Navigating Difficult Conversations: A Guide for Small Business Owners

If you dread difficult conversations in the workplace, you’re not alone. 

One study demonstrated that 70% of employees avoid difficult conversations with a boss, colleague, or direct report, and 53% handle “toxic” situations by ignoring them. 

A different study corroborates these findings: 80% of respondents were afraid of a conversation they knew they needed to have, many avoiding it or putting it off for an extended time. 

While it’s common to avoid or delay these tough conversations, it’s not effective. Common sense tells us that dealing with a problem when it arises is the best way to move forward for all parties. 

Here we offer key insights on how to navigate difficult conversations as a small business owner so you can create the best possible outcome for yourself, your team, and your business. 

How to Navigate Difficult Conversations at Work

The list of difficult conversations that arise in the workplace is not short. Consider these common scenarios that may require a tough discussion: 

• Employee underperformance or change in performance. 
• Team morale issues (i.e., gossip) and motivation. 
• Breaking policies and procedures. 
• Layoffs due to financial reasons or changing corporate structure. 
• Interpersonal conflict. 
• Unexpected circumstances (i.e., illness, death in the family) that impact availability and performance. 
• Differing opinions on work projects. 
• Opposite work styles and conflicting management approaches. 
• Dissatisfied customers. 
• Illegal activity. 
• Changing company strategic direction. 

Some of these can be resolved by building strong team rapport and encouraging open lines of dialogue in the workplace. Casual conversations among colleagues can help build strong relationships that squash any potential conflict before it arises. 

Remote work can, however, complicate the matter. Without ongoing in-person conversation and team-building, many issues are left to fester unresolved. Leaders and managers need to be even more intentional in managing team dynamics with a remote team and realize conflict resolution will look a little different. 

This is one reason why coworking spaces like The Post Workspaces can be integral in building positive team rapport—they bring colleagues together physically and allow you to operate flexible, remote, or hybrid operations without giving up in-person communication. 

Challenging conversations are necessary in the workplace. It’s not about “if” they’ll happen, but “when.” Here’s how to prepare before, during, and after the conversation.  

Before the Conversation

You can’t completely avoid tough conversations at work, but you can minimize them by creating a positive workplace environment with clear leadership and expectations. You can also be proactive at the first sign of any challenge or issue, ideally resolving it before it comes to a head or at least adequately preparing for a difficult discussion. 

Here’s what to do before a tough conversation at work: 

1. Open Lines of Communication

Prioritizing building trust at your workplace by opening lines of communication. This means: 

• Prioritizing employee check-ins so you know how each team member is doing. 
• Leading with vulnerability and not being afraid to—appropriately—share personal information to build rapport. 
• Organizing team-building activities or icebreaker questions that help people get to know each other and build rapport. 
• Offering opportunities to give feedback so employees know their voices are heard. 

By doing these things, you’re creating a workplace where people feel comfortable to talk to each other. This can help mitigate interpersonal conflict and resulting issues. It can also help you stay informed of what’s going on to adequately address any potential issue or challenge. 

2. Document the Situation

When you do notice a challenge or issue that needs to be addressed—an underperforming employee, conflict between colleagues, etc.—start documenting what’s happening. This is important for a few reasons, as thorough documentation:  

• Offers objective observations of the situation, especially if you have emails or other hard data on a situation. 
• Gives “back-up” for your conversation with the employee. 
• May be required for any legal situation or dispute.
• Avoids “he said, she said” disputes because you can refer to something concrete instead. 

Some situations require immediate action—if someone is in danger or there’s a serious threat, then don’t sit around writing things down. But if there is some nuance or complexity to the situation, you can bide your time and collect some data before calling an employee(s) in for a chat. 

3. Prepare for a Conversation

Now that you have observed a situation and have decided to address it in a conversation, prepare ahead of time. This may include: 

• Compiling data or information to reference in the meeting. 
• Contacting the employee and booking a meeting with them. 
• “Role-playing” how the conversation will go—independently consider various scenarios and outcomes so you’re ready for what may occur. 
• Discussing the situation with other leaders or HR, as needed. 

