Difficult Conversations Planner: How to Prepare, Deliver & Follow Up Like a Pro | Ep. #128

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Welcome back to the deep dive the show, where we really try to cut through all the noise and give you actionable intelligence stuff you can actually use to level up your management skills.

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And you know, if you're in any kind of leadership position, I mean, really, if you work with any other human at all, you know that the biggest source of stress, the thing everyone tries to avoid is that dreaded, high stakes, difficult conversation,

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Oh, absolutely. Whether it's, you know, tackling under performance that's just been dragging on, or navigating a really thorny issue with a peer or and this is maybe the most nerve wracking one, giving tough but necessary feedback up the chain to your own boss, these conversations just feel so volatile. It's like you're walking a tightrope. And One wrong word sends the whole thing, the relationship, the outcome, everything just completely off the rails. And

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that feeling, that volatility, that sense of of being unmoored, that is precisely what we're here to eliminate. Today, we are going to be diving into a really structured, two part planning approach that can transform these discussions

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from what emotional confrontations exactly, away from emotional

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confrontations and toward constructive, goal oriented processes. The whole point is to move past that initial fear, that raw emotional reaction, and get to a concrete, measurable outcome.

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And before we get into the nuts and bolts. We should say right up front that the steep dive is produced by new level work, and it's part of the building better managers podcast. Our mission today is to give you frameworks that can turn that feeling of confrontation into well measured and effective collaboration. We're essentially giving you the blueprint for a safety net under that high wire, right? That's a great way to put it. So even if things get a little shaky, little shaky, you can maintain control, maintain your focus,

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and that focus is just so critical. The core idea we're exploring today is this, the success of a difficult conversation is almost entirely decided before you even walk into the room. So it's all in the prep. It's all in the prep. The preparation stage isn't, you know, a nice to have. It's not an optional luxury. It is the central piece that determines whether you succeed

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or fail. Okay, so the power of preparation. Let's unpack that a little, because I think when people hear preparation, they think about scripting what they're gonna say, but it sounds like it's much more than that.

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It is so much more than that. It's primarily about how you manage your own internal state and how you install kind of structure that dictates the flow of the entire discussion. Right? Our source material lays out four main goals that this kind of rigorous pre conversation planning helps you nail down, and they all work together to get you that clarity and reduce that volatility we were talking about.

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Okay, so let's start with the end game. What's the very first step in getting your head right for

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this? First and foremost preparation forces you to well, to clearly think through and define the desired outcome of the conversation, what success looks like. What success actually looks like? Sounds so simple, but I mean, too many people walk into these things focused only on the problem, on the history of the problem, rehashing the past, yes, instead of the future, resolution, if you can't articulate in specific, measurable terms what a win looks like, you can't possibly steer the conversation there. It just becomes, you know, an exercise inventing, not generating change.

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So if the problem is, say, missed deadlines, the desired outcome isn't just stop being late. It's more tangible, like all client deliverables need to be submitted by 5pm on Tuesday so we can maintain our two day review cycle. That's the kind of clarity we're talking about. That

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is exactly the clarity we're aiming for. Now, the second goal is crucial for anticipating resistance and trying to minimize those defensive reactions you always get. Okay, you have to consider the other person's point of view and try to predict how they might

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respond. Put yourself in their shoes 100%

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what are their pain points? What anxieties might this whole conversation trigger for them? You know, fear of failure, fear of being judged unfairly, maybe resentment because they feel like they don't have the resources. If you can proactively anticipate their arguments or their underlying worries, you're not caught off guard,

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and you can even address those things before they fully

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baller up, you can structure your entire approach to address them from the get go. That's

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fascinating. So it's like empathy and foresight baked right into the planning. But what about our own state, our own emotions,

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that leads right into the third goal, which is deeply internal. You have to prepare yourself for the emotions that are going to come up in the discussion and then commit to bringing a sense of calm to the whole thing. That's the hard part. It's a huge challenge. I mean, difficult conversations are basically psychological stress tests, right? They trigger our fight or flight response, which can completely hijack rational thought. So by identifying your own potential emotional pitfalls beforehand, your anger, your frustration, maybe your resentment, you can make a conscious decision to maintain a neutral, composed presence your composure is the anchor. It. That anchor slips the whole dialog just drifts away. I

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think everyone listening can relate to that. You know, walking into a tense meeting and you're already feeling defensive or just resigned, so this prep gives you a chance to manage your own internal temperature before you even open

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the door. And finally, the fourth goal is purely tactical. You need to decide on the best approach and style to bring to the discussion. So what do you mean by style? Well, is this a constructive coaching moment that's focused on skill development? Is it a formal performance warning that could lead to something more serious, or is it more of a collaborative, joint problem solving session about some bigger organizational issue, defining the style in advance, make sure you don't default to an aggressive posture, or, on the flip side, a really wishy washy posture that doesn't communicate how serious the issue actually is.

