Monday: Map the Problem skill

Monday: Map the Problem

Monday sets the foundation for the entire sprint. By the end of the day, the team will have a shared understanding of the problem, a map of the customer journey, and a clear target for the week. Every minute counts: poor Monday execution means the rest of the sprint drifts without direction.

Schedule Overview

Time	Exercise	Duration
10:00 - 10:15	Welcome and ground rules	15 min
10:15 - 10:45	Long-term goal	30 min
10:45 - 11:30	Sprint questions	45 min
11:30 - 12:30	Customer journey map	60 min
12:30 - 1:30	Lunch	60 min
1:30 - 3:30	Ask the Experts	120 min
3:30 - 4:00	How Might We organization	30 min
4:00 - 4:30	Vote on HMWs	30 min
4:30 - 5:00	Pick the target	30 min

Welcome and Ground Rules

Before starting, the Sprint Master should set expectations for the week:

• No laptops or phones during exercises (breaks are fine)
• Silence during individual work phases
• The Decider has final say on all tie-breaking votes
• Timers are strict: when the bell rings, pencils down
• Write on sticky notes in thick marker so everyone can read from a distance
• Every voice matters, but talking happens in structured turns

Long-Term Goal Exercise

Purpose

Align the team on what success looks like. The long-term goal creates a north star that keeps every subsequent decision anchored.

How to Facilitate

1. Hand everyone a sheet of paper
2. Ask: "Imagine it is two years from now. Our sprint was a massive success. What changed? What is true about our product, company, or customers?"
3. Give 5 minutes for individual writing (silence)
4. Go around the room. Each person reads their goal aloud
5. Sprint Master writes each goal on the whiteboard
6. Discuss for 10 minutes: where do we agree, where do we disagree?
7. The Decider picks one goal or combines two

Example Long-Term Goals

Company Type	Long-Term Goal
B2B SaaS	"Enterprise customers renew their contracts at 95%+ because the product is indispensable to their daily workflow"
E-commerce	"First-time buyers come back within 30 days and recommend us to friends"
Healthcare	"Patients manage their chronic conditions without needing to call the clinic"
Fintech	"Users trust us enough to consolidate all their finances in one place"
Education	"Students complete the full course and can demonstrate the skill in a real job"

What Makes a Good Goal

• Focuses on the customer, not internal metrics
• Describes a changed behavior or belief
• Is ambitious but plausible in 2 years
• Can be broken into testable assumptions

Sprint Questions Exercise

Purpose

Surface the risks, assumptions, and unknowns that could prevent the long-term goal. Sprint questions flip optimism into productive skepticism.

How to Facilitate

1. Reframe the prompt: "To reach our goal, what has to be true? What could go wrong? What are we most uncertain about?"
2. Give 5 minutes for individual writing on sticky notes (one question per note)
3. Collect all sticky notes and read them aloud
4. Group similar questions on the whiteboard
5. The team votes (2 dot stickers each) on the most critical questions
6. The Decider selects the top 3 questions for the sprint to address

Example Sprint Questions

• "Will users understand what our product does within 10 seconds of landing on the page?"
• "Can we convince busy professionals to complete a 5-step onboarding flow?"
• "Will customers pay a premium when a free alternative exists?"
• "Do users trust an AI recommendation enough to act on it?"
• "Can non-technical users configure the product without support?"

Template

We believe [assumption].
If we are wrong, [consequence].
Sprint question: Will [specific user] actually [specific behavior]?

Customer Journey Map

Purpose

Create a shared visual model of how a customer moves from discovery to success. The map becomes the sprint's playing field.

Step-by-Step Process

1. Draw the frame: A horizontal line across the whiteboard with "Discovery" on the left and "Success" on the right
2. List the actors: Write customer types and key players above the map (e.g., "New user," "Admin," "Sales rep")
3. Map the steps: The Sprint Master asks the team to call out each step. Write them left to right as simple boxes connected by arrows
4. Keep it simple: Aim for 5-15 steps. If it grows beyond 15, you are going too deep
5. Use plain language: "Sees an ad" not "Awareness phase targeting via programmatic display"

Example Map: Project Management Tool

Hears from    Visits      Watches     Signs up    Creates      Invites     First       Weekly      Upgrades
colleague --> website --> demo    --> for free --> project  --> team    --> meeting --> routine --> to paid
                         video       trial                    members    review

Common Mapping Mistakes

Mistake	Problem	Fix
Too many steps	Map becomes unreadable	Merge similar steps, stay at 5-15
Internal process focus	Map shows your workflow, not the customer's	Always start with a customer action
Branching paths	Map becomes a flowchart	Pick one primary path; note alternatives as sticky notes
Skipping early steps	Map starts at "uses product"	Include how customers discover and evaluate

Ask the Experts

Purpose

Bring specialized knowledge into the room. Experts share what they know so the team operates from facts, not assumptions.

