Dear Boss · by Sandra Quill
120 polite notes, a fill-in performance review and signature pages, as an instant PDF the team can sign.
Dear Boss is a funny gift for your boss from the team by Sandra Quill. It holds 120 short, affectionate and deeply polite notes about meetings, email, deadlines and pizza parties, a Performance Review of the Boss to fill in, a Certificate of Excellent Bossing and signature pages, and it downloads instantly as a 114-page PDF.
- 120 polite notes in nine sections
- A Performance Review of the Boss and a Certificate of Excellent Bossing
- An instant PDF the whole team can print and sign
- 120
- polite notes
- 9
- sections
- 114
- pages, PDF
- 16 Oct
- Boss's Day
Why a Funny Gift for Your Boss From the Team Needs the Team's Voice
Your boss is good. Your boss also scheduled a meeting to discuss why you have so many meetings. This is the gift that says so, kindly.
- A group card collects signatures and no ideas.
- Everyone chips in, and the gift is a gift card.
- The gift has to be funny without being a career risk.
- Boss's Day arrives on 16 October, and shipping takes longer than that.
- You want something the boss can show off, not hide in a drawer.
Dear Boss Says What the Team Thinks, Politely
Pick a section to read its first entry, lifted straight from the book.
Section 1 · the first entry, from the book
Meetings and Calendars
We love it when a meeting ends early. For about eleven seconds, we believe we have been promoted.
Section 2 · the first entry, from the book
Email, Chat and 'Quick Questions'
Dear Boss, marking a routine status update 'High Importance' is like blowing a foghorn to announce a bagel.
Section 3 · the first entry, from the book
Deadlines, Priorities and 'Urgent'
You said the deadline was flexible. We flexed it. It snapped back with interest.
Section 4 · the first entry, from the book
Feedback and Performance Reviews
The performance review said 'exceeds expectations.' The raise said 'meets budget.' We understand the math is complicated.
Section 5 · the first entry, from the book
The Open-Door Policy
You said, 'Don't hesitate to reach out.' We reached. You were in a meeting about availability.
Section 6 · the first entry, from the book
Pizza Parties and Mandatory Fun
Dear Boss, three slices of lukewarm pizza as thanks for forty hours of overtime is an interesting exchange rate.
You said the deadline was flexible. We flexed it. It snapped back with interest.
Read a few pages first
1 / 4
How to Give Dear Boss in Five Steps
It is a gift for the whole team, so plan a short pass-around before the big moment.
-
Print one copy
Print the PDF at actual size on 5 x 8 inch paper, or fit it to US Letter or A4 and trim, and staple it as a booklet.
OUTPUT A booklet with writing pages.
-
Pass it round the team
Everyone adds a note on a signature page, each with its own prompt.
OUTPUT A note from every person.
-
Fill in the review together
Complete the Performance Review of the Boss as a team, using categories such as Calendar Realism and Urgency Calibration.
OUTPUT A review the boss can frame.
-
Sign the certificate
Everyone signs the Certificate of Excellent Bossing.
OUTPUT A document with team signatures.
-
Read the best note aloud
Present it on Boss's Day, a promotion or a birthday, and read the best note aloud.
OUTPUT A boss who laughs first, then reads on.
What Is Inside Dear Boss
- 120 quick reads in nine sections
- Meetings and Calendars, Email and Chat, Deadlines and Priorities, Feedback and Reviews, The Open-Door Policy, Pizza Parties and Mandatory Fun, Remote and Hybrid, What We Really Think When You Leave the Room, and What We Genuinely Appreciate.
- A Performance Review of the Boss
- Fill it in as a team, with categories such as Calendar Realism and Urgency Calibration.
- A Certificate of Excellent Bossing
- A page to sign as a team.
- Pages for the whole team to sign
- Each one has a prompt, so the notes are worth reading.
- A 114-page PDF, cover first
- Sized 5 x 8 inches, with a short second PDF on printing and stapling it.
