Mastering Difficult Conversations: A 5-Step Guide for Business Success


Are you familiar with that sinking feeling before a tough conversation? 

For many, it’s hard to conduct a tough conversation both personally and professionally, and thus try to avoid it at all costs. However, as with most things you try to dodge, you pay for it in other ways, such as frustration, stress, loss of trust, and even broken relationships.  In business, the costs are often lost productivity, employee dissatisfaction, and revenue decline.  

For example, if you have an underperforming employee and you avoid addressing the situation. Not only does it affect their work, but typically also the performance and morale of the entire team.

Why do we tend to evade those conversations?

Often, it’s fear of upsetting or angering others, potential explosions, or the dread of exacerbating the situation further. The truth is that navigating through challenging discussions isn’t a skill we’re typically taught. Many of us stumble through, improvising as we go, and even rehearsing the entire conversation in our heads, only to find ourselves in situations far from what we anticipated.

So, if you would rather avoid these conversations altogether, today is your lucky day because I’m sharing a 5-step resource to confidently tackle those tough conversations.

  1. Preparation:

Don’t just dive into the conversation, take the time to plan and organize your thoughts. Jot down key points you want to address but never plan out the entire conversation. I’ll explain why later. When you take the time to outline your key points and objectives for the conversation, you mitigate the risk of feeling lost or tongue-tied midway through the discussion. It sets the foundation for a structured and productive exchange.

  1. Timing and location:

Choose the right timing and setting for your conversation. You certainly don’t want to spring a tough performance conversation on an employee because you run the risk of them feeling ambushed and becoming very defensive. Opt for a time when all parties are alert and focused and ensure a location that allows open communication without distractions. Timing is not just about time and location but also duration; it’s about allowing adequate time, so you don’t feel rushed because it could escalate tensions unnecessarily.

  1. Control:

Maintaining control—I’m not talking about being in charge but being in control of your emotions. Practice deep breathing to stay calm and composed. It is crucial to approach the conversation with an open mind, ready to understand the other person’s perspective. Remember to focus on the problem at hand rather than directing blame or criticism towards the individual. By keeping your emotions in check, you pave the way for a more rational and constructive exchange.

     4. Active Listening:

Your mother was right—you do have two ears and one mouth for a reason. But what she forgot to tell you is that your eyes are just as important because active listening means paying attention to the entire person. Pay close attention to non-verbal cues like tonality and body language. Want proof, just notice how your pet reacts when you take an aggressive stand and speak sternly versus happily and lovingly. It doesn’t matter what you say; they react to your posture and tone of voice. It’s the same with people. We respond to the emotional queues long before we hear what’s being said. Active listening also requires curiosity and genuine intrigue. As mentioned before, if you rehearse the entire conversation in your head, you typically only hear what you want to hear and disregard crucial facts.

  1. One Topic:

In the heat of the moment, it’s easy to veer off course and bring up unrelated grievances. Stay focused on the primary topic, concise, and to the point. This will help you maintain clarity and prevent the conversation from becoming overwhelming or convoluted. I know it’s so easy to get sidetracked, especially if you don’t resist the temptation to introduce irrelevant issues. However, by maintaining a laser-like focus, you increase the possibility of resolving the issues respectfully. Also, remember it’s never about the person, it’s about the behavior.

 Final thought. When we coach our clients on how to handle tough conversations, they realize that it’s about showing humanity, empathy, and mutual respect. You see, mastering these conversations isn’t about avoiding differences of opinion, or only telling people what they want to hear, but about maximizing the likelihood of fruitful dialogue. It’s also about appreciating it as an opportunity for growth.

By following these five steps—preparation, timing, control, active listening, and staying on topic—you’ll be well-equipped to navigate challenging discussions with confidence and effectiveness.

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