The one-upmanship driving CEOs

The audience that bosses are often most anxious to impress is their peers

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    • CEO roundtables can be a source of comfort if others can validate their beliefs or give some reassurance that their choices are the right ones.
    • CEO roundtables can be a source of comfort if others can validate their beliefs or give some reassurance that their choices are the right ones. PHOTO: PIXABAY
    Published Tue, Nov 25, 2025 · 07:00 AM

    AS FIREFIGHTERS doused the flames that engulfed Notre-Dame in 2019, Francois-Henri Pinault, the business leader whose family controls the luxury group Kering, put up an eye-watering 100 million euros (S$150.6 million) to rebuild the historic French cathedral. Just hours later, rival chief executive officer Bernard Arnault of LVMH shot back with a 200 million euro gift. It was the perfect display of CEO one-upmanship – philanthropy, but with an element of competition.

    Bosses talk endlessly about customers, investors and employees, yet the audience they are often most anxious to impress is each other. From industry conferences to LinkedIn posts, these are arenas for peer rivalry – who is portrayed as the most visionary, whose message is going viral or whose approach to artificial intelligence or sustainability is best.

    “Ultimately, CEOs are competing against each other,” one headhunter told me. For publicly listed companies, “their primary obligation is to perform better than other CEOs in their sector”. Board directors and investors prioritise relative performance, and these executives know it.

    CEO roundtables and private dinners with peers can be a source of comfort if others can validate their beliefs or give some reassurance that their strategic choices are the right ones, especially in a business environment that is tricky to navigate and mis-steps are punished quickly. It is no wonder that so many turn up at the World Economic Forum’s January gathering in Davos year after year.

    But such meetings are also a way to size up the competition in an era where judging power, influence and status can be difficult. Titles alone mean little, informal networks are all-powerful, and an ability to exert authority outside the workplace is as valuable as inside.

    While a company share price is a crude performance metric, it is pay that becomes an irresistible proxy for worth. “What often bothers very wealthy CEOs – they are human, after all – is that other CEOs are getting even richer,” Warren Buffett noted in his latest annual letter. “Envy and greed walk hand in hand.” Journalists, like the public more broadly, are endlessly fascinated with how this manifests. 

    The comparisons can become farcical, particularly for the mega-rich – who owns the larger superyacht, who has a better doomsday retreat in the event of the apocalypse or who can lob the highest investment pledge in the direction of an erratic political leader.

    Few executives admit to any of this. One CEO told me comparison is “a waste of time” while another said he did not like to speak ill of others, yet had spent the previous hour explaining the inadequacies of his counterparts in the sector.

    Not only does the habit fuel personal rivalries, it can compound the anxiety that comes with the top job. Alan Guarino, a vice-chair at executive search firm Korn Ferry, estimated that two-thirds of the CEOs he encounters have imposter syndrome and “the final third are ... delusional and are imposters” and so should not be in the job.

    That is anecdotal but when the challenges facing executives seemingly multiply each week, it is not hard to see why leaders focus on what they are lacking versus others, rather than what they have achieved. It matters because insecurity at the top has a way of cascading downward, shaping outcomes for employees, shareholders and customers alike.

    Comparison is not always corrosive. Benchmarking a company against competitors can highlight gaps and sharpen strategy. Watching a rival execute a bold move can propel others into action.

    But Tomas Chamorro-Premuzic, author of the new book Don’t Be Yourself, told me that the cocktail of traits that often drives people into these roles – ambition, anxiety, narcissism and, let us be clear, just being male – also makes it hard for them to feel satisfied. It is rarely about the money, he adds, but that “there is always something or someone else to beat”.

    Zak Brown, chief executive of McLaren Racing, put it bluntly in a podcast interview last week. As the boss of a Formula 1 team where the tiniest of margins differentiates the winners from the losers “you’re constantly... unhappy, because you can always be doing better”.

    The reality is that what can look like swagger is often a manifestation of feeling inadequate. For some, the endless obsession to compare can inspire, but for others it can be a quiet, destabilising force. One adviser to CEOs told me that for many, “it is very difficult to get off that treadmill”. There is no such thing as “enough”. FINANCIAL TIMES