You know those really difficult conversations, the really hard ones that feels like you've got a big rock in the pit of your stomach? Yeah, those. Well, if you've been following my work for any length of time, you know that I have a methodology for difficult conversations. And what I've done recently is I've updated it and given you a seven step checklist to go through to prepare for your own hard conversations. From everything that happens before the conversation happens to the resolution that you're going to get at the end, and every awkward thing in between.

Today I'm going to go through at a very high level that seven point checklist with you so that you generally know what's in it. And in just listening to this podcast, it's going to give you a great methodology for holding your next difficult conversation, whether it's planned or whether it catches you by surprise. Because we know a lot of times they just catch us by surprise. I'm also going to give you, at the end of the episode, a place where you can go and download the full checklist, which is much more comprehensive than we have time to cover here on the podcast. And so that is what's coming up and what's in store for you today in this podcast.

Now, we know that having difficult conversations is challenging. Nobody likes to have them, and of course that doesn't make them any easier. So we call this the hard Conversation Checklist. It's ideally for technical managers, but even if you're not a technical manager, or maybe you're not a manager, it's okay, you're still going to get a ton of value out of this checklist and out of this methodology. So without any further ado, let me just jump into it and let me give you the steps. And these steps are a bit different from what I've talked about before. My methodology has evolved and changed over time. So now here's where we're going to get into it and I'm going to give you again the kind of the high level step. And then you'll also get an opportunity to go grab this whole checklist and download it as a PDF so that you can use it in your next difficult conversation.

So step one is to name the real issue. So often we name the symptoms, we name what's happening as a result of somebody's behavior. Let's say somebody's missing deadlines. Well, we're talking about with them oftentimes what happens downstream from them missing the deadline, as opposed to talking about missing the deadline. Or maybe the real Issue is even something that comes before the deadline. So we have to absolutely name the real issue as and not the symptoms.

Now, if you can't describe the issue without using words like attitude, vibe, energy, words like that, then you're not ready to take it up with that person yet. Because when you're talking about somebody's attitude, that's not the issue. Now, maybe that's what's manifesting and what you'd like to talk about. But you have to peel back the layers and kind of get under the hood, if you will, and find out what's going on with that person such that they have what you perceive as a bad attitude. Because a bad attitude is not something that can be quantified. It's not something that, that we can pin down like a fact. So we really need to make sure we're getting all the conjecture out of it and we're getting to the actual real issue. Sometimes that's underneath the symptoms that are manifesting. Okay, so step one, name the real issue.

Now step two, and I was just hinting at this one, and that is separate the facts from the assumptions. So the assumptions is the story you tell yourself about what's happening. And the facts are, if an external third party came in to observe the situation and document what they saw, like the situation was being audited, what would the auditor see? What would the auditor write down in their report? And so those are the kinds of things that are fact based. So you were late three times to work in the last two weeks, audience. On this date you were four minutes late. On this date you were 17 minutes late. And on this date you were 43 minutes late.

Okay, Those are facts. Now we sometimes will couch those facts again in a story that we're telling ourselves. Like, this person doesn't value punctuality. Okay, that would be an assumption. We don't know if they value punctuality or not. We just know that there were three times in the last two weeks that they were these many minutes late. So teasing that apart because we don't want to be speaking to the other person from a basis of assumptions or the stories that we're telling ourselves about the situation, we need to be grounding the conversation in facts again, not what somebody else felt or thought or, but what are the actual facts of the situation. Now, hard conversations will derail the fastest when assumptions are treated as facts.

So in this checklist, I go through and give you a few deeper questions to dive even deeper so that you can do a better job Sorting out what is an assumption you might be making about the situation that you will take as the God's honest truth. This is factual. But then all of a sudden, when you say, well, like, okay, show me. Show me those facts, then it's a little harder to actually show you. So this checklist is going to give you some ideas about how you can spend specifically in very, you know, indisputable detail, share the facts with the other person, because then there's nothing for them to push back against or resist. Now, that was step two, separating the facts from the assumptions.

And when we go into step three, this is really where you're thinking ahead about the conversation and you are planning the outcome that you want to have at the end of this conversation. So when you step into that conversation, you should have already predetermined what you expect the outcome will be. Now, in some situations where you are going in, knowing that there's lots of information you don't know, you might go into the conversation with the outcome and the intended outcome being, I want to discover. What I'm missing in this conversation is we're not ready to make a decision or to take any action on this yet. This is more of a discovery conversation, and that would be a perfectly acceptable and clear outcome about what you wanted to get.

