How to Run Your First Planning Poker Session

Running your first planning poker session feels intimidating. You're guiding your team through estimation, keeping everyone engaged, and making sure the process actually works. But here's the truth: with solid preparation, your first session can be smooth and productive.

This guide covers everything—from prep work two days out to the follow-up email you'll send afterward.

What is Planning Poker and Why Does It Matter?

Planning poker is a consensus-based technique where team members use numbered cards to estimate effort for user stories. Unlike traditional estimation methods where one person calls the shots, planning poker taps into your entire team's knowledge.

It works because it:

• Prevents anchoring bias (when the first estimate sways everyone else)
• Sparks discussion about different views on complexity
• Surfaces hidden assumptions and dependencies early
• Builds shared understanding

Your goal as a first-time facilitator? Create space for productive conversations. Perfection comes later.

Pre-Session Preparation: Setting Yourself Up for Success

Your session's quality gets decided before anyone shows up. Here's what to do.

Two Days Before the Session

1. Review and Refine Your Backlog Items

Get your user stories ready. Each one needs:

• Clear title and description
• Defined acceptance criteria
• Documented technical dependencies
• Reasonable size (nothing too massive to estimate)

Work with your product owner on this. Vague or oversized stories? Split them or add detail now.

2. Choose Your Estimation Scale

Stick with the modified Fibonacci sequence: 1, 2, 3, 5, 8, 13, 20, 40, 100. It gives you enough granularity without fake precision on big items.

Make sure your team knows what these numbers mean. Story points? Ideal days? T-shirt sizes converted to numbers? Document it and share it.

3. Select Your Planning Poker Tool

Physical cards work for in-person sessions, but most teams need digital. Pick something intuitive. Planning Poker has a clean interface for remote and hybrid teams—no account needed for participants.

Set up your session and test it. Know how to:

• Add items
• Reveal votes
• Record estimates
• Reset for re-estimation

One Day Before the Session

4. Send a Pre-Session Email

Tell your team what to expect:

• Date, time, duration (60-90 minutes for your first run)
• Session link
• Story list (5-10 stories is reasonable)
• Quick process explanation for newcomers
• What to review beforehand

Sample Email Template:

Subject: Planning Poker Session - [Date] at [Time]

Hi team,

We're running our first planning poker session on [Date] at [Time]. Plan for 90 minutes.

What is Planning Poker?
We'll use numbered cards to estimate effort together. This taps everyone's expertise and surfaces important discussions early.

Before the Session:
Review the user stories in [backlog tool/link]. We're estimating about 8 stories from the upcoming sprint.

How to Join:
Click here: [planning poker session link]
No account needed—just enter your name.

What to Prepare:
Read through the stories and note any questions for the product owner.

See you there!
[Your name]

5. Prepare Your Facilitator Script

Don't memorize it word-for-word. Just have a loose outline:

• Opening explanation
• Ground rules
• How you'll handle disagreements
• Time management approach

Specific scripts are in the next section.

Day of the Session

6. Final Checks (30 Minutes Before)

• Test the tool again
• Confirm all stories are loaded
• Grab reference materials (definition of done, team velocity)
• Ready your timer
• Join 10 minutes early

Opening Your First Planning Poker Session: The First 15 Minutes

The opening sets your tone. Here's what to say.

Your Opening Script (5 Minutes)

"Thanks for joining our first planning poker session. For anyone new to this, here's how it works.

Planning poker lets us estimate user stories as a team. Instead of one person guessing, we all weigh in—which gets us closer to reality.

The process:

1. I'll read a story, then our product owner explains what we're building
2. Ask questions about requirements and approach
3. Everyone picks a card privately
4. We reveal simultaneously
5. Big differences? The highest and lowest explain their thinking
6. Re-estimate until we agree (or mostly agree)

We're using 1, 2, 3, 5, 8, 13, 20, 40, and 100. Story points, not hours. They show relative effort compared to other stories.

Ground rules:

• All questions are valid
• No wrong estimates—we're learning
• 5-minute timebox per story
• We need consensus or close to it

Questions?"

