Interview Script·45 min·10 questions
Reconstructing why teams abandon project management tools after switching successfully
You're seeing teams churn from your project management tool at the 4-6 month mark, right after they've successfully onboarded and seemed engaged. The timing doesn't make sense — they've invested effort in the switch, trained their team, and appeared to be getting value. Yet they're still leaving for competitors or reverting to old systems.
Why standard questions fail here
Direct questions about why teams switched tools miss the emotional and practical journey that led to their decision. This script works backward from their switching moment to reconstruct the complete timeline — the accumulating frustrations, the breaking point, and the evaluation process. By anchoring in specific past behaviors rather than asking for general opinions, you'll uncover the hidden patterns that predict whether a tool switch will stick or fail.
Sample Questions
Grounded in The Mom Test and Jobs-to-be-Done.
JTBD principle: understand the context and job performer before diving into the job itself
Listen for their language - do they say 'projects', 'tasks', 'workflows'? Mirror their terminology throughout the interview
- How big is your team typically?
- What kinds of projects do you usually work on?
- Generic job descriptions without personal connection to project management
JTBD core technique: identify the struggling moment that triggered the job-to-be-done
Use the timeline technique - ask them to walk through it chronologically, day by day if needed
- What was the specific moment when you thought 'we need to change this'?
- Who else was involved in recognizing this problem?
- Vague complaints like 'it wasn't working' without specific incidents
- Rational post-hoc explanations that skip emotional triggers
Mom Test principle: ask for specifics in the past rather than general opinions
Probe for concrete details - names, dates, specific features that failed
- How did that impact the project outcome?
- What did you do as a workaround?
- How did your team react when this happened?
- Generic statements like 'it was hard to use' without specific examples
Customer Journey Mapping: understand the consideration and evaluation phase
Map their journey step-by-step - use phrases like 'and then what did you do?' to keep them moving chronologically
- What sources did you trust most for recommendations?
- What were you specifically looking for that your old tool didn't have?
- Jumping to the final decision without explaining the process
JTBD: understand the moment of switching and what progress they were hoping to make
Focus on their decision criteria, not features - what outcome were they hoping to achieve?
- What alternatives were you considering at the same time?
- What would have happened if you hadn't found a solution?
- Feature lists without connecting to desired outcomes
Customer Journey Mapping: capture the onboarding and early experience phase
Ask for a week-by-week breakdown - 'Tell me about week 1, then week 2' to get specific details
- What surprised you most during those first weeks?
- Tell me about the hardest part of getting your team on board
- Overly positive summaries that skip over friction points
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