The nine questions
1. What percentage of the surface will you scrape, and how did you decide?
The single most revealing exterior question there is. A contractor who has actually inspected the house will give you a number and point at the walls. One who has not will change the subject to paint brands. Prep is where quality lives and where bids diverge.
2. Are your crews employees or subcontractors?
Neither answer is automatically wrong, but it changes what you are buying. Employees mean consistent standards, direct supervision, and workers' compensation coverage that unambiguously applies. Subcontractors mean you should verify the sub's insurance, not just the general's. Ask who will physically be at your house, and whether it is the same people all week.
3. Can I get the certificate of insurance directly from your insurer?
This is the question almost nobody asks, and it is the most important one on the list. A PDF a contractor emails you proves nothing. A certificate sent directly by the insurance agent, listing you as certificate holder, is verification. If a contractor is uninsured and someone falls off a ladder on your property, that becomes your problem in a way most homeowners do not anticipate.
4. What is your EPA lead-safe firm certification number?
Mandatory for any paid work disturbing paint in a pre-1978 home, which is roughly half of Madison. Certifications are public and searchable through the EPA. Ask for the number, then look it up. Two minutes.
5. How many coats, and what happens if it does not cover?
Two coats should be standard. What matters is the answer to the second half: if you chose a deep color that needs three, is that a change order or is it included? Get it in writing, because it is one of the most common sources of end-of-job friction.
6. What product, specifically, and what line?
Not the brand, the line. Every major manufacturer sells a builder-grade product and a premium one, and the gap between them is real. A contractor who cannot name the specific product line they intend to use has not decided yet, which means the decision will be made on price at the counter.
7. What is your warranty, in writing, and what does it exclude?
Exclusions tell you more than the term does. A three-year workmanship warranty that excludes peeling is not a warranty. Read what it actually covers, and expect legitimate exclusions for substrate failure, moisture intrusion, and structural movement, because no coating survives those.
8. What does the daily routine look like in an occupied home?
You are going to live in this. Ask what time they arrive, whether furniture is moved and restored daily or staged for the week, what happens to switch plates and hardware, and how the job site looks at 5 PM. The answer tells you whether they have thought about you or only about the walls.
9. Can I see work you did five years ago, not five months ago?
Any paint job looks good the week it is finished. The interesting question is what it looks like after four Wisconsin winters. A contractor with local history can point you at older work, and that is worth more than a portfolio of fresh photos.
Red flags
- A bid substantially below the others, presented as a deal rather than as a different scope.
- A large deposit demanded up front. A modest deposit for materials on a big job is normal; half the contract before anyone shows up is not.
- Pressure to sign today, or a price that expires at the end of the visit.
- No written scope, just a total.
- Reluctance to provide an insurance certificate directly from the insurer.
- On a pre-1978 home, no mention of lead-safe practices at all.
- Cash-only, no contract, no invoice.
How to actually compare three bids
Line them up on scope, not on total. Make a simple grid: surfaces included, ceilings yes or no, prep described, number of coats, product line, warranty term, timeline, crew type.
In our experience most homeowners discover in the middle of that exercise that they are not comparing three prices for the same job, they are comparing three different jobs. That realization is worth more than any negotiation.