Align Roadmap to Customer Pain | Dataford Interview Questions

Company Context

TaskFlow is a B2B SaaS work-management platform used by 25,000 small and mid-sized businesses for project tracking, approvals, and cross-functional collaboration. The company is growing steadily, but leadership believes the product roadmap has become too influenced by internal stakeholder requests and large-customer escalations rather than broad customer pain.

Problem

Over the last two quarters, TaskFlow shipped 14 roadmap items. Only 4 reached meaningful adoption, and NPS has remained flat at 31. Churn analysis shows that teams with fewer than 10 weekly active users are 2.3x more likely to cancel, and recent customer interviews repeatedly mention three pain points: onboarding complexity, notification overload, and poor visibility into task ownership. Meanwhile, Sales is pushing for more enterprise-specific requests, and Engineering wants to reduce platform debt.

You are the PM for TaskFlow’s core product. Your VP asks: How would you make sure your team’s priorities consistently reflect real customer pain points rather than the loudest internal voices?

Deliverables

Explain how you would identify and validate the most important customer pain points.
Describe the process you would use to translate those pain points into roadmap priorities.
Show how you would balance customer pain with business goals, technical constraints, and stakeholder pressure.
Define the artifacts, rituals, and decision rules you would put in place so this becomes repeatable across quarters.
Specify how you would measure whether the team is actually improving prioritization quality.

Constraints

You have one product analyst, one user researcher shared across three teams, and a 7-engineer squad.
The next quarterly planning cycle is in 4 weeks.
You can only fund 3 major initiatives next quarter.
At least 20% of engineering capacity must remain allocated to reliability and technical debt.
Leadership expects a clear prioritization method that can be explained to Sales, Support, and Engineering.

Problem

Company Context

Problem

Deliverables

Explain how you would identify and validate the most important customer pain points.
Describe the process you would use to translate those pain points into roadmap priorities.
Show how you would balance customer pain with business goals, technical constraints, and stakeholder pressure.
Define the artifacts, rituals, and decision rules you would put in place so this becomes repeatable across quarters.
Specify how you would measure whether the team is actually improving prioritization quality.

Constraints

You have one product analyst, one user researcher shared across three teams, and a 7-engineer squad.
The next quarterly planning cycle is in 4 weeks.
You can only fund 3 major initiatives next quarter.
At least 20% of engineering capacity must remain allocated to reliability and technical debt.
Leadership expects a clear prioritization method that can be explained to Sales, Support, and Engineering.

Problem

Company Context

Problem

Deliverables

Explain how you would identify and validate the most important customer pain points.
Describe the process you would use to translate those pain points into roadmap priorities.
Show how you would balance customer pain with business goals, technical constraints, and stakeholder pressure.
Define the artifacts, rituals, and decision rules you would put in place so this becomes repeatable across quarters.
Specify how you would measure whether the team is actually improving prioritization quality.

Constraints

You have one product analyst, one user researcher shared across three teams, and a 7-engineer squad.
The next quarterly planning cycle is in 4 weeks.
You can only fund 3 major initiatives next quarter.
At least 20% of engineering capacity must remain allocated to reliability and technical debt.
Leadership expects a clear prioritization method that can be explained to Sales, Support, and Engineering.

Problem

Company Context

Problem

Deliverables

Explain how you would identify and validate the most important customer pain points.
Describe the process you would use to translate those pain points into roadmap priorities.
Show how you would balance customer pain with business goals, technical constraints, and stakeholder pressure.
Define the artifacts, rituals, and decision rules you would put in place so this becomes repeatable across quarters.
Specify how you would measure whether the team is actually improving prioritization quality.

Constraints

You have one product analyst, one user researcher shared across three teams, and a 7-engineer squad.
The next quarterly planning cycle is in 4 weeks.
You can only fund 3 major initiatives next quarter.
At least 20% of engineering capacity must remain allocated to reliability and technical debt.
Leadership expects a clear prioritization method that can be explained to Sales, Support, and Engineering.