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11 Tips for Coaching Difficult Employees

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When you get along with your team members, and they’re doing incredible work, it’s fairly easy to be a manager or leader.

However, that’s not always real life — other times, you’ll have an employee who underperforms, makes a mistake or gets on your last nerve.

Delivering constructive criticism to a somewhat difficult employee can be painful, but the point of feedback is to help them grow, which in turn, benefits your entire organization.

Here are 11 coaching tips to keep in your back pocket as a manager, so you can survive any challenging conversation with an employee who needs a push in the right direction.

Don’t Avoid Conversations

As a manager, supervisor or leader, you might be tempted to put off hard conversations with a particular employee — but experts advise against this approach.

Discussions about feedback or performance should happen regularly, without any sense of “surprise,” versus waiting for annual reviews. And if there’s a need to talk about a specific situation with an employee, try to address it in real-time and with confidentiality as much as possible.

“Your employees expect you to deal with performance issues when they occur,” says Dr. Kim Turnage, senior leadership consultant at Talent Plus. “What you do has the potential to either increase or decrease trust. Starting with empathy, asking questions and being straightforward set the right expectations and have the greatest chance of getting results.”

Time and Location Are Key

According to life and career coach Jacqueline Miller, timing and location are everything.

“The content of the conversation has its greatest impact when it is timely,” she notes. “Address situations as they happen rather than delaying for the purpose of creating a laundry list of complaints. Of course, the conversation should occur in private.”

“With difficult employees, managers may find that they either avoid having hard conversations about performance or are constantly critiquing the employee’s work,” says Molly Hetrick, a professional development coach. “It’s a hard balance to make, but it’s critical to try to treat all of your employees in a similar manner, to the extent possible.”

Assume Positive Intent

Khalid Saleh, CEO of Invesp, says the most important thing to remember in difficult conversations at work is that “most people are good and can do good.” Challenges are usually related to poor communication or a mismatch in expectations, not because an individual is intentionally trying to be frustrating.

“Most problem employees are meaningfully unaware of their problem employee status,” states Dr. Todd Dewett, leadership and workplace expert. “As the boss, it’s your responsibility to help them understand. Meet them in a private setting out of respect. State your observation of the recurring problem behavior. Note the outcomes associated with the behavior (e.g., conflict, work delays). Articulate the consequences associated with continuing the behavior. See input and understanding, but stay in control of the conversation. Accept no blame or denial. In the face of elevated negative responses, notify the person of a formal notice being placed in their file. Repeat the above and ask them to acknowledge.”

Emphasize Personal Development

Another option is to help your employee acknowledge the issue, and then emphasize how their words or actions are impacting business, which may make feedback seem a little less personal.

“Get them to provide solutions for how they can better support the company mission, which their challenging behavior is not in alignment with,” says Miller. “Most employees, even the difficult ones, will want to be on board with the concept of being a positive contributor. If positioned to them correctly, it may be viewed as the organization’s commitment to their personal development, as opposed to a reprimand.”