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Episode 90

HOW TO HANDLE DIFFICULT PEOPLE: FROM CONFRONTATION TO CONVERSATION

Keywords confrontation, conversation, professional relationships, connection, resistance, difficult people, empathy, communication Summary In this episode, Dalton Anderson tackles the…

Nov 11, 202500:23:04
Listen to the episode00:23:04

Keywords

confrontation, conversation, professional relationships, connection, resistance, difficult people, empathy, communication

Summary

In this episode, Dalton Anderson tackles the challenge of dealing with "difficult" people, arguing that confrontation is best resolved by transforming it into a conversation. He explains that people are rarely difficult without a reason, as being difficult costs energy and is uncomfortable. The key, he suggests, is to build a genuine personal connection, which allows you to pull someone aside and understand the true reason for their resistance—be it fear, misinformation, or hidden constraints.

Takeaways

People are rarely difficult for no reason; being confrontational requires energy and effort. The best way to solve confrontation is to have a conversation. To have a successful conversation, you must first build a genuine personal connection with the other person. Genuinely connecting with colleagues allows you to understand their perspective and remove ego from the situation. It's your job to uncover why someone is being resistant, whether it's fear of change, lack of information, or past experiences. If you are incorrect, admit it immediately and respectfully; this builds trust. Before confronting someone, you better be sure you are correct, similar to how HR already knows the answer before asking a question. There is almost always something blocking the "easy path" (the path of least resistance); find out what it is.

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E90 HOW TO HANDLE DIFFICULT PEOPLE_ FROM CONFRONTATION TO CONVERSATION

Transcript

Dalton Anderson (00:01.006) Welcome to MedStep Podcast, where we discuss entrepreneurship, industry trends, and the occasional book review. We've all had them, the difficult client, the resistive team member, unresponsive stakeholder. We label them as difficult, but people are really difficult for no reason. Typically, people would take the path of the brief resistance and being difficult is not easy. It requires energy.

effort and one is very uncomfortable. So there's got to be a fundamental reason why people are acting this way on your personal or professional initiatives. And that's what this episode today is going to be about. But before we dive in, I'm your host Dalton Anderson. My background is a bit of programming and technical on the insurance side. I used to work in data science and

do all sorts of things, but in my free time, I have this podcast, like to read, work on my side business and learn. And also a big announcement is this is episode 90, which is really great. I know that you're super excited and I like to take a moment and let everybody clap.

Dalton Anderson (01:29.87) Thank you so much. Appreciate the encouragement. That was awesome. Thank you so much. So episode 90, one thing I will call out is Spotify is still on my back about not having as much followers as my listeners or my listener to follower ratio is out of whack where I have too many listeners compared to my followers. And then,

Sorry, I also have like some kind of cough thing going on. I actually, this is one of the episodes that I've recorded the most ever. think is this is the record and I've earned the right to talk about how many times I've recorded this episode because I recorded one take episode and I was nine minutes in and I randomly got some insane coughing attack.

that ruined the episode. Like the last four minutes of whatever it was, I was just like coughing, you know, it's just like, okay, people aren't going to want to listen to this. So I took cough syrup and then I took some cough. Ricola's I got the honey, the honey herb on me. So I'm taking those. that gets me gets me in a great place to where I'm not coughing because I was coughing too much.

And so I'll try to hold it in and.

and keep in my cough demons from disturbing your ears. That's a goal of mine. But before I get too distracted, Spotify's pushing me. Get more listeners, or you've got enough listeners. You need to get your listener to follow or raise you up. You're underperforming against your peers. Understood. Please, if you liked this episode, like, subscribe, follow. Do your thing. And then also something that's pretty cool is on YouTube.

Dalton Anderson (03:27.412) I'm almost at a hundred subscribers. It's pretty interesting. I'm almost at a episode per subscriber ratio. Hopefully we could get that up a little bit, maybe like two subscribers per episode eventually, but I am thankful for anybody even listening to the show. So it's all good. Like don't stress, but if you're feeling thoughtful and want to provide a little encouragement, I'm almost at a hundred.

