Many great books have been written about difficult conversations, but I’d like to revisit this topic with you, my readers. With a twist of my own experience, I hope you’ll leave with actionable advice to handle these conversations better — without needing to read a stack of books.

What’s Difficult About It?

First, let’s clarify what I mean by a “difficult conversation.” It’s any discussion where the stakes are high. Often, you’ll anticipate it, feeling your blood pressure rise beforehand. But sometimes, it sneaks up on you when a casual chat escalates, leaving you with a sweaty forehead and a racing mind.

6 Principles

Through my work with my engineering leadership team, I’ve developed six principles to prepare for and navigate difficult conversations. Some can even be applied on the fly if you’re caught off guard. More on that later.

#1. Preparation, Preparation, Preparation

If there’s only one takeaway from this post, let it be this: you can never be too prepared for a difficult conversation. Plan ahead:

  • What is your main message?
  • When and where will the conversation happen? Consider time, place, setting, and attendees.
  • How will you structure and present your key points?

Think through all the details in your control beforehand. This isn’t overthinking — it’s freeing mental space for the unexpected. By preparing thoroughly, you won’t need to stress over what’s already accounted for.

Difficult conversations aren’t public speaking, but similar advice applies: practice. Start alone — use a mirror or record yourself. For instance, while I’m confident in writing, the same sentences may sound awkward when spoken aloud. Identifying and adjusting these will boost your confidence immediately.

Next, practice with someone you trust — a mentor, manager, peer, friend, or spouse. The feedback is valuable, but even more so is the experience of voicing your thoughts to another person. It helps you anticipate both your emotions and possible reactions during the real conversation.

Finally, decide and write down your objective. Keep it in front of you. Is your goal to give feedback? Share news? Address behavior? Let someone go? Defining this will guide you when the conversation gets tough.

#2. Don’t Beat Around The Bush

Be clear and direct with your main message. This is harder than it seems, as it’s easy to dilute your point.

In The Culture Map, Erin Meyer highlights cultural differences in presenting decisions. While I advocate for following this advice in formal settings, for private, difficult conversations, lead with the “what.” People are sharp — they’ll sense where you’re headed and may stop listening while trying to guess your point. Breaking the news early avoids this.

Also, avoid softening your message to match the other person’s mood. Doing so risks muddling your point and causing confusion, especially in multicultural teams where English may be a second language.

Be concise and lay your cards on the table. You can elaborate or provide details if needed, but you’ll likely find that it’s less often required than expected.

#3. Stick to Facts

Rely on 100% accurate, indisputable facts. Prepare these thoroughly, ensuring clarity for everyone involved. Keep them at hand during the conversation.

Both parties need to agree on the facts, though they don’t have to agree on their interpretation. For example, if you’re addressing low performance, the fact might be that an engineer completed two tickets last month. This is provable. Whether that’s acceptable or not is open to discussion. Your decision may involve interpretation, but the supporting evidence must remain factual.

Avoid rumors, unclear data, or second-hand information — they’ll only complicate matters. When referencing feedback from others, tread carefully, as it often carries inherent bias. Only use such input if absolutely necessary, and ensure you’ve gathered as much context as possible.

#4. Prepare for Emotions

You can’t fully prepare for an emotional response unless you’re a machine — but you can brace yourself. Expect emotions to surface and allow space for them. Don’t rush; continue only when both parties are calm. If needed, take a break to let emotions settle.

You’re not immune, either. Even with preparation, the real moment can hit hard. And that’s okay. Pause if necessary. Sometimes, simple actions like grabbing coffee, opening a window, or stepping away briefly can help you regain composure.

If emotions overwhelm the discussion, it’s better to reschedule than push through without clarity.

The remaining principles for managing difficult conversations will be shared soon!

Photo by Matt Hardy