Episode 49: The Art of Navigating Difficult Personalities with Cliff

Episode 49: The Art of Navigating Difficult Personalities with Cliff

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Hello and welcome to The Thoughtful Realtor podcast. This is a podcast where we sit down for insights, stories, and conversations about all things real estate, running a team, a real estate team here in California–NorCal and SoCal–and how we find our way as leaders and business partners.

My name is Cliff Tsang, one of the founders and partners of Willowmar Real Estate and today's episode, it's a one on one, just between you and me. And, we're chatting about a challenge that comes across at some point whether in life or at work: difficult personalities. 

And so, whether a mild annoyance or even a really serious concern when things might get a little hostile, sometimes difficult personalities can be just unavoidable. In our line of work, those difficult personalities can arise either with a not-so-friendly listing agent or buyer's agent, or sometimes, our clients can be tricky personalities as well. And this is a topic near and dear to me because sometimes, if I'm being honest, I wonder if I might be that difficult personality.

So it's something that I've put a lot of attention on: to work on myself. And, I feel like I've gotten that feedback from my wife a lot about being a potentially difficult personality with strong preferences. And so, this has opened up my perspective on the importance of growth, trying to seek your blind spots, and really trying to be a bigger and better person–and really just growing.

I wanted to start off by sharing an example of a difficult personality, and maybe that can set the stage for us to dive into it a little bit more and talk through some ways of dealing with a person, difficult personalities, what things have worked for me, what things haven't worked over the years.

And the example that comes to mind is one with a client when, very early on in my real estate career, it was with a seller who came to the table with very strong preferences. It was their first time selling a home, yet they somehow knew how this process should go. 

And, in particular–and maybe let me set the stage for those of you who  don't work in the industry. Typically on the listing process, not only do we navigate and guide the seller through all of the steps in terms of paperwork and documentation, and put together a go-to-market strategy, and get the photos done, and the videography and all of that, whatever you'd see online on MLS, Redfin, Zillow. But on the backend, we're helping set the stage for all of that marketing.

We're putting in staging, oftentimes moving out their furniture, putting in staging, we're repainting the home, we're updating light fixtures, doorknobs, even sometimes helping with some pretty extensive renovations too: redoing the kitchen, the bathroom, all of that. You know, and guiding the seller based on our expertise and what sells and how we know we can get the best price and best value for the seller.

But this seller came to the table not wanting to hear any of that, and had their thoughts on, well, not what furniture, but they wanted to keep all of their furniture in place. And they had a very specific design aesthetic, to put it nicely. Some of the rooms were painted a very bright, ostentatious color that was the preference of the seller and the colors that they liked. 

Really, just along the way, they weren't really willing to take on any of our suggestions to bring on more neutral, different colors and design choices that would appeal to a wider audience. And also, related to pricing the listing as well here in the Bay Area, the price that you list at is imperative, and it's not a market where you just list high hoping to get someone to submit an offer. 

We're a market where you underlist and everyone kind of knows that's the name of the game, and you tack on an additional–on average, just call it 20 percent–so buyers kind of mentally do that math, going, “Okay. This home is listed for a million. It's gonna sell for one point two.” So, if you list at one point two, people are thinking that might sell for one point four plus, and they might not even show up to your open house thinking that the price is going to go too high, if that makes sense. 

So anyway, this seller hired us, but they really wanted to run the show, and I remember this was early on in my career, and I didn't really know how to navigate this type of seller, this type of personality. And, going back to the table with Connie and Kenny, I remember them giving me some really sound advice at the time.

But I also didn't know how to navigate it, so I didn't really maybe take it to heart. And they said, “Hey, this might be a situation where you need to have a really tough conversation upfront to set the stage and set the tone. Otherwise, you're kicking the can down the road, and you kind of know what's likely going to take place. And furthermore, if this is a client who's just not willing to budge at all, this might be someone that we as Willowmar might need to move on from.” 

And as a new agent, that to me was kind of a nutty idea, right? Thinking that I even had a choice to move on from this difficult client. Fast forward a few months, the listing goes live, really not much activity at all, and the listing doesn't get sold. 