It'd be great to get 100 subscribers before I get 100 episodes, which would be in nine weeks. So let's see if we can get that done. Okay, so this episode is all about confrontation. And the first thing that I think that helps with confrontation is to instead of being confrontational, be conversational and.

To do that, you need to connect with that person on a personal level, genuinely connect with them on a personal level. You can't just be like, okay, I'm gonna connect with all these people on a personal level because I wanna influence them. That's not gonna work. People are gonna call you out on your stuff and they're not gonna trust you. So don't do that. You have to genuinely connect with that person and that is probably your most powerful influencer tool, the ability to...

connect with somebody when you're having confrontation with a conversation and then respect you not only at a professional level but at a personal level is a really great, great tool to have. That doesn't necessarily follow for personal life but in a personal life you should know the person personally and if you're confrontation with somebody random,

It doesn't even matter. So you can just go away unless they're threatening to hurt you or you can't get away. And that's different. But for the most part, the first step would be to exit that situation. And then if you can't exit the situation, then you have to to try to have a conversation like what is going on here. And then if you can't have a conversation, then you've got to have a confrontation. Right. So.

Dalton Anderson (05:51.33) but this is really about, on this instance, if like connecting with somebody on a personal level, this is really only tied to a professional setting. Okay, so the first step would be genuinely connecting with your colleagues. That allows you to pull somebody aside and understand their perspective and where they're coming from. And it's less of a you versus them or a ego thing or

the person that want to be wrong or to bruise their reputation. And. Everybody's occasionally wrong, right? Like or even a broken clock is right twice a day. So everybody is wrong occasionally, and I I find that when I am incorrect. I immediately call out, hey, you're wrong, I'm right. That's my bad. And I think that provides a lot of.

respect from or demands a lot of respect. Like I don't demand it, but when somebody hears that

from the person who is incorrect and they're not defensive. They're just like, hey, you know what? You're right on this one. I'm incorrect, my bad. And move on. But a lot of times people hear is they'll say, well, you I didn't know that or, you know, no one told me that or, you know, I wasn't in that meeting or I didn't know about it. It's just like, you're responsible for it.

So just take ownership of the mistake. But anyways, so I think that also helps. Like if you actually are genuinely incorrect, then call that out that you are incorrect and let them know that you are incorrect and you're correct. And the other person is correct. People really do respect the humility of someone being wrong and then acknowledging that they are wrong and then acknowledging that they are correct. It.

Dalton Anderson (07:58.414) is just the respectful thing to do if you are incorrect. also if you're going to call somebody out, you better be pretty sure that you're correct. Like you're almost like HR at that point, like, hey. And like HR is like, hey, do you have some kind of mouse jiggler? If HR asks you if you have a mouse jiggler or like, hey, are you working remote? Like outside of the country, they already know the answer.

Like HR doesn't ask you questions unless they already know the answer, by the way. So it's kind of the same situation. Like if you're going to call somebody out, you better know. But that's a separate, separate topic. I don't want to get too distracted. So would say the first thing is connecting, genuinely connecting with somebody, being able to pull somebody aside, have that conversation, remove the ego, remove the, the us versus them, remove the bruising of reputation. And after that,

you have that second piece, that second layer is that people are rarely confrontational for no reason. And to be confrontational, as I mentioned earlier, costs a lot of energy. It's uncomfortable. People don't like it. It requires energy and effort and no one is like, yeah, let me be confrontational for no reason. And so it's icky. The whole process is icky and it's not comfortable.

