Current state How does this get done today? · Who's involved in that process, start to finish? · What tools/systems are in play right now? · How long has it worked this way? · What's already been tried to fix it? Pain & impact What breaks, specifically, when this goes wrong? · How often does that happen? · What does it cost — time, money, risk, morale? · Who else feels this pain besides you? · What's the knock‑on effect three steps downstream? Urgency & priority Why is this a priority now, versus six months ago or six months from now? · What happens if nothing changes this year? · Is there a specific date or event driving the timeline? · What's competing with this for budget and attention? Decision process & criteria Who else needs to be convinced before this moves forward? · How has a decision like this been made here before? · What would make this an easy yes versus a hard no? · Who signs off on budget of this size? · What's the procurement/security review process look like? Technical / architecture What must this integrate with, and who owns those systems? · What constraints — security, compliance, data residency — are non‑negotiable? · What's the scale this needs to handle, realistically, in 2 years? · What's failed technically in past attempts, and why? Success criteria What does "this worked" look like in six months, in your own numbers? · Who else needs to agree it worked? · What would make this a clear failure? · How will this be reported upward?