And at that point, I then have a much firmer, tougher conversation with the seller. This was about maybe 90 days on the market. Ultimately, getting them to acquiesce and to see things from a different perspective, because they saw it as, “Hey, all of these decisions” that they had made weren't bearing fruit.

And so, in the end, we reworked all of that. We put in staging, we repainted the home, came back on market, and then we're able to get two offers. But ultimately, it ended up being a six-month process versus a two-month process call. And I remember so vividly the seller on that call when we wrap up and congratulate them and talk about how escrow closes and all of that, they muttered something along the lines of, “Well, hey, this would have been a lot easier if we went with your suggestions from the beginning”.

That to me was just a difficult situation that I really learned a lot from, and that, along with other relationships, other things in my life, I think I've pieced together some things that have worked over the years and also some things that haven't worked over the years, and I wanted to share that with you all.

In terms of what hasn't worked or examples of unproductive ways of dealing with difficult personalities, I would say the first thing is coming to the table with a me-versus-you attitude. And what I mean by that is, oftentimes, I think someone who is difficult to deal with, I–at least in my head–I'm already starting to make the list of like, “Okay, well, when they say this, I'm going to say this to attack that point,” kind of think of the rebuttal to what they're saying. 

And what I've learned over the years is when you come to the table like that, you're already setting the stage to be quite hostile. And you're coming to the table with not really an open-mindedness for yourself to change as well.

Because if you really think of a relationship or a personality as a two-way street, you will likely also need to make changes in how you're either communicating or approaching the situation to find common ground. Because, very unlikely, is that other person completely wrong and you're completely right.

But if you come to the table thinking that way, that there's really only “their way or my way,” you're just setting the stage to make things more difficult. And also, related to that, I have found that when I'm in that rebuttal approach, what's happening is: I'm not listening to them as they're speaking. I'm really not taking it to heart. I'm not coming to the conversation with an open heart, open mind, and that can lead to that person not being felt and heard. 

Which may, at the crux of it, be the reason why they are being difficult to begin with. Maybe, like going back with this seller situation, this wasn't true because they hadn't sold a home before.

But, commonly, in dealing with sellers who have very strong preferences, when you dig into the situation, it likely is because they sold a home previously, wherever they lived or in the same city, and dealt with a listing agent who did not listen to their preferences at all and felt like that situation turned out to be negative. So now they're coming to this situation going, “I need to be extra, extra firm with this new listing agent.” 

Secondly, kind of related to the first, I found that an unproductive way is being extremely combative. This combativeness point is actually a fine line to toe because I think how you approach the conversation is really important because there needs to be firmness.

You don't want to be a pushover either, right? You want to convey your points and get your message across, but you also don't want to be combative. Because, I think, once emotions and tension arises in the conversation, it's really difficult to de-escalate. And folks, I think oftentimes–when they're being in an emotional state–both sides, you're not really able to be productive.

It’s difficult for a productive conversation to be held when both sides are just really emotionally charged. So, yeah, I think to summarize, there's that firmness that you need to have where you're conveying your information, but you also don't want it to spill into combativeness and being highly charged or emotional.

And then, how you approach the conversation in terms of tone and energy. You very much want to come with this gentleness. And, I think that gentleness actually stems more from a curiosity and open mind. And the tone of curiosity and open-mindedness is very different, I think. It's hard to quantify or describe but I'm sure everyone listening: when someone has talked to you with genuine curiosity, you felt that, you know, when that other person is wanting to listen and asking questions to learn.

And so, the flip side to talk about productive ways, I said coming to the conversation with curiosity and an open heart, I think that is the most important piece when dealing with a really difficult personality, because that allows you to try to find common ground and establish that common ground before you start to move onto other topics.

And, I mentioned this before, but I think in terms of someone being difficult, oftentimes, if you dig into the situation further, you might understand what led to that difficult approach and really you can only uncover that by coming to the conversation with curiosity.

For me, one of the most productive ways to uncover that, and really dig into that, is asking better questions. And what I mean by that is: I think helping that person achieve self actualization. 

