Letter of Recommendation for Someone with a Criminal Record (The Felon’s Guide to Creating Ass-Kicking Reference Letters)

Updated:2024 Edition

In this article, we will go over the value, importance, and overall effective power yielded by a well-executed reference letter. This will be particularly useful for any individual who’s incurred some legal setbacks.

Understanding the criminal justice system can help in crafting effective reference letters that positively influence the court’s perception of the defendant.

Over the years I’ve used many reference letters to assist me in court, securing a place to live, building credit, and most notably-employment. After reading this, you will be able to as well.

WHAT ARE CHARACTER REFERENCE LETTERS?

A character reference letter is a letter in which the author explains and endorses the character traits and qualities of a particular individual (in this case – YOU – the convicted felon).

A reference letter is normally used for scholarship or job applications but can also be used to secure housing and even in legal matters.

The right words said of you by someone in an authoritative position can make all the difference in achieving your objective. It has become more common to directly attach a character reference letter as opposed to merely providing contact details.

We all know that life is not easy, and it is a tough world out there for someone overcoming a felony conviction.

It is a fact that the biggest barrier to an improved quality of life is good and steady employment, and as it stands in the current job climate, employers are very spoiled and are cherry-picking, due to the overwhelming number of applicants.

So, for a would-be applicant to include a little hiccup like their felony conviction, many prospective employers tend to pass and not take a risk on that person.

The applicant wants to get to the point of being face to face with a decision maker or hiring manager to explain why they’d be a great hire.

With that, I vividly recall the uneasy feeling of having to repeatedly explain my checkered background. The facial expressions I got. The terrible awkwardness to it all.

I knew I was qualified; I just did not know how to go about explaining my felony conviction. Not only that, but the people interviewing me made me feel extremely uncomfortable. I know they didn’t know me, and it’s not their fault. It’s just how the world operates.

I didn’t help matters though, as the mounted frustration building in me was evident. Putting on the fake smile and explaining my past digressions to countless strange faces was incredibly overwhelming. And annoying.

Mind you, this was all in an effort to get the opportunity to just be in a position to have an opportunity. Let me repeat that – I just wanted the opportunity to have an opportunity. Does that make any sense to you?

I don’t want to make excuses, and nobody likes a crybaby, but a felony conviction on your record negates a lot of opportunities I would have otherwise qualified for. Just saying.

But hey, I’m upfront about my background in interviews. Why skirt around it? Even worse, pretend it’s not there.

I’ve known plenty of qualified individuals who have gone through the screening process without mentioning a word of it, with everything going so well.

Then they submit to the dreaded background check and then things go quiet. They wonder and agonize as they wait for what seems like an eternity, hoping to hear something; anything.

When they don’t, (out of desperation they finally break the silence and do say something) it’s usually not good and/or too late and is now damage control. A would-be comedy of errors and looks like they’ve been hiding something all along (which they have – a criminal history).

Given the situation, I believe in putting it all out there. Why hide it? They are going to find out anyway (most likely). Plus, I’ll sleep better at night knowing I put all the cards on the table.

To each his own, but why not try and dictate the course of events by controlling how it’s presented? You see, it is all in the execution, and the delivery to it.

We all know having to explain certain situations can be a bit daunting. It’s awkward. Awkward as hell. And awkwardness kills many things.

Awkwardness can kill conversations. It can kill conversations in your business relationships. In your relationships, and it kills opportunities.

People want to feel comfortable and to feel secure. They want to want to trust you. And it’s your job to put their mind at ease, making them comfortable with you, and with your story.

It’s an art, NOT a science. There’s no right way to do it, but there are plenty of wrong ways that I’ve seen over time.

Having said all that, I’ve been through the job interview process hundreds of times. Before my legal woes and after. Been on both sides of the table. The one conducting the job interview, and the one applying for the position and sitting there smiling (trying to impress).

I think about what someone could have said (or not said) that would have changed my mind. What little things could have been done to make a difference in swaying the decision? What could have helped in producing a different outcome?

I think back on what I could’ve said in that moment, while I had that person’s attention and eyes drawn on me.

I mean, you have to agree, in this attention-deficit world we live in, where people can’t be bothered to even look up from their phone; to have someone focus on little old you for that moment is – well, somewhat special.

What do you do with that? What do you say? The vast majority are very nervous in that situation. Even more, if one has a criminal conviction they are trying to work around it.

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There to help you speak, so you don’t feel all alone in those situations, are character reference letters.