Setting Expectations About Time (2 Minutes)

"We've got 90 minutes and 8 stories. About 10 minutes each. Some faster, some slower. If we run long, we'll schedule a follow-up.

Let me show you the tool..."

Tool Walkthrough (3 Minutes)

Share your screen:

1. Where to see the current story
2. How to pick a card
3. Where estimates appear
4. How to view full story details

Run a practice round. Try a warmup like "How many story points to eat a pizza?"

Establish a Baseline (5 Minutes)

Give your team a reference point:

"Here's a story we finished recently: [reference story]. We called it a 5. Use this as your baseline. Simpler stories get smaller numbers, tougher ones get bigger."

Concrete references beat abstract concepts every time.

Running the Estimation Process: Story by Story

Here's how to handle each story.

Step 1: Present the Story (1 Minute)

Read the title and description. Hand it to your product owner:

"[Product Owner name], walk us through what we're building and why."

Step 2: Facilitate Questions and Discussion (3-5 Minutes)

This is where value happens. Your job:

• Encourage questions
• Keep discussion on scope and approach
• Avoid deep implementation rabbit holes
• Watch the clock

Good prompts:

• "Questions about this story?"
• "Any technical dependencies?"
• "Assumptions we need to clarify?"
• "I'm hearing two approaches—let's align on which one we're estimating"

Past 5 minutes? Step in:

"We're at 5 minutes. Let's estimate, then continue if needed."

Step 3: Estimate Privately (30 Seconds)

"Pick your card based on effort and complexity versus our baseline. Don't show it yet—we reveal together."

If someone's slow:

"[Name], need more info, or should we skip you this round?"

Step 4: Reveal Simultaneously (Immediate)

"Reveal on three. One, two, three!"

Step 5: Interpret the Results

Scenario A: Everyone Agrees (or Close)

Same estimate or within one number:

"Consensus at [number]. Final concerns? No? Moving on."

Scenario B: Moderate Spread (e.g., 3, 5, 5, 8)

"Range from 3 to 8. [Person with 3], why smaller? [Person with 8], what complexity are you seeing?"

Then:

"Based on that, let's re-estimate."

Second rounds usually converge.

Scenario C: Wide Spread (e.g., 2, 5, 13, 20)

Big difference in understanding:

"Wide range means different assumptions. [High estimator], what are you picturing?"

After discussion:

"Sounds like we need to clarify [specific aspect] before estimating. Let's table this and return once we know more."

Step 6: Record and Move Forward

"Recording as [number] points. Next story..."

Common First-Time Issues and How to Handle Them

Challenges will pop up. Here's how to handle them.

Issue 1: Someone Estimates Based on Time

What happens: "I think this is 8 hours, so I'll say 8."

Handle it:

"We're using story points, not hours. Points show relative effort versus our baseline. If our baseline 5-pointer took a day, is this more or less effort?"

Issue 2: The Team Defers to One Person

What happens: Everyone copies the senior developer's estimate.

Handle it:

"Let's make sure everyone weighs in. [Junior developer], you've worked with this code recently—what's your take?"

Remind them: "Everyone's view matters. Frontend complexity, testing, deployment—it all factors in."

Issue 3: Discussion Gets Too Technical

What happens: Two developers debate implementation details.

Handle it:

"Great discussion, but let's not solve implementation now. Can we agree on a general approach for estimation?"

Can't agree quickly? "Sync after this session and we'll re-estimate once you've aligned."

Issue 4: Someone Always Estimates High or Low

What happens: One person consistently estimates 2-3x higher than everyone.

Handle it:

Private conversation after: "I noticed your estimates run higher. What are you factoring in that others might miss?"

They might see testing, documentation, or past gotchas. Their perspective can help the whole team.

Issue 5: Running Out of Time

What happens: 4 stories done, 6 to go, time's almost up.

Handle it:

"We're 45 minutes in with 4 stories estimated and 6 left. Let's hit the top 3 for the sprint and schedule a 30-minute follow-up for the rest."

Better to do fewer stories well than rush all of them.

Managing Energy and Engagement

Estimation sessions can drain energy. Keep it up.