I know that's like, I don't know, maybe a difficult word to understand, so let me explain that a little bit more. But what I mean by self actualization is asking questions that allow that person to come to the conclusion. It's almost like leading the horse to water, so to speak. So related to that seller that we were first talking about, some questions that I could have asked were, “Hey, seller, the furniture that you've picked is really nice, but it's all a specific video game theme. Do you think that applies to a wide enough audience and will that generate the most traffic for your home?” 

You could word it differently, right? But that's the gist of “Hey, you have a really strong preference and we're trying to make this appeal to as many people as possible. Will that achieve that related to the really bright colors on the wall? That's your favorite color; do you think others will have that exact same favorite color as well? What if someone really hates green? For whatever reason, how do you think that they would feel with your home? Do you think a more neutral color like white or an off-white might be helpful to get as many people to your open house as possible?”

And, in my experience, the reason why these kinds of self-actualization questions are really, really important is because then that person comes to the conclusion on their own. And oftentimes, with a difficult personality, they don't want to be told what to do, because maybe in the past they've gotten burned by someone telling them what to do, and they followed that.

So, by asking these types of questions, they come to that conclusion on their own, and now they are incentivized. They understand why they want to move forward with that same decision that you might have told them directly. And then, lastly, I think, one book that I'd recommend for folks to check out is a book called Crucial Conversations.

It's a really solid book. I read this in the last six months, and it was recommended to me by some friends who–I really respect their opinion. And the reason why the book is super helpful is it provides a really great framework for approaching conversations that are crucial, that are likely really charged, that are high stakes, and difficult to navigate. And it gives you a framework for how to approach those conversations–really, what we're talking about today, which is difficult conversations. 

Next, I want to talk a little bit about how I've changed over the years in dealing with these difficult personnel personalities. I think if you've tuned into this podcast for long enough, we've talked about the journey that a real estate agent needs to go through to become a better real estate agent. 

And, to build your business because your business–and I think this applies to anyone who's self-employed or maybe entrepreneurial, running their own company–your business becomes a pure reflection of, really, who you are and how you're perceived by your clients. 

And people generally are drawn to people who they want to work with and who they think will do a good job in real estate selling their home or helping them buy a home, and negotiate, and has their best interest at heart.

And so, for me, in dealing with these difficult personalities, I think it's been twofold. One, I've learned how to deal with more difficult clients and be firmer and stronger as a personality, stronger as a person in conveying my thoughts, and navigating those difficult personalities. It really becomes a puzzle piece or a puzzle situation, as you can imagine. 

Clients come in all different shapes and forms and different personalities, right? How you deal with the couple that might not–they themselves might not have the best decision-making processes between themselves with such an important, expensive financial decision, asking those self-actualization questions, and guiding them to that.

It's a different situation navigating a client who is a first-time homebuyer, who is a single woman, who is really nervous potentially going through the process, and you needing to build trust with them, and maybe them not having a good experience with a previous real estate agent, and you having to overcome that.

And then, the third kind of different personality, it might not be as difficult per se, but it's different and requires you to change as a real estate agent. Think about navigating a close friend or friends from college who know you a certain way, and maybe your experiences over the years have been spending time with them going to the bar, drinking and watching football games. 

And now, you're put in a situation where you need to be more of an advisor and guide them and your relationship has really never cultivated into that type of dynamic before. So, I don't want to say it's a difficult personality, but it's difficult in the sense that it's awkward. 

And similar to the tips that we've talked about, I think helping the person navigate those situations as a real estate agent really comes down to coming to it with good questions, helping understand what they really want in the home-buying process or the selling process, and then guiding them to that, and gaining their trust overall. 

I think that whole journey has really just made me a more empathetic person, a person who really wants to listen before speaking, and I'd like to think that it's made me a better husband, a better son, a better brother, a better colleague, and all of that.

And really, I can't take credit for doing this all on my own because I think on other podcast episodes, I've mentioned that I have a communications coach. Her name's Liz Coleman. And that has just been really instrumental for my growth as well, because I think what we're talking about today is the art of communication.

Dealing with a difficult personality really comes down to: how do you communicate with different types of people? To talk a little bit more about difficult personalities, in terms of positive ways for us to work through that, for me, it's been helpful to reframe, oftentimes.

When it comes to a difficult personality, I'm sure everyone has one with their family, for example, or it can even relate to a client if you're in business, or a colleague. Reframing it down to the basics helps before I have that conversation with them. 

