A few years ago, Nassim Nicholas Taleb was in Mumbai for a short lecture. A colleague at this newspaper took me along to listen to this fool-unsuffering, dogma-demolishing, turtle-neck-wearing, facial-hair-manicuring giant of the banker-bashing industry. This must have been some time in 2008 when Taleb, Nouriel Roubini, Meredith Whitney and perhaps John Paulson were all revered as prophets of the financial apocalypse. The hotel ballroom was packed. Every conceivable Mumbai big shot was present: from central bankers and chief economists to CEOs. Of course this was way back when everyone liked Taleb, and he hadn’t gone and pissed off everybody in the world by compulsively being himself.

The entire point of his lecture, and most of his books, was that we vastly overestimate how much we know and understand. Banks, governments, regulators, economists, taxpayers, Vodafone... everybody creates systems that are built, as it were, on a deep foundation of “certainties". This could include everything from an established notion of how inflation impacts employment, to the belief that US housing prices can never collapse. All of which are true...until they aren’t. Boom. Twelve months later, young Spaniards with PhDs are running to London to make espressos for a living.

More recently, and especially after his most recent book Anti-fragility, Taleb’s ideas have come in for a lot more criticism. Partly, I suppose, this is down to the cyclical nature of public opinion. One minute everyone loves the Backstreet Boys. The next minute everyone in your boarding school is laughing at your Backstreet Boys bedsheet. Cruel.

Some critics said that Taleb was beginning to milk big, fat book contracts out of simplistic ideas. Anti-fragility means you need to be prepared for shocks and uncertainties, right? No, Liverpool Sherlock! What is your next book? “Black and Blue: How falling down from height can hurt"?

Still I think Taleb has a point.

I don’t even presume to understand the mathematics behind Taleb’s work or those of his critics. But if his complaint is that too many people seem too sure of themselves, then I am with the Great Bearded One. Because we really are a society that is obsessed with certainty and fetishizes decisiveness. Just see, for instance, your resume, or the resumes of the thousands of people who apply to your meritorious organization on a daily basis. What do you notice? They are all go-getters! Decision makers! Some are even decisive go-getters! They are all about execution, execution, execution!

Who in the name of Jesus ‘Sanjumon’ Christ, then, is going to do any thinking in the office? Who is going to sit for a moment and think over what has to be done? Before just ‘going and getting’ like anything?

Have you ever seen anyone submit a resume that says: “My greatest strength is an ability to really think and question assumptions and act after rumination"? Of course not! Sacrilege! The modern corporate workplace has no place for such indecisive come-givers. Or why not leaf through any of those candidate information forms that business school students are asked to fill in during campus placements?

“Give us an example of a situation where you took a concept and successfully executed it? Feel free to make things up."

“In not less than 7,000 words excluding diagrams explain a situation where you expressed leadership in a team environment and helped the team achieve a deliverable."

“We are a dynamic organization that thrives on initiative, crony capitalism and insider trading. Give us an example of an incident from your curricular or extra-curricular life where you took initiative without being asked and solved a large problem. All answers must be submitted in the form of contemporary dance."

And what is one question you never come across?

“We understand that not everybody knows what to do always. We are all humans. Give us an example of a situation where you were faced with a crisis, took stock of all your options, realized you didn’t know what to do, and asked around for help. What did you learn from this?"

Instead, what we often have is a professional environment that mocks people at the merest sign of vacillation, rumination or hesitation. The problem with this system, I feel, is that it strips organizations of all self-awareness. It reinforces established ways of doing things and rewards velocity at the cost of acuity.

A few weeks into my very first job, after I’d already started making a fool of myself eagerly biting off more work than I could chew, a manager gave me some interesting advice. “Be shameless about expressing your ignorance in a meeting," he told me. People, he said, were always keen to show off their confidence. Mostly, this got them into trouble, usually by committing them to bad projects. Instead, he suggested, I should say ‘maybe’, ‘let me think’ and ‘no’ once in a while. “At least, it’ll make you sound a little more thoughtful compared to the other robots."

So has this strategy worked for me? Maybe. I need to think about that. Let me get back to you.

Cubiclenama takes a weekly look at pleasures and perils of corporate life. Your comments are welcome at cubiclenama@livemint.com.

To read Sidin Vadukut’s previous columns, go to www.livemint.com/cubiclenama---