You have to know what questions to ask about your business before you can install a successful IT system. Just ask the FBI.

Lucky me. I received a phone call from an obscenely rich organization that genuinely believed that the best way to solve a problem was to throw a lot of money at it. They wanted "world class". And I was hired to help them get it.

The challenge? This financial services company wanted to dramatically improve the quantity and quality of collaboration within its enterprise. Top management had decided that collaboration was to be their new core competence. I was to recommend the best software, systems and apps for achieving this. No expense would be spared in procuring that technical infrastructure. A "smart" client with money to burn — what an opportunity!

I could barely keep the drool from dribbling down my chin. This would be the client that would pay for my children's Ivy League educations. And I don't even have children.

Then, I made the mistake of asking the obvious question: How does the business share information and collaborate now?

Don't really know, don't really care and doesn't really matter, said my client dismissively. You're not here to diagnose our current behaviours; you're here to help us implement our vision of the collaborative future. We need you to make sure we buy the best collaborative technologies in the world.

Of course, I could have taken both the hint and the (lots and lots of) money. Alas, I had to ask the follow up: What other C-level initiatives is the company taking to assure that this cultural transformation to collaboration will work?

The client's eyes rolled: We're signalling our commitment to collaboration by our huge investment in this world-class collaborative infrastructure. We're telling our people to collaborate. This investment removes the technical obstacles that keep them from doing so. They'll do what we want.

Not good. The client could not — would not — give real answers to obvious questions. They hadn't even thought about them. Even worse, these questions had obviously annoyed them. A lot. They now promised to get back to me. I knew they never would. And they didn't. That night, I cried myself to sleep. No Harvard, Yale or MIT for my (virtual) kids. Unlucky me.

Of course, the collaboration initiative went nowhere. Tens of millions of dollars were wasted — and none of it on me. In truth, the company possessed a spiteful, ruthlessly competitive culture that thrived on political infighting and cutting ethical corners. Management cared most passionately about the size of the annual bonus and behaved accordingly. Between the Securities and Exchange Commission's investigations and incessant executive infighting, its best clients scattered. The company was acquired within 18 months of my failed dream of consulting riches. Can you say schadenfreude?

This column is about managing the obvious. Too many C-level executives and their direct reports don't ask the simplest, most fundamental, most essential questions about what they're trying to accomplish. It's as if the obvious is taken for granted.