Discovery Questions Cheat Sheet

(print this page — one page, three lanes)

PAIN — find the real problem

1. What's the actual trigger that got you looking at this now?
2. Walk me through what this looks like on a bad day.
3. What have you already tried, and why didn't it stick?
4. What's the workaround you're using today?
5. If nothing changes, what happens in six months?
6. Who feels this the most on your team?
7. What's the difference between how this should work and how it actually works?
8. What's the one thing about this that frustrates you most?

IMPACT — put a number on it

1. What does one instance of this going wrong cost you?
2. How many hours a week does your team spend on this workaround?
3. What would you do with that time/money if this were solved?
4. How does this show up in a number your boss cares about?
5. What's the compounding effect if this drags on another quarter?
6. On a 1–10, how big a deal is this — what makes it that number?
7. Who above you sees the effect of this problem?
8. What's it costing you to keep doing nothing?

URGENCY — test the compelling event

1. What's forcing a decision by a specific date?
2. What happens on your end if this slips to next quarter?
3. Is there a board date, renewal, or budget cycle tied to this?
4. Who set that deadline, and how firm is it really?
5. What would need to be true for this to not be urgent?
6. If we solved this today, what would you do next with that win?

MULTI-THREAD — find the other stakeholders

1. Who else has a stake in this decision?
2. Who would be upset if this decision got made without them?
3. Has anyone tried to solve this before — what happened?
4. Who signs off once we have a recommendation?

WHEN THEY SAY 'EVERYTHING'S FINE'

1. Fine's a strong word — what would 'great' look like instead?
2. If you had a magic wand, what's the one thing you'd change?
3. What made you take this call if things are fine?