6 Strategies for Mastering Difficult Conversations

By Hardeep Kaur, Director of People, Demandbase

At any point in one’s career, having difficult conversations can be nerve-wracking, leading to sleepless nights and anxiety. When the moment arrives, it’s easy to stumble, leaving the other person unclear about your message. Many professionals struggle with difficult conversations, whether addressing a subordinate’s poor performance, saying no to an authority figure, or other challenging topics.

Here are six strategies to navigate difficult conversations more effectively.

1. Be committed to having the conversation – Let’s face it, having a difficult conversation takes courage, and it’s common to hesitate or postpone it. So first off, consider what the goals are and whether the conversation is necessary. Is it to prove a point or is it something that can be let go? Being clear on goals is crucial before proceeding. If the conversation does need to happen, it’s best to get it done as soon as possible. Some people may feel guilty about having the conversation, worried about damaging the relationship, but delaying a tough conversation can give the other person the false impression that everything is fine, depriving them of the opportunity to know the truth and do something about it. This does more harm than good, hence it’s crucial to have the conversation sooner rather than later.
2. Understand what’s at stake – Difficult conversations can lead to a desirable outcome only if they are authentic and honest, starting with oneself. It is important to reflect on the emotions involved – is it insecurity, fear, a bruised ego, or something else? Consider whether there’s a need to protect self-image and identity, which may feel threatened. It’s also important to remember that the other person is likely trying to protect their own identity as well. By understanding what’s at stake for each party, it becomes easier to relate to each other and find common ground.
3. Plan for the conversation – It’s always helpful to jot down the key points to discuss and the desired outcome. Scripting the conversation isn’t usually effective, since discussions rarely unfold exactly as anticipated. Hence, writing the main points and considering possible scenarios is more productive. If taken by surprise during the conversation, it is fine to buy time and revisit the topic later rather than addressing it on the spot without having given it the proper consideration.
4. Understand the problem – There’s often a belief that the issue is well understood, leading to a greater need to explain oneself than to listen. However, it is essential to get the other person’s perspective and hear the situation in their own words. Active listening is key – listen to understand, not just to respond, and ask questions to clarify any assumptions. Exploring both perspectives helps to understand the problem and move the discussion forward.
5. Behave the way you’d want to be treated – Typically, people respond in kind to how they’re treated—whether positively or negatively. To encourage an authentic interaction, it’s important to lean on the reciprocity principle – behave in a way that encourages the other person to reciprocate in a similar manner, like being respectful, projecting consideration and compassion, etc. The choice of words can significantly impact whether the other person will engage or shut down. In addition, it’s important to focus on facts rather than attacking the other person’s character and to express personal feelings without placing blame.
6. Find a resolution that both parties will agree with – When a difficult conversation is perceived as a zero-sum game, it’s more likely that someone will avoid or abandon it. However, when both the parties agree on who or what will benefit from the resolution, they’ll be more motivated to move forward. It’s vital to find a win-win solution and agree on the next steps. It is also possible to agree to disagree and still reach a resolution.

The outcome of a difficult conversation may differ from what was initially envisioned, but each one can provide valuable lessons for the future. It’s important to reflect after every conversation  to better understand the emotions, biases, and triggers involved, and to continually develop a more empathetic and constructive approach to handling them moving forward.

Difficult conversations are not black swans. With practice and over time, one can improve at having them. While the initial reluctance may not completely disappear, recognizing when these conversations are necessary and addressing them promptly becomes easier.

Also Read: Empowering Women in Tech by Embracing Workforce Diversity