Introduction

Asking someone “would you like to sign this contract” can often feel like navigating a tightrope. Too pushy, and you risk coming off as aggressive. Too casual, you might seem unprofessional or unclear. But when done right, it can be a straightforward, no-sweat experience. Whether you’re closing a business deal, onboarding a supplier or sealing a partnership, here’s a clear step-by-step guide to asking for that all-important signature without making it awkward.

Read: How to structure milestone payments in contracts

Step 1: Prepare before you ask

Before you even think about requesting a signature, make sure you’ve got all your ducks in a row.

Review the contract

Don’t just skim it like you’re speed-reading a boring novel. Read the contract word-for-word to make sure it’s got everything you and the other party agreed on. Nothing says “red flag” like last-minute changes. You can do this manually, hire a legal professional or use Cobrief to do the review in minutes.

Understand the terms

You should be ready to explain every clause and comma in that contract. If you fumble or look unsure, it’s going to raise eyebrows and probably a few doubts. Whether it’s the fine print on indemnification or the scope of services, be prepared to clarify any question that might come your way.

Confidence is key—if you look like you don’t know what’s going on, why would they feel comfortable signing?

Gather all supporting documents

Think of these as the side dishes to your contract’s main course. Appendices, exhibits, or any referenced documents need to be prepped and ready. Make sure they’re correctly linked to the contract so there’s no confusion.

There’s nothing worse than scrambling to find an appendix mid-meeting and realizing it’s nowhere to be found. Having everything at your fingertips shows you’re organized and professional.

Step 2: Choose the right moment

Timing is everything. Don’t drop the contract bomb in the middle of a casual conversation or at a time when the other party is clearly distracted or busy. Instead, schedule a dedicated meeting, whether in person, over a call, or virtually, and let them know in advance that the purpose is to review and sign the contract.

This approach shows respect for their time and keeps the process professional. It’s much better than a casual “Hey, can you sign this real quick?”

Step 3: Introduce the contract and its purpose

Start the conversation by summarizing the contract's purpose. This sets the context and reminds the other party of the mutual benefits outlined in the agreement.

For example, you could say, “I’m excited to finalize our collaboration on this project. The contract outlines the terms we discussed, and I’d love to go through it with you to ensure we’re both on the same page before signing.”

This introduction sets a positive tone and signals that you’re open to discussion, not just pushing for a signature.

Read: How to handle contract disputes without going to court

Step 4: Highlight the key points

Before you ask for that all-important signature, make sure you walk the other party through the main points of the contract. No one wants to feel like they’re signing a mystery document. This isn’t about reading every word out loud like storytime; it’s about giving them a clear summary of the essentials. Here’s how to do it.

Scope of work

Start with what’s being agreed to in plain terms. Explain the services or deliverables involved, so there’s no confusion about what’s expected. For example, if it’s a marketing contract, spell out if you’re handling social media, content creation, or just the ad campaigns. The goal is to ensure both parties know exactly what’s being delivered and by whom.

Deadlines and timelines

Cover the critical dates and milestones. Are there specific deadlines for deliverables, or is the timeline flexible? Make sure these dates are realistic and agreed upon, so no one’s scrambling to meet an impossible deadline down the road. If there’s a launch date or key checkpoint, highlight it to keep everyone aligned.

Compensation and payment terms

Break down how and when payments will be made. Is it a lump sum, or will payments be staggered based on project milestones? Clarify the payment schedule, any deposits required, and how invoices should be handled. It’s also a good time to mention late fees or payment penalties, just in case.

Responsibilities

Detail what each party is responsible for. Who’s providing what, and by when? If one side is handling the creative while the other is responsible for approvals, make that clear. This avoids any “I thought you were doing that” moments later on. Set clear expectations so everyone knows their role in making the project a success.

Termination clauses

Discuss how either party can exit the agreement if things don’t go as planned. Can someone pull the plug without reason, or does it require a breach of terms? Are there penalties for early termination? Outlining this upfront means no one feels trapped if the relationship sours.

By covering these points, you reassure them that they’re not signing a document full of surprises.

