Sample Email to Old Boss for Job: How to Write a Convincing Message

Have you ever found yourself in a situation where you’re on the hunt for a new job, but you’re not sure where to start? Maybe you’ve been out of the workforce for a while, or you’re ready for a change but unsure of where to turn.

One potential solution: reach out to your old boss.

Now, before you jump to conclusions, hear me out. Your old boss — assuming you left on good terms and maintained a positive relationship — could be an invaluable resource in your job search. After all, they know your strengths, your work ethic, and your personality better than most. They may even have new, relevant positions available or know of interesting opportunities in your field.

But how do you go about sending that initial email? What should you say without coming across as desperate or presumptuous?

Never fear. We’ve compiled some sample emails for you to use as a starting point. You can edit them as needed to fit your particular situation and tone. With a few tweaks and a little confidence, you might just land your dream job.

The Best Structure for a Sample Email to Your Old Boss for a Job

Emailing your old boss for a job can be a nerve-wracking experience. It’s important to craft a message that is both professional and persuasive. In this article, we’ll discuss the best structure for a sample email to your old boss for a job. With this structure, you’ll be able to effectively communicate your interest in the position and highlight your relevant experience and skills.

Paragraph 1: Greeting and Intent

The first paragraph of your email should take care of two things: greeting your old boss and stating your intention to apply for the job. Keep in mind that your old boss may have received a flood of emails and may not immediately recognize your name. Therefore, it’s important to include a quick reminder of who you are and where you worked together. For example: “Dear [Old Boss’s Name], I hope this email finds you well! It’s [Your Name] from [Previous Company]. I wanted to reach out to express my interest in the [Position Name] role that recently opened up at [Current Company Name]…”

Paragraph 2: Relevant Experience

The second paragraph should be devoted to highlighting your relevant experience and skills. Here, you should briefly touch on your accomplishments in your previous role and how they align with the requirements of the position you’re applying for. Most importantly, you want to demonstrate to your old boss that you have the necessary qualifications to excel in the role. For example: “During my time at [Previous Company Name], I was responsible for [Accomplishment A] and [Accomplishment B], which gave me the experience and skills needed to excel in the [Position Name] role…”

Paragraph 3: Reasons for Job Change

The third paragraph is where you should address any questions your old boss may have about your reasons for leaving the company in the first place. Be honest and transparent about the reasons for your departure, but make sure to highlight that you’re eager to return to the company and bring value to the team. For example: “I was excited to hear about the opening at [Current Company Name], as I have been following the progress of the company and I believe that I can make a valuable contribution to the [Department Name] team…”

Paragraph 4: Conclusion

The final paragraph should be a concise conclusion that restates your interest in the position, thanks your old boss for their time, and invites them to discuss the position further. For example: “Thank you for taking the time to review my application. I look forward to hearing back from you about the possibility of joining the [Company Name] team once again. If you have any questions, please don’t hesitate to reach out to me. Thank you!”

In conclusion, emailing your old boss for a job requires a professional and persuasive message. Following the above structure will help you effectively communicate your interest in the position and showcase your relevant experience and skills. Remember to be honest, transparent, and concise in your message, and you’ll be on your way to landing your dream job!

7 Sample Emails to Old Boss for Job

Seeking a Job at Your Company

Dear [Boss Name],

I hope this email finds you well. I am reaching out to you today because I am actively seeking employment at your organization. As you may remember, I worked with you at [previous company] and I have always admired your leadership and management style.

In my current job, I have gained extensive experience in [relevant skills and job duties]. However, I believe that your company would be the perfect place for me to grow and further develop my skills.

If there are any open positions that you think would be a good fit for me, I would be grateful for your consideration and recommendation. Thank you for your time and consideration.


[Your Name]

Recommendation for a Job at Your Company

Dear [Boss Name],

I hope this email reaches you well. I am writing to you today to recommend [Name of Recommended Candidate] for any vacancies at your company. [He/She/They] was a colleague of mine at [previous company], where we both worked under your leadership.

[Recommended Candidate] is a hardworking, dedicated and driven individual. During our time at [previous company], [he/she/they] demonstrated excellent [relevant skills or job duties they excelled in]. Furthermore, [he/she/they] possesses a superb [relevant skill or characteristic] that is valuable in any job [he/she/they] takes on.

I believe that [Recommended Candidate] would be an asset to your team and I strongly recommend [he/she/they] for any open positions. Thank you for your time and consideration.


[Your Name]

Returning to the Workforce after a Break

Dear [Boss Name],

I hope this email finds you well. It has been [length of time since you left previous company] since I left [previous company] to take a break from my career. During this time, I [briefly mentioned reason for break]. After taking this time to focus on myself, I am eager and ready to return to the workforce.

Given my previous experience and success working under your leadership at [previous company], I am writing today to inquire if there are any current open positions at your organization that you believe would be a good fit for me.

I am looking for an opportunity to grow, learn and contribute as a valued member of your team. Thank you for your consideration, and I hope to speak with you soon.


[Your Name]

Transitioning into a New Career Field

Dear [Boss Name],

I hope this email finds you well. As you may know from my work at [previous company], I have always been passionate about [previous career field]. However, in the recent years, I have felt a growing desire to transition into a new career field, specifically [new career field].

