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A Small Business Owner’s Guide To Difficult Conversations With Employees

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Janey Velasco
Janey Velasco
6 min read
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One of the benefits of being a small business owner is that you have full control over how you manage your business, schedule, and team. A downfall to that, however, is that you often have to tackle sensitive and difficult issues on your own.

As the pandemic continues to put a strain on many small businesses across the country, owners have had to make tough decisions, including letting employees go, reducing work hours, and temporarily closing their doors. All this in addition to worrying about the health of their customers, team, and family.

But whether it’s going through an unprecedented crisis or simply managing the day-to-day tasks and issues that come up when running a business, having a plan on how to manage difficult conversations with your employees can help resolve issues efficiently and improve work culture.

Below are simple steps you can take to ensure any difficult conversations you need to have are productive and leave both parties feeling heard. Whether it’s a not-so-positive employee review, an internal conflict, listening to a team member’s personal struggles, or even letting someone go, these steps will give you the tools to handle any situation professionally and gracefully.

Prepare in Advance

To prepare, determine the main goal of the conversation. Keeping this goal in mind will help you map out possible outcomes—both good and bad. Difficult conversations can often get messy, so this will keep you and the employee from going off on tangents.

Under the main goal, list each point you want to cover. If applicable, leave room for the other party to discuss their perspective or reasonings.

Don’t: Make a script. It’s impossible to predict the answers, feelings, and reactions of another person, so keep an open mind when it comes to the flow and direction the conversation could take.

Find the Right Place and Time

Two people having a conversation in front of a computer.

When it comes to difficult conversations, you want to block off enough time in your schedule to avoid interruptions. Be sure to let appropriate parties know you’ll be unavailable and silence your phone. This will not only help you and the other person stay focused on the topic at hand, but it helps show respect and investment in the discussion.

Don’t: Have the conversation outside or in public. Oftentimes, people take discussions outside of the office, especially if you work in an open space, to avoid other team members from listening. Instead, schedule a time either in the morning or evening to be able to have a private discussion at the workplace.

Create a Safe Space

In addition to having your conversation in a private setting, you want to ensure your team members that they’re in a safe space to give feedback and express their concerns. This is particularly important when you want to show support.

For example, if you suspect an employee hasn’t been meeting their goals recently due to issues at home, creating an encouraging environment can help you and your employee find a solution that works for everyone.

Don’t: Mention other team members. It goes without saying that these difficult conversations should remain confidential. However, a good way to instill trust with your team is to avoid mentioning other employees by name if it doesn’t contribute positively to the conversation.

Be Direct but Positive

Female business owner speaking to her employee.

Studies have shown that supportive and frequent feedback greatly improves employee growth and development. In fact, about 86% of business leaders believe employee recognition programs help with employee relationships and organizational culture.

In short, feedback is good. However, to be effective, your feedback should be constructive, direct, and positive (when applicable). Of course, if you’ve had a similar conversation with this employee a few times before and haven’t seen a change, your critique can take a harder approach.

Don’t: Over-compliment. Positivity lies in the solutions or alternatives you’re providing. If you’re hoping to see an improvement, discuss ways to reach those goals. If you’re letting an employee go due to business setbacks or hardships, offer a stellar letter of recommendation or referral.

Give Specific Examples

When possible or necessary, be as specific as you can and give examples. If you want to change a process, walk them through each step of the new process. If you’re discussing unpleasant behavior, describe the instances you’re referring to and detail what you want to see in the future.

Don’t: Fall victim to biases. When critiquing behavior and managing a diverse team, make sure you check in with personal biases before you decide on an approach. Behavior that you consider rude, unfriendly, or dismissive may just be a matter of cultural differences.

Keep Your Emotions Under Control

Three people having a conversation in a bike shop.

When bringing up uncomfortable issues, you may get an emotional reaction. To avoid escalating the situation, you need to keep calm and your emotions under control. If you’re anxious about the conversation or expect a negative response, mentally prepare by clearing your mind before the meeting. Practice breathing exercises, do some morning yoga, or go for a walk.

Don’t: Get defensive. As the business owner, it can be hard not to take things personally. However, this job is also your employee’s livelihood, so sticking to a fact-based conversation can help you reach an understanding amicably.

Offer Solutions

If this is a conversation to provide constructive criticism, think of a few solutions you can discuss with your team member. If you don’t have one, honesty is your best policy. Let them know you don’t have an answer but that you’re open to coming up with a solution together.

Don’t: Give broad goals or expectations. If you’re having a difficult conversation with an employee, most likely it’s for a very specific issue or situation. Make sure you set clearly defined expectations for them to work on.

Show Empathy and Compassion

Older man speaking to an employee at a hardware store.

In a time of crisis, many decisions may be out of your control. However, when letting an employee go, cutting back their hours, or even providing feedback on a fall in productivity, showing some empathy can go a long way.

A recent study even found that 90% of employees consider empathy to be important in the workplace while 76% believe it contributes to their productivity.

Don’t: Make comparisons. During difficult events like a global financial crisis or a pandemic, some people may be able to pull themselves by the bootstraps and tough it out. However, hardships affect everyone differently. Avoid using yourself or other employees as examples of how to navigate these situations and encourage them to prioritize their mental health instead.

Make Room for Feedback and Questions

For your conversation to be productive, allow for feedback and questions. Listen with an open mind and consider the other person’s perspective. This will help clear up any miscommunications and encourage a more positive reaction from your employee.

Don’t: Rush your response. After listening to an employee’s feedback, take a moment to process your thoughts and consider your words. If you need more time or suspect the conversation won’t lead to a productive outcome, consider rescheduling or letting them know you’ll get back to them after some thought.

Review the Conversation

Two in an office having a conversation.

Always try to get your conversations on paper (or email). Send a follow-up message that includes both your talking points and your employee’s feedback. Ask for a confirmation that they received the email and leave room for questions. This is a great way to show you listened to what they had to say, ensure nothing got lost in translation, and reiterate any next steps or solutions you both agreed on.

Don’t: Forget to follow up. If you notice an improvement, schedule a quick chat to acknowledge the change and encourage them to keep up the good work.

By following these tips you’ll be ready to turn these uncomfortable conversations into constructive and productive plans to improve your team and company’s culture.

We know hiring, training, and managing a team, however small, can be incredibly time-consuming. Luckily, running your business doesn’t have to be. Start your free account with GoSite and enjoy the benefits of an all-in-one platform to manage your payments, bookings, customer communications, and more from the palm of your hand.

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