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So to recap, we're pre loading the desired outcome. We're anticipating their reaction. We're managing our own emotional state, and we're choosing our tone deliberately. That is a really powerful foundation. Okay, let's move into section one and talk about how you take that mindset and actually craft the talking points the principles of delivery,

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right? So the underlying philosophy of this whole preparation strategy is to bring a, I'd say, a radically neutral, resolution oriented structure to the whole exchange. You're basically replacing the ambiguity of your personal feelings with the clarity of a method,

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and that method, it starts with controlling the delivery of the core message. The first principle the source highlights is one that I think a lot of people stumble on. Be direct and quick. Why is that so critical? Why not ease into it? You know, make some small talk,

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because anxiety and confusion just thrive in that vacuum of ambiguity. Imagine you call an employee into your office, you offer them a coffee, you chat about the weather for five minutes. I'm already getting nervous just thinking about it exactly. They're spending that entire time just guessing right? Am I about to get fired? Did I offend someone? What is this about their cognitive load just spikes and they stop listening to what you're saying, because they're so focused on interpreting the context, getting directly to the point like thanks for coming in. We need to discuss the q3 budget submission deadline. It reduces that anxiety immediately. It signals seriousness and it respects their time. It pulls them right into problem solving mode. It

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stops them from wondering if they're about to be ambushed. It sets the stage for a business discussion, not a personal attack, exactly.

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And that directness has to be paired with the second, and I think maybe the most foundational principle, which is also the hardest to do, well, focus relentlessly on behaviors and impact and provide specifics. This is the bedrock, right? This is the bedrock of non accusatory, objective feedback. You have to talk about what the person did and what result that action had, not about who the person is or why you think they did it. Okay, let's

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dig into that distinction, because this is where so many conversations just derail. We all naturally default to judging motive or character. We say things like, you seem checked out, or you're not showing leadership. How do we translate those subjective judgments into objective behavior and impact? The key

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is to ask yourself, what specific action made me think that? So if you think someone seems checked out, the objective behavior might be you arrived 15 minutes late to the last three team meetings, or you haven't contributed during the last five brainstorming sessions. Those are facts, verifiable, verifiable. Now compare the impact saying you're a lazy employee that attacks their identity, it guarantees they'll get defensive, but saying your q3 sales reports were delivered five days late, which directly prevented our team from adjusting our inventory forecast, and that cost the company an estimated X dollars. Well, that links an objective behavior to a tangible, measurable consequence.

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That makes perfect sense. It's so much harder to argue with facts, it shifts the entire conversation from, am I a bad person to okay, how do we fix this process?

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And that leads right into the third point, strictly avoiding accusatory language. I'm talking about phrases that generalize or inject extreme judgment you always or you fail to, or any language that assumes you know their intent was malicious,

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it just puts them on the defensive. Immediately, instantly neutral

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descriptions like observing a specific action at a specific time prevent the other person from throwing up those walls. Remember, we're looking for collaboration here, not combat. If they feel judged, the conversation stops being about the problem, and it becomes about defending their own integrity.

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So we've covered what to say, but delivery is just as key. The source says we have to maintain a neutral but firm tone. That's a tricky balance. How do you pull that off?

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Well, the firmness conveys that the boundary is serious and the stakes are real. It's about clarity that change is necessary. The neutrality means delivering that message without the heat of anger or, you know, personal resentment or defeat or defeat exactly, if your tone is too passive, if you sound apologetic or uncertain, the message just won't land. It the way it needs to. And if it's too aggressive, then they shut down. They only hear the emotion, not the content, the neutral, firm tone signals I take this issue seriously, but I'm here as a composed, rational partner to solve it with you.