Who to Interview

• CEO/Founder: Vision, business constraints, strategic bets
• Sales/Business Development: What customers say before buying, common objections
• Customer Support: What customers complain about, where they get stuck
• Engineering Lead: Technical constraints, what is easy vs. hard to build
• Marketing: How customers find the product, messaging that resonates
• External expert (optional): Industry analyst, advisor, power user

Interview Format

Phase	Duration	What Happens
Introduction	2 min	Sprint Master explains what we need from the expert
Expert presentation	10 min	Expert shares their perspective on the challenge
Q&A	10 min	Team asks clarifying questions
HMW notes	During all phases	Team writes How Might We notes in real time

Good Questions to Ask Experts

• "What is the number one reason customers leave?"
• "What do customers say they want that we do not offer?"
• "What surprised you most about how customers use the product?"
• "If you could fix one thing, what would it be?"
• "What would a competitor need to do to beat us?"

Tips for the Sprint Master

• Keep each expert to 20 minutes total
• Gently redirect if the expert goes on tangents
• Remind the team to write HMW notes continuously
• Do not let one expert dominate Monday afternoon

How Might We (HMW) Notes

Purpose

Transform problems, insights, and complaints into opportunities. HMW notes reframe negatives as design challenges the team can solve.

How to Write HMW Notes

1. Listen for problems, pain points, and unmet needs during expert interviews
2. Rephrase each one as "How might we...?" on a sticky note
3. Write in thick marker, one idea per note
4. Keep them concise: 5-10 words after "How might we"

Conversion Examples

What You Hear	HMW Note
"Customers never finish onboarding"	HMW make onboarding feel worth completing?
"People don't understand our pricing page"	HMW make pricing instantly clear?
"Users create an account but never come back"	HMW give users a reason to return on day 2?
"Enterprise buyers need approval from 3 people"	HMW help champions sell internally?
"Support tickets spike every Monday"	HMW prevent the Monday confusion?

Common HMW Pitfalls

• Too broad: "HMW make the product better?" (not actionable)
• Too narrow: "HMW add a tooltip to the settings gear icon?" (already a solution)
• Contains a solution: "HMW add a chatbot?" (should be "HMW provide instant answers?")
• Negative framing: "HMW stop users from leaving?" (reframe: "HMW make users want to stay?")

Organizing and Voting on HMWs

1. After expert interviews, collect all HMW notes (expect 30-80 notes)
2. Read each one aloud quickly (2-3 seconds each)
3. Organize on the whiteboard by theme (group similar notes together)
4. Place themed groups near the relevant part of the customer journey map
5. Give each person 2 dot stickers
6. Vote silently (no discussion during voting)
7. The Decider gets 4 dot stickers

Target Selection

Purpose

Choose the single moment on the customer journey map that the sprint will focus on. Without a target, the team tries to solve everything and solves nothing.

How to Select the Target

1. Review the map with HMW clusters and vote dots visible
2. Look for the intersection of: high risk + high opportunity + answerable in one week
3. The Sprint Master asks: "Given our goal and our sprint questions, where should we focus?"
4. Brief discussion (10 minutes max, not a debate)
5. The Decider makes the final call

Target Selection Criteria

Criteria	Question to Ask
Impact	"If we solve this, does it meaningfully move us toward the long-term goal?"
Risk	"Is this the area where we are most uncertain?"
Feasibility	"Can we prototype and test a solution for this in 4 days?"
Learning	"Will testing this answer our most important sprint question?"

Example Targets

• "The first 5 minutes after signup: do users understand what to do?"
• "The pricing page: do visitors understand the value and choose a plan?"
• "The handoff from sales demo to first login: do buyers become users?"
• "The weekly report: do managers find it useful enough to keep paying?"

Monday Checklist

Before leaving for the day, confirm:

• Long-term goal is written on the whiteboard and agreed upon
• Top 3 sprint questions are identified and visible
• Customer journey map is complete (5-15 steps)
• At least 3 experts have been interviewed
• HMW notes are organized by theme on the map
• HMW votes are complete
• The Decider has chosen a target on the map
• Everyone knows the target and can explain it
• Tuesday agenda is confirmed

Common Monday Mistakes

Spending Too Long on the Goal

Problem: The team debates the long-term goal for 90 minutes, compressing everything else. Fix: Time-box to 30 minutes. The goal does not need to be perfect; it needs to be directional. The Decider breaks ties.

Mapping Internal Processes Instead of the Customer Journey

Problem: The map shows "engineering builds feature" and "QA tests" instead of the customer's experience. Fix: Start every step with a customer verb: "Customer sees," "Customer clicks," "Customer decides."

Expert Interviews That Turn Into Debates

Problem: The team argues with the expert instead of listening. Fix: Sprint Master enforces a "no debating" rule. The team asks questions and writes HMW notes. Disagreements become sprint questions.

Picking a Target That Is Too Broad

Problem: The target is "the entire user experience" or "our go-to-market strategy." Fix: A good target fits on one section of the map. If you cannot prototype and test it in 4 days, narrow it down.

Skipping HMW Notes

Problem: The team listens to experts but does not capture opportunities. Fix: Remind the team every 10 minutes to write HMW notes. Provide sticky notes and markers on the table before interviews start.

No Decider in the Room

Problem: The person with authority is "available by phone" or will "review the decisions tomorrow." Fix: Do not start the sprint. The Decider must be present for all key decisions, especially target selection. Reschedule if necessary.