The more prepared you are for a tough conversation, the more empowered you are to have it. If you feel yourself delaying or avoiding a discussion you know you need to have, turn on your preparation mode—it will help you move into action instead of staying stuck. 

During the Conversation

Now we’re at the crux of the matter—the actual conversation. It’s important to handle a tough discussion with tact and professionalism. Here are three key tips to employ: 

1. Choose The Right Environment

Where you choose to have a difficult conversation is key to its success. It’s inappropriate to have a private conversation where other people can hear, and some locations may enhance counterproductive power dynamics. 

And, simply put, meeting with someone face-to-face is always better. Whenever possible, this should be a priority. Here are some ideas to consider when choosing the right environment: 

• If possible, choose something other than your office or the HR team’s office. This helps keep the environment neutral for both parties. 
• Book a meeting room at a coworking space if you have a remote team or don’t have your own private office. Meeting rooms are private, secure, and professional, which is appropriate and important when having a tough conversation. 
• Select an appropriate time of day to have the conversation—mornings are typically best, as waiting until the afternoon may increase the nerves of both parties. Make sure there is also time after the appointment to regroup. 

2. Be Clear and Kind

Professor and author Brené Brown’s years of research led to a simple but transformative principle: Clear is kind. Unclear is unkind.  

So, as you are conversing with your employee or team member, ask yourself: Am I being clear? Clarity is: 

• Straightforwardly presenting facts. 
• Keeping the conversation short and not over-explaining. 
• Referencing company policies, procedures, or previously agreed-upon decisions. 
• Avoiding blame, shame, or finger-pointing. 

When you handle a situation this way, you are being kind. The opposite approach—talking about someone rather than to them, blaming and pointing fingers, going on and on and on—are all unkind behaviors. 

So, be specific and clear, speak with kindness, and your conversation will resolve in a better way.

3. Listen and Create Solutions

After you’ve said your piece, make sure you offer the other party a chance to respond. Practice active listening so you hear what they are saying, and be empathetic to their point of view. What they say may not change the outcome of the conversation, but it will help someone feel heard and valued. 

Depending on the situation, you may wish to brainstorm solutions together. How can the situation be resolved? Ensure they are on the same page as you by including them in the conversation, rather than speaking to them and dictating what needs to happen. 

After the Conversation

Phew, the conversation is over. You can just forget all about it now, right? While that may be tempting, the better approach is to spend time after the discussion on these two action items: 

1. Reflect

Both immediately and a few days after, take a bit of time to reflect on the conversation. Here are some guiding questions: 

• What went well? What didn’t? 
• Did the conversation go how I expected? Why or why not? 
• Do I need to make changes as a leader or in our organization? 
• How did I feel before and during that conversation? How is that different from past discussions? 

This reflection helps you become better at having these tough conversations in the future. Self-awareness always supports growth and development as a leader. 

It may also lead to practical changes or new ideas. For example, you may notice a lot of petty interpersonal conflict that’s coming up between team members. Perhaps this is because colleagues are not spending a lot of time together to build strong rapport. Switching up your office arrangement and utilizing a coworking space may be a better option for your remote team. 

2. Follow-up

Finally, following up with the colleague or team member is often a good idea. Some situations may not require it, but even a quick check-in can help solidify the positive resolutions you made in the meeting. 

You can also follow up in a less direct way through regular employee check-in meetings. This is a way to keep a finger on the pulse of what’s happening in the office and if negative situations have been resolved. 

Difficult conversations in the workplace are inevitable and important. By being intentional in building a strong work culture, planning for the meeting, being clear and kind, and following up, you can work towards positive outcomes for all involved. 

Looking for a cost-effective professional workspace where you can manage your team and grow your small business? Book a tour of The Post today.