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And once you establish that tone, you have to commit to relentless focus, not being distracted by tangents. What happens when the other person inevitably tries to derail the conversation because they will,

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oh, they will. It's a classic defense mechanism, often subconscious. When the topic gets uncomfortable, people try to shift the focus, they'll bring up some unrelated grievance from the past, or cite personal hardship or deflect blame. Well, John does it too, right? The preparation is your shield here. Yeah, because you did that internal audit and you locked in your one or two core issues, you can gently but firmly redirect them. You might even want to rehearse a few phrases, like, I appreciate that context, but let's circle back to the q3 budget deadline we need to resolve

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today. Or that sounds like a separate issue we should definitely talk about later. But for now, let's stay focused on the impact of this specific behavior Exactly.

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If you let yourself get pulled down those rabbit holes, the resolution gets diluted and the seriousness of the main issue is just totally undermined.

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Okay, I love this focus on structure, but it can sound a little cold, a little robotic. How do we keep this process from sounding like you're just reading an HR memo, the source mentions two critical soft skills, being prepared to listen and bringing empathy to the discussion.

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Yes, these two are the humanizing counter balance to the whole structured delivery. You have to build in space for the other person to respond to offer their context or explain their perspective without being interrupted or judged active listening is so essential, because their response might reveal that the issue isn't behavioral at all, but systemic.

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Ah, like a problem in the process you didn't even know about right? For

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example, that late report wasn't because of neglect, but because of some technical blocker or maybe a competing directive from another manager that they were told was a higher priority,

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which would expose a failure in organizational communication, not just one person's motivation, precisely.

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Yeah, and the empathy piece is just as critical. You can be absolutely firm about a necessary boundary the report must be on time, while still being empathetic about how difficult that change might be or the stress that led to the behavior

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in the first place. So empathy doesn't mean you're excusing the behavior,

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not at all. It just means you recognize the person's humanity and the difficulty of navigating professional life.

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What's really fascinating here is that the structure and the empathy, they don't contradict each other. It sounds like they actually enable each other. How does using a neutral structure allow for more genuine empathy?

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It's a psychological safety mechanism for you, the manager, when you strictly rely on the structure on specific observable behaviors and measurable impacts, you successfully remove your own personal bias and emotional charge from your side of the conversation, and because you aren't fighting your own rising anger or frustration, you suddenly have the cognitive and emotional bandwidth to genuinely listen and respond thoughtfully to their side of the story. The structured approach removes the personal heat, creating a vacuum that can be filled by objective light and genuine

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empathy. That's a fantastic principle. Structure eliminates the bias, and that enables the listening. Okay, now that we've got the right mindset and the core principles for delivery, let's get into the detailed nuts and bolts of the preparation itself. This is the seven step internal audit, the work you do before you say a single word to the other person,

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right? This first major tool is a mandatory seven step approach that focuses entirely on your own internal reflection. It's about defining the scope, managing your personal reaction, all before you ever engage the other party, so

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you're clearing the fog from your own mind before you try to navigate the high seas with someone else.

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Exactly this internal audit is your commitment to honesty and clarity. It ensures that when you finally do start the dialog, you're not contaminating it with your own confusion or personal resentment or mixed messages. It's the groundwork.

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It makes sure you know exactly why you're having the conversation and what success is going to look like. Okay, let's start with the foundational steps one and two, which are all about definition and objective description.

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Step one, identify the pressing issue. And we need radical clarity here. You have to write it down definitively the single most urgent issue I intend to resolve in this conversation. This conversation is and the discipline here is to avoid

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scope creep. Don't bring a laundry list. Please

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don't. If you have five things, you have to pick the one that is the most urgent or the most consequential. Trying to solve five things at once just guarantees you'll do a surface level job and probably fail at all

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of them. So you focus on the single point of failure, the most critical behavior. Then comes the detail work. In step two, describe the issue.

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This is where you move past generalizations and you ground the problem in observable reality. You ask yourself, what specifically is going on? How long has this been happening? How serious or important is this situation? That forces you to be specific. It does instead of something vague, like the team atmosphere is poor. You describe it like this, for the last six weeks, Project X has missed all three of its internal milestones, which required me to intervene on two separate occasions. The seriousness level is high as this now risks a three year client relationship.

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That description of length and seriousness is crucial because it justifies why you're having the conversation in the first place, right?

