3 Emails to Disclose Your Controversial Past to Your Boss

Stressing about how you’re going to disclose your criminal record to your boss? Has your name been previously caught up in a scandal?

Take a deep breath. Perfection in human beings doesn’t exist and we can all take comfort in the fact that almost everyone has something they would rather erase from their past.

For some people, this is achieved by simply not mentioning aspects of themselves that they’re not so proud of, but for others, this isn’t so easy.  

Maybe there are publicly accessible records of your not-so-finest moments, you might have a criminal record, featured in controversial posts, or had compromising photos of yourself leaked on the web.

Whilst our first point of call would do the best you can in cleaning up your online reputation sometimes you’ve got no other option than to own your previous mistakes. 

For a career to thrive in any company, it’s important to have a good working relationship with the majority of senior staff and your colleagues.

When it comes to you and your boss, this is even more important as both of you are likely to spend your full working days together, discussing new innovative ideas, highlighting the goals of the month, and then working extremely hard to achieve those targets.

The best working relationships involve trust, reliability, professional distance, and understanding.  

What kind of information would we recommend you disclose to your boss? 
Criminal convictions/ arrests. 

There is always the risk that your employer will independently discover information about you that you did not first disclose to them initially.

This could result in disciplinary or termination. Despite the legal implications varying from state to state country to country, it’s probably best to start any kind of relationship (not just working ones) with honesty. 

Publicly accessible information about yourself that could result in damaging the reputation of the company. 

It’s always better to talk about any issues that may affect your working relationship BEFORE they surface. Very often, you’ll find that even if people are initially shocked, they’ll be more likely to commend your honesty. 

We understand that sharing sensitive information about your past with people who barely know you isn’t easy, and you risk getting stuck with a reputation based on judgmental preconceived notions.

However, it’s better to inform your boss of any damaging news before they find out themselves as lying by omission is very often perceived far worse.

To help you with this tricky task, we’ve drafted these three emails that will ease your way to disclose the controversial past: 

Email Template 1 | Speak with Confidence and Honesty 


Good morning [Insert Your Boss’ Name],
I hope the email finds you well. It’s been six months since I have started working with you. During my stay, I have not only elevated my department sales but have also initiated a couple of new projects with my team. I am sure you have noticed my enthusiasm, energy, and wholehearted dedication to the work. All of this wouldn’t have been possible if you had not put so much confidence in my capabilities.
I have tried my best not to disappoint you in the past and will continue to do so in the coming days. Since you have put so much trust in me, I wanted to do the same for you. That’s why I am opening up to you today about one of the “stories” that still haunts my professional career.
To avoid any misunderstandings, I wanted you to hear it from me first instead of another source. If you are happy me to do so I would like to explain my side of the story.

As we have stated earlier, professional relationships work on the very same principles as our personal ones. If you made a mistake in your romantic relationships, (for example) the best way to deal with the issue is to communicate with your partner.

The same works for professional relationships. Talk to your boss and tell them that you could have kept your past quiet, but have decided to open up because you value their trust.

By doing so, you are talking to your boss in confidence, and they will likely be less judgemental when they hear your side of the story.

The core purpose of this email is to inform your boss about your past so that mutual understanding doesn’t get affected.

And one of the main reasons is that you want to disclose the controversy first is so they don’t uncover the information by themselves.

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Email Template 2 | Explain Your Side of the Story 


Good morning [Insert Your Boss’ Name],
You may have heard my name appear in the “Campbell controversy” that stirred a long-heated debate in the corporate sector and remained in the headlines for a few days. Unfortunately, I was among the accused of assisting the illegal activity; however, after the week-long hearing, I was dismissed. The court issued me a warning for not reporting the incident on time. 
At the time, I was struggling as I had just gotten out of a messy divorce. I know professional ethics says that your performance should be not affected by personal circumstances, but unfortunately, during that period of my life, I let my things cloud my judgment. I thought it would be better to inform you now before anyone drew your attention to it, or you came across some of the articles yourself.
I admit it was a terrible mistake on my part. I should have seen that whole tragedy coming, but I was just so involved in my mess that I ignored all the signs coming in my way.

