How to identify and have a Crucial Conversation

This is the first-ever guest post on Barely Managing. I couldn’t be more excited that it’s by one of my favorite people, David Klemenz. David and I worked together at Segment. He was my HR business partner and my executive coach. We were partners in crime on two big topics I’ve written about: Career Ladders (a.k.a. Competency Maps) for Managers and Career Conversations. 

The value I’ve gotten out of David’s coaching is extraordinary: I’d come in with some kind of a mental block (e.g., “I feel like I add no value to managers that report to me and are more senior than I am”) and walk out with a clear path forward.

This post is about Crucial Conversations. The key insight is that we aren’t having nearly enough of them. I hope you (like me, with David’s help) will learn to spot when you could benefit from a Crucial Conversation and how to have one! I now leave you in David’s hands:

I recently had an introductory coaching conversation with someone – let’s call her Maria – who felt frustrated about being stuck in her middle management position. Maria had reached a similar role at her last company, and she saw the trend repeating itself in her current one. ‘I want my work to speak for itself,’ she told me, ‘and I do good work. What’s worse, they promoted my colleague in the last cycle. He’s dramatic and talks about himself all the time in front of the leaders. My team is much more effective than his.’ I asked her what feedback she had received; she told me she had been praised for building a good team, but she hadn’t received any real constructive feedback. I asked her what she wanted to do about the situation. She sighed and said she was hoping she wouldn’t have to do anything. ‘My work should speak for itself,’ she repeated. ‘Why do I have to convince others, especially my boss, that I deserve to be promoted? He seems to like the work I do but doesn’t respect me enough to tell me why I’m not ready for promotion.’

As I listened to this new prospect, I immediately recognized someone who wasn’t having a crucial conversation. In my experience, more than half of the coaching sessions I have with people who feel stuck in their careers or who are stepping into new leadership roles involve a crucial conversation that they’re not having. 

What are Crucial Conversations?

According to the best-selling book, Crucial Conversations, they are conversations between people in which there are (1) high stakes, (2) strong emotions, and (3) differing opinions.

Let’s return to Maria. What’s at stake? She wants a promotion to a higher level leadership role, which qualifies as high stakes for her, her manager, and the company. What emotions does she feel? She is upset because she perceives that she’s being passed over. And what differing opinions exist? She thinks she’s ready for the next level whereas her manager and the company do not, or at least did not in the last promotion cycle. 

What commonly happens when we are presented with a challenging conversation? We freeze, flee, or fight. The mere consideration of a difficult conversation causes us to sense danger. And when we sense danger, we stop thinking rationally. Instead, our reptilian brain – the amygdala – takes over. Thus we move to silence – the freeze and flight response – or violence – the fight response. We don’t realize there’s a third option, dialogue.

Sounds like an impossible place to be. What can you do? I will focus on three recommendations that have been most helpful for my clients.

How to have Crucial Conversations

Get Unstuck. The quickest way to move out of the reptilian brain is to ask questions. But that’s not the first step, at least not for those who haven’t practiced switching back to the rational brain after an irrational response. 

First, find some space to externalize and reflect on your thoughts and feelings. 

  • If you’re an internal processor, find a space away from others. My clients generally like to journal. You can simply start writing, if you’re not a fan of structure. For those who like structure, my clients have found a ‘heart journal’ or ‘feelings journal’ helpful. Begin every sentence with the words “I feel [emotion]…” For example, you can write, “I feel calm” or “I feel angry because he interrupted me.” Do not write, “I feel like he isn’t listening” or “I feel as though it was too loud.” If the heart journal isn’t for you, focus on answering a question, e.g “What do I want?”. I focus mainly on writing because that’s what most of my clients do. But you can also sing, dance, or cook. Feel free to bring your thoughts and emotions into the world in any way you’d like.
  • If you’re an external processor, go find someone you trust and who is a good listener. Then, talk it out. Feel free to vent in a stream-of-conscious way. Use a whiteboard or hand gestures or both. Just get it out.

Only then can you ease into asking yourself – or having someone else ask – questions that help you get unstuck. For Maria, those questions could include a few of the following. What do I really want in this situation? What is upsetting me? Which problem am I trying to fix? 

Separate facts from stories. When you get into a more rational frame of mind, pay attention to the stories you have told and are telling yourself. What’s wrong with stories? By themselves, nothing. But when we’re in our reptilian brains, the stories are usually focused on keeping ourselves safe. They can be about blaming yourself or others. They can justify and rationalize. They can pit you against everyone around you. When you’re in the middle of those stories, it’s hard to think that anything else can be true, even if you are in a rational frame of mind. Let’s return to Maria. She claims her manager doesn’t respect her enough to tell her why she’s not ready for a promotion. She calls her colleague dramatic and says that he talks about himself in front of leaders all the time. She also claims that her team is more effective. Without proof, those are all stories. 

What can we do when we are focused on these stories? We can rewind the story past the thoughts and feelings, all the way back to the observable and measurable facts. Only when we look at the facts, without tying thoughts and feelings to them, can we begin to see that it is possible to tell other stories based on those facts. In Maria’s case, we know she was not promoted. We know her colleague was promoted. And let’s say that there are metrics that prove her team has been more effective than her colleague’s. What are some other stories she could tell? Maybe she is missing a development opportunity and isn’t ready for promotion. Maybe her boss didn’t realize that her team was more effective. Maybe her boss advocated strongly for her in the last promotion cycle and didn’t tell her because he felt ashamed about not making it happen. And maybe he advocated just as strongly against her colleague’s promotion but was overruled. 

Use a specific framework when having the Crucial Conversation. Now that we have gotten unstuck and separated the facts from the stories, we’re ready to prepare for the conversation. If you want to have a Crucial Conversation, you can follow four tactical steps. In addition, there are two specific ways to deliver those steps. I’ll cover the steps and their delivery below.

Step 1: Share your relevant facts. Facts become a firm foundation on which to build your conversation. They are persuasive and not divisive. 

Step 2: Tell your story. This is not a novel; it is not a list of all your grievances against this person, their role, or their department. Instead, this is your chance to put the facts together in a way that explains to the other person how the situation is impacting you. I often like to begin the story explicitly with, “The story I’m telling myself is…” 

Step 3: Ask what they think or how they feel about what you said. There are many ways to phrase the question. The key is to ask an open and honest question. 

Step 4: Listen to understand, not to respond. Stay open to what you hear without getting defensive. More often than not, you’ll be surprised by what they say. 

As for delivery, remain (1) tentative and (2) curious. Being tentative ensures that you are not conveying the steps in a manner that causes the person to become defensive, and staying curious enables you not to devolve into the reptilian brain.

Let’s return to Maria one last time. How might she prepare?

Step 1: Start with the facts. Maria’s colleague was promoted in the prior cycle, and she was not. And let’s say that she has metrics from the past year showing her team’s effectiveness. 

Step 2: Tell her story. The story Maria tells herself is that she deserves to be promoted because she and her team do objectively good work, and because her work is as good as, if not better than, her colleague’s. In addition, she has received no constructive feedback from her boss. So, she is at a loss about why she hasn’t been promoted.

Step 3: Ask what they think or how they feel. Maria can ask her boss, what do you think about what I’ve said?

Step 4: Listen to understand. Maria can prepare by ensuring that she is open and curious going into the conversation. It is best if she can set it at a time when she believes she will not be anxious or stressed based on other stimuli.

Now you’re ready to practice crucial conversations. Think about those situations in which you’re avoiding dialogue and try to put these tips to use. Ping me if you’d like to chat at [email protected]. And visit me at

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