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Questions to ask before you hand over a key

The scope conversation gets all the attention. This is the one that actually deserves it.

September 1, 2026 · 2 min read

Questions to ask before you hand over a key

Almost every conversation about hiring a cleaning contractor is about scope and price. Both matter. Neither is the part that should keep you up, because the genuinely unusual thing you are about to do is give someone access to your building at a time when nobody else is in it.

That deserves five specific questions. Here they are, along with what a good answer sounds like and what a weak one sounds like.

1. When does screening happen?

Not whether. When. The difference between screening before orientation and screening at some point during employment is the difference between a policy and an intention.

A good answer names the checks and puts them before training: reference checks, a criminal background check and a drug test, all completed before the person reaches orientation. A weak answer is any sentence containing the phrase we make sure without a point in time attached to it.

2. Will I be able to tell who they are?

If someone from your building works late and encounters a stranger in the corridor, what happens? The answer should be that the stranger is wearing a visible photo ID badge and is therefore not a stranger.

This sounds like a small operational detail. In practice it is the single thing that converts an unsettling moment into a non-event, and it is worth asking about explicitly.

3. Are you insured and bonded?

Insured and bonded are two different things and it is worth hearing both words. Insurance covers damage. Bonding covers loss. A contractor who is fully insured and bonded is telling you that the risk of handing over a key is not one you are carrying by yourself.

4. What happens on a night that goes wrong?

Ask before you sign, not after it happens. The useful version of this answer is a written remedy that does not depend on how well the conversation goes.

Ours is that if you are not satisfied with a day's service you call the following business day and you do not pay for that day. That is deliberately mechanical. A remedy that requires goodwill is a remedy that quietly evaporates the moment goodwill is under strain, which is precisely when you need it.

5. Where does your work come from?

This is the question that is hardest to answer dishonestly, because the answer is either specific or it is not.

A contractor whose work has come mostly by referral over many years is describing something that cannot be manufactured for a proposal: a run of clients who stayed satisfied long enough to put their own reputation behind a recommendation.

What the answers tell you together

Taken individually these are five reasonable questions. Taken together they test one thing, which is whether the company has thought about being trusted with an empty building, or has only thought about cleaning one.

Any contractor can clean a floor. The reason this list exists is that the floor was never the risky part.

If you are weighing up a contractor for a building in Saint Paul or the surrounding east metro, ask us all five. We would rather answer them at the start than have you wondering about them later.

Great Lakes Janitorial Services, (651) 253-2239

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