- A former Facebook executive said employees once let Mark Zuckerberg win when playing a board game.
- The incident sparked a debate about the potential pitfalls of playing a game with your boss.
- Business Insider asked workplace gurus how competitive you should be in such situations.
A new memoir by former Facebook employee Sarah Wynn-Williams included a claim that workers let Mark Zuckerberg win a game of Settlers of Catan. Her former colleague, who was also there, hit back and denied the claim.
The episode sparked a debate about the risks for employees of going head-to-head with their bosses in ostensibly friendly games.
Business Insider asked workplace gurus for their thoughts — and experiences — of playing games with a boss.
Elizabeth Hines recently started a new role as an HR manager. She told BI her new boss uses table tennis to chat and share business details with employees. “After I beat him several times, he no longer invites me for a game.”
Hines said her boss has started talking to her less during the day and they had no personal contact at all for a week recently.
“I hope it’s a coincidence, and it’s temporary, but I definitely want to ask him about it later because it bothers me a lot,” she said.
‘How you lose reveals your character’
Jenn Whitmer, a leadership coach and speaker from Missouri, told BI that she had beaten bosses at games before.
“The healthy ones, even the competitive ones, take it in stride,” she said. “The toxic, unhealthy ones became like toddlers. How you lose reveals your character.”
Whitmer described one time when her then-boss while she was an assistant head teacher of a school who “shut down” and was “sullen and sulky” after losing a game.
Joaquin Paolo Arellano, a freelancer from Toronto who worked in customer-success roles for more than a decade, told BI he once beat a boss at a pickup basketball game — and he took it well.
It also had a positive effect on his career, he said, “perhaps because he can relate to me better.”
Appreciating the losses
Joe Galvin, the chief research officer at Vistage, an executive coaching organization based in San Diego, said that leaders who take losing badly don’t foster a healthy working environment.
“The best leaders understand that success isn’t about always winning; it’s about fostering an environment where employees feel challenged, engaged, and motivated to do their best,” Galvin told BI. “If a boss expects to win every time — whether in a board game or in a board room — they’re not just stifling competition, they’re also stifling innovation.”
He added that a leader’s ability to handle losing “can also have significant impacts on employee engagement, company culture, and, ultimately, retention.”
Nikki Innocent, a leadership coach and diversity, equity, and inclusion consultant in New York, told BI it could be healthy to “celebrate” losing and that a boss who doesn’t create an environment where they can lose means they’re not developing their resilience.
“It does a disservice not only to the individual person’s ability to develop in life, but it does a disservice to the business’s ability to weather the obstacles of the future,” she said. “I wish we celebrated losing a little bit.”
What’s the vibe?
Hayley Lewis, a chartered member of the British Psychological Society who specializes in leadership and management, told BI that people judge whether it is “safe” to be competitive.
“That’s the judgment we make based on the data we have around us. What do I see other people doing in the organization? What’s the vibe I get from my boss? Am I likely to be more accepted if I just let this go and let the boss win?” Lewis said.
Anyone whose boss becomes upset after being beaten should consider how bad the response was, in her view.
If that response is abusive, Lewis said HR should be involved. If the boss was merely a bit grumpy, she suggests treating the incident as a learning moment: “The next time we all go out as a team, and somebody wants to play a game, I know not to win.”
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