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Follow These 5 Steps to Make Your Next Difficult Conversation Easier

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As a police sergeant, defensive tactics instructor and member of the regional crisis negotiation team (outside of Boston, Massachusetts), Din Jenkins in no stranger to difficult conversations and high-stakes scenarios. Jenkins is also the CEO of his own company, Supply the Why, which focuses on conflict resolution and DEI training.

In recent years, Jenkins has found himself facilitating a number of difficult conversations between police and civilians regarding the appropriate use of force and other tactics. He joined Negotiate Anything to share his simple, five-step framework for successfully navigating conversations where the subject-matter may be especially sensitive or difficult.


Start Small

According to Jenkins, some of our most difficult conversations are those that emotionally charged and/or involve a highly polarizing topic. Because these conversations can’t be avoided, especially in today’s society, it’s important to approach them in a manner that will be safe for all involved.

Start with a small group; a one-on-one conversation is ideal. The goal is to avoid large groups where multiple people’s ideas align and one or two people feel outnumbered or ganged-up on.

“We tend to gravitate towards people who share our ideologies and values,” Jenkins shared.

In emotionally-charged conversations, this can lead to a pack-mentality and ultimately, an unproductive (and potentially highly confrontational) conversation.

Be Realistic

It’s important to remember that complex situations cannot and will not be solved in one conversation. From reproductive rights to foreign affairs, there is no shortage of complex issues to discuss in today’s world.

To solve some of these problems and the associated tensions, difficult conversations are necessary. That said, realistic goals should be set from the start. One of the best ways to do this is to acknowledge that a follow-up conversation (or multiple) will likely need to be had. Then, allow the first conversation to be all about exchanging ideas and building trust.

“Once you have that foundation of trust, people feel safe to have more of these conversations,” Jenkins explained.

Stay Focused on One Topic

When we’re involved in highly emotional discussions, it can be hard to stay focused on one topic. Once our emotions become triggered, logic and rational thought sometimes go out the window.

“This is the one that really requires the greatest amount of internal discipline,” Jenkins said.

To keep the conversation on track, and avoid any potential attacks, slow down and try to stay on one topic at a time. Then, take the opportunity to let your conversation partner ask their questions and seek clarification.

Do Your Homework

In emotionally-charged conversations, especially where issues related to identity are being discussed, participants will often want to validate their argument with data.

With a long career in law-enforcement, Din is familiar with this tactic but advises against it. Not only can statistics be manipulated to support varying sides of the same argument, but should those stats be incorrect or misrepresented, trust will likely be compromised.

Not only do you lose credibility but this can also cause the opposite site to retreat back into defensiveness.

While Jenkins generally advises against the use of data, he has advice for how to safely incorporate facts into the conversation.

“The best way: let everybody get their turn talking,” He explained. “You have to be patient and there has to be that trust that both people will get the opportunity to present.

Don’t Try to Win the Conversation

Finally, though it seems counterintuitive, Jenkins encourages people to enter the conversation with a collaborative mindset (where possible).

Because so many of these conversations involve highly-sensitive topics and passionate people, oftentimes the focus of the conversation becomes “winning” or proving that one perspective is best.

When dealing with complicated matters like politics and race, it’s unrealistic to expect to change somebody’s opinion in one conversation. Rather than viewing the discussion as an argument or debate, seek to exchange ideas and thought processes. Then plan to follow-up at a later time.

Equally important is identifying your personal goal in the conversation. Oftentimes these discussions take place because two or more people will be interacting on a regular basis (at work or in social environments) or because one or more parties is seeking mutual understanding in a close, personal relationship.

If this is the case, mutual understanding and respect should certainly be one goal. That said, take time to discuss your hopes for the conversation and future-relationship.


To learn more about Din Jenkins and his 5-step approach to difficult conversations, listen to the full episode or visit www.supplythewhy.com.

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