Character reference letters are your cheerleaders and supporters, speaking well of you on your behalf. They address your (criminal) past in the present, while still having the ability to talk about you in the future, long after you’ve left the room.

WHO SHOULD WRITE A CHARACTER REFERENCE LETTER?

When it comes to writing a character reference letter, you want to make sure you’re picking the right people to vouch for you. Think of it like assembling your own personal Avengers team – you need folks who know you well and can speak to your transformation and positive qualities. These are the people who can paint a picture of your honesty, integrity, work ethic, and contributions to the community.

So, who should you ask? Here are some top picks:

• A close friend or family member: These are the people who have known you through thick and thin. They can provide a heartfelt and genuine perspective on your character.
• A mentor or employer: Someone who can speak to your professional qualities and work ethic. They’ve seen you in action and can vouch for your dedication and skills.
• A community leader: Maybe you’ve been involved in community activities or volunteer work. A leader from these circles can highlight your contributions and commitment to giving back.
• A teacher or professor: If you’ve been in school, a teacher or professor can speak to your academic abilities and personal growth.

The key is to choose individuals who are credible and can provide a unique perspective on your character. Avoid asking people who might have a personal stake in your case or who can’t provide an objective view. You want your character reference letters to be as impactful and authentic as possible.

Identifying the right individuals who can vouch for your character and provide a credible perspective on your transformation.

Character recommendation letters (another term used), are a game changer, allowing one the opportunity to change the mind and opinion someone may form and feel about you.

The letter writer plays a crucial role in presenting character references, ensuring that the letter includes necessary elements and considerations.

This is done by the explanation of your background and story (giving specific examples and mentioning good character traits) and having these letters support you on that.

A character reference is an endorsement. Figure out who can endorse you. Who do you know that can add support, influence, and positive things to your life story? Use your connections. Don’t have any? Please…. You have to have some.

GOOD CHARACTER REFERRAL SOURCES

• Family
• Friends

It is crucial to consider the credentials and background of the person writing the character reference letter, as reputable individuals carry more weight in court.

GREAT CHARACTER REFERRAL SOURCES

• Co-Workers
• Employment Supervisors
• Human Resources
• Teachers
• Attorneys
• Probation Officers (If they’ll commit due to liability)
• Ministers and Church Faculty
• A Community Leader
• Charitable organizations
• Small Business Owners & Operators
• Respected authority figures, and anybody with power or influence, who is respected by the community

It is important to note that letter writers play a crucial role in crafting character recommendation letters. Their responsibility is significant as they can influence a judge’s decision and may even be contacted by the court to verify the authenticity of the letters.

Let your character reference letters speak for you, highlighting personal qualities and different traits you possess that benefit the other party. When compiling your collection of character recommendation letters, certain key words need to be emphasized.

Family, growth, clarity, hardworking, driven, purpose, character, trustworthy, team player, experience, punctual, learning from mistakes, determined, change, positive, focused, responsible, helpful, hope, work ethic.

Now I’m going to give you an outline of a good sample character reference letter to have in your possession. Please do not copy this word for word.

It is merely to give you an idea of how to structure the character letters, what to ask for, and what you want it to accomplish (the trait you want to highlight). You should plug and play different things to fit your own situational needs. These letters are here to help build a story. Your story as a person.

**FOR YOUR BENEFIT.****FOR YOUR STORY.**FOR YOU.

The Felons Guide to Ass-Kicking Reference Letters

Example 1 – The Co-Worker Character Recommendation Letter

Example 2 – The Big Brother Character Recommendation Letter

Example 3 – The Past Employer Character Reference Letter

Example 4 – The Supervisor Character Letter

Notice how the recommendation letters all drive home the point of what kind of valuable asset and worker, but more importantly, the person you are.

That you are enjoyed and respected by your team, and all those around you. Your dedication, focus, and commitment to creating a better quality of life for you and your family members is recognized.

A recommendation letter is powerful and effective. They should be clear and to the point without rambling. They support you and allow you to tell your story when sitting in front of somebody.

A single good character letter is great, but several character reference letters collectively working together speak volumes.

Psychologically, it relieves you of some pressure and the dilemma when going about explaining your background and conviction.

It also puts both you and the other party more at ease (less awkward), as they have something physical to look at while you’re talking. So, somebody is not staring you down throwing you off your game.

I can’t stress the pivotal role these character reference letters play, as many people have gaps in their employment history due to incarceration or unemployment.

Simply put, these character reference letters work for you, yet not very many people have a collection working for them. Now why is that?

