b Cause Work Doesn't Have to Suck

309: How to Handle Tough Conversations Without Losing Your Cool with Gabe Karp


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Life isn't all smooth conversations and easy people. Sometimes it's messy, uncomfortable, and straight-up frustrating.

In this episode, Erin sits down with former trial lawyer turned entrepreneur and conflict expert Gabe Karp to talk about how to handle tough situations without spiraling, avoiding, or blowing things up.

Because here's the truth: conflict isn't the problem. How you handle it is.

Gabe shares practical strategies to help you stay grounded, take control, and walk away without regret… even when the other person is making it hard.

Here's what you'll hear:

- Why there are always "two tokens" in every situation and how to choose wisely

-The 5 traps that quietly sabotage your ability to handle conflict

-A simple shift that helps you stay calm when things start going sideways

-Gabe's least proud leadership moment and the lesson that stuck

-The subtle behavior that might be holding others back (and you don't even realize it)

Website: GabeKarp.com

LinkedIn: www.linkedin.com/in/gabe-karp-1b772a1b

Check out Gabe's TED Talk, How To Thrive With Difficult People: https://youtu.be/ggOQg6uUV2M?si=nKviXwvHJkGgvLGk

If you'd like quick tangible tips and practical corporate career advice to level up your authentic leadership, download the 10 simple "plays" to stop selling out and start standing out at https://bauthenticinc.mykajabi.com/freebie

To connect with Erin and/or Nicole, email: [email protected]

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  • DISCLAIMER: This episode is not explicit, though contains mild swearing that may be unsustainable for younger audiences.

    Tweetable Comments

  • "Everyone knows what "better" looks like. They just don't know where to start."

  • "When you really screw something up for a client, that is an opportunity to make the relationship stronger and better."

  • "Mistakes are inevitable and a real true test of character is how we react once we recognize we've made a mistake."

  • "You cannot drive growth and innovation without conflict."

  • "What do you get out of being mad?"

    Episode Transcript

    This transcript has been lightly edited for clarity and readability.

    In this episode, Erin Hatzikostas talks with conflict expert Gabe Karp about how to handle difficult workplace conversations, give feedback without becoming the bully, manage conflict with bosses and clients, and use practical tools like the "two tokens" theory, the "shopping list voice," and the penguin philosophy.

    Why Conflict Is So Hard at Work

    Erin: I'm really excited to talk to you today. I think we can never have too many episodes about tough conversations. Conflict is the word you use, and our audience is working in a very Game of Thrones-type environment — corporate America.

    Erin: You are a conflict expert. Was there a moment when you realized this was the work you wanted to do?

    Gabe: There was. I spent ten years as a litigator, mostly in commercial litigation and legal malpractice. If you think a normal lawsuit is contentious, suing lawyers for screwing up is that on steroids.

    Gabe: I learned a lot about anger and how it flows through a room. For all the wrong reasons, I loved it.

    Gabe: Then I left private practice and joined a startup. We were growing fast, and whenever there were issues — a client problem, an internal mistake, anything — I wanted to jump in and fix it. But everyone around me was uncomfortable with conflict, and I didn't realize that at first.

    Gabe: I realized we couldn't fix what needed fixing if everyone was tiptoeing around issues. I had to consciously find ways to help people feel comfortable having difficult conversations.

    Can People Get Better at Conflict?

    Erin: Do you think people can transform? A lot of people listening may think, "I just naturally run from conflict."

    Gabe: Absolutely. I think it's nurture, not nature. We all have the same fight-or-flight instinct. But the ability to pause that instinctive response in the moment is something people can learn.

    Gabe: The thing I've found most effective is helping people find the right entry point into a difficult conversation. One line I use all the time is, "If I were in your position, I'd want someone to tell me this."

    Gabe: Once people have that one sentence to break the ice, all the things they need to say can come out in a productive, respectful way.

    Erin: So one of the most important things is the entry point into the conversation.

    Gabe: Exactly. Most people have a sense of what needs to happen. They just don't know how to begin.

    When Your Boss Keeps Changing Priorities

    Erin: Let's take a common scenario. Someone's boss keeps changing priorities. One week it's one thing, the next week it's another. The employee is overwhelmed and hasn't said anything. How should they approach that conversation?

    Gabe: You want to bring awareness to the boss. It's like holding up a mirror and letting them see what their behavior looks like.

    Gabe: In the moment, you might say, "It sounds like this is important, but two days ago you told me the thing I'm working on now had the same level of urgency. If I drop this, it remains unfinished. If I move to this new thing and then two days from now we switch again, that becomes difficult for me because I don't know what's actually important."

