Playing a game with your boss? Just let them win.

• A former Facebook director said that employees once let Mark Zuckerberg win when playing a board game.
• The incident led to a debate about the potential pitfalls of playing a game with your boss.
• Business Insider asked the workplace gurus how competitive you should be in such situations.

A new memoirs from former Facebook employee Sarah Wynn-Williams contained a claim for employees Mark Zuckerberg to have a game of Settlers from Catan win. Her former colleague, who was there too, hit back and denied the claim.

The episode led to a debate about the risks for employees of justice with their bosses in apparently friendly games.

Business Insider asked the 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 that her new boss uses table tennis to chat and share business details with employees. “After I have defeated him several times, he no longer invites me for a game.”

Hines said that her boss started talking to her less during the day and that they recently had no personal contact at all.

“I hope it's a coincidence, and it's temporary, but I certainly want to ask him about it later because it bothers me a lot,” she said.

'How you lose your character' reveals'

Jenn Whitmer, a leadership coach and speaker from Missouri, said Bi that she had previously defeated bosses during competitions.

“The healthy, even the competitive, get it going,” she said. “The poisonous, unhealthy became like toddlers. How you lose your character.”

Whitmer once described when her boss at the time while she was an assistant head teacher of a school that “stopped” and was “Nors and Sulky” after losing a match.

Joaquin Paolo Arellano, a freelancer from Toronto, who had been working in customer success roles for more than a decade, told Bi that he once beat a boss at a pick-up basketball game and he took it right.

It also had a positive effect on his career, he said, “Maybe because he can better relate to me.”

Losses

Joe Galvin, the Chief Research Officer at Vistage, an Executive Coaching organization based in San Diego, said that leaders who lose poorly, do not promote a healthy working environment.

“The best leaders understand that success is not always going to win; it is about promoting an environment in which employees feel challenged, involved and motivated to do their best,” Galvin told BI. “If a boss expects to win every time, regardless of whether they are in a board game or in a boardroom, they not only suffocate the competition, they also suffocate innovation.”

He added that the ability of a leader to lose “can also have significant consequences for employee involvement, corporate culture and, ultimately, retention.”

Nikki Innocent, a leadership coach and diversity, fairness and inclusion advisor in New York, told BI that it can be healthy to “celebrate” losing and that a boss does not create an environment where they can lose means that they do not develop their resilience.

“It is a bad service, not only for the ability of the individual person to develop in life, but it is a bad service for the ability of the company to endure the obstacles of the future,” she said. “I wish we celebrated a bit.”

What is the atmosphere?

Hayley Lewis, a chartered member of the British Psychological Society who specializes in leadership and management, said BI said that people judge whether it is “safe” to be competitive.

“That is the opinion that we make based on the data that we have around us. What do I see other people in the organization doing? What is the atmosphere I get from my boss? Have I probably accepted more if I just let this go and let the boss win?” Lewis said.

Everyone whose boss Van Streek touches after he has been beaten must consider how bad the answer was, according to her.

If that answer is offensive, Lewis said HR should be involved. If the boss was only a bit grumpy, she proposes to treat the incident as a learning moment: “The next time we all go out as a team, and someone wants to play a game, I don't know how to win.”