Read: What you should do if a client refuses to sign your contract

Step 5: Address any concerns openly

Encourage the other party to voice any questions or concerns they have about the contract. This step is crucial for building trust and showing that you’re transparent and open to dialogue. If they raise any issues, don’t brush them off—take each point seriously and address it thoughtfully. If there’s something you can’t answer right away, be honest and promise to get back to them with the information they need.

You might say something like, “If there’s anything you’re not clear on, let’s go through it now. I want you to feel completely comfortable and confident before we move forward.” This approach shows that you’re not just interested in getting the contract signed, but in ensuring they fully understand and agree to everything.

It also prevents any “I didn’t know that” surprises down the line, keeping the process smooth and professional.

Step 6: Request the signature confidently, but respectfully

Once you’ve reviewed the contract and addressed any questions, it’s time to ask for the signature. Be direct but respectful:

“I’m confident we’ve covered everything. If you’re happy with the terms, are you ready to sign?”

This phrasing is polite but firm, indicating that you’re expecting the next step but not pressuring them unduly. Avoid passive or uncertain language like, “So, um, do you maybe want to sign it now?”

Step 7: Provide clear signing instructions

If the contract is physical, make sure they have a pen and know where to sign. If it’s digital, guide them through the e-signature process. You can use tools like DocuSign or Dropbox to speed up the e-signature process. Avoid assuming they know what to do—this little step can save a lot of unnecessary back-and-forth.

Step 8: Express appreciation and confirm next steps

After they sign, thank them for their time and trust. Then, outline what happens next—whether it’s a project kickoff, onboarding, or delivering the first service.

“Thanks so much for signing! I’ll send you a copy for your records and get started on [next step]. Looking forward to working together!”

Step 9: Follow up with a signed copy

Once the contract is signed, make sure they receive a final, executed copy for their records. You normally don’t have to do this if e-signature software is used, but it’s always worth double checking. This shows professionalism and ensures everyone has the same version of the agreement. It’s a simple but often overlooked step that can prevent confusion later.

Read: How can I get out of a business contract?

Step 10: Avoid these common mistakes

When asking someone to sign a contract, it’s easy to slip up and turn a smooth process into an awkward mess. Here’s how to avoid some classic blunders.

Don’t rush it

Pushing someone to sign quickly is a surefire way to come across as desperate or, worse, untrustworthy. If you’re shoving a pen in their face like it’s a high-pressure sales pitch, they’ll wonder what you’re trying to hide. Instead, give them time to review and consider the agreement.

The devil is in the fine print

Skipping over the nitty-gritty because “it’s all standard stuff” is a rookie mistake. What seems trivial now can become a big issue later if misunderstood or overlooked. Go through the key points and make sure everything is crystal clear.

It’s like skipping the instructions on flat-pack furniture—you’ll regret it when things start falling apart.

Personalize your pitch

Everyone’s different. Some folks prefer a formal approach with lots of “therefores” and “herebys,” while others would rather have a relaxed, straightforward chat. Tailor your pitch to match the person in front of you. If they’re buttoned-up and businesslike, go with a polished presentation. If they’re more laid-back, keep it casual and friendly. This shows you’ve done your homework and respect their style.

Conclusion

Getting someone to sign a contract is all about clear communication, respect, and timing. By preparing thoroughly, addressing concerns, and being clear about the process, you can make the experience smooth and professional for both parties. After all, it’s not just about getting a signature—it’s about starting a partnership on the right foot.

So, take a deep breath, follow these steps, and you’ll be a contract-signing pro in no time.

Read: What happens if you breach a contract?

How Cobrief can help with contract review

Reading your business contracts can feel overwhelming as an owner-manager of a small to medium-sized business. That’s where Cobrief comes in. Cobrief helps business owners and operators review their business-to-business contracts for legal risks.

Upload your contract to Cobrief's AI contract review software, click review and you’ll get a list of all the risks, in plain English. This helps you decide whether to sign, negotiate or reject the terms of your contract, or hire a lawyer. Think of it as a heat map for your contracts.

Get started here.