Sample Email To Old Boss For Job: Free & Effective

I’m sharing my personal experience and a guide on how to write an email to a former boss about a job opportunity. I’ve been in this position and understand the nuances involved in crafting such an email.

Key Takeaways

  • Understand the Purpose: Reaching out to a former boss for a job opportunity.
  • Personalize Your Approach: Tailor your email to reflect your previous relationship and experiences.
  • Be Professional and Concise: Maintain a professional tone while being clear and to the point.
  • Highlight Your Achievements and Growth: Share your accomplishments since you last worked together.
  • Show Enthusiasm and Respect: Express genuine interest in rejoining the organization and respect for your former boss.
  • Follow-up Respectfully: If necessary, follow up in a respectful manner.

Step-by-Step Guide

Step 1: Reflect on Your Relationship

Start by recalling your working relationship with your old boss. Was it formal, friendly, or somewhere in between? This will guide your tone.

Real-Life Example: When I reached out to my former boss, I remembered our casual yet respectful rapport, which helped me set the tone for my email.

Step 2: Draft a Clear Subject Line

Your subject line should be straightforward, indicating your intent. Example: “Exploring Potential Opportunities – [Your Name]”.

Step 3: Start with a Personal Greeting

Begin with a warm, personalized greeting. Mention something memorable from your time working together to reconnect on a personal level.

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Tip: Avoid overly casual greetings; maintain a balance of warmth and professionalism.

Step 4: State Your Purpose Clearly

Get to the point quickly. Express your interest in rejoining the organization and why you are reaching out to them specifically.

Step 5: Highlight Your Achievements

Since leaving, what have you achieved? Briefly mention new skills, experiences, or accomplishments relevant to the role or company.

Since LeavingAchievement
Year 1Skill A
Year 2Experience B
Year 3Accomplishment C

Step 6: Show Enthusiasm for the Company

Demonstrate your knowledge of and enthusiasm for the company’s current direction or achievements.

Step 7: Be Respectful of Their Time

Acknowledge that they are busy and express appreciation for considering your request.

Step 8: Close with a Call to Action

Politely suggest a meeting or phone call to discuss potential opportunities.

Step 9: Proofread and Send

Always double-check for errors or typos before sending.

Email Template

Subject: Exploring New Opportunities – [Your Name]

Dear [Boss’s Name],

I hope this email finds you well. I often reflect fondly on our project [X], which was a significant learning experience for me.

Since leaving [Company], I have honed my skills in [New Skill] and achieved [Accomplishment]. I am excited about [Company’s recent achievement or direction] and believe that my recent experiences align well with these developments.

I am reaching out to explore any potential opportunities for collaboration or rejoining the team. I would greatly appreciate the chance to discuss how my current skill set and experiences could contribute to the continued success of [Company].

Thank you for considering my request. I understand you have a busy schedule, and I appreciate any time you can spare. I am available for a call or a meeting at your earliest convenience.

Looking forward to the possibility of working together again.

Best regards,
[Your Name]


Reconnecting with a former boss for a job opportunity requires a blend of professionalism, personalization, and respect.

Remember to be concise, highlight your growth, and express genuine interest in the company’s future. A well-crafted email can reopen doors and pave the way for new professional endeavors.

Comment Request

I’d love to hear your thoughts and experiences on this topic. Have you ever reached out to a former boss for a job? What strategies worked for you? Share your stories in the comments below!

Frequently Asked Questions (FAQs)

A middle-aged Hispanic woman in business casual attire

Q: How Should I Start the Email to My Old Boss for a Job Opportunity?

Answer: When reaching out to an old boss for a job opportunity, it’s crucial to start your email with a warm and professional greeting. 

I usually begin with “Dear [Boss’s Name],” to keep it formal yet personal. In the opening line, I mention how they have been impactful in my career and express genuine interest in reconnecting. 

For instance, “I hope this email finds you well. I’ve often reflected on the valuable experiences and lessons learned under your leadership at [Company Name].”

Q: What Information Should I Include About Myself in the Email?

Answer: In the body of the email, it’s important to briefly update your old boss on your professional journey since you last worked together. I focus on key achievements and skills that are relevant to the job or the company I am interested in. 

For example, “Since leaving [Company Name], I have enhanced my skills in [specific skills] and have successfully [mention any notable achievements].” This helps in positioning yourself as a strong candidate.

Q: How Do I Express My Interest in the Job Opportunity?

Answer: Expressing your interest should be done clearly and concisely. I always ensure to directly state my purpose for writing. For instance, “I am writing to express my interest in the [Job Title] position I saw advertised on [where you found the job posting]. I believe that my experience in [relevant experience] makes me a suitable candidate for this role.”

Q: Should I Mention Our Past Working Relationship?

Answer: Yes, definitely. I make a point to refer to our positive past working relationship, as it can be a significant advantage. I usually include something like, “I have fond memories of our collaboration on [specific project or task], and I am eager to bring that same level of commitment and innovation to [Company Name].”

Q: How Do I End the Email Professionally?

Answer: Concluding the email professionally is as important as the beginning. I always thank them for considering my application and express my willingness to discuss my candidacy further. 

A good closing line would be, “Thank you for considering my application. I am very enthusiastic about the possibility of rejoining [Company Name] and would welcome the opportunity to discuss how I can contribute to the team. Please let me know a convenient time for a conversation.”

Q: Is It Appropriate to Attach My Resume?

Answer: Absolutely. Attaching your updated resume is a must. I usually mention it towards the end of the email, “I have attached my updated resume for your review. I look forward to the possibility of working together again.”

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