Avoiding Court Through Communication

Southbridge attorney Rob Caprera discusses three ways good communication can avoid problems. Presented in Worcester on January 10, 2015.

This is part of the Worcester Rental Real Estate Networking and Training series.

Avoiding Court Transcript

[Start 0:00:00]

Rich: I’ve been coming to this. I’ve been a part of this organization since ’02. That’s a little while now, and I don’t remember us actually dedicating an evening to communication before. Does anybody else remember anything like that? It was actually suggested by the first speaker, and we all just kind of looked at each other and so that’s a really good idea. This guy has some really good ideas. Do you guys like really good ideas?

Audience: Yeah.

Rich: All right, terrific because is communication important?

Audience: Yeah.

Rich: Everybody has heard the expression, “It’s not what you say. It’s how you say it.” Do we always get what we want with our tenants?

Audience: No.

Rich: No. Who’d like to increase our success rate? We would, right? I think we all would. It’s a component that we don’t normally focus enough on, so our first speaker is going to be Attorney Rob Caprera. I know we hear from attorneys from time to time, but we don’t get to hear from them on a subject as day-to-day as this is. We hear about things like a lot of other legal things what to do in court, and how to file this form, and how to do that stuff. That’s not stuff we do everyday, is it? Do we communicate everyday? Every day, right? We should.

This first fellow is coming up. His name is Attorney Rob Caprera and he’s based in Southbridge. He actually is a landlord himself. He actually owns some commercial properties as well. He knows what he’s doing. He’s been an attorney for a long time, and he’s actually a tough guy to get because everybody wants him to speak at their groups, so we’re lucky to have him. I’m going to shut it down and going to bring up, help me welcome up Attorney Rob Caprera [applause].

Rob: Thank you, Rich. This is a pleasure for me to be here tonight, and I’m having more fun now than I thought I ever would. I am a landlord, and I’ve been through it all and I know the deal and I feel like with a bunch of gazelles around the watering hole with the big cats lurking in the weeds trying to get us. I heard about your group, but I didn’t know the dynamic of it and the spirit of it, and you folks are really helping each other. I would say I don't know too many places other than the church where I would get a sense of a spirit where people are trying to help each other like you’re trying to help each other.

I’ve been practicing 35 years in Southbridge. I went in with my dad in 1979. I’m in general practice. I do everything but divorce and bankruptcy, so that means I’ve done a lot of trial work and I’ve done a lot of landlord-tenant work. My preference is landlord. You can send up a cheer. I do have some tenants every once in a while, and they’ll come in and I’ll tell them, “Do you think you can live there for free? Well, then you need to find a place. When are you going to get a place?” It’s that simple, right?

In the work that I’ve done as a landlord, certainly I have worked through a lot of problems, and I would tell you as I communicated with Rich before this evening and he invited me here is a lot of the problems we encounter are not legal problems, but people problems. People problems oftentimes are communication problems.

I’m not here to teach any law topic as such but to hopefully encourage awareness in communication, and I want to touch on three areas and maybe we’ll have some time for questions. I don't know if that’s how you do that, but your position as a landlord with your tenants, your position as a landlord with perhaps if you’re big enough your employees, and your position as a landlord with municipal inspectors and people who work in the municipalities and oversee what you do.

I have had at my height or one could say my worst moment 19 tenants a one time. They have been apartment residential tenants. They have been storefront commercial tenants ‑ office, professional, doctors, clinic, restaurants, realtors. My father started it out and passed it on to me. I would probably frankly tell you that I wouldn’t have gone looking for it myself, but I inherited the fun, and I know what you go through, and I’ll just lay it right on the line right off the bat.

Sometimes you win, sometimes you lose; my worst was $14,500 I left behind with a tenant, a residential tenant. You’d think that ‑ yeah I know it makes me sick to even say it, but you’d think that as a lawyer I would have been able to get myself out of that mess better. That’s the best I could do. I actually paid him $2,000 to leave.


Being a landlord sometimes is not fun. It’s very difficult in Massachusetts. We know that the law is stacked in favor of the tenant. It’s very complicated. Security deposits – I’ve gone to the point now where I often tell my clients don’t take one. Why walk through the minefield? Just don’t take it. Don’t give them a chance to gripe and fuss with you at court. Just don’t take it and go your way and hope they don’t trash your place because even if they have the security deposit, many of the tenants – I come from Southbridge, and it’s not a very affluent area with a lot of tenement buildings. If they’re going to leave you and they’re going to leave you in a mess, you’re not going to be able to chase them and get money. It may not be to your best benefit to have a security deposit.

