4 Tips for Handling Difficult Conversations at Work: A Guide for Small Business Owners

We all know how the story goes, especially these days. Something or someone has slowly started being brought up more and more often, distracting or disrupting the day to day operation of your business. It feels natural to want to ignore it. You think “this is something that could resolve on its own” or “any action feels like an overreaction”. But as if a check engine light has come on, this is likely just the beginning.

There are a lot of reasons you might be ignoring your check engine light. Maybe you don’t have time, maybe you have higher priorities, maybe this vehicle is better than no vehicle right now. Maybe you just don’t know where to start.

As a small business owner, it’s true that a big advantage you have is the ability to manage your own schedule, your entire business and your team. When situations get difficult or sensitive issues come up, you don’t have to tackle those alone. Don’t let an addressable situation become toxic to the rest of your business, costing you much more time, energy and money in the long run. Using these tips should get you started, but this also might be the right time to enlist the help of a trusted HR partner like Approach. 

Conquer your fears

You are not alone. Many managers spend too much time delaying addressing an issue because they’re not sure how to approach the situation or how to handle emotional employees. 

Often, leaders fear the conversation won’t go well and, while that concern is valid, avoiding hard conversations with employees often leads to making everything worse. The longer you wait, the more it begins affecting your workplace environment, culture and productivity.

Keep in mind the bigger picture that is the mission of your business. Not all employees understand how their behaviors are affecting others around them or the environment overall. It’s hard for employees to hear that they’re failing, making mistakes or that they need to majorly course correct to get back on track. Most difficult conversations aren’t about isolated incidents, but rather a long term issue that will take a long time to resolve. 

Focus on the steps you’ll need to take together that will help improve life for everyone.

Be prepared

Preparation never made anyone worse. For any difficult situation, you cannot rely on observations or informal notes, you need to make sure that you’ve properly researched and documented the situation you’re about to address. 

So often employees want to know why or to drive the conversation into an unrelated direction. Plan out ahead of time what you are going to say, keep it short, relatable, understandable and repeat (even until you feel awkward). 

Whether you’re an owner or manager, you’re the leader of the business and a coach for your employees. It’s up to you to set them up for success with the right tools and direction. So, make sure you can explain how they are missing the mark and what the next steps will be.

This may also be your chance to evaluate your company’s written policies. Having a process to document conflicts, policies in place for handling difficult situations and properly documented employee communications (in an employee handbook or other materials) help you outline your expectations. 

Regular, ongoing performance reviews also provide you a way to check in on individual goals and objectives, culture fit and personal progress. Having well-documented evidence leaves less room for interpretation and builds in that chance you’re looking for to face difficult situations head on. 

It’s also important that you don’t leave these as a one-time conversation. Once addressed, you should immediately set up a time to regroup or follow up. Using already scheduled performance reviews also provides the opportunity to highlight progress or resolution (or the lack thereof). By circling back on difficult situations, you demonstrate your continued support of your employees even if it has been solved.

Stay positive

It sounds simple enough, but setting a positive tone at the very beginning can make all the difference. The right approach allows employees the opportunity to better understand versus feeling defensive or getting argumentative.

No matter what, your meeting should always be based in fact. Keep your emotions in check and avoid saying things like “I’m disappointed”. There are ways to be supportive without using personal language. If emotions rise, pause the meeting and set up a time to reschedule.

Present solutions for every issue that is addressed. While every situation is different, you can put yourself in their shoes. How would you prefer to hear this news? If you can spin the context of the conversation with a positive approach, open communication is much more likely.

We’ve seen it happen a lot where a difficult conversation (even with the best of intentions) leaves an employee feeling discouraged. The most difficult topic of conversation we’ve helped support is around termination, but if that’s not the goal of your meeting it is important to keep a positive tone and end the meeting on a positive note, you are more likely to leave an employee thinking they can do better - that you are giving them the opportunity to do better. You want them to feel accountable and committed to any goals you’ve set for them to improve.

Find the right place and time

Just like a positive attitude, you should be mindful that you choose the right setting. An office or other private space is usually an acceptable location. Depending on the topic (and the individual), you might be better talking to them over coffee or lunch. This could lessen their chance of feeling embarrassed or cornered. However, this more informal approach might not be interpreted well or appropriate for the situation. 

Difficult topics can range anywhere from poor performance to something much more severe such as breech in confidentiality, sexual harassment, stealing, insubordination, etc. The point being there are lots of options, but every set of circumstances should be evaluated for the best fit.

This includes consideration of whether this conversation should be held in-person or virtually. While it could create more conflict to force an in-person conversation, we don’t recommend ever addressing difficult topics over the phone. If it must be virtual, try to accommodate a video chat so as to better empathize and read emotional responses.

Again, depending on each individual situation, including a witness might be a good idea. When it comes to dealing with policy violations, behavioral issues or anything requiring disciplinary coaching, consider pulling in a qualified HR professional. Never involve another employee. This third party should be unbiased and briefed on the situation to ensure you are both clear on what each other's roles and responsibilities will be.

In any case, it’s most important to choose a safe environment that makes everyone comfortable.

Difficult situations will come up. It’s inevitable. Especially as the pandemic continues to put a strain on many small businesses, owners have to make tough decisions including termination, reducing hours, temporarily closing doors, setting standards for vaccinations (on top of the worry about the health of customers, teams and your own family).

But whether it’s going through an unprecedented crisis or simply managing the day to day issues that come up while running a business, having a plan for how to manage difficult conversations with your employees helps bring resolution and can even improve work culture.