Questions You Should Always Ask Before Signing a Contract

A Practical Guide for Business Owners, Freelancers, Renters — and Anyone Who Wants to Avoid Regret

Contracts are everywhere – from employment offers to freelance gigs, gym memberships, apartment leases, and business partnerships. But how many times have you actually read a contract all the way through before signing? The truth is, most people sign contracts far too quickly – often without fully reading or understanding the terms. In fact, a recent Adobe Acrobat survey from January 2025 reported that 69% of consumers admitted to signing contracts without reviewing their contents. Maybe we’re afraid to look like we don’t understand, or we trust the other person, or we just feel rushed. But here’s the thing: a contract is a legal commitment. Once you sign, you’re expected to follow it.

Understanding the Importance of an Agreement:

An agreement is more than just a signature on paper — it’s a legally binding document that protects everyone involved by outlining clear expectations, responsibilities, andoutcomes (Federal Trade Commission, nd.). Even for everyday agreements, the American Bar Association (ABA) recommends reviewing all terms and asking questions about anything unclear. Taking the time to understand what you’re agreeing to isn’t just smart – it’s a necessary step to protect your interests and avoid future complications.

5 Risks of Not Reading the Final Contract

1. Hidden fees → Unexpected charges or costs later on
2. Auto-renewals → Getting locked into a long-term commitment
3. Ownership confusion → Losing rights to your own work or property
4. One-sided clauses → No protection if the other party breaks the agreement
5. Legal liability → Being held responsible for things you didn’t realize you agreed to

So before you sign (or click “I agree”)

• Read the full contract — no skipping
• Highlight confusing sections
• Take your time — don’t let anyone rush you
• Get legal help if needed

Then, ask the following 9 important questions in this guide — explained, with real life examples, so you know exactly what to look for and what to avoid.

9 Questions to Ask Yourself before Signing a Contract

1. What exactly am I agreeing to?

This is the most basic – and most important – question. Make sure you understand the actual deal. What are you supposed to do? What are they doing in return? What are the key promises, services, or products being exchanged?

Watch out for: Vague terms like “industry standard” or “as discussed.” Ask for clear, written descriptions of services, deadlines, or responsibilities.

Example: A freelance designer is hired to “create marketing materials.” What does that mean? One flyer? A full campaign? Clarify before signing.

2. How long does this contract last?

Contracts often have a time frame — sometimes clearly stated, sometimes hidden in the fine print. Knowing the length of your commitment helps you plan ahead and avoid being stuck in something longer than expected.

Look for: Start and end dates, renewal terms, and what happens at the end (does it auto-renew?).

Example: A cleaning company contract might say “initial term: 12 months” and then auto-renews unless canceled 30 days before the end date.

3. What are the payment terms?

Money can get messy if it’s not clear upfront. Always know:

• How much you’re paying (or getting paid)
• When payment is due
• How payment is made
• Whether there are late fees, deposits, or refunds

Tip: A contract with unclear or shifting payment terms is a red flag.

Example: A wedding photographer contract may require a 50% deposit upfront, 25% before the event, and the final 25% after delivery. This should be written down.

4. Can I end the contract early?

Life changes. Sometimes, you may need to exit a contract — and knowing how to do that without huge penalties is crucial.

Ask:

• Can I cancel early?
• How much notice do I need to give?
• Are there cancellation fees or “lock-in” periods?

Example: You join a co-working space with a 6-month contract. Two months in, your business moves. If the contract says you owe the full amount anyway — that’s a problem unless you read and negotiated it ahead of time.

5. What happens if something goes wrong?

Contracts should cover the “what ifs”: delays, broken promises, bad service, non-payment. If there’s a problem, how will it be resolved?

Check for:

• Dispute resolution (court, mediation, arbitration)
• Refund or repair policies
• Penalties for breaching the contract

Example: If a builder doesn’t finish your kitchen, can you get a refund? Will they redo the work? This should be in the contract.

6. Are there any important deadlines or tasks I need to remember?

Even a “simple” contract can include deadlines you must follow — or risk breaching the deal.

Look for:

• Payment due dates
• Delivery schedules
• Required paperwork or reports

Example: A service agreement might require monthly reports by the 5th of each month. Missing them could violate the contract.

7. Who is responsible for what?

Responsibilities should be spelled out clearly for both sides — not just you. This avoids finger-pointing later.

Ask:

• Who pays for what?
• What happens if someone doesn’t deliver?

Example: If you’re hiring a videographer, make sure it says whether you are expected to provide the script or they are. Who books the location? Who edits the footage?

8. Are there any restrictions, rules, or hidden clauses?

Contracts sometimes include extra rules you might not notice — non-compete clauses, confidentiality requirements, usage restrictions, or exclusivity terms.

Look out for:

• Language that limits your future work (non-compete)
• Clauses about what you can’t say publicly (NDAs)
• Exclusivity — agreeing not to work with competitorsExample: You sign with a modeling agency, and later learn you can’t work with any other brand while under contract — even as a freelancer. That should have been clarified upfront.

9. What happens when the contract ends?

Some contracts don’t really end — they “auto-renew” or include obligations that survive the agreement.

Ask:

• Will this contract automatically renew?
• Do I need to give notice to cancel?
• Do I owe anything after it ends?

Example: A software subscription may require 60 days’ notice before the renewal date. If you miss it, you’re locked in for another year — with no refund.

Quick Recap: Your Pre-Signing Checklist

You’ve asked the right questions — now take a moment to scan for any warning signs. Even if a contract seems to check all the boxes, these red flags can reveal deeper issues or hidden risks. If you notice any of the following, pause before signing and get clarification in writing

Contract Red Flags

• The contract is super short (vague and missing key details)
• The other party says “you don’t need to read it”
• You’re told to “just sign it now — we’ll fix it later”
• You can’t get a clear copy in advance
• Key terms are only mentioned verbally, not in writing

Final Advice

You don’t need to be a lawyer to ask good questions. And you don’t need to feel embarrassed for slowing down the process. Asking the right questions doesn’t make you difficult – it makes you smart. At the end of the day, contracts aren’t just legal documents — they’re about trust. But trust should never replace clarity. No matter how friendly the relationship feels at the start, things can change — people forget, companies shift priorities, and memories fade. That’s why a well-written contract protects both sides. It forces everyone to slow down, get specific, and agree in writing to what really matters. You’re not being difficult by asking questions — you’re building a foundation that’s fair, professional, and future- proof. The strongest deals don’t rely on handshakes — they rely on clarity. If something feels unclear, confusing, or risky — don’t sign yet. Ask, clarify, or get help. A few extra minutes now can save you months of stress later. If you have any questions or need help reviewing a contract, feel free to reach out to the team at Pierce & Kwok LLC. We’re here to help you protect your interests with confidence.