Interview Script·45 min·10 questions

Understanding why agency clients abandon project tools after three committed months

You're seeing a clear pattern: creative agency clients who seemed engaged with your project management platform are canceling right around month three. You have the usage data and cancellation timing, but the exit surveys aren't telling you why clients who made it past the initial setup and first few projects suddenly decide the tool isn't working for them.

Why standard questions fail here

Direct questions about why people cancelled miss the gradual shift that happens between month two and three. This script reconstructs the specific moments when successful workflows started breaking down, anchoring in actual project timelines and client situations rather than asking people to rationalize decisions they made weeks ago.

Sample Questions

Grounded in The Mom Test and Jobs-to-be-Done.

Q1 Can you start by telling me a bit about your agency - what kind of creative work do you focus on, and what's your role there?
Why ask this?

Moment-Driven methodology: establish context before diving into specific moments

Technique

Let them talk freely for 2-3 minutes. Note their language choices about their work and responsibilities.

Follow-up Prompts
  • How many projects do you typically juggle at once?
  • Who else is involved in project coordination?
Watch out for
  • Generic company descriptions without personal role details
Q2 Think back to before you started using any project management software - can you walk me through what a typical project looked like from start to finish? What tools were you using?
Why ask this?

JTBD: understand the struggling moment that triggered the search for a solution

Technique

Use the narrative technique - ask for a specific project story, not general descriptions

Follow-up Prompts
  • What was the most frustrating part of that process?
  • Can you tell me about a specific project where things went wrong?
Watch out for
  • Vague generalizations like 'we were disorganized' instead of specific pain points
Q3 What was happening in your agency that made you think 'we need to find a better way to manage projects'?
Why ask this?

JTBD: identify the catalyst event that triggered active searching

Technique

Push for the specific trigger moment - use the 5 Whys technique if they give surface-level answers

Follow-up Prompts
  • Was there a particular project or client situation that was the final straw?
  • Who else was feeling this pain?
  • What did you try first before looking for software?
Watch out for
  • Generic answers like 'we needed to be more organized' without specific incidents
Q4 Walk me through how you found and evaluated project management tools - what was that process like?
Why ask this?

JTBD: understand evaluation criteria and decision-making process

Technique

Get the chronological story - who was involved, what did they compare, how did they decide

Follow-up Prompts
  • What other tools did you seriously consider?
  • Who was involved in the decision?
  • What made our tool stand out?
Watch out for
  • Hypothetical 'we looked for the best tool' instead of actual evaluation steps
Q5 Tell me about your first few weeks using the project management software - what was that experience like?
Why ask this?

Moment-Driven: capture the critical onboarding moments that predict retention

Technique

Focus on specific moments of friction or delight - ask for day-by-day details if needed

Follow-up Prompts
  • What was harder than expected?
  • What worked better than you thought it would?
  • How did your team react?
Watch out for
  • Generic 'it was fine' responses without specific moments or emotions
Q6 Can you walk me through how your usage of the tool changed over the first three months? What was different in month 1 versus month 3?
Why ask this?

Behavioral journey mapping to identify the critical 3-month inflection point

Technique

Use timeline probing - get them to think month-by-month about specific changes in behavior

Follow-up Prompts
  • What features did you start using later that you ignored initially?
  • Which team members adopted it fastest? Slowest?
  • Were there any moments where you almost stopped using it?
Watch out for
  • Vague timeline descriptions without specific behavioral changes

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