So, for example, if it's a family member, right, boiling it down to: I love this person, I want to have a relationship with this person. And thinking about that before you approach the conversation really changes, I think, your heart and how you–the tone of everything that you say.

And I would recommend to say that to them as well, right? I think laying the ground for the conversation, whether it's a family member or difficult colleague, whatnot, saying, “Hey, I know that we've had some bad conversations in the past, but I see you as a valuable colleague. I want to build this relationship with you because our teams need to work together going forward.”

And then, starting that conversation, because I've often found that with relationships, I see it as a door, you know, the door needs to be opened by someone first. I think, maybe this example relates to folks, which is–maybe in elementary school, you had your best friend. And, at some point, someone needs to articulate that, right? “Hey, you. We're best friends. Let's go hang out after school,” and that’s usually what happens. 

I was actually in elementary school–the one that received that–I was always nervous and shy to say, “I think we're best friends,” but I didn't want to say it to the other party.

But I remember receiving that and going, “Oh my gosh, we're best friends. Yeah, let's hang out more.” And it really opened my heart up and opened me up. 

And I think, similar to that in conversations with difficult people, someone needs to lay the common ground first. If you're listening to this podcast, it likely means that you're at least open to changing your ways to have better conversations with people.

And my recommendation would be to not be afraid of being that person, to lay that down, because someone needs to do it. And then the other tip, related to all this, it's a different advice, which is also learning to walk away from really, really difficult personalities.

I think everything I've said up until this point has been how to deal with those personalities so that you navigate it, so that you can find common ground. But I think part of growing up for me has been realizing some toxic relationships, some personalities, it might just be easier to walk away from, and it's not easy, depending on that relationship and how long you've known that person. 

But, I think that's also an important piece to recognize, which is: if you've given an attempt, to try to find common ground and make the relationship better, but the other person–because you can only really control your side of the equation–if that other person does not have the willingness or the crack in their heart to try to want to mend the relationship with you, it might also be easier for you to walk away. 

And, I'm a firm believer that the relationships and the people around you really spark energy to me, and in the same way, that if you're around someone who has negative energy, they can really be pulling you down as well.

And then, the last piece that I wanted to end with, just to wrap up: I think it's important for everyone to realize that learning to communicate, learning to deal with difficult personalities, is what I like to call an “infinite game.” 

Simon Sinek talks about how some things in life are just an infinite game: going to the gym, your health, taking care of that. There's no end to it, right? You go to the gym for a hundred days in a row that–you don't just stop at that point, right? It is infinite. Until we die, pretty much, we're going to be working on our health and fitness. 

And similar to that, dealing with difficult personalities, learning how to better converse with them is, in my opinion, an infinite game as well. So, I think we also need to give ourselves grace and just empathy to ourselves to really go, “Hey, these tough conversations are really really tough, and they're ever-changing too,” which is kind of crazy to think about. 

My wife and I are expecting in July and I know that once I have a kid, and those difficult conversations with my kid, and things in fatherhood are going to be so different than things that I had to deal with 20 years,10 years ago. It was breaking up with someone, quitting a job. Twenty years ago, I was telling someone, “Hey, we're maybe not as good of friends anymore.” Those types of things. 

And nowadays, it's communicating with my wife. I'm setting boundaries with in-laws and different conversations and different dynamics that I just never have dealt with before. 

The final thing to wrap up on is just understanding these difficult conversations are difficult for everyone and we're all going to need to adapt and change over time. So wow, I didn't expect that would be 25 minutes already. 

Thanks again for tuning in! That wraps up this one-on-one episode. I really hope my experiences with difficult personalities and different ways to navigate those and converse with people really provided some food for thought. 

And, I'd love to hear from you. What about you? How have you navigated difficult personalities? Please drop us a comment or just, you know, let us know how you've navigated those difficult personalities. You can find us at @willowmar.com or Instagram at @thoughtfulrealtor, and reach out to us directly. 

And if you haven't already, please hit that subscribe button and leave us a review. We read each and every one of your reviews and really appreciate when you share the love. So, thanks so much for listening And until next time, bye!

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