So people typically wouldn't be doing it for no reason. So there's gotta be a reason why they're doing this. They must be under some guidance from their managers or they may not feel comfortable with change or they may not understand the solution or the solution wasn't explained to them. There's gotta be a reason. Like they might be missing information. They might be...

making their assumptions off of previous bad information that's dated, they might be making their assumptions off of previous information like from a prior job. All of that can influence them and how they feel. It's your job to uncover why they're feeling that way and either acknowledge their issues and deal with them or to acknowledge them and

Dalton Anderson (10:22.413) make them feel comfortable with the current solution. Those are those are the two things like either lower the hurdles of their concerns by providing remedies or you acknowledge their concerns on, hey, like I'm not comfortable with change because I've done it this way for a while. Like acknowledging that and understanding where they're coming from.

and making them feel more comfortable with the change. And so there's a whole bunch of reasons. I almost let the cough demon out there. But it's much easier to do that when you're genuinely connecting with the person and getting to know them as friends and genuinely caring about them, like understanding their family and what's going on. And some people just straight up aren't gonna be cool with that. Like they're not gonna wanna connect with you.

you always should try to. And one thing that would help is being less formal and more personable, like being jocative and, and not in a bad way, but you know, being easygoing and easy to deal with and like easy to collaborate with, but also driving a hard bargain when it matters and like when it's important. But in a general sense,

If you connect with somebody and the faster that you can connect with somebody at a personal level allows you to one, grow your relationship with that person, two, understand when there is conversation that you could pull that person aside and have a genuine conversation with them. listen, like I'm really, really having a hard time understanding what's going on with your apartment. I'm hearing this and it just doesn't make sense. Like, can you provide some insight here? Like what's off the record, what's going on?

And that stuff helps like to get that extra info or that extra ammo to navigate a dangerous situation is a big deal and it helps out a lot. But anyways, so the faster that you can get from, Hey, this is just a singular professional relationship to having a duality about your conversations or it's like a personal and a

Dalton Anderson (12:50.997) a professional and then the next step would be to make things way less formal and make them informal. But you've got to make it informal slash formal where it's not too informal to where things are the balls dropped on different things and you don't have the right processes put in place.

but also not too formal to wear like things are uncomfortable.

You get what I mean. You want to make it conversational, not confrontational. And then the next thing is I talked about earlier is this was an off shoot or an off conversation with my boss, Eric Rupert, where we were talking about some issues that were ongoing that I'm not going to talk about here, but we'll talk about some examples that are made up. But.

People are rarely difficult for no reason. Typically people take the path of least resistance. Right, so if somebody is being difficult, then why do we have this conversation? Like why is there this flag in the ground and they're just standing on it? They're standing on their hill and they're not getting off their hill. it's just, sometimes it's a funny case of.

It's just sometimes it's so funny, but you gotta figure it out. And sometimes when you do figure it out, you're like, that was the reason? That was the reason why we had this great battle, the battle of battles? Well, there's something blocking the easy path and it may be out of their control. It may be prior experiences I talked about, but in general, you'd wanna discover what is...

Dalton Anderson (14:40.981) the reason of the confrontation and then what is blocking the easy path? Like what is blocking the solution here? And if you can't find it, I coughed. If you can't find it, look harder. And if you can't find it after you look harder, then we're just out of luck. There's gotta be some kind of competing priority or lack of understanding.

or personal fear or past experience or this, this hidden constraint that you weren't aware of.

So that being said, let's talk about some situations.

Dalton Anderson (15:20.919) Sorry, Mike.

but we're nearing the end of the episode, so I think it's okay that I got a couple coughs in. I'm sorry that my cough piece came out.

But all right, so let me let me I'm going to zoom in. I'm just going to read this briefly.

