Lessons on Leadership

Three Surprising Tips for Getting the Most Out of Contentious Conversations

By Jacquelyn Adams and Guest Contributor Becky Pocratsky

Dear readers, this week, we are treated to another article from my delightful editor, Becky Pocratsky. And if you happen to have missed her most recent article, click here to learn how to leverage someone else’s words to deepen our relationships. 

After butting heads with one of my coworkers multiple times, she has made the following bizarrely adorable statement: “I hate arguing with you because it’s like getting into a fight with a Disney princess. I always end up being the bad guy who loses.”

Ummmm…. thanks?

While being compared to a cartoon character is certainly not my number one life goal, I will not lie and say that I hate having that edge. So let’s take a moment to flesh out some communication/emotional intelligence techniques I have used to diffuse awkward situations, engage in hard topics, and other tips for being more complete as a professional and also as a person. In this article, we will delve into the top-secret arsenal that I rely on to ensure success, regardless of any unexpected turns in the conversation.

Pick your timing

The first step is to gauge your colleague’s mood — and your own — when choosing the right time to have a conversation. Are emotions running high on either side? Will the conversation be rushed? Or, perhaps, would it be beneficial to take a moment to stage the discussion by requesting a meeting, explaining what the topic entails, and scheduling a time to have it? Sure, it might seem a bit formal, but giving them some time and space to consider the topic can result in clearer, healthier and more productive communication. This can be especially true when it comes to communicating with introverted personalities.

Additionally, it can be helpful to continue assessing the situation as the conversation goes along. It might reach a point when it is best to take a pause to regain composure, or mull over what was said so far and reconvene later. In those moments when we need to break away, we could say something like, “You have given me a lot to think about. Can we pause this conversation and come back to it later today/tomorrow/Friday, once I have had time to process and/or research the points you’ve made?” Taking time to consider your colleague’s insights demonstrates your desire to truly engage, and shows respect for their side of the discussion.

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Understand the other side

Please-in-the-name-of-all-that-is-good do not be that person who is already lining up their counterargument while “listening.” This is not listening. We cannot process and digest what someone else is saying if we preplan our response. Instead, consider what they are saying and ask questions to where you need them to clarify their position. This keeps us from simply fighting a strawman. When we use phrases like, “So, what I understand you to be saying is…” it helps guarantee that both parties are on the same page. When we aren’t really listening or asking good, clarifying questions, we risk arguing against a point that the person doesn’t hold… which is just a waste of time and energy for both of you.

Admit when you’re wrong

“Arguing with an engineer is like wrestling with a pig. After a couple of hours you realize the pig likes it.” – Unknown

I will be among the first to admit I enjoy a solid debate, and even better, when it is an existential one that is hard to answer. However, we all know at least one person who can’t concede a single point. Ever. Every hill will be the one they die on, and they are so stubborn that they are deemed irrational by everyone around them. The result is that they can’t be taken seriously in an argument.

Sometimes we have to lose a battle to win the war. Whether it’s conceding one point or the whole argument, making concessions is a necessary part of having future conversations and debates. So let’s all practice together, “Huh… that makes sense. I never thought about it like that before, but I think you’re right.” From personal experience, it hurts less the more you say it, and it sets you up for success next time.


And that, my friends, is a quick peek into my secret arsenal. Do you have any tips or tricks of your own that you employ during contentious conversations? Leave a comment below or message me on LinkedIn. In the meantime, let’s leave the wrestling to the pigs and fill our conversations with thoughtful questions.


Jacquelyn Adams is a storyteller and an award-winning CEO. She lives in a world of constant exploration, whether it’s summiting Mount Kilimanjaro, vlogging about the future of work… or discovering how she’d do in a chocolate eating contest (answer: last place). Find more of her Lessons on Leadership articles here or connect with her on LinkedIn here.

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Becky Pocratsky is a freelance editor and writer. She works from home with her two sweet (loud, energetic, help me!) daughters. Also she is a super geek who went to Hobbiton on her honeymoon.

Jacquelyn Adams

Jacquelyn Adams, founder and CEO of Ristole, uses her column to delve into the wild world of leadership. Whether the article is about her days as a Peace Corp volunteer, exploring corporate training, or even grabbing lunch at Chipotle — she will come out with a story and her “top tips.” As she passionately believes in leveraging her platform to share others’ voices, her column welcomes guest bloggers to create a fuller and more diverse pool of experiences for her readership. So, welcome to “Lessons on Leadership” where you never know what the next article will hold: online networking advice, guidelines for creating a joyful workplace, or even puppies. Just keep reading to discover what’s next!

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