11 Tips for Coaching Difficult Employees

Giving feedback is never easy but it's essential for any good leader. Here’s how to do it well.

11 Tips for Coaching Difficult Employees

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.”

Think About Your Desired End Result

“Before initiating a conversation with an employee to give feedback, first ask yourself the purpose of giving the feedback,” says Janelle Coleman, managing partner for Four Letter Consulting, which focuses on leadership development and organizational culture. “Are you giving the employee feedback to help their professional development? Or are you giving them feedback to better meet your own preferences? Either one is fine, but being clear about the purpose is critical.”

And remember — it might be stressful for you to deliver constructive criticism, but it’s actually even more stressful for the person receiving it.

“As human beings, we are hardwired to assume the worst, so to be an effective leader it is important to make coaching as painless as possible for your team members,” says Amber Hunter, director of people strategy at Helpside. “Tell them up front what you want to discuss, so they aren't running through a list of potential missteps in their minds, not really even listening to what you are saying.”

Start With a Piece of Praise

“Start by letting the employee know what they’re doing right,” suggest Shannon Falvey, a Boston-based communications consultant who works with startups and small businesses. “Even with the most difficult employees, there are always positive attributes — keep looking until you find them. Suggest ways this employee can parlay these skills into areas of improvement. For example, if he’s great at taking charge but terrible at listening to others, suggest he use his leadership skills to ensure that everyone’s on the same page — have him reconnect with his teammates after a meeting to make sure they’re really being heard.”

When you highlight what’s working well, says Falvey, you are essentially telling your employee that they’re capable of excellent work and growth, and you believe they can move forward in the right direction. Your coaching is then intended to help build confidence around doing so, and feedback can provide advice around adjustments that will allow them to succeed.

Aim for Clarity and Objectivity

“All difficult conversations are, well, difficult,” says Anne Miner, president and CEO of The Dunvegan Group. “[But] feedback is information — information that the recipient may choose to act upon to improve their own performance or, up their game. When you cast the conversation in this light, it may help the recipient to receive the information in a positive light.”

Try to be as objective as possible, too, and frame your feedback up as something you’ve noticed that needs to be discussed, says Dr. Dewett, versus making it about who they are as a person. Saleh agrees, even recommending that managers avoid using terminology like, “don’t take this personally, but . . .” Instead, make it about the work itself, and give your employee a chance to weigh in on next steps.

Dory Wilson, founder of Your Office Mom, also believes in the power of reframing negative feedback.

“[For example] Instead of saying, ‘I am still getting complaints that your monthly reports are not well-organized,’ make the feedback clear and actionable. Saying, ‘Overall, the data in your monthly report looks excellent. I would like to talk about ways to organize the data to make it easier for our executive team to review and take action. I want to get your ideas, but I think adding a pivot table, and a separate summary page would be helpful. What ideas do you have?’”

Be as compassionate as possible.

“More often than not, a difficult employee is an insecure employee — either insecure in their role at work, at home or in some other area of life — so when you’re giving constructive criticism, be kind and compassionate,” says Falvey. “Nobody likes to hear they’re doing something wrong, even the most secure among us.”

It can be useful to talk about moments when you’ve had to learn from mistakes, says Dr. Dewett, to be more relatable and help employees understand you’ve been in their shoes before. Also, spend at least two-thirds of the time or even more listening, says Hunter, because it’ll most likely lead to further insights.

“Constructive criticism is supposed to be just that: constructive,” says career coach Carlota Zimmerman. “It’s supposed to help the employee learn and do better. Don’t spend so much time emotionally beating the employee up that finally, as their self-esteem has left the office, you remember to say, 'Oh, but hey, I know you’re trying, so um, thanks I guess.' Crucially, if in the midst of the meeting, you realize that the employee is crying, or trying not to cry, be human. Stop talking and connect. Make eye contact with the employee, and ask what’s really going on. That may seem like a scene from a bad 1960s movie, but many 'difficult employees' are just people going through some difficult things.”

Give your employee a little space to react and reflect.

Wilson likes to remind managers to give employees time to process after receiving feedback, so they can reflect on the information they’ve been given and think about what could be done differently going forward. But too often, leaders expect employees to have an answer on the spot, which isn’t fair.

“You have had time to think about your feedback, process what you are going to say and prepare in most cases,” agrees Hunter. “The receiver is typically hearing the message for the first time, so give him or her some time to process. Share facts. Facts help establish a baseline as to why you are giving the feedback. Next, share how you have interpreted the facts. Lastly, check in for understanding.”

Keep building a positive relationship

Once you check a difficult conversation off your list, you’ll probably feel relieved and somewhat “done” — but you still have a few things to do, such as continuing to build a strong relationship with the same employee and following up on any improvement plans.

Offer genuine support and praise if the behavior at hand changes as desired, says Dr. Dewett.

Don’t forget to follow up.

And Wilson says to make yourself available to answer questions or give additional feedback as well, so employees know if they’re on the right track.

“Giving negative feedback can be difficult for even the most seasoned managers,” says Dr Turnage. “But honest feedback grounded in a sincere desire to help people improve can be constructive. The effectiveness of those kinds of conversations has a lot to do with your credibility as a manager, the trust people have in you, and the quality of relationship you have established with your team members. Invest in those proactively, and difficult conversations can become less daunting.”