Dalton Anderson (15:47.054) All right, so you're working on a project and the other stakeholder in a different department is slow to respond to your emails and is missed meetings and it's seem to be blocking your progress as of like this week and say it's Wednesday. So it's been a couple of times or that they haven't been responsive or like call it three business days, call Thursday. So three business days, they haven't gone to your meetings, they haven't responded to your emails. You just, don't really know what's going on with

Typically the confrontational approach would be emailing them again, CCing their boss. We've all had that where, hey, it's been like half a day and then somebody just straight up CCs their boss on this email and they're trying to like flame you and they CC, they see your boss and it's just like, okay, like what, why, why are you doing that? What you really should do is pull a person aside,

and ask them like, hey, what's going on? It seems like this current project that's really important to me is just potentially something else on your list, like just one more thing on your list, like what's going on right now? And then that person might say like, hey, I've got this high priority request that I got from the state and there's some kind of audit going on and.

Yeah, like, I'm sorry, like I've just been crushed with this, this, I should have communicated better, my bad. Like, I'm finishing everything up, like end of day to day, let's circle back and let's get this, project started. That makes things so much easier, so much easier. Instead of making everybody, like, instead of making the whole situation a hassle, you just make it easy. Like, the first thing is,

you should try to genuinely connect with why you're having a confrontation. And you do that by having a conversation. It's straightforward, I'm not sure, but.

Dalton Anderson (17:53.993) The next thing would be like you're implementing a new CRM. When you're seeing your salespeople, it's openly critical in the meetings and they keep saying this is a waste of time, the spreadsheet works fine.

I personally have had, like I've had situations like that, like not at my current company, but prior company where we're, we're working on this system upgrade or doing something. And somebody's like, why, why are we doing this? Like such a waste of time. And it doesn't really help me with my job or what's going on. And what you really hear when you dig a little deeper is a lot of times in these situations when you have somebody very senior,

and their position. They've been doing the same thing for 20 years. They know the ins and outs of what they're doing in that system. They're just straight up afraid of change. Like they're just not comfortable with the change. And so you've got to make them, you've got to make them feel comfortable.

So like in this example, like pulling that person aside, like what you could say is,

you pull them aside and say this is the new way, get on board or find a job. That's confrontational. So you're forcing them to be

Dalton Anderson (19:14.293) like either you submit to the new idea or get out of the way. And I'm not saying that's never an option. Like there are some times where you do need to come down pretty hard, but for the most part, the conversational way would probably work in this scenario. And so this would be like, Hey, I really value your experience. I'm surprised you're not a fan of this new tool that we're rolling out. What's your real concern here?

Help me understand what I don't see. And you hear that like the real blocker is the fear of changing to this new tool. Like they've done the old tool for decades and they feel like potentially like their value that they've created or like how good they are with that tool is lost, which is a problem.

Okay, so the next scenario is a client is constantly nitpicking every deliverable, asking for endless revisions.

Dalton Anderson (20:24.224) Sorry, sorry, like almost gonna cough. And they seem impossible to please.

Dalton Anderson (20:32.97) The confrontational thing would be sending an email of original scope of work attached, highlighting these revisions are out of scope and it will be extra.

Dalton Anderson (20:43.74) Or he'd ask like, Hey, we've been through a few rounds of revisions. I'm feeling we're not really hitting the mark for you. Can you walk me through what a home run looks like? And what's the one thing that your boss would want to see from this? And there are scenarios to where you feel like you're being taken advantage of or where you feel like there was a miscommunication. If it's a miscommunication,

then that's fine, go for the home run scenario. If you feel like you're getting taken advantage of, that's out of scope. And so you let them know, like, like we can do these things on a on a separate request and you'll be billed for that piece.

But in general sense, this episode was really about confrontation and the best way to solve confrontation is to have a conversation. And to do that, you need to connect with somebody on a personal level and genuinely connect with them and be interested in their personal life. And then from there, you need to understand why are they blocking you? Like, why are they being difficult? People are not difficult for no reason. Being difficult costs a lot of energy. It's frustrating and it's uncomfortable.

And people typically like to take the path of release resistance. So why are they deciding to go that way? All of those things need to be answered for you to get stuff done, which is important. Confrontation is something that you have to deal with in relationships, personal life, friendship, professional, your professional career. It's everywhere. And so you can't escape it. So you might as well dive straight into it. And I hope

A couple of these items were interesting enough and or help with you dealing with confrontation.

