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How to Message a Former Boss You Haven't Talked to in a While
Send a short note that names something real from your time working together. Share one line of your news, and ask for nothing. Something like: "Hi [Name], it's been too long. I still use the [specific habit] you taught me at [Company]. I'm now at [New Company] and doing well. How are things with you?" Detail makes it read as real, not as a favor hunt.
A former boss is one of the most valuable people in your network. They know your work firsthand and can vouch for you. They often move into roles where they hire, buy or refer. Years of silence don't end that bond. But they do make the first message feel heavier than it is.
What makes the message land is proof you remember them as a person, not as a contact. Mention one thing they taught you or did for you. Give a quick update, and leave the door open. Keep it short enough to answer from a phone in under a minute.
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Free, no signup. The example is filled in: press the button, then replace it with your own situation. In Capstone, a message like it is written for each person you know when their check-in is due.
11 examples to copy
One message is easy. Hundreds of people, all year, is the hard part. Capstone Outreach puts everyone you know on a rhythm you pick, from weekly to every three months. When someone is due, a message like these is already written in your voice from your history with them. You approve it, and it goes from your own email or phone. See how it works.
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Everyone on a rhythm. Who is due, and when. Recorded in the app on a demo account.
1. After two years of silence, no ask (email)
Subject: Long time no see, [Name]
Why it works: A real memory plus a clear "no agenda" removes any pressure and makes replying easy.
2. Quick text when you still have their number (text)
Why it works: Naming yourself and your old company up front avoids an awkward "who is this?" moment. They may have lost your number.
3. Sharing a win they helped make possible (email)
Subject: You had a hand in this
Why it works: Most managers rarely hear how their coaching paid off. Giving them credit makes this a message they'll remember.
4. Congratulating them on a new role or milestone (email)
Subject: Congratulations on [new role]
Why it works: Their news gives you a natural reason to write. A real compliment shows it isn't a copy-paste congrats.
5. Reconnecting before you may need a reference (email)
Subject: Catching up, and a heads-up
Why it works: Being honest about the ask early, with an easy out, respects their time and builds trust.
6. Sending something useful you came across (email)
Subject: Saw this and thought of you
Why it works: Leading with something of value gives them a reason to reply that has nothing to do with duty.
7. Short note on a professional networking site (message)
Why it works: Replying to something they just shared shows you're paying attention. It gives the message an easy starting point.
8. Coffee invite when you're visiting their city (email)
Subject: In [City] on [date], coffee?
Why it works: A set date and place turn a vague "let's catch up" into a yes or no they can answer right away.
9. Clearing the air after an awkward exit (email)
Subject: It's been a while
Why it works: Owning the awkward part briefly, without too much sorry, resets the relationship on better terms.
10. Holiday or birthday text that reopens the door (text)
Why it works: A day that already invites good wishes makes a message out of nowhere feel natural.
11. Reconnecting when you have a business reason (email)
Subject: Long overdue hello (and an idea)
Why it works: Naming the business reason openly is more respectful than hiding a pitch inside a friendly hello.
Sending these to more than a few people? See how people keep track of who to follow up with, and when: what a personal CRM does and the best personal CRMs, compared.
When to send it
- Reach out when nothing is at stake. Write at least a few weeks before you might need a reference, an intro or a favor.
- Use a natural hook when one appears. That could be their promotion, company news, a post they shared, or your own news that ties to them.
- Send emails Tuesday through Thursday mornings. Inboxes are lighter than on Monday, and focus is better than on Friday afternoon.
- If you're traveling to their city, write one to two weeks ahead so a coffee invite is easy to fit in.
- Holidays, work anniversaries and birthdays are fine for a short text. Skip the busiest stretch of late December for longer emails.
Subject lines
- Long time no see, [Name]
- It's been too long
- A hello from your old [Company] team
- You had a hand in this
- Saw this and thought of you
- Congratulations on [new role]
- Still using what you taught me
- Catching up, and a heads-up
- In [City] on [date], coffee?
- Long overdue hello (and an idea)
- Quick update from [Your Name]
- Thinking of our [project name] days
- A belated thank you
- Hello from [New Company]
- It's been a while
- Remember [specific shared moment]?
What to avoid
- Don't open with a long apology for the silence. One line that mentions it is plenty.
- Don't make the first message a favor request dressed up as a hello. They will notice.
- Don't send a generic note that could go to anyone. One real memory is what makes it personal.
- Don't write a life story. Keep your update to one or two sentences.
- Don't bring up old office politics, complaints about the company or former coworkers.
- Don't use slang or memes with a boss you only knew at work, even over text.
After you send it
If you don't hear back, wait two to three weeks. Then send one short, friendly follow-up. Ideally, add something new, like an article that fits or a bit of your news. If there's still no reply, let it rest. Try again in a few months without mentioning the silence. Once they respond, keep the bond warm with a light note every three to four months. Congratulate their wins, share useful finds, and plan a coffee or call about once a year.
Building the habit: how to keep in touch with contacts and what a personal CRM does.
Don't let it be years again Once you reconnect, put your old boss on a rhythm, like every three months. Capstone writes each check-in from your last talk. If you spoke in between, it waits.
Start 14 days free, then $25/mo
A study of 20 million LinkedIn members found that acquaintances, more than close friends, led to new jobs (Science, 2022). Capstone keeps those people warm. You approve every message, and it goes from your own email or phone.
Frequently asked questions
How can I say "long time no see" in a formal way?
Say "It's been a long time since we last spoke" or "It's been too long since we were last in touch" instead. Both carry the same warmth with a more formal tone. In an email to a former boss, follow it with a real memory and a short update. For example: "It's been a long time since we last spoke, and I still think about the [project] we led at [Company]."
What to say for a Long time no see?
Say it, then make it specific. Pair "long time no see" with a real detail from your shared past and a quick update. The phrase alone sounds empty. The detail shows you actually remember them, and it makes them want to reply. For example: "Long time no see! I still use your [habit] at [New Company]."
How to reply to a Long time no see message?
Reply warmly, match their energy and ask a question back. If they mention a catch-up, suggest a set time. If your former boss reached out first, thank them, since that small effort deserves it. Something like this works: "It really has been too long! Great to hear from you. I'm now at [Company] working on [area]. How are things with you?"
How do I write an email to someone I haven't seen for a long time?
Keep it short, specific and pressure free. Use a clear subject line and open with a line that notes the gap. Mention one real memory and give a one or two sentence update. End with an easy question or open invite. Aim for under 150 words. Skip long apologies for the silence, and save any requests for a later message.
Is it weird to message a former boss after years of no contact?
No. Most former managers are glad to hear from people they worked with. Reconnecting is a normal part of work life, and a thoughtful note usually reads as flattering, not strange. It only feels awkward when the message is vague or comes with a quick request. Lead with a real memory and let the talk grow naturally.
Should I ask my former boss for a reference in the first message?
Only if you need it soon, and then be upfront about it. If you have time, send a no-ask hello first and make the request a few weeks later. If you're already job hunting, pair a real catch-up with a clear request that's easy to decline. Offer to send your resume and a summary of the roles you want.