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If it's a one time low impact thing, maybe you just handle it with a one minute coaching moment, not this whole formal process, but if it's an ongoing high stakes pattern, the seriousness justifies the intense prep we're talking about. The prep has to match the stakes

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makes sense. The audit ensures proportionality. So next, we move into steps three and four, which you called the emotional check. This is where we assess the current impact and map out the future, all while keeping an eye on our own internal

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reactions. Step Three determine current impact. This means quantifying the tangible effects. You have to ask, How is this issue specifically impacting me? How is it impacting others, the team's performance, or even the wider organization? This immediately moves the problem outside of your personal feelings and frames it in a shared organizational context.

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So the impact isn't just I'm annoyed by the late report, it's I now have to work late to fix the errors, or the marketing team can't launch their campaign until my team's data is approved, or even our department's efficiency rating dropped by 5% Exactly.

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And here's the crucial internal part, when I consider the impact on myself and others, what are my personal emotions? You have to name those specific feelings, frustration, anger, fear of failure.

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Why is naming them so important?

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Because if you don't name them, you can't contain them. It's that simple. Unnamed emotions are guaranteed to leak out in your tone, your body language, in passive, aggressive phrasing, no matter how neutral your script is. So acknowledging, for example, I feel significant resentment because this issue is adding four hours of extra work to my week. That is an act of self management. It lets you separate that understandable but highly personal frustration from the objective behavior you need to address. You acknowledge the feeling, you set it aside and you commit to being professional.

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That's incredibly powerful. It stops that resentment from becoming the fuel for the whole discussion. And step four looks forward. It raises the stakes. Right? Determine future implications.

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Right? If nothing changes, you have to map the trajectory. What is the likely outcome, if this keeps going, what's the risk? What is truly at stake? For me, for others, for the organization, this is about defining the urgency for the other person, which starts by clarifying the urgency for yourself.

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So does this minor pattern, if it continues, lead to a formal warning termination? Does it lead to losing a client? Team morale collapsing

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exactly by mapping out that future risk, you transform the immediate discomfort of having this conversation into a necessary preventative action,

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and once again, that internal emotional check comes back when I consider these possible implications. What are my emotions?

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This usually identifies the deeper emotional anchors, often fear or deep disappointment. Fear the business will suffer, fear the person will quit, fear the relationship will be ruined, understanding that fear helps you calibrate your delivery. If you walk in there operating from a place of panic, you might rush things or become overly punitive to try and assert control. Naming the fear allows you to prioritize a calm, constructive dialog over just, you know, getting rid of the thing that's making you anxious. Okay,

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let's talk about step five. This is where, for me, the framework separates the good managers from the truly great ones. It's the moment of truth, the commitment to self accountability. Examine your personal contribution to this issue.

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This step is absolutely non negotiable for anyone leading a team, but honestly, it's valuable in any relationship. Asking yourself, How have I contributed, even accidentally, to this problem's existence or its continuation? That question fundamentally shifts the entire premise of the dialog away from blame and toward a shared resolution.

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Let's give the listener some complex examples here, because it's really easy for a manager to just say, Nope, I didn't contribute and move on. What does real self accountability look like when you're addressing, say, a consistent quality issue?

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It means you have to look past the individual failure and into the systemic factors. So if the issue was low quality, a manager's contribution might be, I contributed by celebrating speed and rapid turnaround in public, so I unintentionally incentivized rushed work over quality control. Oh, wow. Or if the issue is poor communication, it might be, I contributed by allowing a siloed team structure to develop, which meant the employee didn't even know who to talk to when they hit a roadblock or the most common one. I contributed by letting this behavior continue for two months, because I was avoiding the confrontation

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that is a powerful admission by owning your piece of the puzzle, your process failure, your misaligned incentive. Own failure to act sooner, you disarm the other person, almost instantly, you're showing vulnerability and a commitment to fixing the system, not just finding a scapegoat. And

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that shared vulnerability is so effective, you're signaling I get that this isn't all on you. I'm willing to change my behavior, my processes or my resources to support the change we need from you that dramatically increases the odds of a successful collaborative outcome. You've gone from being a judge to being a

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partner, Okay, moving to the final two steps, which pull us forward, away from the problem and toward the solution. Step six, describe the ideal outcome.

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This is where you define that aspirational target, that North Star we talked about. You ask yourself, when this issue is totally resolved, what positive results will I see? What positive results will others see? This isn't just about stopping a past problem. It's about defining the shared positive future you're both moving toward. It reframes the whole conversation as aspirational, not punitive.

