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New Year Messages to Send a Former Boss
Send your former boss a short, personal note with no ask attached. Thank them for one specific thing they taught you or did for you. Add a one-line update on where you are now. Then wish them well for the year ahead. The specific detail is what makes it work. It proves you remember them as a person, not a name on a list.
A former boss is one of the most valuable people in your network. They've seen your work up close. They can vouch for you in ways no one else can. A new year message is a natural, low-pressure reason to stay on their radar without needing anything from them.
What makes it land is being specific. Generic holiday wishes get skimmed. A note that names the lesson, the project or the moment they helped you gets read and remembered. It often gets answered, too. Keep it short and about them. Save any request for later.
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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. Email: Thanking them for one specific lesson, no ask
Subject: Something you taught me
Why it works: Naming one real lesson shows true gratitude and gives them a good reason to reply.
2. Email: After two years of silence, no ask
Subject: Happy New Year from an old team member
Why it works: It names the gap honestly and clearly drops any ask, so reconnecting feels easy, not awkward.
3. Text: Short note to a boss you still text
Why it works: It reads in two seconds, but the one real detail keeps it from feeling like a mass text.
4. Email: First new year since you left the company
Subject: My first January without your kickoff meeting
Why it works: Thanking them for a graceful exit builds goodwill just when the relationship could start to fade.
5. Email: Sharing a career win that traces back to them
Subject: A win that started on your team
Why it works: Managers love hearing that their bet on someone paid off, so this reads as credit to them, not bragging.
6. Email: To your former boss and the old team
Subject: Happy New Year to the old [Team name] crew
Why it works: Praising the team in front of the boss compliments their leadership and keeps you close to several people at once.
7. Email: New year note with a light ask for advice
Subject: New year, and a quick question
Why it works: The ask is small, specific and easy to turn down, and it says why their view in particular matters.
8. Text: Light and funny, for a boss with a sense of humor
Why it works: Poking fun at yourself while paying them a compliment is warm and safe, even with someone senior.
9. Email: Former boss who has retired
Subject: Happy New Year, and how is retirement treating you?
Why it works: Retired leaders rarely hear about their lasting impact, so this note may mean more than anything else they get in January.
10. Text: A slightly late new year message, mid-January
Why it works: Owning the lateness up front keeps it relaxed and still reaches them while a new year note feels natural.
11. Email: New year note asking them to be a reference
Subject: Happy New Year, and a favor if you're open to it
Why it works: It gives early notice, ties the request to work they saw, and promises to make the favor easy.
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
- Send between January 2 and January 10. The holiday inbox flood has cleared, but the year still feels fresh.
- Email on a weekday morning. Tuesday through Thursday works well, when they're really reading mail.
- Text only if you texted while you worked together. Send it at a decent hour on New Year's Day or the day after.
- If you miss the first two weeks, a note up to about January 20 still works. Just admit it's a little late.
- If your note has an ask, wait until the second week of January. Then it won't compete with their first-week catch-up.
Subject lines
- Happy New Year, [Name]
- Something you taught me
- Happy New Year from an old team member
- A win that started on your team
- Thinking of my [Company] days
- New year, and a thank you
- My first January without your kickoff meeting
- Happy New Year to the old [Team name] crew
- New year, and a quick question
- Still using your [specific detail] rule
- Happy New Year from [New City]
- A quick hello for the new year
- Wishing you a great year ahead
- Happy New Year, and a favor if you're open to it
- Happy New Year, and how is retirement treating you?
- A little late, but Happy New Year
What to avoid
- Don't send a generic wish like "Happy New Year to you and yours" with nothing personal. It reads like a mass message.
- Don't make your first message in years a job or referral request. It makes the whole note feel like a deal.
- Don't vent about your old company, your new company or anyone you worked with, even as a joke.
- Don't write a long life update. One or two lines about where you are now is plenty.
- Don't overdo the humor if your relationship was formal. Match the tone to how you really worked together.
- Don't add them to a group text or a long CC list with dozens of others and call it personal.
After you send it
If they reply, answer within a day and keep it brief, so the exchange stays easy. If you hear nothing, wait two to three weeks and let it go. A new year note doesn't need a follow-up. Then plan a light touch every three to four months. Congratulate them on a promotion or send an article on a topic you both cared about. Or share a win tied to their coaching. Small, regular notes keep you remembered without feeling like work.
Building the habit: how to keep in touch with contacts and what a personal CRM does.
One note a year isn't much of a link Set a light rhythm for your former boss, like every three months. Capstone drafts each check-in from your last talk, so it never sounds like a form letter.
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
What should I write in a message to my former boss?
Thank them for one specific thing they did for you. Add a one-line update on where you are now and a warm wish for the year. Keep it to a few short sentences. Mention a real detail, like a project, a lesson or a moment, so it feels personal. Leave out any request, unless you've stayed in regular touch.
What is the best way to write an email to your old boss?
The best way is short, specific and easy to answer. Use a clear subject line. Open with a greeting and your reason for writing. Mention something you worked on together, give a brief update and close warmly. Aim for under 150 words. If you need something, keep the ask small. Say why you're asking them, and give them an easy way to decline.
Is it weird to send a new year message to a former boss?
No, it's one of the most natural reasons to get back in touch. New year notes are expected and low pressure, so they work even after years of silence. Most former managers are glad to hear from people they led. That's most true when the note thanks them for something specific and doesn't ask for a favor.
Should I text or email my former boss for the new year?
Email is the safer default for a former boss. Text only if you texted often while you worked together, or still do. Email gives you room for a short update and a specific thank you. It also fits a professional relationship. A text works best for a quick, warm wish to someone you're already close to.
How long should a new year message to a former boss be?
Keep it short: two to four sentences for a text, and about 50 to 140 words for an email. That's long enough for one specific detail and a brief update. It's short enough to read in under a minute. A brief note is easier to reply to, and it shows you respect their time.
Can I ask my former boss for something in a new year message?
Yes, if you keep the ask small and clear, like a short call or asking to list them as a reference. Lead with the new year wish and a personal note. Explain why you're asking them in particular, and make it easy to say no. If you haven't talked in years, send a no-ask note first. Save the request for later.