Having said that, let me say a little bit about communication with your tenants. I come from probably one side of the spectrum with respect to drafting documents, to practicing law. I see Attorney Craig Ornell here, and I have known Craig for many years. He’s a very good lawyer and he’s practiced in housing court and other places. We’ve had cases. I’m not quite sure your style, but I would say my style is a minimalist.

I am very reluctant to put my tenants on a 20-page lease. I just hit 60 and I think I hearken back to a different era, and if your handshake doesn’t do it, 20 pages or 30 pages aren’t going to do it. It’s the agreement. It’s that relationship that you develop with your tenant. By throwing paragraph on paragraph on paragraph in a lease, I’m not sure it’s going to work.

We even try to put in that special clause that if we have to evict them that the costs of collection and cost of eviction would be reasonable attorney’s fees and interest in clause. We put that in all of our documents, our promissory notes, our leases, everything. But let me just ask. I was curious and I wasn’t sure if I was going to do it, but I’m going to do it.

How many of you in here are landlords? Okay. Keep your hands up. Of all of you landlords, how many had to evict someone? If you haven’t, put your hand down. Okay, so you’ve had eviction. If you’ve evicted someone, have you gone to the housing court and worked with the housing specialists who mediated and settled the case? You’ve done that? How many of you, who have evicted someone, have had to go to a full-blown trial? Okay, so hands have gone down. For those who have gone to the full-blown trial, how many of you have gotten an award for attorney’s fees, not for costs because they always spell that in costs and service, but for attorney’s fees? How many have gotten an award for attorney’s fees? I see one hand, two hands. Of the two of you, how many have turned that award for attorney’s fees from a white execution paper to green money? Did you get it all?

Male Audience 1: Yeah.

Rob: Good for you. But you can see that what happens and this happens with 93A claims, the unfair and deceptive trade practice, do you think they’re going to triple up on you? Do you think you’re going to get attorney’s fees and costs but what happens most cases settle. When a case is settled, the lawyer is left out of the mix. Isn’t that right, Craig? Yeah. They’re not going to settle and throw the fee on it. They might double the thing and think they’re getting out with an offer of double instead of triple, but they won’t put the attorney’s fee in there, and so clients will come to me all the time and ask, “Will you take this 93A claim? It’s a slam dunk.”

I say, “I will but even though the law says there’s attorney’s fees, the greatest likelihood is you’re not going to get it from the other side. I’m going to have to charge you. Is that okay?”

It’s very tricky to go the whole distance and most people if they can negotiate and housing specialists are great and they close a lot of the cases. They’ll negotiate for you. What you need negotiate, you’re very really going to negotiate the attorney’s fees and those things in there.

Putting those kind of sharp teeth in the bite clauses in your leases page after page after page, I don’t personally see on the whole ‑ some situations yes ‑ but on the whole, I don’t see that as being the best way to go. I see after 35 years of practicing, the best way to go is get to know your tenant as best as you can. Certainly, references, certainly check them out. Meet them. Try to get to know them as best as you can before you begin to dance.


First time in my practice this year it’s happening. I represented a couple of large landlords in the Southbridge Sturbridge area. In March, I evicted one tenant. They went to another place. I’m evicting them again for the other client, and I’m thinking, “The screening on this, something disconnected here.” But it’s the first time I’ve ever had this experience. Get to know your tenant, and when you’re talking to your tenant about the lease, the tenancy, the occupancy, you need to know who you are.

I’ve found many, many times that the landlords when they come for eviction don’t know who they are. They may have a trust. They may have an LLC. The owner of the property may not be who’s managing the property. Husband and wife, and the husband comes but not the wife but they’re both on the deed, and so it’s complicated. You need to know who you are, but then you need to know who they are if it’s going to be a husband and wife, it’s going to be boyfriend/girlfriend, if they’re going to be other occupants.

