
Hello Everyone & Happy Wednesday!
As we embrace all things spooky, let’s talk about what really keeps professionals up at night! 😱
What’s Your Career’s Biggest "Fright"? 👻
🧙♀️ Vote below and let us know what spooks you the most!
Which of these "scary" career situations gives you the most chills?
Plus, share your tips for overcoming these career fears by responding to this email! (If we love your advice, we’ll share it in tomorrow’s newsletter)🎃
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In Today’s Newsletter:
Addressing Background Check Issues - How to tell employers something will come up when they run a background check.
In The News - The current state of the white-collar job market & Walgreens rolls out a student loan 401(k) match program.
J.T. Talks Jobs - How to find companies you’ll love to work for.
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The Right Way to Address Background Check Issues With Employers

The Background Check Dilemma
One of the most anxiety-inducing moments in any job search is knowing that something will come up on your background check. Whether it's a DUI, a misdemeanor, or any other issue, the fear of rejection can be overwhelming. However, as a career coach who has helped countless professionals navigate this challenge, I can tell you there's a right way to handle it—and it can actually showcase your character rather than diminish your chances.
Timing Is Everything
The key to addressing background check issues lies in the timing. Don't wait for the employer to discover the information on their own. Instead, wait until you've successfully completed the interview process and sense that an offer is imminent. This is typically when background checks are initiated, and this is your moment to be proactive.
The Power of a Personal Conversation
Here's the crucial part: request a phone conversation with your primary contact in the hiring process. This might be the recruiter, the HR representative, or the hiring manager—whoever you've built the strongest rapport with throughout the process. It must be a phone call, not an email. Why? Because they need to hear your voice and your sincerity.
The Conversation Framework
When you get on the call, here's how to approach it:
Start with expressing your enthusiasm for the company and position
Acknowledge the difficulty of the conversation
Be direct about the issue
Take full ownership
Express genuine remorse
Emphasize your growth and learning
For example, you might say: "This is really difficult for me because I love your company and want this job so badly. It's actually because I respect you so much that I need to tell you something. When you conduct the background check, you're going to find that I have a DUI on my record. I own this mistake completely. It happened [timeframe], and I'm mortified about it. It hasn't happened since, and it will never happen again. I wanted you to hear this directly from me rather than discovering it during the check."
Why This Works
This approach demonstrates several important qualities employers value:
Integrity and honesty
Professional maturity
Accountability
Respect for others
Proactive communication
Personal growth
Many hiring managers and HR professionals understand that people make mistakes. What they're really evaluating is how you handle those mistakes. By coming forward proactively, you're showing them that you're someone who faces challenges head-on and communicates openly—qualities that are invaluable in any employee.
Moving Forward
Remember, this conversation is actually an opportunity to demonstrate your character. It shows that if something goes wrong on the job, you'll be the type of employee who comes forward, takes responsibility, and addresses issues directly rather than hiding them.
Need More Career Guidance?
If you're struggling with background check issues or other career challenges, you don't have to navigate them alone. At Work It DAILY, we specialize in helping professionals overcome obstacles and achieve their career goals. Take advantage of our free 7-day trial to access expert career coaching, resume reviews, interview preparation, and a supportive community of professionals who understand what you're going through. Don't let past mistakes define your future—let us help you show employers your true potential.
P.S. - Use code NEWSLETTER10 to get $10 off your membership if you decide to stay.
Go get ‘em!
J.T. O’Donnell
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