Email To An Ex-Boss After A Long Time: How To Draft It Right!

In this article, I’ll share a step-by-step guide on how to craft an effective email to an ex-boss, including a customizable template.

Key Takeaways:

  1. Purpose of the Email: Understand the reason for reconnecting – networking, job opportunity, reference, or a personal update.
  2. Tone and Formality: Maintain a professional yet warm tone.
  3. Personalization: Reference past experiences and achievements shared with your ex-boss.
  4. Clarity and Brevity: Keep the email concise and to the point.
  5. Call to Action: Clearly state what you are hoping to achieve from the email.
  6. Proofreading: Ensure the email is free of errors.
  7. Follow-up: Be prepared to send a gentle reminder if you don’t hear back.

Step-by-Step Guide

Step 1: Define Your Purpose

Why are you reaching out? This will shape your email’s content. Possible reasons include seeking job opportunities, asking for references, or sharing personal updates.

Step 2: Craft a Compelling Subject Line

Your subject line should be clear, concise, and intriguing. For instance, “Catching Up and Sharing Exciting News” strikes a balance between personal and professional.

Step 3: Start with a Personal Greeting

Begin with a warm, personalized greeting. For example, “Dear [Ex-Boss’s Name], I hope this email finds you well…”

Step 4: Reintroduce Yourself

If it’s been a long time, a brief reintroduction might be necessary. Mention your previous role and any significant project you worked on together.

Step 5: Get to the Point

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Be clear about why you’re reaching out. Avoid beating around the bush.

Step 6: Keep it Professional Yet Personal

Share a brief update about your professional life, but also add a personal touch by recalling a shared positive memory.

Step 7: Be Respectful of Their Time

Acknowledge that they might be busy and express appreciation for any time they can give to read or respond to your email.

Step 8: Include a Specific Call to Action

What do you want from this interaction? Be it advice, a meet-up, or a job reference, be specific.

Step 9: Close with Appreciation

Thank them for their time and the impact they had on your career.

Step 10: Proofread

Review your email for any spelling or grammatical errors.

Email Template

Subject: Catching Up: A Note from a Former Team Member

Dear [Ex-Boss’s Name],

I hope this message finds you well. It’s been a while since we last connected. I was working as [Your Role] in [Company/Department], where we collaborated on [Project/Event]. I wanted to reach out, share some updates from my end, and also inquire about how you have been doing.

Since leaving [Company], I have moved on to [Brief Professional Update]. I often recall our time working on [Specific Project or Experience], which was a significant learning experience for me.

I am reaching out specifically to ask for [Your Request – e.g., reference, advice, etc.]. I understand you have a busy schedule, and I truly appreciate any assistance you can provide.

Thank you once again for the mentorship and guidance you offered during my time at [Company]. It would be wonderful to catch up over a coffee or a call if your schedule allows.

Looking forward to hearing from you.

Warm regards,

[Your Name]


Reconnecting with an ex-boss can open new doors and rekindle valuable professional relationships. Remember to be respectful, clear, and genuine in your approach.

Your email should reflect a blend of professionalism and personal touch, showcasing your growth while acknowledging past shared experiences.

We Want to Hear from You!

Have you ever written an email to a former boss after a long time? What was your experience? Share your stories and tips in the comments below! Your insights could be invaluable to others facing similar situations.

Frequently Asked Questions (FAQs)

A professional office setting with a young woman sitting at a desk, working on a computer

Q: How Do I Reconnect with an Ex-Boss After a Long Time?

Answer: I recently reached out to an ex-boss after several years. I started with a friendly email, mentioning a fond memory from our time working together. 

I updated them briefly about my career progress and expressed genuine interest in how they had been doing. Keeping it warm, professional, and concise worked well for me. They replied positively, and we’ve since rekindled a great professional relationship.

Q: What Should I Include in an Email to an Ex-Boss?

Answer: When I emailed my ex-boss, I made sure to include a brief introduction reminding them of who I am and our time working together. I briefly mentioned my current role and achievements, which were partly thanks to their mentorship. 

I also asked about their current endeavors and expressed my appreciation for their past guidance. This approach helped me maintain a professional yet personal tone.

Q: Is It Appropriate to Ask for a Reference in the First Email After a Long Time?

Answer: In my experience, it’s better to rebuild the connection first. I didn’t ask for a reference in my first email. Instead, I focused on catching up and re-establishing rapport. 

After a couple of exchanges, when the conversation naturally progressed, I then mentioned that I was exploring new opportunities and politely asked if they would be comfortable providing a reference. This patient approach was well-received.

Q: How Can I Apologize for Losing Touch with an Ex-Boss in the Email?

Answer: When I reconnected with my ex-boss, I acknowledged the time gap since our last communication. I apologized for not keeping in touch, citing my focus on career and personal development. 

I made sure to express that reconnecting with them was important to me. This honesty helped make our communication more open and sincere.

1 thought on “Email To An Ex-Boss After A Long Time: How To Draft It Right!”

  1. This is an incredible, useful, and practical guide for reconnecting with former bosses. The detailed steps and email template are particularly helpful in navigating this often-tricky communication

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