6 Tips to Master the Art of Difficult Conversations

As a business leader, one of the most challenging aspects of the job can be having difficult conversations with employees or colleagues. These conversations may involve performance issues, conflicts between coworkers, or even termination. However, it's essential to approach these conversations with a strategic mindset and effective communication skills to ensure a positive outcome for all parties involved.

In this blog, we will discuss the art of difficult conversations and how leaders can navigate them successfully. Keep reading for the 6 tips to navigate these challenging conversations.

  1. Plan ahead
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  2. Start with a being honest
    It's essential to begin the conversation with being honest and communicating clearly. In our leader Wendy's words, "It became apparent to me over time that the best way to manage tough conversations is to be direct, to not sugarcoat the problem. I've also learned the discussion becomes less difficult if I start it out by saying "This is going to be an awkward (or a tough, or a challenging) conversation. There's no easy way to say this.".

    Acknowledge the person's strengths and contributions to the organization. This approach will help the person feel more comfortable and open to the conversation. Also, it will build trust between you and the employee or colleague.

  3. Be clear and specific but also relatable, where possible
    When having a difficult conversation, it's crucial to be clear and specific. Avoid using vague language or ambiguous terms. Use specific examples to illustrate the issue you're discussing, and provide clear expectations for improvement. It's essential to avoid any personal attacks or judgments and focus on the behavior or performance that needs to change.

    "And then I state the issue in as clear and simple terms as possible. I try to be as matter of fact as I can be. This clearly opens the door for anything needed to be said. And I also try to inject humour into what I say if it's suitable for the situation. This can be a fine line because you need to ensure the person hearing the message understands the seriousness of the issue, or the point of the conversation is lost." – Wendy

  4. Listen actively
    Active listening is a critical skill in difficult conversations. Listen carefully to the person's perspective and concerns. Avoid interrupting or dismissing their opinions. Repeat back what the person has said to show that you understand their perspective. Active listening can help defuse any potential conflicts and find a common ground to move forward.

  5. Offer solutions
    Once you've discussed the issue, it's time to offer solutions. Brainstorm together with the person to find solutions that work for everyone involved. Offer support and guidance to help the person improve their behavior or performance. Be willing to provide additional resources or training if necessary.

  6. Follow-up
    After the conversation, it's essential to follow-up. Check in with the person regularly to ensure that they're making progress towards their goals. Offer positive feedback for improvement and address any issues that arise promptly. Following up will show that you care about the person's success and are invested in their growth.

"In my own consulting practice, I have had to have difficult conversations with my consultants. Like most business owners, I have a model of doing business I want my people to emulate. Over the years I think I'm doing a good job at picking the right people to espouse our values and service but at times, I can also misjudge. When I receive poor feedback from clients on one of my consultant's performance, it is difficult for me to have those conversations with that person. I am good at coaching others about what to do but when it is in my own shop, it becomes harder. So, I stick to the same advice I give my clients – be honest and upfront. I lay the issue out on the table without anger or blame. We then talk about what we can do to fix the problem. I have to say this works almost 100 percent of the time, when it hasn't, it usually results in a parting of the ways. If someone isn't open to working towards a solution, that may end up being the only answer." – Wendy

In conclusion, having difficult conversations can be challenging for leaders, but it's an essential skill to master. By planning ahead, starting with an honest note, being clear and specific, actively listening, offering solutions, and following up, leaders can navigate difficult conversations successfully. With the right approach, difficult conversations can become an opportunity for growth and improvement for all parties involved.

If you are looking for support either with hiring, onboarding support, or other areas of HR, our team is here to help! Reach out to our experts at Wendy Ellen Inc. to assist with all your organization's HR practices.



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