Skip to content

The Time is Right: How to Approach Uncomfortable Conversations with Your Employees

Read time: minutes

Table of Contents
    Add a header to begin generating the table of contents

    I grew up without cable, which left us with limited tv options. Somewhere between Judge Judy and before American Idol, we indulged in gameshows. 

    As a kid, they’re riveting. As an adult, they induce anxiety. You’re more familiar with the hardships of day-to-day living and expenses. That loss of money, which is your freedom out of debt and worry, becomes very real. 

    Work can kind of be like a game show for business owners. Sometimes, you’ve got to take a chance to win big. That chance could be a partnership, a new hire, or a renovation. 

    Sometimes, you find yourself in an awkward situation, stumped, and unable to solve a problem that’s so simple. But the anxiety and pressure completely cloud your judgment and ability to face the issue. 

    One common issue is having an uncomfortable conversation with an employee. Navigating the issue, the employee’s feelings and your own anxiety aren’t easy, yet it’s critical for the well-being of your team and the reputation of your business. 

    In this article, we’re going to help you tackle four common uncomfortable situations, and how to address them best as an employer. If you sweep these issues under the rug, it just creates a larger mess down the road. 

    The more you create transparency with your team, the more you foster trust. And fostering trust lays the foundation for a strong company culture. 

    I’d Like to Buy a Vowel

    Before you approach any of the following situations, remember to do the following: 

    1. Explore your emotions, so you can…
    2. Empathize with your employee, so they can feel…
    3. Encouraged to share, and you can…
    4. Equip them with the tools they need, so they know they’re…
    5. Empowered to excel.

    1. Late Employees

    For some industries, showing up late isn’t a major offense. But for others, it makes or breaks their business. A restaurant owner can’t rely on consistently late servers. It means disgruntled employees eager to get home, and impatient customers. 

    But maybe the consistently late server is amazing at their job and is mentioned by name in several Google reviews. How do you approach the issue without potentially losing your best employee?

    First things first: remove your emotion. Maybe you’re frustrated, disappointed, or just simply stressed out. It’s important to work out all of those feelings before having the official conversation. 

    Next, think about why they may be late. Maybe they’re a single parent juggling a difficult schedule. Maybe they’re forced to rely on Uber for transportation. Or maybe they really struggle with managing their time. 

    Regardless of what it is, practice creating a safe, empathetic space for your employees to discuss issues that are affecting their work – without getting too personal. You both want to feel like the conversation was productive, and not just a catch-up session. 

    Lastly, ask what you can do to help them excel in their role. Is carpooling an option? Does a different shift work better for their schedule? Or do they simply need to make being on time a priority? 

    Explain to them why you care and why it matters for them to be on time. If they value their job and want to be a part of your business, they’ll strive to correct their behavior.

    2. Bad Grammar

    If you’re in a customer-facing industry where communication is essential to your business, poor spelling and grammar can affect your credibility and professionalism. 

    The most obvious answer seems like autocorrect, but it isn’t a catch-all. You have to address these issues for the benefit of your employee, which may be embarrassing for them. 

    Approach your employee from a place of empathy and understanding. Explain to them why it’s important and how it can help them excel in their future at your company, but also in their career. 

    You can also offer to review documents or emails, which makes your employee feel like they’re in a safe space and helps build trust. 

    “I wonder if you would be open to feedback for something that might be holding you back.”

    Skip Wesiman, SHRM

    A good leader will recognize that and have the conversation, no matter how difficult it is. If it’s an issue that reflects your brand, it matters. By taking the time to develop, train, and coach your employee, you’re showing them how invested you are in their role and future at your company. 

    3. Gossiping

    “Cliques didn’t work in high school; they are not going to work now. You are far more productive when everyone works together.”


    Office gossip is like reality television: once you start watching, it’s hard to stop. By identifying a common enemy, the illusion of bonding with your coworkers appears. In reality, it’s creating unnecessary drama that distracts you from your work, damages your relationships, and breeds tension in the workplace. 

    Gossip invites negativity into your team. When it’s not addressed, it gives license to your employees to continue doing it. So how do you stop it? 

    Tally the Votes

    First, recognize that there’s a difference between gossiping and venting. Coworkers need to vent to each other every now and then – it creates camaraderie and garners trust. When a mean spirit is attached to it – that’s gossip. 

    As the employer or manager, assess your company culture. 

    • Are you investing more time and energy in certain employees?
    • Are there team members that feel left out?
    • Have you addressed your team’s questions and concerns? 

    The Tribe Has Spoken

    People want to be seen and heard. Taking the time to understand the heart of the problem can turn a disgruntled employee into a grateful one. 

    This is why it’s important to create a safe space for your employees. They need to feel like they can express their frustrations and concerns in a reasonable way without getting fired.

    We’ve all had bad days and felt like the world was out to get us. In those moments, kindness means everything. 

    Bring Me Your Torch

    Lastly, lead by example, otherwise, you become a warning. If you’re the owner and you’re engaging in office gossip, you’re telling others that they can behave the same way.

    By being passionate, dedicated, and empathetic, you’re encouraging your team to do the same. 

    4. Personal Matters

    We’ve saved the worst for last: conversations about personal matters. Whether it’s an employee who doesn’t maintain proper hygiene or one that wears too much perfume, addressing a personal issue is never easy to navigate, because the employee isn’t doing anything wrong and it’s not affecting their performance at work. 

    Ask yourself these questions: 

    1. Is it affecting others at work? 
    2. Is this person in a customer-facing position? 
    3. Is there an underlying issue related to the lack of personal care?

    The perfume/cologne debacle is the easiest one to address. Several people are sensitive to certain aromas and it triggers migraines. Come from a non-judgemental place and keep it light. There’s no need to overthink it and make it more serious than it is. 

    Personal care, however, is a different issue. One option is to revise your employee handbook and review your hygienic policies. Ask your employees to review and sign it before their next shift. 

    25 Words or Less 

    “Hey [name], this is super awkward for me, but you’ve got to address [insert issue]. You’re the best at what you do, but we’re dealing with customers, and you know how people can be. If there’s anything I can do, please let me know, and please don’t take this personally.” 


    Employ the help of one of your employees – and one of their coworkers. It’s way easier to hear your best friend joke around with you and address the issue lightheartedly. Make sure that you can trust the employee to approach it in good spirit and not gossip about it. 

    What is, Ignorance is Bliss

    Your last option is to ignore it and hold off on addressing it until it becomes a bigger issue. You never know what’s going on in someone’s personal life. Maybe they’re battling a medical issue, struggling financially, or going through a hard time emotionally. 

    Err on the side of grace and ask your team to do the same. 

    I’ll take Employee Happiness for $1,000 

    While uncomfortable conversations can seem like a gamble, the reward is transparency between you and your team, which builds trust, strengthens your company culture, and helps you retain great employees. 

    If you’re struggling with having uncomfortable conversations, and you want to strengthen your team’s trust and your company culture, we encourage you to book time with our team to see how our HR guru Greg can help you build a better back office.