    Gabe: You're not attacking them. You're helping them see the pattern. Most people don't want to be perceived as the person who creates fire after fire after fire.

    Erin: I think one of the most important things you said is to address it in the moment. A lot of people wait for the next one-on-one, and by then they're nervous or the meeting gets delayed.

    The Two Tokens Theory

    Erin: Let's talk about customer conflict. How do you handle a situation where you have to tell a client that something you promised isn't going to be delivered?

    Gabe: There's a concept I love called the choice between two tokens. In every customer service complaint, there are two tokens on the table: the "it's not a big deal" token and the "this is the end of the world" token.

    Gabe: Whoever picks up the first token forces the other side to pick up the only token that's left.

    Gabe: If a customer has a serious complaint and you minimize it, they are forced into the "end of the world" position. But if you immediately take accountability and say, "This is unacceptable. We failed you. We're going to fix it," the customer often becomes the one to say, "Okay, it's not that bad."

    Gabe: In business, there is almost no downside to taking accountability first, even if you don't know all the facts yet. If you later learn the other side was also at fault, you'll have more credibility because your default response was accountability.

    Gabe: When you really screw something up for a client, that can actually become an opportunity to make the relationship stronger. Mistakes are inevitable. The real test is how you respond once you recognize the mistake.

    Erin: I love that metaphor. I've never heard it explained that way, but I've seen that strategy work.

    Why Conflict Drives Growth

    Erin: You say conflict can drive growth and innovation. Tell us more about that.

    Gabe: You cannot drive growth and innovation without conflict. It's impossible.

    Gabe: Companies where everyone is a yes person and no one raises their hand when there's a problem will kill innovation. The same is true for careers. People grow when they receive feedback, learn from mistakes, and get better.

    Gabe: If someone is repeatedly making a mistake and you know exactly what they're doing wrong, but you withhold that information because you don't want them to feel uncomfortable, you're depriving them of the opportunity to become the best version of themselves.

    Gabe: People often think avoiding feedback is kind. But sometimes it's actually cruel because you're withholding information they need in order to grow.

    Gabe: You can say something like, "If I were in your position, I'd want to be told this," or, "I think you're being perceived in a way you don't want to be perceived." Then get specific.

    Gabe: It's not enough to tell someone what they did wrong. You also need to give them something they can take away and use to improve.

    Feedback as a Leadership Gift

    Erin: That reminds me of a boss who once gave me feedback after I ran a town hall. I thought I had crushed it, and he told me I said "I" a lot — "I think," "I want," "my vision." It stuck with me because he was right.

    Erin: If he hadn't told me, he would have deprived me of becoming a better leader.

    Gabe: That's huge. Whether or not he was your favorite boss, that was a real service he did for you.

    Don't Get Mad at Penguins

    Erin: We have to talk about penguins. Your book is called Don't Get Mad at Penguins. Why?

    Gabe: Don't get mad at penguins because they can't fly.

    Gabe: It's a lesson in acceptance. We need to accept people, limitations and all, and stop expecting them to do things they are not capable of doing.

    Gabe: The hard part is that limitations are often hard to see. A penguin is a bird. It has wings and feathers. Everything about it suggests it should be able to fly. But it can't. Flight is literally beyond its ability.

    Gabe: People often say, "Of course this person is capable of behaving differently. They're smart. They can analyze other people's behavior." But that doesn't necessarily mean they can see or change their own behavior.

    Gabe: If someone behaves the same way every single time, and you know there's a 100% chance they'll do it again, why keep getting mad? Sometimes you have to accept the limitation.

    Gabe: The penguin analogy helps people separate themselves from anger. They start picturing the difficult person as a little penguin who can't fly, and it takes the hot air out of the situation.

    Erin: I love that. Think of people as penguins.

    The Five Conflict Traps

    Erin: You talk about five traps that turn conflict against businesses. What are they?

    Gabe: The five traps are the bully trap, the need-to-win trap, the liar trap, the avoidance trap, and the judgment trap.

    Gabe: These show up in all human interaction, not just business. Things like anger, fear, ego, and judgment are not always bad. In healthy amounts, they can be useful. Anger can motivate you to fix something broken. Fear can protect you.

    Gabe: But when those things move outside their healthy range, they become toxic.

    The Bully Trap

    Gabe: The bully trap is not about a playground bully who enjoys hurting people. It's a situation where someone, because of urgency, fear, or passion, behaves in a way that is perceived as bullying.