As your boss was not around at the time, they are unlikely to have in-depth knowledge of what happened. All they know and can react to is your version of the story.

Please do not make a desperate attempt to make yourself the victim, as it’s unlikely to provoke sympathy, think honesty and ownership, and you are more likely to gain respect.

While writing the email, re-read it 4-5 times before hitting a send button. Try to read it from a third-person perspective to see if it makes sense.

Make amendments accordingly. Take your time, and remember that you’ll only get the chance to explain yourself once.

If you're looking to develop your communication skills for professional environments even further, we think you’ll like the following video course from LinkedIn Learning.
Click here for full access to "Holding Yourself Accountable" On LinkedIn Learning
In this course, personal branding expert Dorie Clark helps you adopt the accountability mindset. Dorie outlines specific, practical steps you can take to implement accountability.This course teaches you to amplify the urgency of your mission, understand why it matters, and know how taking responsibility helps you become the kind of person you want to be.

Email Template 3 | Ensure Your Boss that The Past is the Past


Good morning [Insert Your Boss’ Name],
I wanted to take this opportunity to disclose some information regarding my criminal conviction.
Four years ago, in [Insert Location], I received a twelve-month prison sentence for [Insert the Crime]. I accepted full responsibility for my involvement and admitted the offense immediately. While in prison, I attended a program specifically for people convicted of similar crimes, and this enabled me to get a better understanding of my underlying issues. I have dedicated myself to working on improving myself ever since.
I deeply regret my mistake, but I have grown into a better person because of it. I’ve seen the impact that my conviction has had on those closet to me, and I now know that I am much better able to deal with adverse situations constructively and positively.
If you would like to discuss further, I would welcome the opportunity to explain this in more detail in person.
[Insert Your Name]

Accept your mistake, make peace with it, and move forward. Let bygones be bygones. Make a way to come out of it, and there is still a long way to go.

If you're looking to develop your communication skills for professional environments even further, we think you’ll like the following video course from LinkedIn Learning.
Click here for full access to "Creating Great First Impressions" On LinkedIn Learning
In this course, Vanessa Van Edwards—lead investigator at Science of People, a human behavior research lab—shares research-backed strategies that can help you make the first few seconds of any interaction count. Vanessa dives into the body language that is essential to an engaging first impression, the vocal cues that help you sound confident both in person and on the phone, and the best opening lines for sparking a great conversation. Plus, get tips for changing dull small talk into a lively and memorable conversation.

These email templates were written as an example of how to write a typical disclosure email. Your situation will likely differ; controversies are all different, ranging from a small forgery in documents to court cases. That said, the main objective is the same. Speak with confidence, narrate your account, and reassure your employer that history will not repeat itself. 

We have provided you the basic guidelines to use them to craft an email that will turn the odds in your favor. Good Luck, and we wish you a fulfilling career!

At Never the Right Word, our aim is to give you practical examples of how to handle life’s difficult conversations. If you have an awkward situation that you’d like example templates for, request a topic here.  

If you’re interested in further reading, we’ve also included links to our trusted resources and related posts below. To find out more about NTRW and our recommended tools, you can do that here.

Lastly, if you found this content helpful or want to share your own examples, let us know in the comments. We’d also be delighted if you shared this article and joined us on social media too!

Article by Never the Right Word

Scripts & Templates for Life’s Uncomfortable Conversations. Learn more about NTRW here. NTRW is supported by adverts and affiliate marketing links. For more info, please see our Earnings Disclosure.

This site does not constitute legal, mental, or medical health advice, please consult a competent licensed professional. If you have questions please Contact Us.

Never the Right Word

Never the Right Word

Hi there! I’m Amy, and I’m the person behind Never the Right Word. I’m a designer-by-day who’s fascinated by human psychology; you’ll find me learning about what makes others tick through all types of media and good old-fashioned conversation. Learn more about me here.

In 2019 Never the Right Word was born to fill the gap of ‘how-to’ websites with copy and paste examples showing you EXACTLY what you need to say to steer difficult conversations into positive outcomes.

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