Dalton Anderson (22:38.884) And if it did, like and subscribe. And if it didn't, let me know what you do when you're in a confrontational situation. But of course, wherever you are in this world,

Dalton Anderson (22:56.502) Good evening, good afternoon, good morning. Thanks for listening and listen in next week.

SourcesFollow the source trail.

E090 Sources

Executed research records

[[Conversation Boundary and Escalation Research Note]] defines the ordinary-friction, boundary, formal-process, and immediate-safety routes.

[[Resistance Diagnosis and Change Research Note]] records the constraint map, organizational-change evidence, trial design, and stop conditions.

[[Decision Ready Communication and Scope Research Note]] records the stakeholder and client decision structures.

Preserved episode evidence

[[E90 - Transcript]] is the canonical raw monologue. It preserves Dalton's professional examples involving an unresponsive stakeholder, resistance to a CRM change, repeated client revisions, relationship-building, private conversation, and escalation.

[[E90 - How to Handle Difficult People - From Confrontation to Conversation]] is a retained legacy note. It correctly identifies the episode as operating commentary, not HR, legal, safety, conduct, or workplace-policy guidance.

The transcript supports Dalton's viewpoint that apparent resistance often deserves investigation before judgment. It does not establish that every resistant person has a benign or hidden reason.

Informal conflict and mediation

acas.org.uk/the-power-of-informal-conflict-resolution-at-work

Acas describes informal resolution as catching some workplace issues early through voluntary conversations where people feel safe to speak. It also emphasizes that context determines the appropriate response. This supports an early-conversation path, not a rule that every conflict should remain informal.

cipd.org/uk/knowledge/guides/workplace-mediation

CIPD describes mediation as voluntary and useful for some relationship breakdowns, differences of opinion, and personality clashes. It also states that serious harassment complaints are better addressed through formal procedures. Use it as professional guidance, not United States law.

Harassment and retaliation

eeoc.gov/laws/guidance/what-you-should-know-what-do-if-you-believe-you-have-been-harassed-work

The EEOC explains that a person who is uncomfortable confronting a harasser can use employer policy, a supervisor, or HR, and that reporting harassment is protected from retaliation under the laws the agency enforces. Any legal applicability depends on jurisdiction, employer coverage, facts, and filing deadlines.

eeoc.gov/retaliation

The EEOC describes protected activity and examples of conduct that may constitute retaliation. This source establishes why a casual "just have a conversation" framework is inadequate for discrimination or harassment complaints.

Threats and workplace violence

osha.gov/workplace-violence

OSHA defines workplace violence broadly to include threats, harassment, intimidation, and physical violence at a worksite. It recommends prevention programs and prompt investigation. This supports a safety-first exception to the episode's informal-conversation approach.

osha.gov/shms/chapter-10

OSHA's internal safety manual directs employees to remove themselves from threats, report incidents, and avoid engaging or antagonizing a person threatening violence. The page applies directly to OSHA employees, so public work should use it as a concrete safety principle rather than a universal workplace procedure.

Evidence boundaries

The package is about ordinary professional friction, coordination, adoption, scope, and communication. It must not recast harassment, discrimination, retaliation, threats, violence, coercion, or serious power abuse as a misunderstanding that the affected person is responsible for resolving privately.

The transcript's examples are Dalton's recollections. They can illustrate a method but do not prove the other person's motive. Public work should model questions that uncover constraints without claiming to read someone's mind.

Draft-time checks

Identify the jurisdiction before making legal claims. Use an organization's policy and formal reporting process where applicable. Preserve contemporaneous records when conduct, commitments, or escalation may matter. Include a direct safety route for threats or violence, and never recommend private confrontation when the reader feels unsafe.

HOW TO HANDLE DIFFICULT PEOPLE: FROM CONFRONTATION TO CONVERSATION