Navigating the Complexities of Asking Your Former Boss for a Job

Asking your former boss for a job can be a delicate situation. However, with the right approach, it can be done effectively. Here's a step-by-step guide to help you through the process.

1. Reflect on Your Reasons: Identify Why You Want to Return

The first step in approaching your former boss for a job is to clearly identify why you want to return. Consider what skills and experiences you have gained since your last stint at the company, and how they can be beneficial to the current team.

2. Choose the Right Timing: Find an Appropriate Moment

Selecting the right moment to reach out is crucial. Try to connect with your former boss during a time when they might be more receptive. This could be after a successful project or during a quieter period in the office.

3. Craft Your Message: Use a Professional Tone

Whether you're sending an email or making a phone call, maintain a professional tone. Your message should convey a sense of respect and appreciation for the opportunities you had in the past.

Subject Line if Email: Keep it clear, e.g. “Reconnecting” or “Exploring Opportunities.”

4. Structure Your Communication: Greeting, Expressing Gratitude, and Requesting a Meeting

Greeting: Start with a friendly greeting. Express Gratitude: Thank them for past opportunities and experiences. State Your Intent: Clearly express your desire to discuss potential job opportunities. Highlight Your Skills: Briefly mention any new skills or experiences you've gained since leaving. Request a Meeting: Ask if they would be open to catching up over coffee or a call to discuss possibilities.

5. Follow Up: If You Don't Hear Back, Consider Sending a Polite Follow-Up Message

If you don't receive a response within a week or so, consider sending a polite follow-up message. This shows your enthusiasm and commitment to the potential opportunity.

Example Email Template

Subject: Reconnecting

Hi [Former Boss’s Name],

I hope this message finds you well! I’ve been reflecting on my time at [Company Name] and wanted to reach out to express my gratitude for the opportunities I had while working under your guidance.

Since then, I've gained [briefly mention any relevant new skills or experiences]. I am very interested in exploring potential opportunities at [Company Name]. I believe my [specific skills or experiences] could bring value to the team.

If you have some time, I would love to catch up and discuss any possibilities. Please let me know if you're available for a coffee or a call.

Thank you for considering my request and I look forward to hearing from you!

Best regards,
[Your Name]
[Your Contact Information]

6. Be Prepared for Any Outcome: Stay Positive

Understand that they might not have an opening or may not be able to rehire you. Regardless of the outcome, stay positive and thank them for their time.

By approaching the situation thoughtfully and professionally, you can increase your chances of a positive response.