Roger Duguay

As managing partner at Boyden, one of the world’s top executive search firms, Roger Duguay has interviewed countless people with big egos.

The headhunter says he’s developed a keen sense for distinguishing bravado from earned confidence. But when he met one of his heroes, Tibetan Buddhist monk and Dalai Lama confidante Matthieu Ricard, he was expecting a deservedly bold answer to one of his favorite interview questions: “On a scale of 1 to 10, where are you versus the person you want to be?” Ricard responded with, “Oh, maybe a 4 out of 10.” Duguay was shocked. The reply further enforced his idea that a senior executive referring to himself as a 9 should be a major red flag.

Duguay spoke with Business Insider ahead of the announcement that Boyden CEO Trina Gordon named him, in addition to his current role, leader of the firm’s Global CEO & Board Services Practice. It was a recognition of the work he’s done over the past five years building up the firm’s Montreal office — and it means Boyden will incorporate more of his talent-placement practices across its 65 offices around the world.

Over his Boyden career, Duguay has placed more than 100 people into executive, CEO, or board roles in both the private and public sectors (he estimates he’s gone through 1,000 candidates). In that time, he’s determined what qualities are necessary for a chief executive, and why anyone answering “9.5” for the question he asked Ricard is not going to end up in the role.

“If you are in the typical C-suite,” Duguay said, “you have the CEO, and after that you have the team. If you’re the CEO, you have to manage a full board and you have to manage your C-suite. It’s not the same skill. We’ve seen so many CEOs with big egos not be able to manage a board or play with the board.”

As Duguay sees it, a CEO’s role is to have a continuing dialogue with a board that is mutually beneficial, and also inspire the entire company. He said that his experience has shown him that CEOs struggle when they lack respect for their board, considering them an unfortunate but necessary team of people who don’t get it, rather than as a team of experienced leaders to utilize.

When he’s trying to find someone with this capacity, Duguay searches for evidence of some level of humility.

A few months ago, Duguay had an interview with a candidate for a CEO position. Duguay asked him, “If you had to do it all over again, is there anything in the last five years you would do differently?” He said he wouldn’t. “Well, that’s a pretty bad sign!” Duguay told us.

“If you’re not able to tell me 5 to 10 big mistakes you’ve done in the last five years, something’s really wrong with you,” Duguay said.

He likes to refer to these mistakes as “scars.” This isn’t to say he wants a candidate to explain all the ways they’d be terrible for the job, but he wants to see evidence of how failures became learning experiences — and he does not want a CEO who tries to cover up those moments.

Duguay interviews CEO candidates for two hours, and is primarily focused on assessing their personality — the skillset qualifications are a requirement for even being in the room.

“At the end I’ll always ask, ‘Tell me the exact reason why I will not hire you if you don’t get the role?”” Duguay said. “Now I can see in their eyes, ‘Oh, do I tell him the truth, because maybe he doesn’t know this? Those two flaws, and I really know they are my flaws, am I going to tell him? He’s going to add them to this count of flaws… Or do I just play that answer?'”

As you can probably tell by now, Duguay is looking for a genuine assessment of weaknesses, and not of the “My flaw is that I work too hard” variety. Still, Duguay has found that about half the candidates he asks this question give a “wrong” answer — i.e. a disingenuous one. He wants to find a CEO who is honest, confident, humble, self-aware, and authentic.

“I always make the parallel to personal relationships and work because I think the key is to be the same individual,” he said. “You should not play a game when you go to work.”