6 Common Character Reference Letter Mistakes

Imagine this scenario! What if you could go to a sentencing hearing or hearing to try to keep your professional license with all of the inside information you need to put yourself in the best possible position to succeed?Does that sound like something that would interest you?

If it does, please watch this video because I’m going to give you this inside information that I’m going to channel in part through a federal judge who was interviewed by my business partner, Michael Santos. I’m going to put up a two and a half minute clip to that video with the judge at the end of this video.

What I’ll cover in this video today is not just the importance of character reference letters, but some common mistakes that people make. After all, it does no good to go through an extensive mitigation strategy, in some cases, over a period of months and years to then have one word, one statement, one line, derail all the progress you’ve made. And that absolutely can happen.

We’re dealing with cynical stakeholders here, probation, officer, a prosecutor, a judge: you need the right content at the right time to influence these people favorably. So you’ve got to invest the time you have to do the work.

So about six weeks ago I sent an email to our list, highlighting a defendant who called after sentencing to tell me that his judge had lambasted him and his white collar defense lawyer by essentially turning in letters that looked boiler plate. Further, he admonished the lawyer and asked the lawyer, “did you even read these character reference letters?” I’m not so sure you did.” So all of the other good stuff this white collar defendant had done worked against him because the judge spoke at length about the mistakes in these character letters. So let’s jump right in with some common mistakes to ensure that you don’t make them.

Character Reference Letter Mistakes:

#1: Wrote that it wasn’t the defendant’s fault

Well in the sentencing world one common mistake is the writer writing that it wasn’t the defendant’s fault. And you may be thinking, well I didn’t have bad intent and I want the judge to learn more about the circumstances through the person writing the letter. That is not the intent of the letter.

And at the end of this video, I’m going to close with three very easy to follow takeaways to help make your letter great. And I’m going to read an excerpt from a letter that I turned in at my sentencing, that Judge Wilson discussed and referenced. You cannot in the criminal justice world have your cake and eat it too. In other words, you can’t plead guilty and then say, well I didn’t really do it, or I didn’t mean to do it. It may be true, it’s not the right message at the right time. So too many letters in our experience, character reference letters, convey, if not directly, it wasn’t the person’s fault, they insinuate in a matter of fact sort of way. And that can be very off putting to a judge. And if you have a lawyer that’s not dissecting and reviewing every single letter and editing and removing, you’re going to have a problem. So that’s the biggest mistake that I see again and again, and again, people writing that it wasn’t the defendant’s fault.

#2: Stated that the government or jury got it wrong

The second mistake I frequently see is that the government or jury kind of got it wrong. And again, kind of aligns with the first fact. The government overcharged. The government sends too many people to prison. This is not a good use of our tax dollars. This is a first time non-violent offender, or there are no victims. There’s no financial loss, as of as the case in the varsity blues case for example. Maybe true, technically no victims, no financial loss, but is that the right message in a character reference letter for a judge who’s deciding, your contact, your supporter or the people with whom we’re writing letters for you, how long you should serve in prison? So it is a common mistake stating the government or jury got it wrong. If you’re going to have someone write that sort of letter, don’t have them write a letter, just don’t turn it in. If they write it, thank them. It shouldn’t be turned in. Okay. I just see it too frequently.

#3: That the defendant should not be going to federal prison

Another problem, and a common mistake in character reference letters and you’re going to hear Judge Bennett discuss this at the end of the video is someone writing a letter than telling the judge the defendant shouldn’t go to prison. And it’s just terrible, this is a federal judge appointed by a sitting president who has a great deal of power and responsibility. I can assure you, as Judge Bennett will discuss at the end of this video on character reference letters, I can assure you the judge does not want to be told what the sentence should be or that you shouldn’t be going to prison. It’s obvious you don’t want to go to prison. It’s obvious your support network doesn’t want you to go to prison. Do not make that mistake of telling the judge that defendant shouldn’t go to prison. When you do that, you’re essentially trying to do their job for them. It goes poorly.

#4: Followed a template that many others wrote

Another common mistake and my lawyers did this, I mean, the defendant gets in trouble, the lawyer says collect letters. Here’s a template, here’s a form letter, here’s something to follow. Well, if the proper amount of time isn’t invested in getting great letters and I’ll put up a URL here to characterletters.com, it’s a free course our team teaches where I walk you through my letters, why they were helpful, what judges tell us. So you can have access to all of these letters and learn the makings of a great letter so I encourage you to go to characterletters.com.

But when you read the letters that were turned in on my behalf, you will learn not one of them was templated.

Not one of them look like the same person wrote them. It was in the voice of the person writing it. Now I may have had some suggestions. I think it’s good to give guidance like, don’t tell the judge what to do. Don’t say that it wasn’t my fault. Don’t say that I shouldn’t go to prison. Common mistakes I’ve just addressed. Do not follow a template. Judges see through it. It’s lazy. It’s boiler plate. And again, it can derail all of the good work and mitigation that’s been built up. So I am concerned sometimes when a lawyer sends a template to their client that says, here’s the guidance and templates on how to get letters. I think it’s lazy. It’s not specific.

It’s not extraordinary turning in templated, garbage stuff.