Take Breaks

After 45 minutes: "5-minute break. Stretch, grab water, then we'll tackle the rest."

Use a Warmup for Re-engagement

Energy lagging? Quick non-work estimation:

"How many story points to plan a birthday party for 20 people?"

Lightens the mood.

Celebrate Consensus

Quick agreement? "That was smooth! We're getting this."

Positive reinforcement matters.

Watch for Zoom Fatigue

Remote sessions? Suggest turning off self-view. Gallery view beats staring at yourself.

Closing the Session: The Last 10 Minutes

Recap What You Accomplished

"Great work. We estimated 8 stories totaling 42 points. Solid foundation for sprint planning."

Gather Feedback

"First session done. What worked? What should we change?"

Listen without defensiveness. Common feedback:

• "Stories need more detail" - Work with PO on this
• "Discussion time felt short" - Adjust for next time
• "Still not sure what a 5 means" - Need more reference examples

Preview Next Steps

"We'll use these estimates in sprint planning on [date]. Thanks for the thoughtful discussions."

Follow-Up Email

Send within 24 hours:

Subject: Planning Poker Session Summary - [Date]

Hi team,

Thanks for a productive first session! Here's what we accomplished:

Stories Estimated: 8
Total Story Points: 42
Estimated Stories:
- [Story 1]: 5 points
- [Story 2]: 8 points
- [etc.]

Action Items:
- [Product Owner] to clarify requirements on Story X
- [Developer Y] and [Developer Z] to sync on technical approach for Story W

Your Feedback:
We'll improve pre-session story prep for next time on [date].

Next Steps:
These estimates go into sprint planning on [date] at [time].

Great job!
[Your name]

Post-Session: Learning and Improving

First sessions are learning experiences. Improve for next time.

Reflect on What Happened

Within a day, write down:

• What went smoothly?
• Where did you struggle?
• Which stories took longest and why?
• What patterns emerged?

Review Time Management

Track story duration. Consistently over 10 minutes? You might need to:

• Improve pre-session prep
• Set stricter time limits
• Use a parking lot for technical decisions

Analyze Estimate Patterns

Look for:

• Wide disagreement stories—what made them unclear?
• Quick consensus stories—what made them clear?
• Re-estimation stories—what info was missing?

These patterns show you how to prep better.

Iterate on Your Process

Make 1-2 small changes for next session. Don't overhaul everything. Common improvements:

• Send stories 2 days earlier
• Add 5-minute refinement before estimation
• Create a reference list of past estimates
• Adjust meeting length

Quick Reference: Your First Session Checklist

Two Days Before:

• Review backlog items with product owner
• Ensure stories have acceptance criteria
• Choose estimation scale (recommend modified Fibonacci)
• Set up planning poker session in tool
• Test the tool yourself

One Day Before:

• Send pre-session email with stories and logistics
• Prepare facilitator script
• Create reference story examples

Day Of:

• Join meeting room 10 minutes early
• Test planning poker tool again
• Have timer ready

During Session:

• Explain planning poker process (5 min)
• Set ground rules and expectations (2 min)
• Demo the tool (3 min)
• Establish baseline story (5 min)
• Estimate stories (10 min per story average)
• Take break after 45 minutes
• Recap and gather feedback (10 min)

After Session:

• Send summary email within 24 hours
• Record estimates in backlog tool
• Reflect on what to improve
• Schedule next session if needed

Your First Session Will Be Imperfect—And That's Okay

One thing to remember: aim for progress, not perfection.

Your first session will have awkward moments. You'll forget to timebox. Someone will ask a question you can't answer. The team might spend 20 minutes on a 3-point story.

Normal.

What matters:

• You created space for discussion
• Different perspectives surfaced
• Estimates beat one person guessing
• You learned for next time

Each session gets easier. The team gets faster. Discussions improve.

Getting Started with Your First Session

Ready to run your first session? Set one up at planning-poker.app. The platform works for teams new to the process, with an interface that lets you focus on facilitating.

Create your session, share the link, use this guide. You've got this.

The most important step? Starting. Your team's ready to collaborate—now go facilitate a great first session.