Now, there are other situations where you might be like, I want to get to the bottom of this. Okay. And in which case you have to get very specific about what getting to the bottom of this means. Does that mean discovering all of the facts, getting all the facts on the table, sorting through them, and then making some sort of a decision or having an outcome or does, you know, getting to the bottom of this mean something different? Now, again, getting to the bottom of this is much more of the story you're telling yourself about it as opposed to something factual, because a difficult situation, does not actually have a bottom. So this is also part of how we start to interrogate whether this is a fact or a story. We're telling ourselves about the set of facts or assumptions we might be making. Okay, but the more you can get really clear on the exact outcome that you want, the more likely the con itself will be productive and won't wander in lots of different other areas, but you'll stay more focused on what you're trying to get out of the conversation.

All right, step four is you're going to choose clarity over comfort. Now, sometimes being vague and, you know, doing an end run around the subject feels like you're being kind to the person. But, you know, here in Minnesota, we call that passive aggressive behavior when you're not naming the issue, but you're doing a 180 around it, or you're doing a big 360 even around it, a big loop around it that creates more confusion and more work down the road than it does solve a problem right now.

So you've also probably heard Brene Brown, who's famous for saying clarity is kind. So here's what we're doing is choosing clarity over comfort. So that comfort is really our own, you know, discomfort and trying to make the other person feel okay. When we're going into a hard conversation, it's not about making the other person feel okay. It's about solving a problem at work. Okay. We just really need to keep the focus on. This is all about solving a problem at work.

This isn't about making you feel bad or trying to protect your feelings or anything like that. When we're vague, it can kind of feel kind in the moment, or at least it makes us feel less uncomfortable. But that does not serve the conversation. So we want to go in with clarity over comfort, thinking about how we can serve the highest good in that conversation.

All right, now we're getting into step five, which is thinking about the language that you're going to use when you open that conversation. And in the checklist, I call this on step five, pressure testing your language. So before the conversation starts, you're going to plan out your opening phrases. And you've probably heard me talk about this in difficult conversations before because this has been a long standing piece of my methodology where we want to open that conversation in a way that doesn't make the other person defensive.

And there are some specific turns linguistically that we can do, some specific word choices we can make to make the other person feel more at ease and to make them feel less like they are being personally blamed in the situation. So everything from how we are, again, choosing those very first words to open the conversation to whether we're using, for example, personal pronouns, if I'm using the word you a lot, it's much more likely that if you are on the receiving end of this conversation, you are going to feel more blamed than if I try to get those personal pronouns out. Out of the tee up of the conversation altogether. It's about the issue, not about you. Now, it probably is the fact that you did this thing or that thing again, going back to the facts that led to this outcome. But we want to stay focused on the facts and the outcomes, not necessarily playing a blame game. And so again, that's where step five comes in, where we're really going to pressure test your language so that we can see that you are indeed focusing on the issue, not talking around the issue, and that your language focuses on behavior and impacts, not on the person's character or their attitude or some of those things that can feel a little bit squishy and a little bit sloppy and isn't going to help the person who's on the receiving end of that conversation know exactly what to do with the information. Okay? So that is step five, pressure test your language.

In step six, we're going to anticipate before we even go into the conversation what the other person's reaction might be, okay? So we don't need to control their reaction. In fact, we can't control their reaction. Sometimes they're going to have a reaction, sometimes they might have a big reaction, they might be feeling all the feels and they might have this big reaction. But that's not ours to own. What is ours to own is that we're having the conversation, that we're holding another person accountable, that we are indeed uncovering the facts and the causes that led to whatever the situation is. But we are going to anticipate what their reactions are so that when we get ourselves into that moment, there are no surprises. We've seen what anger looks like, we can see what frustration looks like, we can see what disappointment looks like, we can see what pushback or denial looks like. So when we have really fully anticipated the breadth of how the other person might react to this conversation, it is far less likely that we are going to find ourselves in a reactionary moment because we're going to just be like, oh yeah, I saw that coming, or oh, that wasn't nearly as bad as I imagined it.

