Valentine's Day retrospective

A warm retro for mid-February: what the team fell in love with, what broke its heart, and a valentine for a colleague who made a difference. In ProstoRetro the template is called My Love.

I fell in love with

People, features, projects, processes

It broke my heart

People, features, projects, processes

Valentines

Give a valentine

Use this template — it's free

What a Valentine's Day retrospective is

The board has three columns. I fell in love with collects what made people happy over the last weeks. It broke my heart collects what let them down. Both columns carry the same prompt: people, features, projects, processes. The third column, Valentines, holds short notes to a specific colleague or team, thanking them for something they did.

Under the hearts, the first two columns are a familiar What Went Well retro. The holiday language changes three things:

• It asks how strongly people feel. "I fell in love with the new deploy pipeline" says more than "deploys improved". Heartbreak is for things people cared about, so that column fills with what actually hurt rather than with small irritations.
• It covers people, not only process. The prompt lists people, features, projects and processes. That invites cards about a teammate who moved on, a feature that was cut, a project that ended — losses a process-focused retro rarely names.
• It gives thanks its own column. Thanking colleagues is easy to intend and easy to skip. Here, appreciation has a place on the board and its own slot on the agenda.

When to use it, and when not to

It suits sessions where warmth matters as much as fixes:

• the retro closest to Valentine's Day;
• after a long, hard stretch, when people need to hear that their work was noticed;
• at the end of a project, or when the team is about to split up or change shape;
• a team that works well together but rarely says thank you;
• a team-building session that should still end with a couple of real actions.

Pick something else when:

• Relationships are strained. Valentines between people in conflict come out forced or sarcastic. Deal with the tension first, for example with Elephant in the Room.
• The theme doesn't suit the team. Not everyone celebrates Valentine's Day, and some people find romance at work uncomfortable. Keep the tone playful rather than romantic, and see the variations below for a version without hearts.
• You need a close look at process. Love and heartbreak are coarse categories. When the team needs to fine-tune its practices, Starfish gives you five directions instead of two.
• Something has just broken. In the week after an incident, hearts feel off. Run a plain retro and save this one for a calmer sprint.

The three columns

I fell in love with: what made you happy

People, features, projects or processes that gave you joy or pride. The test against the Valentines column: a card here is about what you enjoyed, written for the whole team; a valentine is a message to someone in particular.

• Preview environments: every pull request gets its own link to click through
• Async standups in the channel instead of a 9:30 call
• Dark mode shipped, and customers wrote to support just to say thanks
• How fast design and backend agreed on the new API

It broke my heart: what let you down

Things you cared about that went wrong, ended or were taken away. The test against an ordinary complaint: it hurt because it mattered. A slow build is an annoyance; the feature you spent two months on, cut a week before launch, is heartbreak. When a card here is about a person, it is about losing them, never about blaming them.

• Offline mode was cut two weeks before the release
• Ana moved to the platform team, and we lost our best reviewer
• The roadmap changed twice in one month
• The redesign we were proudest of tested worse than the old page

Valentines: thanks to a specific person

A short note to a colleague, or to another team, naming what they did and why it mattered to you. The test: it has a recipient and a reason. "Thanks for everything" is kind; "your comments on my first pull request made me feel welcome" is a valentine.

• To Priya: your review comments taught me more about SQL than any course
• To the support team: your weekly bug digest saved us hours of triage
• To Leo: thanks to your on-call handbook, my first night on call was calm
• To whoever wrote the local seed script: I owe you a coffee

Use this template — it's free

A 45-minute Valentine's Day retro agenda

This plan suits four to ten people. Leave real time for the valentines: people want to hear them read aloud.

1. Warm-up, 5 minutes. Something light from our icebreaker questions — the food questions work well — or a round of Scribbles, the drawing game built into ProstoRetro.
2. Silent writing, 8 minutes. Everyone fills all three columns, with at least one valentine each. Nobody sees the others' cards until the writing ends.
3. Valentines read-out, 7 minutes. When the cards are revealed, read the Valentines column aloud before anything else, naming the recipient first. Valentines are not grouped or voted on; they are delivered.
4. Grouping, 5 minutes. Group the love and heartbreak cards. ProstoRetro can suggest the groups and name them with AI.
5. Voting, 3 minutes. Vote on heartbreaks the team can still mend and on loves worth protecting.
6. Discussion, 12 minutes. Take two heartbreaks — what would mend this, or keep it from happening again? — and one love: how do we make sure we keep it?
7. Action items, 4 minutes. One or two actions with owners and due dates. A light retro is still a retro.
8. Close, 1 minute. One word from each person about the session.

Running it with a remote team

• Sign the valentines, shield the heartbreaks. Cards are anonymous by default, and each person decides per card. Most valentines mean more with a name on them; a heartbreak about a management decision may need to stay unsigned.
• Add a picture. Cards can carry images and GIFs, pasted from the clipboard or a link. On a valentine, a GIF is part of the message.
• Invite the people you want to thank. A valentine to another team lands better when that team is on the call. With the board open to anyone, a colleague from support or design joins from the link with just a name.
• Collect valentines all week. On Monday, open an infinite room, a board with a permanent link, and let people add valentines as they think of them. The cards stay hidden until the meeting, so the surprise holds.
• Keep the thanks in writing. After the retro, every card, valentines included, stays on the summary page, and signed-in participants get it by email.

Variations

Secret valentine

A few days before the retro, draw names so that each person writes a valentine to one assigned colleague, as in a gift exchange. Everyone receives at least one, and it nudges people to notice a teammate they rarely work with. People can still write extra valentines to anyone they like.

Love letter and breakup letter to your product

Point the first two columns at your own product, seen through a user's eyes: what users fell in love with and what broke their hearts. Invite support and sales, who hear both every day. Designers will recognize the idea from the love letter and breakup letter exercise used in user research. Keep the Valentines column for thanking the people who passed the feedback on.

Any time of year

The same structure works in any month — after a project ends, or as a send-off for a teammate who is leaving. If the hearts feel out of season, build a custom template with neutral names, such as "Loved", "Lost" and "Thanks", and your own colors.

Common mistakes

• Valentines that get too personal. Keep them about work: help, skill, kindness. Never appearance, and nothing that could read as flirting.
• Heartbreak turned into blame. "Ana left" is a loss; "Ana dropped the ball" is an accusation. In the discussion, steer cards like that to the situation, not the person.
• No actions because it's a fun retro. The heartbreak column often hides a real problem. Give at least one of them an owner.
• Voting on valentines. Thanks are not a contest. Read them out and leave them out of the vote.
• Forcing the theme. If the team rolls its eyes at hearts, keep the columns and drop the costume.

FAQ

What is a Valentine's Day retrospective?

A themed retro held around February 14. The team lists what it fell in love with and what broke its heart, and writes valentines — short notes of thanks — to colleagues. It ends with a few actions, like any other retro.

What should I write in a retro valentine?

Name the person, what they did and why it mattered to you, in one or two sentences: "To Sam: you answered every question in my first week without making me feel slow." Specific beats sweet.

Is a Valentine's Day retro appropriate at work?

Yes, if the tone stays friendly rather than romantic and the valentines stay about work. Explain the format before the session, and let people who don't celebrate the day join in without the hearts; the columns work without the theme.

Can I run a Valentine's Day retrospective online for free?

Yes. In ProstoRetro the template is called My Love; choose it when you create the board. The app is free to use with your whole team, and everyone joins from a link. New to it? Read how a retro in ProstoRetro works, or see all retrospective templates, including Three Wishes, another light format.