How to coach a problem employee: The insecure employee

Help your employees have more confidence in their work.
By Matthew Philpott

All the corporate world's a stage — at least from time to time.

"We call meetings the 'corporate theater,'" said Diana Faison, leadership development consultant and author at Flynn Heath Holt, a Charlotte, N.C., firm focused on developing women leaders. "It is a stage of sorts where everyone is watching."

And whether that "stage" is an all-hands meeting, a small group brainstorming session, or even a one-on-one over coffee, not every employee is comfortable being the focus of attention.

Faison, co-author of The Influence Effect: A New Path to Power for Women Leaders, said that when an employee is not expressing his or her views or volunteering to take assignments it can be a sign he or she lacks confidence or is working against self-esteem issues.

If you're managing an employee who's reluctant to speak up, there are some things you can do to give that employee faith in his or her abilities. Here are some tips to help struggling employees find their place in the spotlight.

  • Make a connection. Getting to know your employees better can help them find the confidence to speak up.
  • "Give them the space and the grace to show you themselves in their preferred mode," said Heather Kephart, CPA, director of financial reporting at Koniag Inc., an Alaska Native Corporation in Kodiak, Alaska. "Find something that they like to talk about and build their confidence that way."

    Kephart recalled a technically capable, but insecure, employee who happened to be an avid player of a popular video game.

    "You get him going on ' and he just bursts out of his shell," Kephart recalled. And while Kephart said she knows little about the game, she believes making those personal connections, and providing a friendly face in the audience, can help an employee find a comfort zone. 

    "I think him knowing someone else knows what he is good at gave him extra firepower," Kephart said.

  • Create a sense of safety. An important part of taking on a new job or role is accepting that coming up short is part of growth. For some, a fear of failure may be the root of the self-confidence issues keeping them from taking center stage.
  • "Especially in public accounting, it's hard to set yourself up knowing you are potentially going to fail," said T.J. O'Neill, CPA, senior tax accountant at Mueller Prost in St. Louis. "Sit with them and let them know, 'We want you to make mistakes because it's how you're going to learn.'"

    O'Neill suggested asking employees to reach while providing the safe space to break a few eggs as they find their path to success. That freedom can produce great work results, and that can boost self-confidence.

    "They will put a little extra work behind [what they do], and if you set that expectation upfront that it's OK to fail, it really sets the tone and brings the pressure down," O'Neill said.

  • Help them prepare for big events. Facing down company leaders or a big networking opportunity can make nearly anyone nervous. Faison suggested helping employees in this situation beat the jitters by helping them form a clear idea of how they want to "show up."
  • Encourage them to rehearse or to dress in a way that makes them feel confident, she suggested. Taking time with your employees to practice and prepare, all the way down to their chair posture and handshakes, will help build their confidence.

  • Let them play to their strengths. O'Neill suggested allowing employees to embrace their true strengths.
  • "You need to sit down with them and identify what their strengths and weakness and their true passions are," O'Neill said. "Give them the opportunity to spearhead something they believe they can succeed in."

    Giving established employees the opportunity to specialize, when appropriate, can allow them to find their way forward within the organization.

    "Everyone thinks they need to be a jack of all trades," O'Neill said. "But if you have someone in your organization who is stronger on business development, chances are you have someone on the other side strong technically." Giving employees the tasks they're best suited for can make your team stronger overall.

  • Find the format where they're most comfortable. No matter what, some people simply operate better in small groups.
  • "You can't fix some of these deep-seated issues," Kephart said. "But you can find your way around them."

    Kephart said it's often the people who don't share their ideas who have the best ideas. Ultimately, to draw those ideas out, you may need to engage them in a more personal setting.

    "I'm not going to put them in a situation that will make them uncomfortable," Kephart said, so she will meet with them in small groups instead.

Matthew Philpott is a freelance writer based in Durham, N.C. To comment on this article or to suggest an idea for another article, email senior editor Courtney Vien.

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