I've been saying yes to the wrong freelance projects for ten years. The pattern is always the same: client sounds reasonable, scope sounds clear, timeline sounds fine. Three weeks in, I'm rewriting the same feature because the requirements changed three times and the original budget is gone.
I now run five questions before I say yes. They've saved me from at least four bad engagements in the last six months.
Question 1: What's the deliverable, in one sentence?
If the client can't describe what they're buying in one sentence, they don't know what they want. That means scope will drift.
Question 2: What's the budget, and is it actually enough?
If they say "we don't have a big budget" but the scope is 3 months of work, that's a no. If they say "$50k" but the scope is a landing page, that's also a no — they don't understand what they're buying.
Question 3: Who else is involved in approving this?
If there's a chain of approvers, every decision will take a week. If it's just the person I'm talking to, decisions happen fast.
Question 4: What does success look like in 30 days?
If they can't describe what shipped looks like in 30 days, the engagement will drift. If they say "we'll know it when we see it," that's also a no.
Question 5: What's the political context?
Why now? What changed? Who's pushing for this internally? If the answer is vague, the project might get cancelled mid-flight for reasons outside your control.
I keep these (plus 65 more prompts) in a kit: https://gobvan.gumroad.com/l/yxqiuq ($12).
The prompts are designed for solo founders and freelancers. Free sampler: https://gobvan.gumroad.com/l/erkjry.
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