businessproduct-management
Stakeholder Interview Guide
Design and conduct stakeholder interviews for requirements elicitation — with structured question frameworks, active listening techniques, assumption surfacing, and synthesis into actionable requirements.
interviewsrequirementsstakeholderselicitationdiscovery
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crm-migration-interview.md
Markdown
| 1 | # CRM Migration — Stakeholder Interview: VP of Sales |
| 2 | |
| 3 | ## Preparation |
| 4 | |
| 5 | **Stakeholder:** Dana Whitfield, VP of Sales, 14 direct reports, approves all sales tooling changes |
| 6 | **Project:** Migrate from Salesforce Classic to HubSpot CRM across a 120-person sales org |
| 7 | **Known context:** Contract with Salesforce expires in 5 months. CEO approved migration budget of $380K. Sales ops has documented 43 custom Salesforce workflows. |
| 8 | **Interview goal:** Discovery — understand Dana's team's daily CRM usage, pain points, and non-negotiable requirements. |
| 9 | |
| 10 | **Assumptions to test:** |
| 11 | 1. The sales team's biggest frustration is Salesforce's reporting speed. |
| 12 | 2. Pipeline forecasting accuracy will be the highest-priority capability to preserve. |
| 13 | 3. Dana will resist the migration due to re-training costs. |
| 14 | |
| 15 | **Project summary for opening:** "We are migrating from Salesforce Classic to HubSpot over the next 4 months to reduce licensing costs and improve sales workflow efficiency. This interview is about understanding what your team needs from the new system so we don't break what's working." |
| 16 | |
| 17 | ## Questions (sequenced broad to specific) |
| 18 | |
| 19 | ### Problem discovery (primary) |
| 20 | 1. "What are the top 3 things your reps complain about with Salesforce today?" |
| 21 | 2. "Walk me through what happens when a rep needs to log a deal from first contact to closed-won." |
| 22 | 3. "If you could fix one thing about how your team uses the CRM today, what would it be?" |
| 23 | |
| 24 | ### Process mapping |
| 25 | 4. "Describe how your team runs the Monday pipeline review — what data do you pull, and from where?" |
| 26 | 5. "Where do handoffs between SDRs and AEs happen? What information gets lost at that point?" |
| 27 | |
| 28 | ### Constraint surfacing |
| 29 | 6. "What would make this migration a failure in your eyes?" |
| 30 | 7. "Are there integrations — Gong, Outreach, CPQ — that are non-negotiable?" |
| 31 | 8. "What is the maximum amount of downtime your team can absorb during cutover?" |
| 32 | |
| 33 | ### Priority alignment |
| 34 | 9. "If we could only migrate three capabilities on day one, which three matter most?" |
| 35 | 10. "What does 'good enough for launch' look like versus the ideal state?" |
| 36 | |
| 37 | ## Post-Interview Synthesis |
| 38 | |
| 39 | ``` |
| 40 | Stakeholder: Dana Whitfield, VP of Sales |
| 41 | Date: 2026-02-12 |
| 42 | Interviewer: Marcus Chen, Business Analyst |
| 43 | |
| 44 | Key requirements identified: |
| 45 | 1. Pipeline forecasting must match current accuracy within 5% — Priority: High |
| 46 | Source quote: "If my Monday forecast breaks, I lose the CEO's trust in a week." |
| 47 | 2. Gong and Outreach integrations required at launch — Priority: High |
| 48 | Source quote: "Reps will revolt if call recording stops syncing to deal records." |
| 49 | 3. Custom lead scoring model must be replicated — Priority: Medium |
| 50 | Source quote: "We spent 8 months tuning that model. Starting over is not an option." |
| 51 | 4. Mobile CRM access for field reps — Priority: Medium |
| 52 | Source quote: "Half my enterprise team lives in the app on their phones." |
| 53 | |
| 54 | Assumptions tested: |
| 55 | - Reporting speed is the biggest frustration → Corrected — data entry burden is #1. |
| 56 | Dana said reps spend 40 min/day on manual logging; slow reports ranked third. |
| 57 | - Forecasting accuracy is top priority → Confirmed — Dana was emphatic about this. |
| 58 | - Dana will resist migration → Nuanced — she supports it IF reps get fewer clicks |
| 59 | per deal update. She's frustrated with Salesforce, not attached to it. |
| 60 | |
| 61 | Constraints uncovered: |
| 62 | - No more than 4 hours of CRM downtime during cutover (weekend only) |
| 63 | - Outreach contract renews in 3 months — integration must be live before then |
| 64 | - Sales comp data cannot leave Salesforce until finance validates HubSpot reports |
| 65 | |
| 66 | Conflicts with other stakeholders: |
| 67 | - Sales Ops wants a phased rollout by region; Dana wants a single cutover to |
| 68 | avoid running two systems. Resolution needed: Yes. |
| 69 | |
| 70 | Open questions for follow-up: |
| 71 | - How does the CPQ workflow interact with HubSpot's native quoting? |
| 72 | Assigned to: James (Solutions Architect) — Due: 2026-02-19 |
| 73 | - Which 43 custom workflows are actually used weekly vs. legacy? |
| 74 | Assigned to: Sales Ops — Due: 2026-02-26 |
| 75 | ``` |
| 76 |