How To Write An Old Boss To Say Hi (Sample Emails)

It is always nice to catch up with people you used to know. Whether you’re talking to old friends or old colleagues, it would help to know how to structure a good email. This article will explore how to say hi to an old boss via email.

How To Write An Old Boss To Say Hi

1. Choose The Right Subject Line For Your Catch-Up Email

Step one is potentially the hardest part for some people. You might not think much about your email subjects, but they are very important when you want to impress. Make sure you pick the right subject that tackles the main point of the email.

When emailing a former employer, it’s likely that you’re looking to catch up with them and their life, or you’re looking to be hired by them. Either way, it’s good to make sure you set up a strong subject that covers the reason why you’re emailing.

For example:

  • “About a job”

Isn’t a great choice. Sure, you might be very familiar with your old boss. You might also know that they prefer informal talk in emails. Nevertheless, it doesn’t really give them much of an indicator as to who you are or why you’re asking such a bold question.

Instead, you might want to try:

  • “Hey (name), it’s been a while.”

Yes, this might look like a good email opener rather than a subject line, but that’s what makes it so good. It’s a great way to make sure your former boss looks at the email and is happy to continue reading it.

2. How To Start An Email To Your Old Boss

Next, it would help to know how to start the bulk of the email. Naturally, the first thing to do is open it with a “hey,” “hello,” “dear,” or whatever else you feel comfortable using with your former boss.

Introducing yourself with a “hello” message is standard practice in emails. An email without a suitable greeting is rarely seen, and many people will think of it as far too rushed to be taken seriously.

So, you might want to try one of these:

  • Hey there, (informal)
  • Hi sir/ma’am, (a good sign of respect)
  • Dear (name), (formal choice)

Once you’ve established a suitable greeting, there are a few things you’ll want to get out of the way in the subject of the email.

Ask How They’re Doing

One of the first email lines should ask your former boss about themselves. You should say something like “How are you” or “I hope all is well.” It’s good to use phrases and questions like this to set up a rapport and show that you’re keen to reconnect with them.

Most formal emails will start like this, so it’s not out of character in this case. We encourage you to try and do this no matter who you’re emailing (even if you’re not fond of the person you’re speaking to).

Start With Small Talk

After asking how they are, introduce some small talk. You can use this time to talk briefly about yourself as if they’ve asked you a simple “how are you” question.

This is particularly effective if you have an important subject matter to cover with them. The more small talk you can get into your email, the less your former boss will need to ask you about.

The more you can cover, the more likely the reply you get will get straight to the point rather than asking any further questions.

Make Sure They Remember You

Funnily enough, this is a big one, and people forget it too often. Make sure your boss remembers you. If it’s been a few years, they might have moved on since when you worked together, and they may need a slight refresher about who you are.

Don’t be upset if they don’t remember you. Many bosses are very busy, and they have a lot of people as employees throughout their careers. It can be hard to keep up with all of these people.

3. Share What You’ve Been Up To Recently

The next step is to talk more openly about what you’ve been up to recently. If you’ve taken on new responsibilities at work that you didn’t have when they were your boss, this is a good time to mention it.

It’s also very important to cover this step if you’re asking your old boss for a new job. The more you can sell yourself and prove to them that you have new duties, the better off you’re going to be.

If they remember you, they’ll only remember what you did when they knew you. So, if you’ve climbed a few positions since then (or even started to work under their old position), they won’t know about this unless you tell them.

As always, when you’re talking to employers, don’t sell yourself short. Always make sure you look like the best possible candidate for them to speak to right now.

4. Move On To The Main Subject Of The Email

Now is the most important part of the email. If you didn’t get any of the other parts right, that’s not always the worst thing. Step four is where it counts. Get this wrong, and you might as well have sent an empty email to your boss.

Step four requires you to move on to the main subject of the email. Be bold about this. You want to make sure your former boss knows the exact reason why you are emailing them.

The reasons are plentiful. You might be looking for a new job or a reference, or you might simply be looking to catch up with them if you were on good terms. Whatever the case, make sure you cover this in the email content.

This is the main hook of the email. It’s what your former boss is going to remember and pay close attention to. If you can make sure you grab their attention quickly be using snappy phrases like:

  • I’m writing to find out if you have a position for me


  • I’m just checking in to see how you’re doing

Then you’ll be in a much better position to capture their attention.

5. Sign Off With Intention

Finally, you need to sign off with intention (and the correct tone). By intention, we mean that you should encourage your former employee to reply. Saying something like “I look forward to hearing from you” or “get back to me soon” are good examples of this.

Also, you’ll have to make sure you get the right tone. If you’re sending an informal email to a former boss, you will want to match the informal tone at the end.

You want to match energies like this:

  • Hey Michael,
  • Email contents
  • All the best,
  • Dan

But if you overlap informal with formal, you might end up with a weird combination that looks out of place:

  • Hey there, Stacy,
  • Email contents
  • Yours sincerely,
  • Mr. Smithers

Asking Your Previous Employer For A Job (Sample Email)

  • Subject: Hey Matthew, I have a query for you
  • Dear Matthew,
  • How are you doing? It’s been a while since we last spoke, and I’ve been very busy with my work over the last few weeks.
  • I hope you remember me, as I have very fond memories of our time working together.
  • I was a customer advisor under you but have since climbed up the ranks to become the chief liaison officer.
  • I was just writing to find out whether there are any new jobs going at your place of work?
  • I feel like I would be a great candidate.
  • I’m looking forward to hearing from you,
  • Thomas

Following all the points from above is what makes this email so perfect. We can use this to guarantee that we’ll get a response from our former employer. With luck, they’ll also offer us the job (or at the very least an interview).

Asking Your Former Boss For A Reference (Sample Email)

  • Subject: I would like to ask you about a reference
  • Hello Maria,
  • I hope you’re doing well! I know it’s been a while since we last spoke, but I’m eager to learn how you’re getting on with your new job.
  • I was your chief analyst back when you worked at The Pie Co. I hope you remember the great times we had together.
  • Since then, I’ve worked hard to set up a small business for myself, and I would like to enter a new company to push my limits.
  • I was wondering if you would be a reference for me, as they are looking for someone I used to work under.
  • Thank you so much for your consideration,
  • Jan

Writing Your Old Boss Just To Keep In Touch (Sample Email)

  • Subject: How are you doing, Amy?
  • Hey Amy,
  • It’s been a long time! How have you been? I can’t believe we haven’t been able to stay in contact as we promised.
  • Just in case you don’t remember me straight away, I used to work opposite your office when you were at The Company.
  • Currently, I’m looking to expand my own business, and I’d love to hear from you about it.
  • I think it would be of real interest to you.
  • Anyway, I would love to hear what you’ve been up to lately!
  • I can’t wait to hear from you,
  • Mitch