What Is Questimate?

Planning poker that your team actually looks forward to. Same estimation rigour, significantly less dread.

The Short Version

Questimate is a free, web-based planning poker tool that wraps sprint estimation in a cooperative RPG adventure. Your team picks character classes, votes on story points using Fibonacci cards, earns XP and loot, and — if you connect Jira — syncs the agreed estimates straight back to your backlog. It’s the estimation ceremony your team has, but with character sheets instead of spreadsheets.

Why Does It Exist?

Sprint estimation is one of the most important agile ceremonies. It determines what your team commits to building for the next one or two weeks. Get it right and sprints are predictable. Get it wrong and you’re either crunching or twiddling your thumbs.

It’s also one of the most dreaded ceremonies. In most teams, estimation looks like this: someone reads a ticket title, people silently hold up numbers, someone types the result into Jira, and this repeats for 30–60 minutes. Engagement drops, estimates get sloppy, and by the tenth story everyone’s just voting whatever the senior dev voted.

Questimate exists because we believe the problem isn’t estimation itself — it’s the ceremony around it. The mechanics of planning poker are sound. The experience just needs to not be boring.

How It Works

The DM hosts a session. One person creates a session (we call them the Dungeon Master) and gets a 5-character code to share. They can add stories manually, import from Jira, or start empty and add on the fly.
The party assembles. Team members join with the code — no account needed for guests. Everyone picks a character class (Warrior, Mage, Rogue, or Cleric) and an avatar.
The quest begins. Each story becomes an “encounter.” The DM presents it, the team reads the details, and everyone plays a Fibonacci card simultaneously.
Cards are revealed. If the team agrees, the encounter is defeated and the party earns XP and loot. If estimates diverge, Parley mode triggers a structured discussion before a re-vote.
Rinse and repeat. The party progresses through encounters, with tavern events between stories to break up the session. At the end, results can be exported or synced to Jira.

Key Features

Character Classes & Progression

Four classes — Warrior, Mage, Rogue, Cleric — each with unique avatars. Players earn XP for voting, reaching consensus, and participating in tavern events. Characters persist across sessions, so your team’s Mage is still levelling up next sprint.

Parley Mode

When estimates diverge significantly, Parley mode activates. It’s a structured discussion phase where outliers explain their reasoning before the team re-votes. This turns “why did you vote that?” from an awkward moment into a productive one.

Jira Integration

Connect your Jira Cloud account via OAuth, import issues from a sprint or board, and write agreed story points back with one click. No Jira plugin required — just a secure OAuth connection. Learn more about the Jira integration.

Loot & Tavern Events

After encounters, players can receive loot drops (Common through Legendary). Between stories, tavern events give the team a quick vote-based interlude — a palate cleanser that keeps the session from feeling monotonous.

Guest Access

Only the host needs an account. Everyone else joins with a session code and a display name — no signup, no install, no friction. Guests can create an account later to keep their character.

What It’s Not

Questimate isn’t a project management tool. It’s not trying to replace Jira, Linear, or whatever your team uses to track work. It does one thing — sprint estimation — and tries to make that one thing genuinely enjoyable.

The RPG layer is a bit ridiculous, and we know it. But “a bit ridiculous” turns out to be exactly what a 45-minute estimation session needs. We take the estimation seriously. We just don’t take the ceremony seriously.

Under the Hood

Real-time WebSocket sync — votes and reveals are instant
Works on desktop, tablet, and phone (PWA supported)
Fibonacci scale: 1, 2, 3, 5, 8, 13, 21, plus ? and infinity
Up to 5 active voters per session, plus unlimited observers
Free for all team sizes, no trial period
No cookies beyond authentication — we don’t track you