Laziness, shame, maybe even embarrassment. Thinking it’s beneath you to ask someone for a referral. C’mon, get over yourself, and play the game man.

For the individual who’s incurred legal complications, a well-put-together character reference letter speaks loudly in a silent way.

The Educated Felon

A few final tips:

• Letterhead-written character letters are much more official and should be the way to go if and when possible.
• Pay close attention to grammar and correct spelling PLEASE! Nothing worse than sloppy character letters riddled with mistakes, where your character references end up hurting you rather than helping.

When you submit recommendation letters, consider the strategic timing and proper methods. Submitting them well in advance of hearings allows for thorough consideration. You can submit them digitally or in hard copy, and it is important to keep copies for your records.

WRITING A CHARACTER REFERENCE LETTER (A Breakdown)

Alright, so you’ve got your dream team assembled. Now, it’s time to craft a character reference letter that packs a punch. Here’s how to do it:

1. Start with an introduction: Begin by introducing yourself and explaining how you know the person you’re writing about. This sets the stage and establishes your credibility.
2. Highlight positive qualities: Provide specific examples of the person’s positive traits and characteristics. Talk about their honesty, integrity, work ethic, and any other qualities that make them stand out.
3. Address past challenges: Don’t shy away from mentioning past mistakes, but focus on how the person has grown and learned from them. Show that they’ve turned things around and are on a positive path.
4. Emphasize strengths and accomplishments: Talk about the person’s achievements and how they contribute to the community. This helps paint a picture of their potential and future contributions.
5. Keep it professional and respectful: Avoid making excuses or blaming others for past actions. Keep the tone positive and respectful, and make sure your letter is well-written and free of errors.

Just to offer yet another versatile benefit, here’s another sample character reference letter (addressed to the Judge) to give you an idea of how to structure it and what it should look like:

[Your Name] [Your Title] [Your Address] [City, State, Zip] [Email Address] [Phone Number] [Date]

The Honorable [Judge’s Name] [Court Name] [Court Address] [City, State, Zip]

Dear[Judge Name],

I am writing to wholeheartedly recommend [Defendant’s Name] as a person of good character and integrity. I have known [Defendant’s Name] for [Number] years, and I can confidently attest to their exceptional qualities and strengths.

As [Defendant’s Name]’s [Friend/Family Member/Employer], I have had the pleasure of watching them grow and develop into a responsible and compassionate individual. [Defendant’s Name] is a hard worker, a dedicated member of their community, and a loyal friend and family member.

I understand that [Defendant’s Name] has made mistakes in the past, but I can confidently say that they have learned from those mistakes and have grown as a result. [Defendant’s Name] is a person of great integrity and character, and I do not doubt that they will continue to make positive contributions to their community in the future.

I strongly believe that [Defendant’s Name] deserves a second chance, and I urge you to consider their character and personal qualities when making your decision. If you have any further questions, please do not hesitate to contact me.

Sincerely,

[Your Name]

Remember, your character reference letter should be concise, clear, and respectful. Focus on highlighting the person’s strengths and growth, and you’ll provide a compelling narrative that supports their case.

Crafting a compelling narrative that highlights your strengths and growth, while addressing past challenges.

In a personal letter, it is crucial to highlight the writer’s background and relationship with the person being recommended. This helps explain how the writer knows the individual and why they are qualified to provide a recommendation, along with specific examples of the person’s qualifications and character.

In Conclusion

I could have named this article The Art of Bringing Up Your Criminal Background on a job interview, however, I named it what I did due to the interview process being only one small part of someone’s life, albeit an important one.

The many purposeful uses of these character letters are not to be underestimated. Concerning the interview process, it’s sales to some degree.

You are selling yourself, and people need to feel comfortable with you so you must do an effective job of making them feel as such.

Character references are similar to customer testimonials in a buying sense, where it’s a tool used to gain trust and make one comfortable enough in their decision-making to look past any risk.

You have something to prove, you are a convicted felon.

Let’s say you’ve seen something you want, but are on the fence. You don’t know if you should get it. If you should invest your time, and money, or take the risk.

Wouldn’t it make your decision easier and put your mind at ease if you heard great feedback? People who vouched for it and were satisfied. Not just one, but several.

Don’t you think you would be more inclined to buy despite the risk involved? Based on this positive feedback and testimonials, the same thing goes for character reference letters – only you’re the product they’re buying. Get out there, hit up everyone you know, build that portfolio of letters, and go kick some ass.