You need to know who’s going to be in your place and communicate well and find out at the onset. You need to know how much the rent is. They need to know how much the rent is. They need to know that you’re serious, that the rent is paid on the first of the month. Leases might say there’s a grace without interest or whatever after the fifth day or the tenth day, but the rent is due on the first of the month. That around here, on the sixth, you’re going to get a 14-day notice. That’s just it’s going to be. It’s going to be. You need to communicate that right at the beginning, and so when you give them on the sixth, they don’t give you kind of that deer-in-the-headlights look like, “What the heck are you doing to me?”

“I told you. Remember when we talked? I was sitting in my office there. You were sitting across the desk. We talked. I told you on the sixth day, you’re going to get a 14-day notice. You can bring the rent up to date and you get it by this first time, but next month, if I don’t get it on the first five days, on the sixth, you’re going to get another one and you won’t be able to stop that one with payment.” It’s communicating up front.

Audience: Pets.

Robs: Pets, I heard pets. I had one dog in one of my apartments that scratched the wood. At least it proved to me I didn’t have hollow doors because it scratched way down deep into the wood, but it was a brutal dog. It was a Samoyed or one of those kind of husky-ish dogs. Pets, sometimes if you weigh how good the human tenant is, you get the sense. They pass the smell test, great tenant. If they have a pet, sometimes you go with it, but you have to be forewarned is forearmed: pets are problems. Pets are problems, but you have to know that upfront.

I guess as to tenants, as to tenants, my comment is you really have to become their friend. I recently went to the home of a friend, a client. He’s a landlord. I think he’s a member of your association. He would have been here tonight. He was telling me just recounting stories about working with the tenants. When they went out of work, lost a job, he would go help them apply for work, and get them work so that you win-win. They get a job and he get paid. But being that involved with his tenants, I think is a high standard and a standard to which we all need to aspire. With that communication, with that kind of relationship, the problems are less likely to come. I will not guarantee that they won’t come at all because they will. They just will. Everyone can tell a tenant-from-hell story, right?

Audience: [unintelligible 0:14:16].

Rob: Yeah. Okay, so that’s with tenants. Now if you have people who work for you, and this is a concern because really where it can get messy. In principal agency, you as the principal can put your agents out into the field and what they do in the course and scope of their employment will bind you. If it’s terms between the landlord or the landlord group, the principal and his agent and the tenant, those terms conveyed by the agent, by your worker can bind you, and that person may not say things that you would want them to say.

Your communication really needs to be precise with your employee, what authority they have, what’s their goal. If it’s a negotiation they’re going to enter into with one of the tenants, what authority levels do they have? Where should they try to shake hands at?


The difficulty oftentimes in court is that the landlord has not said or done something but the landlord’s employee has said or done something, and now as a landlord, you’re trying to defend and your client, the landlord hasn’t really done anything wrong, but the representative has put everyone in a pickle, and that can be problematic. That’s not to say don’t have people working for you. I’m just saying in communicating, that scenario where you need to focus on communicating, don’t overlook that. Don’t assume that your representatives out in the field are going to say and do everything right or everything that you would want to say or do.

Then finally, in terms of communicating, I see this as a situation now that I’m town attorney in Southbridge. I’ve been town attorney in Southbridge for the last 5 or so years. One like to think that comments occur like this in meetings, but I have been in meetings in the town with inspectors or town workers or whatever. It’s kind of the comments that teachers will have about students in the teacher workshop. I mean there’s good students, there’s bad students; you try to treat them all the same but everyone knows who’s who.

I have been in meetings where a landlord’s name has come up. Sometimes, “Oh, yeah. We can trust that person. Yeah, they’ll get it fixed. It’s not a problem.” Other times, a person is blowing wind at us, and you got to stay on top of that person because I’ve had some bad experiences. You wouldn’t think that so, but humans are humans, and that’s kind of the way it is.

You can blackball yourself by the way you act with the health inspectors and the building inspectors. I mean you try to fix something and don’t pull a permit and get caught. What do you think they’ll say about you inside the town hall? It may be benign. It maybe a benign kind of thing, but you can cook your own goose if you act that way.

I would encourage you when you are having communications with municipal officials: mean what you say and say what you mean and stick to it and then do what you say you’re going to do. You can build a trust by being trustworthy, worthy of trust. If you have that kind of reputation, it can be a whole lot easier when you’re dealing with the towns and the cities and the inspectors. You’re going to have to deal with them because you own property.