#5: Not addressed to the sentencing Judge:

Couple of other things and then I’m going to turn it over to the video with Judge Bennett, then I’ll read my letter. A letter that isn’t addressed to the judge. So I have seen defendants compile letters, it says to whom it may concern, it doesn’t address the remorse, the shame, the conduct, the crime. And it’s clear someone was asked to write a letter without knowing that, hey, I’m going in front of a sentencing judge trying to avoid prison, or I’m going in front of a board to try to keep my real estate or law license. Our team is working with someone now who has as a civil issue not criminal, trying to keep the law license going in front of the board to try to keep the license. To be clear it’s going to be dressed specifically to the board. In my case, I tried to keep my real estate license when I came home from prison, the new letters that I collected were written specifically to the California Department of Real Estate, the commission who was evaluating my fitness to keep my license based on my conviction as a securities broker. So if you have something that is addressed to whom it may concern, judges are going see through it, don’t turn them in. I beg you!

#6: Too many character reference letters:

The last thing I’ll convey for common mistakes is too many letters. Our team speaks at length about the right content at the right time, you will give specific conduct to a probation officer that may defer to the judge, that may differ to a case manager in prison and a probation officer when you come home, content is key, but it’s got to be the right content at the right time. Too many letters can work against you if your judge favors brevity. In my case, I compiled 16 letters I only turned in six. Judge Wilson commented on all six letters, I don’t know if he had a read 16, but I also know that he favored brevity. So common mistake is compiling 40 or 50 letters, in time they begin to get a little water down and you’re running the risk the judge may not read them all, especially if they all sort of say the same thing.

A caveat to that of course, is some judges will read a great deal of letters.

We’ve had clients, for example, go in front of Judge Hall, a judge in Connecticut, who I believe has commented that she’s open to reading as many letters as will come in. I think that’s an anomaly. I think judges favorite brevity. So it’s okay to compile 10, 20, 30 letters or 40 letters. I’m not telling you to get six letters, in time you will use them at different stages of the journey. You just don’t get content, use it, put it in the shelf and throw it away. Here we go, here’s the shameless plug for Lessons From Prison. No good if this sits in my garage. I’m not going to my Amazon page and selling it to universities or giving it to you for free. It does no good. You use it for the rest of your life. So you may get 30, 40, 50 letters. You may only turn in 10 and that’s okay.

So before I turn it over to Judge Bennett with Michael Santos, I’m going to wrap up the makings of what a very good letter is, and then read a snippet from my letters. It’s very simple. Your letter should show the positive contributions you’ve made to society. Pretty simple. A specific story or detail about your life, your character. I don’t care who it’s from, gardener, your dentist, your friend, your plumber, street sweepers judge Bennett says. It’s not a matter of who’s important or high profile or celebrity, doesn’t matter. Can they speak to your character? Additionally, the letter should discuss candor about your crime and what you’re doing to make things right. That’s a community service component of measurably giving back to the lives of other people, which helps them and helps you. And I guess, lastly, the great component of a good letter is that you have evidence that you identify with the people that you’ve hurt. Your victims if that information can make its way into a letter and show your character and your commitment to reform in yourself, you’re measurably ahead. That’s mitigation. That is mitigation at the right time with the right audience, your federal judge.

So to give you an example of something that really helped me at my sentencing hearing was a letter written on my behalf by who is my dentist, he still is my dentist, a very good friend. I was a real estate agent before I went to prison, as many of you know, I sold real estate at Sotheby’s for three years before I went away. And it was a good time, made a lot of money, really enjoyed it, I like selling real estate. In this letter, my client, real estate client, wrote how I did something that helped him.

“He wrote, legal representation, has been financially draining for Justin. And one would think that he would take advantage of any professional opportunity to alleviate his financial stress. That has not been the case. Early in our relationship. I asked Justin to represent myself and my wife in the sale of our house and the purchase of a new property. Justin would have realized 75,000 in commissions, a lot of money at any time. Certainly in 2007, when I needed to pay the lawyers and come up with money for restitution. Certainly he needed the money, instead, he advised me to wait a year until I turned 55 so then I might benefit from certain tax advantages.”

Judge Wilson spoke that I had reformed myself, that I was making better decisions, that I was doing what I was supposed to do, making good decisions on behalf of my clients. I shouldn’t be lauded or applauded for doing the right thing, which I did, but it spoke to my character and that I was changing. That was more impactful than a letter from my mom or my dad. Letters, frankly, I did not even turn in because you know what my parents are going to say. Learn from people who’ve made bad mistakes, profit from their experience, compiled best in class character, reference letters and avoid these mistakes. And with that said. I’m not going to turn it over to this video with Michael Santos and Judge Bennett. Again, go to characterletters.com, enroll in that course on how to compile best-in-class character reference letters. And of course, if you have questions for our team, while you’re on the White Collar Advice site, schedule a call and we’ll get in touch with you.

Thank you so much for watching this video. And by the way, we went over 6,000 subscribers on the channel. Thank you very much for subscribing and for being a part of our family. I hope you feel comfortable here and find a lot of value continuing to come back.

Thank you,
Justin Paperny

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