So when we can anticipate the reaction without over engineering and without really changing our own tee up of the conversation, but just to imagine what might their response be and then how am I going to continue to hold the space for resolution, for discovery, for curiosity, for all the things that we want to have in that conversation to make it a good exchange of information that really is going to get to the quote unquote bottom of the situation so that we can solve for something, change behavior and clear up whatever this hard situation is. So that is step six, anticipating their reaction or a whole host or a whole range of reactions before we go into the conversation.

And then step seven, decide what happens next. Now this is going to be something that you're co creating in the moment with the other person. So hard conversation without that follow up, without that next step is just sort of like navel gazing and talking about something, bringing up all the fields without actually getting anywhere. So we want to make sure this gets us from point A to point B, even if it gets us partially from point A to point B. Point B, that is, that, that's fine. We gotta get somewhere with it.

So deciding what's gonna happen next, like what's the immediate next step after this conversation? Now you don't have to know that in advance. In fact, you probably shouldn't try to anticipate what happens next before the conversation. Unless of course, you wanted to anticipate a whole range of things. But a lot of times in those hard conversations, the other person has this vital information that we did not know about. And when that information gets disclosed, oftentimes it is just this whole like turns the whole situation on its head and you're like, oh, I had no idea that was going on. That changes everything. So when those surprises come up, which inevitably they do, you can't have already predetermined what's going to happen next because then that's not taking into account the discovery that's going to happen in that conversation. So when you decide what happens next, that is something that you are doing in the moment with the other person in real time and then determining and articulating in that moment what follow up is required. And do we need more meetings after this? Do we need some accountability follow up? Maybe there's additional support that you can be providing to this person that will help get at the root cause of whatever is happening that's leading to the behavior that you needed to have the hard conversation around. And then also after the whole conversation is over and asking yourself, did that work? And doing a little bit of self assessment and evaluation to see if you made significant and substantial progress in that hard conversation.

So that is step seven, deciding what is next. And again, step seven, I just want to double down and reiterate that is not something you do before the conversation, that is something that you're doing in real time as you've heard from the other person and you've again presumably found out more information, new information that you didn't know before. And again, I'll add one more thing here. Sometimes what happens next is we just need some more time to think about this or to strategize what to do about this. Because Especially when new information has come to light, you maybe aren't in a situation where you can just like make a snap decision. You need to investigate something further or just even sometimes sleep on it.

So one last thing I want to just mention about this checklist and hard conversations before I tell you how you can get your hands on it. Preparation, of course, makes hard conversations easier, but it really does not remove the moment itself. A hard conversation is going to be hard, it's going to make you uncomfortable and the more you can ground yourself undeniably in the reality of that, the easier it's going to be. The other thing, and I always tell folks this when I'm doing like a deep dive training on how to have difficult conversations. And I do a lot of those, it's probably one of my most requested trainings is when we're in training like that, what I remind people is putting in the reps is what makes difficult conversations easier. There is no magic bullet, but it's one of those things that the more you do it and the more you have success in doing it, the easier it becomes because you start to develop some confidence in your own competence over time. So let me say that again, you start to develop some more confidence in your own competence at holding difficult conversations over time, the more you do them. So this checklist is meant to help you get clear before the conversation and then follow up after the conversation.

The real work happens during the conversation and when you put in that extra bit of time to get clear on the outcome, outcomes you want and how to pressure test your language and all of those things before the conversation happens, it is much more likely that it is going to be a productive conversation that has a lot of discovery in it and leads to you knowing new things, the other person knowing new things, and to the two of you generating some good solutions to change the circumstances so that this is no longer an issue. When you handle that part, then you've, you've got this ace in the hole. This will be a no brainer. So I want you to have this checklist because it goes into so much more detail than I've had an opportunity to cover here in these 15 to 20 minutes. So you can get that checklist over on my website @janelanderson.com, Janel Anderson J-A N E L A N D E R S O N.com/HCC. That stands for hard conversation checklist. HCC. We'll link that up in the show notes.

The show notes for this episode can be found at janelanderson.com/255 for episode 255. I've got some other episodes about difficult conversations. We can link those up in the show notes for you as well. And again, I want you right now to go over to janelanderson.com/hcc for that hard conversation checklist. You'll just drop your email address in and it will show up in your inbox and you can start using it right away. All right, my friends, be well and have a great week.