If you try to cut corners and if you don’t stay in the high road, you will get caught and it’s going to haunt you. You just don’t need that. It’s going to haunt you all the way around you. If you start winding up in court, trying to evict tenants and one of their witnesses, the health inspector, because they blew the whistle on you and they came with a big list of to-dos. If the court starts seeing that the health inspector is on all of your cases, it’s the human nature. I’m just going to tell you it’s human nature the clerks and the judges ought to think that you’re not shooting straight as you ought to shoot.

Communicating with the building inspectors, with the health inspectors, with police officers if they come on a report of disturbing the peace or something like that, it’s your place. Fire inspectors if there are sprinkler issues or whatever – smoke detector issues, carbon monoxide issues. Just do your best and recognize in your communicating with them, it’s meaningful. It really is meaningful for the work that you’re trying to do as landlords.

That is basically what I would say as the skeleton on which we might hang flesh. I don't know if you have any questions. Again I would specify that me standing up here as an attorney perhaps does not represent all attorneys, and you may have had good confidential conversations with your attorneys and are very comfortable with them and the counsel they’ve given you and I don’t want to disrupt that. I want to say it as sort of a disclaimer that I come into this as much of a minimalist, trying – it’s interesting. I didn’t give it a title, Avoiding Court, but I try to avoid court.


I try to avoid court with my clients and do everything I can for that and try to settle cases too because going to trial, it’s exciting because it’s a jump ball, juries more than judges, but judges can be unpredictable as well. Try to settle cases. Try to stay out of court. I find more that I appreciate my role as a counselor-at-law as opposed to a litigant. If I’m litigating with a long-time client, maybe I have done something wrong. Avoiding court, communicating - those are the things I will encourage. Are there any questions that anyone of you might have? Okay, I ‑ go ahead.

Sandra: Comment regarding‑

Rich: I have another one.

Sandra: Just a comment because I do believe what you said in terms of keeping those lines of communication open as much as possible, but I think what’s also important for us as landlords and that’s documentation especially in conversations that I’m very guilty of this because I get so busy during the day that I forget to do it. But I find that more and more that if you have documentation on this particular day you had a conversation with a client, your tenant. You tell them that their 14th day was coming down the pike and send them out a letter that says, “As per our conversation today and date to date,” at least you have more documentation to bring with you when you do go to court.

I know that my attorney, who’s sitting at my desk here, will always say to me, “Do you have the letter than you sent out? Did you bring it with you?”

Then I start flipping through my files to find out. I tried to get in there as prepared as possible so that he’s a happy camper. I would just offer that as a piece of advice.

Rob: Okay, good point. I’m jumping off of that. So how many have a journal? How many keep records of their daily conversations, daily communications with their tenants?

Female Audience 1: Scattered.

Rob: You scattered. Keep a journal, a formal journal of everything that you do with your tenants. Another point is when you go see tough tenants, bring someone with you as a witness. When you’re communicating with your tenants maybe even by email, don’t be afraid to be self-serving. Write a little story. “Joe, remember when we stood in front of your stove in your kitchen and we looked at the smoke detector that you had pulled off the wall, and you apologized for that. Hopefully it won’t happen again, but as to the problem of the mold…”, so I mean you can just document a lot of your trail with your tenant, and then sort of be patient.

When you’re dealing with your tenant and dealing with anyone, there is this mindset that you can say, “Okay in this checker game, I’m going to do this, then I’m going to expect that the person, the tenant to do that. Then after they do that, I’ll do this and then they’ll likely do that and then I’ll do this, and they’ll do that. We’ll cross the finish line together, win-win.”

That commonly can work if you’re patient and you communicate. But if you’re dealing with alcohol, drugs, or nuts, all bets are off. It doesn’t work. And so, what‑

Female Audience 2: [unintelligible 0:24:06].

Rob: Yes, and that’s the problem. That’s the problem because you hope you don’t get into a pickle where you have to negotiate out, and if you negotiate out, you kind of go on a step process, check the game kind of process, and some people, you can’t play their game with, and then you have to go to court. But hopefully those are few and far between. Yes?

Female Audience 3: [unintelligible 0:24:30] journals. Are texts admissible in court?

Rob: Are what?

Audience: Text, text messages, text.

Female Audience 3: Text messaging.

