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    Tackling Tough Conversations With Your Team

    December 9, 2023

    Let’s chat about those nail-biting, sweat-inducing ‘tough conversations’ with employees. You know, the ones — where your heart races faster than a caffeinated Yorkie? 

    Tackling these chats head-on is not just brave; it’s essential for a thriving workplace and a productive company culture. Avoiding them is like ignoring a squeaky wheel — eventually, the whole cart crashes, but when handled with empathy and clarity, these tough conversations can foster trust, drive growth, and create an environment where issues don’t just hide under the rug. So, let’s get talking! 

    Why Tough Conversations Give Us The Ick

    Have you ever noticed how your palms get clammy at the thought of a tough conversation with a team member? You’re not alone. Feeling discomfort around confrontation is part of our human nature. We’re wired to seek harmony, so the idea of potential conflict or hurting someone’s feelings is nerve-wracking, especially for the people-pleasers of the world!

    But recognizing that running a business isn’t about pleasing people, and being able to have these uncomfortable chats confidently, is what elevates you from a good manager to a great one. Why? Because they are the cornerstone of transparent, authentic leadership. When handled appropriately, these conversations are where trust is built and respect is earned. They’re where problems are nipped in the bud and where personal and professional growth is nurtured.

    Calmly approaching tough conversations shows your team that you value honesty and directness over the comfort of silence, an approach that resolves issues faster and creates a culture of open communication.

    When A Tough Conversation Is Warranted

    Some employee issues can be trickier to spot in the online business world, but are no less critical. Every business is different, and what matters to one leader might be no big deal to another. So, when considering whether a conversation is warranted, you’ll have to consider your company’s unique culture and policies. As a general rule of thumb, if someone’s behavior or performance is impacting your business or your team’s morale, it’s time for a conversation.

    For example, if you have a team member who is a whiz at data analytics but ghosts on team Zoom calls, that’s a red flag for a chat about communication and team engagement.

    Or, if your social media guru who crafts IG captions like a poet struggles with deadlines, turning your content calendar into a wishful thinking list, it’s time to discuss time management and prioritizing tasks.

    You may have a customer service star who shines in client emails but gets tangled up in misunderstandings during live calls. A conversation about clarity and tone in real-time communication is necessary.

    These scenarios are common in online businesses and require a nuanced, empathetic approach. Addressing them head-on resolves current issues and sets a precedent for accountability and continuous improvement in your virtual workspace.

    What’s At Risk By Avoiding The Conversation?

    Avoiding these talks might seem like the easy route, but it’s a one-way street to disaster. When issues are swept under the rug, they don’t disappear — they fester. Unaddressed problems can lead to a toxic work environment, plummeting team morale, and even top talent jumping ship. Plus, it sets a shaky foundation for your company culture that favors silence and avoidance over transparency and resolution.

    The “Right Time” For a Tough Conversation

    Timing is everything when bringing up an issue with an employee. My golden rule: don’t delay. Address the issue as soon as it becomes apparent, but choose a moment when both of you can speak privately and without rush, and approach the conversation with empathy and an open mind. Begin by acknowledging their strengths and the value they bring to the team, then, clearly and calmly state the issue. Go into the conversation with a desired outcome, and be specific about your concerns while expressing your willingness to understand their perspective. This approach will foster a constructive dialogue and reinforce a culture of mutual respect and continuous growth.

    How To Be A Trustworthy Manager (And Why Being Trusted Matters In This Context)

    Becoming that manager everyone trusts will make these conversations easier. If your team trusts that you have their best interest at heart, they will be more receptive to your feedback, even if it is negative. Building that level of trust is all about keeping communication clear, consistent, and transparent. When you’re upfront about what’s happening with the business, the goals, the hiccups, and everything in between, your team feels in the loop.

    Regular check-ins are your best friend for building trust. I’m not talking about ticking off to-do lists….really use these moments to connect and to dive deep into what’s happening in your employee’s world. This way, you’re not just a boss; you’re part of their support system. It’s easier to confront an issue with an employee if they see you as someone in their corner, rather than someone who is out to get them. 

    And most importantly: walk the talk. Show your team that integrity isn’t just a fancy word in your handbook; it’s a part of who you are as a leader. Having integrity means you’re the same person in a board meeting as you are in a one-on-one. It’s about making decisions that are not just good for the business, but also right by your people. 

    It’s also about owning up to mistakes. Nobody’s perfect, and as a leader, showing that you can admit when you’re wrong is powerful in gaining your team’s trust! It tells your team that it’s okay to be human, to learn, and to grow; all of which lays the foundation for a receptive and productive difficult conversation when the time comes.

    Document, document, document!

    If you’re navigating the choppy waters of difficult conversations with your team, remember this: HR documentation isn’t just your life raft; it’s the compass guiding you through. Clear documentation serves a purpose beyond just covering your bases; it’s a tool for clarity, continuity, and growth.

    Before a tough talk, documentation helps you gather your thoughts, set clear objectives, and ensure you’re addressing the real issues. It’s like having a script in a play — your lines, the cues, and the direction of the conversation. This preparation can turn a potentially confrontational dialogue into a constructive one.

    Post-conversation, documenting what was discussed is crucial. It’s not just about keeping a record for compliance or protection (but yes, that’s important, too); it’s about creating a reference point for you and your employee. This record allows you to track progress, follow up on agreed actions, and provide consistent feedback. It’s a tangible way to show your team that their development and your mutual understanding are a priority. Ultimately, effective HR documentation transforms difficult conversations into stepping stones for professional growth and stronger team dynamics.


    Getting good at those tough, heart-racing conversations is key to a productive workplace and stepping into your leadership role. It’s a skill that requires practice, just like any other. You’re not going to wake up tomorrow excited to confront an employee, but over time, you will feel more confident having these discussions on the fly without weeks of mounting anxiety and procrastination. 

    Remember: it’s not just about tackling the tough stuff head-on but also about building a space where trust and growth go hand in hand. Stepping up and being a leader who addresses issues early and with an open heart makes the magic happen.

    Listen Now!






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