What do you ask high-flying ex-diplomat Kishore Mahbubani? How to make it big like him, of course.

It's not every day that you get to spend an hour with a public intellectual of the ilk of Kishore Mahbubani — let alone force him to answer whatever questions you have as we did on the latest episode of Mothership's Help Desk.

Mahbubani's standing in Singaporean society was best illustrated to me by two distinct sets of admirers.

The first were those in attendance at the launch of his latest book Living the Asian Century: An Undiplomatic Memoir; the who's who of the upper class. Former and current bank CEOs, founders of household-named companies, Cabinet ministers, and of course, high-flying ambassadors.

The second was a man who exited the lift at our office building as Mahbubani was entering.

The office worker did a double-take, before stepping back into the lift. "I love your articles Prof," he said nervously.

Mahbubani, who was on the phone at the time, smiled warmly and waved politely.

The former diplomat's appeal runs both wide and deep.

Whenever a new geopolitical conflict emerges, many eagerly anticipate his take on the situation, while his thoughts on the great schism of our generation — the U.S.-China rivalry — are well respected, if not appreciated for their divergence from mainstream Western commentary.

Trivial questions

So when preparing for his appearance on Help Desk, I found myself pondering — might we be better off deviating from the usual chatter of our podcast to ask Mahbubani the serious questions on Ukraine-Russia, U.S.-China, or Harris-Trump?

Or do we continue with the comparatively trivial questions that your guests are subjected to?

If you've watched the episode, you would know that Mahbubani fielded viewer-submitted questions on picking a university course, managing office politics, and how to be successful in life.

Ever-sporting and in his usual charming but measured delivery, Mahbubani offered candid advice while reflecting on his storied career and life experiences.

"It's a huge mistake to spend years studying a subject that you don't enjoy — I almost did that," he said while discussing how one should decide on an area of study, before later musing about his ability to collect detractors in the various organisations he'd worked in.

These are questions that you might ask your friends, or a mentor, or a respected elder, because you trust them. Because it's how someone handles the simple things in life that display the measure of a man. The little decisions we make betray our character and reveal the foundation of who we are. I think.

So no, our interview on Help Desk didn't turn up any solutions for war in Ukraine, nor did it offer any insight into the escalating tensions between an incumbent global power and a rising one.

But it did give us a glimpse into Mahbubani's remarkable rise.

It was a taste of the anecdotes and reflections he's penned in his memoirs, which traces his journey from poverty to the United Nations Security Council, to becoming the dean of the Lee Kuan Yew School of Public Policy.

While today Mahbubani is esteemed for his opinions on complex geopolitical issues, it's the so-called "trivial" decisions that he'd made along the way — the ones that sent him on a path from Joo Chiat to New York — that arguably inform those opinions.

And I think that makes the "trivial" questions worth asking.

Check out the latest episode of Help Desk, featuring Kishore Mahbubani here:

Top image by Mothership