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It gives purpose to the discomfort. And finally, we get to step seven, commit to action and a timeframe

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This is what locks in your own accountability and gets the execution process moving. You ask, what positive outcome am I committed to supporting? What specific expectations do I have for others to achieve this? And crucially, when will I schedule this conversation, you have to treat scheduling it as a non negotiable step in your commitment. The audit has to lead to action or it's just an interesting journal entry, set the date, book the room and commit.

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So these seven steps from defining the issue all the way to that scheduled meeting, it's all internal, private work. It's about clarity, impact, managing your emotions and self accountability. Sounds a lot of work, but absolutely vital. It is a

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lot of work, but it pays off exponentially in reducing stress and increasing success. And that's the preparation phase. Now we have to transition. How do you take all that rigorous internal prep and translate it into effective, neutral, high impact dialog? We move from the internal audit to the external conversation planner,

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right? The seven step audit was the self work. This six step framework is the actual script how you translate that self reflection into a real, neutral conversation. And you mentioned it builds on the SBI model, Situation, Behavior, Impact from the Center for Creative Leadership.

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It does explicitly. The beauty of SBI is how it forces objectivity. Let's break down the first three steps, which are all about presenting your objective observation. Okay. Step one, describe your observation of the situation. This is about setting the context and precision. Here is everything you have to state neutrally when and where the issue happened. Specificity is your best friend. Not in the meeting last week, but at the 10am team review on Tuesday, October 15, when we were in Conference Room B,

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that locks down the reality of the moment. It creates an undisputed historical record, so they can't argue about the setting or the time. They have to focus on the content Exactly.

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Then you move to the action in step two. What specific behavior or action Did you observe? This is the core behavioral observation. You only describe what a video camera with no sound could have captured. And the warning here, which we just cannot stress enough, is do not assume what the person was thinking or intending.

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This is the difference between saying you rush that project because you're sloppy and saying the final report contained 12 formatting errors and three factual inconsistencies. One is a judgment, the other is an observable fact.

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Perfect example. Let's ground this even more if a manager's judgmental thought is this employee clearly lacks commitment. How should they objectively describe the behavior

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they need to find the evidence for that thought,

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right? They should say when I asked you to stay 30 minutes late to finish a client deck on Wednesday, you explicitly said that's not my problem, and you left. Or in the last six project updates, you haven't used the new standardized risk assessment template. We're only focusing on verifiable actions. You have to stick to the tape,

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and the third step closes that observation loop. What impact did you observe? This articulates the consequence which moves it from a personal criticism to a recognized organizational issue.

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Articulate the impact you felt or observed that resulted from that specific behavior. So if the behavior was checking a phone during a presentation, the impact might be I felt distracted, and the silence that followed signaled to the team that the topic wasn't important, which undermined the seriousness of the whole training session, or

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for the late report, the observed impact was that we had to absorb $5,000 in rush fees to meet the client's deadline, which also delayed our internal q4 budgeting process.

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Exactly. It makes the consequences real, measurable and often financial or

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relational. So steps one, two and three, Situation, Behavior, Impact. That is the non negotiable foundation of non accusatory feedback. It's all about objective data. Once you've laid that out, the key is the pivot. How do you gracefully transition from talking about the past to collaborating on the future?

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That happens in steps four and five. This is where. Pivot away from fault finding and towards shared solution building Step Four describe the optimum outcome,

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and this is where we present that positive future we already mapped out in our internal audit.

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Precisely what is the optimum positive outcome necessary for success? Here you state the desired state clearly and positively. So instead of defining the absence of the negative, stop doing X, you define the presence of the positive. The optimum outcome is to ensure all quarterly reports are submitted using the new template by 5pm sharp on the 15th so we can guarantee accurate compliance reporting. It gives them a clear, measurable and aspirational target.

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And then comes the most important, collaborative part of the whole conversation. Step five, discuss solutions, and this has to be genuinely collaborative.