Rob: Bring it in, sure. Sure if you can get into evidences, a piece of evidence, it can refresh your recollection so your lawyer can say, “Did you text your tenant on the 5th of August?”

“I don’t really recall.”

“I’ll show you this document and ask you if it refreshes your recollection.” You look at it. “Does it refresh your recollection?”



Female Audience 3: Okay.

Rob: “Did you text?” Now the judge sees that there was a text that you’ve got into evidence. Whether it’s a printed form, which might be hearsay kind of stuff or whether you just can get it in that way, you can get it in.

Female Audience 3: Okay, thank you.

Male Audience 2: You’ll need a screenshot of text messages printed up.

Rob: There are some evidentiary hurdles that you have to get over to enter that piece of paper in, but you can get it in.

Male Audience 3: I just wanted to stress up on the communication via email, how important it is as Rob was pointing this out. I have a tenant that I was having issues with and then he would do all kind of things, and at some point, I pulled some communication that I had with him via email. That was like 6 months. He was taken back by that because he didn’t think that I was keeping track of every conversation and every detail of everything. That’s how I was able to get rid of him because he saw that I had everything documented.

Rob: Very good.

Rich: I don’t need to refresh other people’s recollection. I need to refresh mine quite a bit. One advantage to doing this and this is one thing that Rob really enforced with me is and what Sandra was talking about is it’s tough to keep up with sometimes if somebody calls you and say that they have a clog. If you’ll just send them a curt note saying, “Hey, thanks for letting me know about that. I’ll give you a call when we can set up the maintenance,” if they have a slow drain or whatever the case maybe. Now it’s in writing when they called in and when you replied especially if it’s something that’s not an emergency that you’re not going to rush over today. You have acknowledged it and there’s a record of it.

I can actually do a search in my phone and figure out when that was because I don’t remember when that was, and if you ask me to guess, I’m probably wrong 99 percent of the time. Do we have other questions?

Female Audience 4: I think it’s more than plumbing [unintelligible 0:27:17].

Rich: I want you to hold on one second. She’s going to tell us that she’s a geek.

Female Audience 4: No. I’m a journal geek, literally every single file. I think more of a comment when a tenant calls me, and I can’t talk or can I call you right back because I’m very disciplined in I got to have that piece of paper, I have to have that pen, and I want to make sure that when I’m talking to whoever the tenant is, I have their undivided attention, so I’m not taken off guard. I would say kind of try not to be impulsive in answering that phone call when it comes through. Make sure that you’re always in a position where you can talk so that you can document. But documentation when you’re before that judge, not that I ever have to be before a judge, but like an attorney, you keep logs. It helps you. It really helps you, so I think that’s really sound advice for this evening. Thank you.

Rob: Good.

Female Audience 5: I want to know what do you do when someone you keep asking for the rent because it’s overdue and overdue and you give them five more days and keep going. Then at the end, you’re texting and they say, “Stop harassing me [laughter].” What do you do with that?

Rob: Well what you’re suggesting is now you’ve gotten to the point where they’ve shown their color, you know what kind of blood runs through their veins.

Female Audience 5: Exactly.

Rob: You have to be careful.

Female Audience5: [unintelligible 0:28:51].

Rob: Yeah, you have to be careful for that. I had a horror show of a client ‑ I mean I would say parenthetically that we’re very fortunate in Worcester County to have I would say very good housing court judges. We practice in a very favorable climate for landlords in fairness, too. I was in Hampden Court in the last 2 years and had one case. It was $500,000 house in East Longmeadow, beautiful house, and the tenants wouldn’t pay and my client called, texted. He was in Florida. It was an old house. He had to move, and we tried to evict them, started in the summer of 2013, had a trial date in October 2013, and the people did not leave until August of 2014. I went to court 12 times.

Female Audience 6: [unintelligible 0:29:55] one of my tenants?


Rob: No. I went to court 12 times. My client walked away from over $40,000 of rent to get them out. It was a nightmare, but one of the counts against him because of in his frustration, he’d lost it a couple of times was that he was harassing the tenant. You don’t want to give tools to the other side. You don’t want to give them bullets for their gun. You have to be careful, so it’s people. It’s communication. It’s dealing with people. At some quick point, you realize that it’s time for an eviction, time to just disengage. You have to work with people but it can be frustrating.

Okay, anything else? Okay. Thank you very much [applause].

[End 0:31:05]





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