With your guidance and mentorship, I was able to gain valuable experience in areas such as [relevant skills or job duties] which, I believe, will be transferable to this new career field. I am reaching out to you today to ask if you know of any open positions in [new career field] or if you have any recommendations for someone who is embarking on this new journey.

Thank you for your time and consideration.


[Your Name]

Entrepreneurial Venture with Boss’s Partnership

Dear [Boss Name],

I hope this email finds you well. After careful consideration and planning, I have decided to embark on a new entrepreneurial venture. My goal is to [briefly describe the venture and its benefits].

After working closely with you at [previous company] and watching you lead with innovation and success, I believe that I could benefit from your experience and potential partnership in this new endeavor.

I am reaching out to you today to inquire if this is something that you would be interested in hearing more about and, if so, if you would be open to discussing potential partnership opportunities.

Thank you for your time and I look forward to hearing from you.


[Your Name]

Reconnecting for Mentorship and Career Advice

Dear [Boss Name],

I hope this email finds you well. Although it has been some time since we worked together at [previous company], your leadership and mentorship had a significant impact on my professional development. Since then, I have had the opportunity to develop new skills in [relevant skills or job duties], and I am grateful to have built a successful career in [current career field].

However, as I approach the next steps in my career, I am hoping to reconnect with you and receive your guidance and advice. In particular, I am interested in hearing your thoughts on [specific career-related topic or question] as I continue to grow and develop as a professional.

If you have the time and willingness to connect with me to discuss any career advice or mentorship that you could offer, I would be grateful. Thank you for considering my request.


[Your Name]

Requesting a Reference for a Job Application

Dear [Boss Name],

I hope this email finds you well. I am reaching out to you today to request a reference for an upcoming job application. As you know from our time working together at [previous company], I pride myself on my work ethic, and dedication to excellence.

In the pursuit of continuing my career development, I am pursuing a new job opportunity at [prospective company] and would be grateful if you could speak to my skills, experience, and work ethic.

Please let me know if this is something that you feel comfortable doing for me, and if so, I will provide you with any information that you need.

Thank you for your time and consideration.


[Your Name]

Tips for Writing a Sample Email to Your Old Boss for a Job

When you are reaching out to your old boss for a job, it is important to approach the situation tactfully and professionally. Here are some tips to help you craft a compelling email that will help you land your dream job:

1. Start with a Personal Greeting

Begin your email by addressing your old boss by name and expressing your gratitude for the time you spent working together. Try to make the greeting as personal and warm as possible, as this will help you build a stronger connection with your boss and increase the chances of them responding positively to your request.

2. Explain Why You are Reaching Out

After the greeting, provide a brief explanation of why you are reaching out. This could include your desire to explore new career opportunities, your passion for your former company and its products/services, or your interest in reconnecting with your old colleagues and the culture of the workplace. Be sure to convey your enthusiasm and interest in the company, as this will demonstrate your commitment to the role you are hoping to secure.

3. Highlight Your Relevant Skills and Experience

Next, you should highlight your relevant skills and experience that make you an ideal candidate for the position you are seeking. This could include any relevant education, training, or certifications you have obtained, as well as your past work experiences and achievements that demonstrate your ability to excel in similar roles. Be sure to focus on your strengths and how they align with the requirements of the role you are applying for.

4. Request a Meeting or Call

Finally, you should conclude your email by requesting a meeting or call with your old boss to discuss the opportunity further. Be sure to express your gratitude for their time and consideration, and provide your contact information so they can get in touch with you easily. By requesting a meeting or call, you will be able to further explain why you are the best candidate for the job and demonstrate your passion for the company and the role you are hoping to secure.

By following these tips, you will be able to craft a compelling email to your old boss that showcases your skills and experience and helps you land your dream job.

Frequently Asked Questions (FAQs) About Writing a Sample Email to an Old Boss for a Job

What should I include in my email to my old boss?

You should include a brief introduction of yourself, explain why you’re reaching out, and attach your resume and a cover letter.

How do I address my old boss in the email?

You should start the email with a professional greeting, such as “Dear [Hiring Manager’s Name],” or “Hello [Hiring Manager’s Name].” If you’re not sure how to address your old boss formally, it’s better to err on the side of being too formal than not formal enough.

What should I say in the body of the email?

You should briefly explain why you’re interested in the job, provide a few highlights of your experience that show you’re a good fit for the position, and express your enthusiasm for reconnecting with the company.

What tone should I use in the email?

You should use a professional and respectful tone in the email. Be polite and convey your excitement for the potential opportunity to work with your old boss again.

How long should the email be?

Your email should be short and to the point. Keep it under 250 words if possible.

When should I send the email to my old boss?

You should send the email to your old boss as soon as possible after you’ve heard about the job opening, and ideally within 24-48 hours.

What should I do if I don’t receive a response?

If you don’t receive a response within a week or so, you can follow up with a friendly email to ask if there have been any updates on the hiring process. But don’t be pushy or overbearing — hiring takes time, and your old boss may be busy with other priorities.

Sincerely Yours!

Thanks for sticking around till the end. I hope that my email sample has given you a heads up on how to compose a professional letter to your old boss. It’s undeniable that reconnecting with former colleagues might become your gateway to a brighter future. So, never hesitate to take that bold move. If you have any queries or want to share your experience with us, leave a comment below. Keep exploring our website, and we promise you’ll find lots of valuable content. Until then, farewell, and we’ll catch up soon!