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This is the payoff for all that self accountability work you did in your audit, because you already asked yourself, how did I contribute? You're now positioned to be a resource provider, not just a critic. You can start by asking, what are some viable solutions or options for achieving this outcome, what support or training or resources would help resolve this

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that just opens the door for the employee to suggest solutions that fit their workflow, or, more importantly, to reveal those systemic issues, the lack of resources, the conflicting priorities, the skill gap, that are the real root of the

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problem. An effective manager knows their job isn't just to spot failure, but to remove roadblocks. If the employee tells you the issue is they lack the technical skills for the new template, the solution is specific training, not moral judgment. If the issue is just lack of bandwidth, the solution might be reprioritizing tasks. You're solving the problem together, not just imposing consequences, but

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what if the employee suggests a solution that you know is totally unworkable or impractical? How do you maintain that collaborative spirit, but also hold that firm boundary?

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That's where your pre work saves you again, since you already defined the optimum outcome in step four, you can gently redirect impractical ideas by linking them back to that objective goal. So if they say, I can only submit the report if I work until 2am every night, you can counter with, we need a solution that's sustainable and healthy while still meeting that 5pm deadline. Given those constraints, let's look at maybe reducing your pre approval workflow instead you acknowledge their input, but you redirect the solution back to the non negotiable definition of success.

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Finally, we get to step six, commitment, time frame and follow up. We have to lock in the change and the accountability. This is all

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about making the resolution concrete and making sure it sticks. You have to agree on a clear time frame for execution, and you have to agree on specific checking points. Change is a process, not a light switch. Accountability needs scheduled reviews, so

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agreeing on a follow up, whether it's a quick check in next Friday or a formal review in 30 days, shows that you're committed to supporting them, not just dropping criticism and walking away. It

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does. And the final critical action step here is follow up in writing. Why

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is the written confirmation so vital for these high stakes conversations.

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It serves multiple purposes, and it protects both of you. First, it locks in accountability. It provides a neutral record in emotional moments, people often mishear or misremember what they agreed to. Second, it serves as a formal action plan that written follow up, which just reiterates the situation, the agreed outcome, the agreed solution and the check in timeframe. It removes all ambiguity. It turns a verbal exchange into a documented commitment. It confirms you've established a shared reality, a shared reality of commitment.

28:35  
Exactly this whole structure from a seven step internal prep to the six step external execution. It's designed to remove the subjectivity and the panic that usually define these conversations. It replaces all that with clarity and joint

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ownership. It moves these necessary discussions from being, you know, exercises in fear and avoidance, which is how most managers treat them, to structured, predictable exercises and problem solving and mutual development.

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This has been an incredibly detailed, deep dive into creating structure around something that most professionals well, they dread, the difficult conversation. Our analysis has really shown that being effective in these moments has less to do with natural bravery and a lot more to do with rigorous structure and honest self reflection

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and to synthesize the core mechanism. Just remember that duality. You use the seven step process your internal audit for your own personal clarity, to manage your emotional leakage and to commit to self accountability. Right then you use the six step process that SBI execution model for a clear, non accusatory delivery that focuses only on observable behaviors and their measurable impacts, and then pivots quickly toward collaborative solutions. And this

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framework, of course, it isn't brand new. It's built on decades of foundational research into high stakes communication. For anyone who wants to go even deeper, this structure really pulls on concepts you'll find in resources like taking the stress out of stressful conversations by Holly weeks. And of course, the classic crucial conversations

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and. Critically, we drew a lot from the core principles of radical candor, that practice of being both intensely caring on a personal level and aggressively challenging directly, this preparation structure helps you execute that challenging part based on objective fact, while your commitment to empathy and listening provides that necessary personal caring.

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Before we wrap up, I want to leave you with one final thought that I think connects the two big frameworks we covered today. Go for it when you really, truly commit to step five of that, internal audit, the hard work of looking at your own contribution to the problem, you fundamentally redefine the power dynamic in the room. That's

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it. You immediately move from being the adversary or the judge to being a fully vested collaborative partner,

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and because you've identified your role in the environment that let the problem grow, you're now empowered to be the resource provider in the execution stage step five of the actual conversation planner, that transformation from someone delivering a verdict to someone offering support and Process correction that changes the entire climate of the conversation,

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and that shift from confrontation to partnership, that's the secret. That's how you transform a conversation you dread into a productive, necessary and ultimately positive outcome. It's about being fully prepared to manage yourself, manage the method, and commit to finding solutions together.

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We hope this deep dive helps you feel significantly more confident and prepared to tackle those essential, high stakes dialogs and to continue your journey in building better management skills. We really encourage you to visit New Level work.com. For more information and resources.

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Thank you so much for joining us for this deep dive into structure and clarity. We'll catch you next time.