life there is still World of Warcraft, try it. I remember that on my last project I earn twice as much because I was working really hard ;> My competitor just got fired, because he wanted to have family, idiot.

    However if tale is for project managers than I think its a good one, it must be really hard to manipulate people to do stupid stuff for a longer period of time. However what do you do if people are not scared of getting fired? i think its important question. As developer I can find job really easy, but some people hate to look for a job. The key should be to hire developers that cant find another job. Maybe offer them 1,5 of what they can get and make them work twice as much. think about it. You just need one developer who knows what hes doing and he will be fixing all the errors.

  13. In my previous job we cut corners to transform something that was impossible to something nearly impossible. After several months of two developers working ridiculous hours, the company got a new E-Commerce system to better sell their products and the two developers got a crippled code base to refactor and reattach the corners. No bonus, no extra vacation time, nothing. Not long after, management was convinced more developers were needed and hired 3 new team members…

  14. washingtonCarver 16 years ago

    seems to me that if “the impossible” is worth something to the managers, that something ought to be spread around, no?

  15. washingtonCarver 16 years ago

    seems to me that if “the impossible” is worth something to the managers, that something ought to be spread around, and phony ass stock options don’t count. yes,no?

  16. Maddog 16 years ago

    Love your writing.

    I thought the best question to consider when faced with an impossible request would be ‘what is his/her motivation?’. Is the idea coming from desperation or inspiration?

    Both can yield amazing results but if you are inspired and bet the company or if you are desperate and dont then i’d guess something special is in the works.

    … or you could be toast. Either way there is so much mediocrity about i’d be tempted just for the ride.

  17. The only guaranteed result of of achieving the impossible is that your boss will add it to the list of your regular duties.