The Battlefield of Difficult Conversations

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A memorable moment for me as a child was going to the Pennsylvania Renaissance Faire. I remember my dad buying me a bright pink princess hat and the thrill of watching the medieval joust battle. It’s hard to imagine fighting like that today.

Prepare for Battle

Facing a difficult conversation can feel like a real-life medieval jousting battle. You must put on protective armor (mental and emotional preparedness), grab your joust (backup documentation, examples, etc.), and suit up your horse/riding partner (compare notes with your witness, etc.) as you prepare to face the opposition (employee, family member, etc.).

No two battles are exactly alike, and the same can be said for difficult conversations. Some go better than expected and others throw you curve balls that you never saw coming. Those more challenging ones can make the experience seem like a battlefield and throw you completely off course. The way in which you respond will ultimately result in either winning (finding common ground) or losing (ending up in worse shape than before the battle). Fear, anxiety, dread, worry, sadness, frustration, and anger are just some of the emotions surrounding a difficult conversation. Those feelings are real and are ok, after all, we’re human. However, having an opportunity to prepare in advance for the conversation and knowing how to respond to surprises helps reduce the level of these emotions.

One of the biggest mistakes with difficult conversations is avoiding them completely. I get it, we all wish that by ignoring a problem it will just magically go away. However, that is a very, very rare occurrence. Procrastinating doesn’t solve problems, but it can create additional issues and even more difficult conversations. Save yourself the trouble and address things when they happen. The goal of having these types of conversations is to resolve a situation, keeping that in mind will help you stay focused on the importance of doing it and doing it well.

What Could Possibly Go Wrong?

Conversations going wrong are extremely common, and a primary reason is that we lead with emotion instead of facts. Every day I hear about situations in which conversations were handled improperly or avoided. The consequences are significant. By not providing real-time feedback or communicating in a transparent way, companies are creating a breeding ground for a disengaged workforce and opening the door to risk.

Let’s consider underperforming employees or toxic individuals. When you fail to address these types of issue, the rest of the workforce is left feeling frustrated, stressed and in extreme cases bullied or harassed. When an employee appears to abuse substances (alcohol, prescription drugs, illegal drugs, etc.) the rest of the workforce must pick up slack because the work of the individual is not meeting standards (quality or quantity) and often excessively misses work or arrives late. Employee morale, culture, effectiveness, and business growth are only a few items that are hindered when workforce issues are not addressed.

Another downside of not properly handling or documenting difficult conversations is the opportunity it can open for people to pursue legal action. It only takes one person to file a complaint, and even if there is no wrongdoing, significant effort and costs will be incurred. Time spent responding to legal action takes away from your ability to focus on the core activities of the company such as increasing revenue, developing new products/services, increasing efficiencies, and improving profitability. Not sure about you, but I would much rather spend my time focusing on these items than to deal with an issue that

Next Steps

While I don’t believe there is any technique that can fully prevent the “pit-in-the-stomach” feeling, there are ways to easily navigate through challenging discussions.  Please watch as I share some of the techniques I have learned over the years to help me approach difficult conversations.


Kristi Weierbach