- A kind ending
- The last section says what the team genuinely appreciates, in a way a boss can show off.
Where to buy, and what each store sells
| Store | Price | Includes |
|---|---|---|
| Whop | $9.99 | Instant PDF download |
| Gumroad | $9.99 | Instant PDF download |
| Etsy | $6.99 | Printable PDF download from Etsy |
Prices checked 10 October 2026. Each store shows its own refund terms at checkout.
When a Funny Boss Gift From the Team Lands Best
Boss's Day is 16 October each year, and many offices mark it on the nearest weekday. The book also fits a promotion, a birthday, the holidays, a manager's farewell and a team lead who has survived another quarter.
And it works because the team gives it together. The review and the certificate turn a joke into a shared activity, and the boss gets something to keep.
The book was written and drawn with AI tools, then selected, reworded and edited by the author, and Sandra Quill is a pen name. The store listings say so, and so does this page.
What You Download
One PDF of the whole book with the cover first, 114 pages at 5 x 8 inches, and a short PDF on printing and stapling it as a booklet. Nothing is shipped.
- 120
- notes
- 9
- sections
- 114
- pages
The review, certificate, signature and writing pages are made to be printed and written on. Print one copy for the boss.
Dear Boss: Frequently Asked Questions
What is Dear Boss?
It's a funny gift for your boss from the team, by Sandra Quill: 120 short, polite notes about meetings, email, deadlines, reviews, the open-door policy and pizza parties. It includes a Performance Review of the Boss, a Certificate of Excellent Bossing and signature pages.
What is a good funny gift for a boss from the team?
One the team makes together. This book gives the team the notes, a review to fill in and a certificate to sign, so the gift reads as a team effort.
When is Boss's Day, and is this a good gift?
Boss's Day is 16 October each year, and many offices mark it on the nearest weekday. Dear Boss works because everyone adds a note and someone reads the best page aloud.
Is it a physical book?
No. It's an instant PDF, so it works when Boss's Day is days away. Print it and staple it with the included guide.
Who is it for?
Managers and team leads, and the teams who want to give them something funny and kind.
What do I get when I buy it?
One PDF of the whole book with the cover first, 114 pages at 5 x 8 inches, and a short PDF on printing and stapling it as a booklet.
Is the humor safe for the office?
Yes. It's clean, with no profanity, politics or religion, and every entry is a fictional composite, not a real person, team or employer.
How much does it cost, and where can I buy it?
As of 10 October 2026 it costs $9.99 on Whop and $9.99 on Gumroad and $6.99 on Etsy. The edition table above lists what each store sells.
More questions
Is Dear Boss a good boss day gift?
Yes. As a boss day gift it works because the whole team takes part: everyone writes a note, the team fills in the review, and the boss gets a book to keep.
What is the Performance Review of the Boss?
It is a page the team fills in together, with categories such as Calendar Realism and Urgency Calibration, as a funny review the boss can keep.
What is the Certificate of Excellent Bossing?
It is a certificate page the whole team signs, to present with the book.
Is it a good gift for a boss who is leaving?
Yes. It suits a manager's farewell, because the last section says what the team genuinely appreciates.
Can the team sign it?
Yes. Print it and pass it round. Every signature page has a prompt, so people write something specific.
Does it work for a team that works remotely?
Yes. It has a section for remote and hybrid work, and you can send the PDF to the team and collect pages one at a time.
Was AI used to make it?
Yes. It was written and drawn with AI tools, then selected, reworded and edited by the author. Sandra Quill is a pen name.
Are there other titles in the series?
Yes. The Nurse's Edition, The Teacher's Edition, The Leaving Gift Book and Reply All are in the series, and the Office Humor Collection bundles all five.
Give a Funny Gift to Your Boss Before 16 October
Sandra Quill wrote the book for teams whose boss is good, and whose calendar is not. Download it, print it and pass it round. It is part of the funny gift books for work shelf.
Buying for more than one manager? The Office Humor Collection has five titles.