“What we have seen is that poor communication on difficult topics gets in the way of relationships, understanding, and productive work. It can also create resentment and strain the relationship, when clear, honest communication could have fostered a strong and healthy relationship.” – Lori Heffelfinger
Difficult conversations are a part of the workplace dynamic, especially for managers and leaders. While the majority of people are uncomfortable with conflict, giving and receiving challenging news or feedback can be an opportunity for teams to address challenges and conflicts head-on. When handled skillfully, challenging conversations can lead to personal and company growth, while building trust and maintaining a productive work environment.
Some examples of difficult conversations in the workplace are performance reviews with a struggling employee, conflict resolution between employees, layoffs during a downsize, or disciplinary actions for employee misconduct.
Leaders who receive quality leadership development and team alignment coaching gain the tools to better handle challenging workplace conversations with confidence, using effective communication that fosters active listening, empathy, and respect.
Why Direct Communication?
When handled with compassion, direct communication can be a powerful tool for building trust and maintaining healthy relationships, both personally and professionally. An effective style of direct communication is assertive communication, which balances confidence with respect. This communication style allows thoughts and feelings to be expressed clearly and directly while maintaining kindness and respect to preserve the relationship.
Some ineffective methods of communication include:
· The sandwich approach—where criticism is placed between two positive messages—was once popular, but it can sometimes feel disingenuous and may dilute the core message.
· Aggressive communication can come across as arrogant and uncaring. It shuts down collaboration and damages relationships by prioritizing dominance over understanding.
· Passive aggressive communication isn’t much better. It presents more softly but is ineffective because it creates confusion, avoids direct problem-solving, and fosters resentment instead of open and honest dialogue.
Being clear yet kind ensures honesty without causing unnecessary harm. Difficult conversations are challenging for both parties, but avoiding respectful directness can lead to misunderstandings, strained relationships, and even resentment.
How to Handle Difficult Workplace Conversations
When it comes to successfully navigating difficult workplace conversations, it’s important to practice your direct communication skills in both personal and professional settings because practice and experience can help build confidence, and allow you to handle conflicts with clarity and respect. Here are several points to help prepare for and handle difficult workplace communication effectively:
1.Set Your Mindset
By labeling a conversation “difficult”, you are more likely to feel stressed and nervous. When you reframe the conversation as an opportunity for a constructive conversation with an opportunity for development, you set the tone for a productive meeting.
2.Prepare But Don’t Script
Collect your thoughts about what needs to be discussed and organize any notes you have made about what needs to be discussed along with any relevant employee files and materials that support your position. Create an outline of how the conversation may unfold and identify statements that you can use to help move the discussion forward in a positive and productive way.
3.Plan for how you will handle different reactions
Employees may react differently to negative news or feedback depending on their personality, what is going on in their personal life, their relationship with the manager, and how the conversation is handled. Cues about the employee’s reaction should be taken from body language, hand gestures, tone, and words. Active listening while showing empathy about how the employee may be feeling can be an effective way to diffuse fraught situations. It is also important to keep responses respectful, always maintaining focus on the behavior or necessary action, not on the employee’s personal traits.
4.Schedule Enough Time
Attempting to rush a difficult conversation can prevent all parties from fully expressing their thoughts. Though you may have an idea of how long a conversation may take, build in some wiggle room to your schedule to prevent either party from feeling rushed or overwhelmed.
5.Be Open to Listen and Receive feedback
Managers should not plan to give news without expecting feedback from the employee. In fact, open conversation should be encouraged so that everyone feels heard and respected and because it can lead to improvements. Do not interrupt and acknowledge the other person’s perspective.
6.Attempt to Give Something Back
If you know that the conversation is going to put the other person in a difficult position such as losing their job, come prepared with how you are going to give back. For example, discuss a severance package (if appropriate) and write a recommendation letter that the employee can use to help them find new employment.
7.Reflect and Learn
After the conversation is complete, it is important to reflect on what went well and what could have been handled more effectively. Identify triggers that caused you to react poorly and how you could better prepare for those triggers before the next conversation.
Case Study
Situation: You disagree with the way one of your coworkers is completing certain tasks and you think it will impact the quality of the team’s work. How should you handle the situation?
Ineffective Approaches:
Gossiping with other coworkers. Discussing your concerns with colleagues who may or may not be involved is unproductive and creates a toxic work environment. Rather than addressing the issue, it fosters negativity and damages team trust.
Immediately going to the boss. Escalating the issue to management without first speaking to your coworker can break trust and make it seem like you are unwilling to resolve conflicts directly. You also miss the chance to understand their perspective and find a mutually respectful solution.
Best Approach:
Address your coworker directly in a respectful and curious manner. Ask questions to understand why they are completing tasks in a certain way and share your concerns openly. A collaborative conversation may lead to an easy resolution or even a better way of working. If the discussion isn’t productive or the issue persists, consider involving your manager as a next step. However, under no circumstances should you resort to gossip, because it harms workplace culture and teamwork.
Learn How to Master Difficult Workplace Conversations Through Leadership Development
Successfully navigating difficult workplace conversations requires clarity, confidence, and compassion. The Heffelfinger Co. equips leaders with the tools to communicate effectively, foster trust, and resolve conflicts through our expert leadership development or team coaching services.
With our support, leaders have strengthened their communication skills and created more collaborative, high-performing workplaces. Please contact us to book your free 20-minute consultation to see if we are the right fit.
Warmly,
James & Lori
James Jackman & Lori Heffelfinger
Sources:
How to Handle Difficult Conversations at Work. Rebecca Knight. 1/15/2025. https://hbr.org/2015/01/how-to-handle-difficult-conversations-at-work. Accessed 2/14/2025.
How to have difficult conversations in the workplace. University of Phoenix. https://www.phoenix.edu/professional-development/blog/handling-difficult-conversations-at-work/. Accessed 2/14/2025.
More Resources: Clear is Kind. Unclear is Unkind. Berne Brown hhttps://brenebrown.com/article...