    Gabe: If someone on my team makes a mistake and I yell at them because I'm angry, I may think I'm giving feedback, but I'm not. I'm just beating them up.

    Gabe: If I want to understand why something happened and I start by yelling, they're just going to defend themselves. There won't be a genuine conversation.

    The Need-to-Win Trap

    Gabe: The need-to-win trap happens when your desire to win a small battle eclipses the reason you entered that battle in the first place.

    Gabe: I experienced this as a litigator. I had a case where I found a smoking gun piece of evidence. I knew I could destroy the other side at trial, and I wanted that moment.

    Gabe: A judge pulled me aside during a settlement conference and reminded me that my job wasn't to win for the sake of winning. My job was to get the best result for my client.

    Gabe: I had become so focused on winning and punishing the other side that I almost lost sight of what was actually best for the client.

    Erin: I think we can all relate to that. Maybe not in a trial, but definitely at work or in relationships.

    The Shopping List Voice

    Erin: Let's talk about detoxing the bully trap. How do you do that?

    Gabe: I love using what I call the shopping list voice.

    Gabe: Imagine someone says, "Hey Gabe, I'm going to the store. Do you want me to pick anything up?" And I say, "Yes, eggs, milk, frosting, and sprinkles." It's matter-of-fact. Neutral. Calm.

    Gabe: Now take a workplace example. A client fires us because someone on my team sent deliverables with mistakes, the client had to redo the work, and they missed a deadline.

    Gabe: I could explode and attack the person. Or I could say in a calm voice, "I just got off the phone with the client. The deliverables had mistakes. They had to redo the work. They missed the deadline as a result. They said this wasn't the first time it happened, and they fired us. That was a $2 million account."

    Gabe: The substance is the same. But in the angry version, the person stops listening almost immediately. In the shopping list voice version, they may not like what I'm saying, but they can actually hear it.

    Gabe: If you're really mad, practice first. If you can't say it in the shopping list voice, you're not ready for the real conversation yet.

    Accountability Plus Reaffirmation

    Gabe: When people screw up, it's also an opportunity. Deliver the feedback in a shopping list voice, then reaffirm the person.

    Gabe: You can say, "This is serious. But you are not horrible. You're smart and capable, and my hope is that this becomes a turning point in your career."

    Gabe: That combination helps you avoid being perceived as a bully. You tell the truth clearly, and you also remind the person that the mistake is not their identity.

    Erin: So it's a one-two punch: use the shopping list voice, then reaffirm the person at the end.

    Bucking the Norm by Having the Hard Conversation

    Erin: We always ask guests for a "buck that" story — a time they went against conventional wisdom. What's yours?

    Gabe: I'll tell you about another mistake I made. When I first moved from litigation into a startup, I was still communicating like a litigator. Lawyers swear at each other all the time and no one is offended.

    Gabe: One night, a sales person made a mistake, and I was dealing with the fallout. I sent him a brutal email with a subject line I should not have written. I copied another lawyer because I thought I was showing how I was managing the situation.

    Gabe: The next morning, that lawyer told me, "You can't do that. These people aren't lawyers. They're real human beings with feelings."

    Gabe: That was a turning point. I realized the way I communicated in litigation wasn't effective in the real world.

    Gabe: The norm I decided to buck was avoidance. So many people avoid difficult conversations, but I made a commitment not to carry anger or frustration around at work or in my personal life.

    Gabe: If someone does something that feels disrespectful of me or my time, I assume first that they don't realize it and are not being intentionally mean-spirited. Then I make them aware of it respectfully and quickly.

    Final Advice to Make Work Suck Less

    Erin: What is your final tip to make work suck less for our listeners?

    Gabe: Think about the things that bother you at work and draw a circle around yourself. Anyone who enters that circle has to adhere to the higher standard you hold yourself to.

    Gabe: When people fall short of that standard, respectfully give them the gift of awareness.

    Gabe: It will make your professional life easier because people will learn how to work with you. It will also help you build the skill of expressing difficult concepts in a way people can actually hear.

    Gabe: If you were about to walk on stage and I saw spinach in your teeth, it would be mean not to tell you. Workplace mistakes are the professional version of having food in your teeth. Tell people. It's a gift.

    Erin: I love it. This has been great, and conflict is such a hot topic with our audience. Thank you so much for spending this time with us.

    Gabe: Thanks for having me.

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b Cause Work Doesn't Have to SuckBy Erin Hatzikostas

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