Project Management Tool for Design Agency

CASE STUDY INTERVIEW QUESTIONS

Customer: 12-person boutique design agency
Product: Project management tool
Interviewee: Founder
Results to Highlight: 50% reduction in client emails, 4.5/5 client satisfaction

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SECTION 1: BACKGROUND (5 questions)
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1. Tell me about your design agency—what services do you offer and what types of clients do you work with?
2. How is your team structured? Who handles client communication and project coordination?
3. Before [Product], what were you using to manage projects and client deliverables?
   Follow-up: What did you like about that approach? What didn’t work?
4. As the founder, how much of your time was spent on project management vs. creative direction or business development?
5. What prompted you to start looking for a project management solution?

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SECTION 2: CHALLENGES (7 questions)
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6. Walk me through a typical project workflow before [Product]. How did you coordinate with clients?
7. What were the biggest pain points your team faced with client communication and project delivery?
8. Can you give me a specific example of a project that got derailed by communication issues? What happened?
Follow-up: How did that impact the timeline? The client relationship?
9. You mentioned client emails were a problem—what was the volume like before [Product]?
Follow-up: What types of questions or requests were eating up your team’s time?
10. How were clients feeling about the design process and communication before [Product]?
11. What was the cost of these communication challenges? (Time, team bandwidth, client retention, creative quality)
12. Had you tried other project management tools? Why didn’t they stick?
13. On a scale of 1-10, how urgent was solving this problem for your agency’s growth? Why that number?

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SECTION 3: DECISION PROCESS (5 questions)
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14. How did you first discover [Product]?
15. What other project management tools did you evaluate?
16. What made [Product] stand out compared to alternatives like Asana, Monday.com, or ClickUp?
17. As a small agency, what were your biggest concerns before committing to a new tool?
Follow-up: Was cost a factor? Learning curve? Client adoption?
18. What was the deciding factor that made you choose [Product]?

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SECTION 4: IMPLEMENTATION (6 questions)
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19. What was the onboarding process like for you and your team?
20. How did your clients react when you introduced [Product] to them?
Follow-up: Were any clients hesitant? How did you handle that?
21. How long did it take before [Product] became your team’s default way of working?
22. Were there any challenges getting your designers to adopt the tool consistently?
23. What surprised you most during implementation (good or bad)?
24. Looking back, what would you have done differently during rollout?

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SECTION 5: RESULTS (9 questions - MOST IMPORTANT)
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25. Let’s talk results. You mentioned a 50% reduction in client emails—how did you measure that?
26. Before [Product]: How many client emails per week was your team handling?
27. After [Product]: What does it look like now?
28. Where did those emails go? Are clients self-serving answers through [Product]?
29. Tell me about the 4.5/5 client satisfaction score—how are you measuring that?
Follow-up: What was your satisfaction score before [Product]? What do clients specifically call out in their feedback?
30. What other unexpected benefits have you seen from using [Product]?
31. Has this impacted your team’s creative output or ability to take on more projects?
Follow-up: Has it affected revenue or profitability?
32. Has [Product] helped with client retention or winning new business?
33. Can you share a specific project that went dramatically better because of [Product]?
Follow-up: What would that project have looked like without [Product]?

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SECTION 6: WRAP-UP (3 questions)
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34. Would you recommend [Product] to other boutique agencies or creative firms? Why?
35. If a fellow founder was considering [Product], what advice would you give them?
36. As your agency grows, how do you see your use of [Product] evolving?

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BONUS: QUOTABLE MOMENT PROMPTS
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• “How would you describe [Product] in one sentence to another agency owner?”
• “Complete this sentence: Before [Product], client projects felt _____. Now, they feel _____.”
• “What’s the one thing that would make you never want to go back to your old process?”
• “If [Product] disappeared tomorrow, what would you and your clients miss most?”
• “What do your clients say about working with you now vs. before [Product]?”