Team Leading 101: How to Gracefully Handle Awkward Talks

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For many small business owners, a big part of the initial appeal of working for yourself was not having a boss. And in those magic early years when it’s just you, or just you and a partner or a great first employee, it really is great to have no one to answer to except yourself. Then your business grows—yay!

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Now you’ve got a little team of folks working for you, and that’s amazing. But suddenly there’s a boss in the room again—and now it’s you. And as a team leader, it’s your responsibility to initiate and facilitate the awkward-but-essential talks that must happen when an employee is doing something that is bringing the team down. Check out our cheat sheet for how to act like a boss when things get uncomfortable. 

Body Odor

If your staff works together in an office, or if your employees see clients, each person’s hygiene impacts the rest of the team, and if someone has body odor that’s a consistent distraction, you need to handle that. It is high-key awkward to have to approach a grown adult about their armpit-washing situation, so tread lightly here.

The person is going to be embarrassed, there’s no way around that, and it’s possible they’ll react defensively. You want to go in with kindness and compassion, keep the conversation short, and give them space to not be around you right afterward so that they can process their feelings in some privacy.  

Because of the sensitive and personal nature of the ask, a convo about workplace body odor is best held in person. Ask your employee if they can meet with you (preferably at the end of the day) and speak to them in a private space. If you’re in an open plan office or on a job site, make it your business to find somewhere private offsite to meet. You want to avoid shaming them as much as possible.

Keep the tone light and the language focused on serving the team. Avoid accusatory language or words like “disgusting” or “overwhelming” or “dirty.” Some people just have more body odor than others, and sometimes it’s an issue of diet or health rather than just “I didn’t take a shower,” so show some understanding while advocating for the rest of your team and clients.   


When an employee consistently fails to show up for work, it hurts your business. While it might be tempting to avoid the conversation, or to come down hard on the often-absent staff member, you need to balance two things in your approach to this situation: the needs of the employee, who may or may not have life or health stuff going on that you are not aware of, and the needs of your business and clients, who need your staff to show up when they say they are going to show up. 

Remember that as an employer you are not allowed to ask questions about protected health information. You can ask a general “is everything okay?” but if you don’t get answers, it can be legally problematic to push for more info. The important question to ask is what you, as the boss, can do to support the employee’s consistently showing up for work.

Sometimes an easy fix like starting the day two hours late to accommodate childcare issues can turn an often-absent staff member back into the star you hired. Be willing to be flexible—but remember that you have your own bottom line to protect, too. 

Inappropriate Comments

When a staff member makes inappropriate comments, such as microaggressions or remarks on someone’s appearance that make others uncomfortable—to a coworker, a client, or to you, you need to take immediate action. You set the tone for the health of your workplace culture, and letting those comments go even once can suggest that your workplace tolerates inappropriate dynamics. 

Sometimes people are genuinely unaware that they’ve made a problematic comment, so you want to approach them firmly but without being accusatory. “It was inappropriate when you said _____. It’s not okay to make ______comments at this company. In the future, please avoid comments of a ______ nature” is a good template. It’s worth considering having this conversation via email so you have a record of your interventions just in case you end up with an HR issue down the line. 

Poor Performance

When an employee’s performance takes a dive, it’s time for you to shift roles a bit, from boss to coach. Before sitting down with them, ask yourself what change you’d like to see from them (and get very specific). Then, ask yourself what you can bring to the table to elicit the performance you desire.

If it’s sales goals or quality of work, what kind of mentorship can you offer that will increase their effectiveness? If it’s a discipline or work ethic issue, what incentives can you put in place that will help them tap into greater motivation? Unless you want to fire the employee (which should not be your first or second move), it’s important to think as a mentor rather than like an underserved client, because positive reinforcement is more effective than punishment or fear.   


Every office has one—the perpetually late employee. Tardiness tends to be contagious, so it’s wise to initiate a conversation with an often-late employee sooner rather than later. Start from a place of observation (“I’ve noticed that ____”) rather than an accusation (“You were late four times this week!”) and let them know what is and isn’t acceptable.

Dress Code

This one is dicey, so tread lightly. The best way to handle dress code issues is to be clear about expectations from the moment you hire someone. It’s important to remember that some of the ways people present themselves (like hairstyles and makeup) are expressions of their culture or gender, and those expressions aren’t yours to manage or police. 

What is fair game are issues of formality—if business casual is standard in your office and industry and one staff member keeps showing up in sneakers, that’s okay to speak up about. If your employees work in a client-facing capacity, it is also reasonable to expect that they be presentable, meaning that they took care with their appearance by wearing clean and pressed clothing and practicing personal hygiene.  


It’s natural for employees to become friendly with each other and perhaps with you—this is the sign of healthy workplace culture! But sometimes when collegial relationships become friendships, workplace boundaries get blurry. If you have an employee who has become overly familiar in the way they speak to clients or staff, who lacks physical boundaries, or who talks about intimate or personal topics during work, sit down with them and gently but firmly let them know that, at work, there are different boundaries than there are at home. 

If you’re thinking that you’re not bothered by relaxed boundaries, remember that it isn’t just about you—as the boss, you are responsible for establishing and maintaining boundaries on behalf of every staff member and client, too. Maybe you don’t mind that one of your staff members is a rampant hugger or overshares about her dating life, but another staff member might be deeply uncomfortable and afraid to speak up. 

Unprofessional Behavior

The standard of what “professional behavior” looks like varies a lot from industry to industry That said, it is reasonable to expect your employees to adhere to the professional standard of their line of work. Sometimes, as the boss, it will be on you to remind them of what those standards are. 

If you have an employee who is on their phone when they are meant to be working, takes extended personal phone calls during work, or swears a lot around clients and coworkers, it’s time for a sit down, during which you should explain to them that such behavior is unprofessional and that they need to make an adjustment. Focus on the behavior (“it was unprofessional when you ______”) rather than their character (“you’re unprofessional”), be as specific as you are able, and give them space to respond.

Bossing Like a Boss

You want your employees to feel valued—in addition to being a good personal and business ethic, it is also the single best way to motivate their work. Your end of that contract is keeping the workplace a safe, hygienic, professional environment to the standard of your industry. When people start edging up to the boundaries of best office practices, you owe it to your business, yourself, and the rest of your team to speak up asap to clarify and maintain those boundaries. You got this, boss.