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Having Tough Conversations With Your Employees (the Right Way)

Hiring a team and delegating your business tasks is all fun and games until something goes wrong. When a team member makes an error or creates a hostile work environment, it’s your responsibility to have difficult conversations to resolve such issues. That’s what you signed up for as a leader!

But those tough conversations can go two ways: constructively or destructively. Clearly, we want to avoid the latter—but it’s not as simple as putting a smile on and setting a feel-good intention. Navigating tense situations requires poise to preserve the integrity of your relationship and your core values.

So how do you make a point to your employees without sowing seeds of resentment? Here’s what the industry leaders suggest. 

Skip the blame game 

There’s no changing the mistake, so there’s no need to discuss who is at fault. While accountability is important, the blame game does little to solve the problem. 

Hustle + Gather’s Courtney Hopper says, “It’s vital to approach difficult conversations with empathy to avoid creating shame or embarrassment. Placing blame is never the answer and can often leave your employees feeling disengaged and unhappy.”

“Discuss the issue as a systematic problem rather than an individual one,” Hopper adds. “Lifting the pressure will help your team members overcome any lingering negativity and open up to ideas for improvement.”

So instead of focusing on who did what wrong, direct the narrative toward how everyone can learn from the issue and improve collectively. 

Be clear and direct 

Awkward conversations aren’t fun, which can lead to dancing around the real problem. However, a vague conversation leaves employees uneasy and without a real solution. 

Rather than beat around the bush, Keith Willard of Keith Willard Events encourages leaders to “be specific. It's easy to start off-topic, especially if an employee has been with you for a long time. However, it's important to state specifically what happened, the action of the employee at the time, and why it needs to be corrected.”

The only way to reach a genuine resolution is to get to the root of the cause, which requires transparency. A little small talk is fine, but don’t avoid the discomfort! 

Choose the right time and place 

A well-timed discussion ensures everyone is in the right mindset to listen actively and participate. It’s not on event day when an employee’s hands are full, nor is it at the team meeting with everyone around the table.

“Timing is everything when it comes to tough conversations,” confirms Jacqueline Vizcaino of Tinted Events. “You don’t want to spring a conversation on an employee when they're stressed. You don’t have conversations in a public place where others can overhear. Choose a time and place conducive to productive discussion.”

The best course of action is to schedule a time on the calendar so all parties can come prepared without distractions pulling their attention away from the situation at hand. 

Arm yourself with a plan 

Criticism without a solution helps nobody. It also makes it seem like you care more about a past transgression than a problem-free future, which can breed resentment.

Before opening the discussion, make sure to “have a plan of action or correction,” Willard urges. “When I have a criticism about the action taken by the employee, I will also need to provide the correct option. Being vague and saying just do better is not an answer.”

If it’s a solution that can help everyone, present it to the rest of the team only after discussing it with the individual first. Otherwise, the employee in question may feel ashamed if you ask others for input on fixing their mistake. 

Don’t forget to follow up 

In a perfect world, we’d only need to have a tough conversation once. Unfortunately, that isn’t always the case–especially if a slip-up turns into a repeat behavior. That’s why regular check-ins are an essential part of problem-solving.

“Once the tough conversation is over, don’t just leave it at that,” Vizcaino reminds. “Make sure to follow up afterward. Set intentional time on the schedule to see how the employee is doing and to check in if there’s anything else you can do to support them.”

Following up on a discussion shows that you hold your employees accountable while offering your support to help them improve as professionals. 

Mistakes happen—it’s part of being human. But when an employee’s mistakes spill over to clients and other team members, they must be addressed swiftly and tactfully.  


Meghan Ely

President, OFD Consulting, Richmond, VA

Meghan Ely is the owner of wedding PR and wedding marketing firm OFD Consulting. Ely is a sought-after speaker, adjunct professor in the field of public relations, and a self-professed royal wedding enthusiast. 

Photo: Melody Smith Portraits