The Top 10 Types of Difficult Conversations Every Business Owner Needs to Have

Mastering difficult conversations at work is an invaluable skill – especially for leaders – but do you know the ten most common types of difficult conversations?

While difficult conversations about performance management are definitely one of the most common types of difficult conversations we see in workplaces, they’re just the tip of the iceberg.

Business owners and leaders will encounter a wide range of challenging conversations with their teams, and knowing how to approach and navigate these difficult conversations is an invaluable skill. 

So, while performance dramas are undoubtedly a significant part of the landscape regarding difficult discussions, it's a mistake to believe that these are the only challenging conversations you'll have as a leader in business.

Why We Avoid Difficult Conversations at Work

There are many reasons why avoiding difficult conversations is bad for business, the most obvious being the creation of a toxic work environment that can be damaging for everyone involved.

What are difficult conversations at work?

When we talk about difficult conversations, we’re talking about any type of conversation that you find hard to do, or carry out. Something that isn’t easy and is seen to be the cause of problems that we don’t want to deal with.

The Top 10 Types of Difficult Conversations

Let’s dive into the ten most common types of difficult conversations we see crop up in the workplace so that you can identify them and prepare for them ahead of time.

1. Offer of Employment & Counter Offers: Crafting an enticing employment offer and handling counter offers can be challenging, especially regarding salary negotiations. As a leader, your ability to navigate these discussions can make the difference between securing top talent and losing them to counter offers from their current employers.

2. Expectation Setting: Setting clear expectations with your team members is crucial, but many find it challenging to articulate their expectations effectively. Leaders often assume that their team members understand their roles and responsibilities, but assumptions can lead to confusion and conflict. Learning to communicate expectations clearly from the outset can prevent misunderstandings that lead to more significant issues later down the track.

3. Delegation Conversations: Delegating tasks can be challenging if you're prone to micromanagement. Many business owners believe they can do a task better themselves, leading to the "I'll just do it myself" mentality. However, effective delegation is essential for business growth and preventing burnout. Learning to delegate efficiently and trust your team is a skill that can transform your business.

4. Performance Reviews: Providing honest feedback during performance reviews can be daunting. No one likes delivering constructive criticism, and no one enjoys receiving it. However, performance reviews are essential for employee development. Avoiding these discussions can hinder your team's growth and the overall success of your business.

5. Salary Negotiations: Discussing salary increases or adjustments can be uncomfortable, but it's a conversation you must have as a leader at some stage. It's not just about the numbers; it's about valuing your team members' contributions while maintaining the financial health of your business.

6. Promotion Requests & Expectations: Addressing requests for promotions and career advancement can be tricky, especially in small businesses. Employees may feel they've outgrown their current roles and want to climb the career ladder. Handling these discussions carefully is essential to maintain team morale, retain top talent and foster long-term relationships.

7. Workplace Flexibility Expectations: Managing employees' demands for remote work or altered hours can be challenging as flexibility becomes the norm. The traditional 9-to-5 work model is evolving, and leaders must adapt to keep and attract the best people for the job. Balancing flexibility with business needs requires open communication, trust and well-defined policies.

8. Conflict Resolution: Dealing with conflicts between team members, customers, or suppliers requires finesse and practical mediation skills. Conflict is inevitable in any workplace, but unresolved disputes can escalate and harm team dynamics. Learning to address conflicts promptly and constructively is essential for maintaining a harmonious work environment.

9. Performance Management: Addressing performance issues within your team is one of the most critical and challenging conversations you'll face. Whether addressing consistent underperformance or managing behavioural issues, performance management discussions can be emotionally charged and tricky to navigate. However, they are essential to maintain a high-performing team so learning how to approach these in a respectful and balanced way is a critical skill for a leader to develop.

10. Termination or Redundancy Conversations: At some point, you may need to exit employees for various reasons, and these conversations are never easy. Whether you're terminating employment on performance grounds or making a position redundant due to business changes, these discussions require empathy and professionalism. Handling them poorly can lead to legal issues and damage your company's reputation, while handling them professionally and with compassion can lead to a more positive experience for all involved.

You can see there’s a wide range of difficult conversations you can be faced with as a leader beyond just tricky performance management conversations.

Strategies to Help You Manage Difficult Conversations at Work

Effective communication is the backbone of any successful business. There are many reasons why we avoid difficult conversations, but they are opportunities for growth and improvement.

Here are some strategies to help you navigate these challenging discussions effectively:

• Prepare Thoroughly: Before entering a difficult conversation, prepare yourself by clarifying your goals and desired outcomes. Anticipate potential objections or questions and plan your responses.

• Active Listening: Listen actively to the other party's perspective and concerns. Understanding their point of view can lead to more productive discussions and solutions.

• Empathise: Show empathy and understanding, even if you don't agree with the other person's viewpoint. Acknowledging their feelings and experiences can defuse tension.

• Stay Calm: Emotions can run high during difficult conversations. Maintain your composure and avoid reacting impulsively. Take breaks if necessary to collect your thoughts.

• Use "I" Statements: Express your thoughts and feelings using "I" statements to avoid sounding accusatory. For example, say, "I feel concerned about..." instead of "You always..."

• Seek Common Ground: Identify areas of agreement and shared goals. Finding common ground can build rapport and create a foundation for resolution.

• Be Solution-Oriented: Focus on finding solutions rather than dwelling on the problem. Collaborate with the other party to explore possible resolutions.

• Follow Up: After the conversation, follow up with clear action steps and timelines. Ensure that both parties understand their responsibilities in moving forward.

Tap into one or a combination of these strategies the next time you face a difficult conversation with your team.

Great Communication Starts With You

The first step is to recognise that mastering difficult conversations is a vital skill for business owners no matter what size your team is. These conversations are not isolated incidents but integral parts of your role as a leader.

By addressing the diverse range of challenging discussions we’ve covered, you'll not only enhance your leadership skills but also foster better relationships within your team at every stage of their journey.

If you find yourself struggling to manage difficult conversations with your team even after using the strategies we’ve covered, give our team at People Powered Business a call.

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