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Home » Bosses Should Encourage Workers to Own Their Mistakes, Take Risks: VP
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Bosses Should Encourage Workers to Own Their Mistakes, Take Risks: VP

arthursheikin@gmail.comBy arthursheikin@gmail.comJune 26, 2025No Comments3 Mins Read
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In a healthy, thriving workplace, colleagues aren’t throwing each other under the bus.

People don’t show up to work at their best when they don’t feel safe, says Leena Rinne, vice president of leadership, business, and coaching at Skillsoft — an educational technology company that produces learning management system software and content.

“The version of myself I bring every day is very different if I’m constantly nervous, if I don’t have the psychological safety, and if I’m not clear on how I contribute here,” she told Business Insider.

A way to build that trust is to encourage making mistakes — and that’s the responsibility of bosses, Rinne said.

“Leaders sometimes feel like they have to have the answers — that’s why they have a hard time asking for input or admitting when they’ve done something wrong,” she said. “But if I’m not afraid to make mistakes, I’m willing to take more risks, which means I’m willing to innovate more effectively.”

Leena Rinne

Leena Rinne is a vice president at Skillsoft.

Skillsoft



Leaders who are able to admit when they’re caught off guard can cultivate a culture where people are not afraid to pivot and try something new when projects don’t go as expected.

“Maybe it doesn’t go well, but we fall back and then we go forward,” Rinne said. “It’s creating an environment where we are actually safe to do that, which comes through being transparent, owning mistakes, calling things out for what they are.”

Some leaders, including Airbnb’s cofounder and CEO Brian Chesky, believe that favoritism and competition among staff breed a culture of excellence. Rinne does not agree.

“I can’t even conceive of how an organization would think that’s the way we should engage with each other — that I’m winning and others are losing,” she said.

“That idea of workplace toxicity through extreme competition or through low trust always comes at a price. It comes at a price of performance, productivity, and innovation.”

‘Mindful maneuvering’

In Rinne’s view, it’s vital that leaders know who their employees really are, and their strengths and weaknesses, to put them in positions where they will flourish.

She calls this “mindful maneuvering — making sure that people understand how they fit into the organization’s goals.”

Workplaces are suffering from disengagement and detachment. Switching the culture from one of shame to one of encouragement could be the antidote, according to Rinne.

“One of the biggest indicators of engagement is that I feel like my work is meaningful — am I doing something that matters or not?” she said.

“If I just focus on being more transparent, if I just focus on giving better feedback as a leader, all of those do add up.”

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