How to Send a Contract Without Sounding (and Feeling!) Like a Jerk

How to Send a Contract

At one of our contract workshops, I mentioned that it’s often better to be the one who offers the contract rather than to be the one who receives it.

It gives you more leverage because (1) you’ll hopefully know what’s in the contract and (2) you can offer something that’s more in your favor. It leaves the burden on the other side to review the contract and bring up things that they want changed.

An entrepreneur quickly shot her hand up and asked this great question:

“How do you suggest I bring up a contract without sounding like a jerk?”

This isn’t the first time I’ve been asked this, especially from newbie entrepreneurs and freelancers. This is a VERY common source of anxiety.

Imagine this: You meet a prospective client or partner. You have a few phone calls or meetings where it’s very clear you both like each other. Those phone calls lead to more serious discussions about working together. Maybe you start hashing out terms like what, when, and for how much.

And then … the moment comes when you wonder if you should bring up a written contract.

I’ve heard entrepreneurs and freelancers describe this moment as “icky”. They fear that mentioning a written contract will “bring up a wall” and “signal mistrust”. And the unfortunate result of this fear is that if the other side doesn’t offer a contract, they move forward without one. 😧

This can result in more time, money, and efforts wasted later on. When there’s confusion about what you’ve agreed to (“You said you would cover my travel expenses, no?”) or even worse, when there is a full-blown conflict (“I’m not paying you, because this isn’t what I wanted!”), not having a written agreement can leave you scrambling.

Why does sending a contract bring up such uncomfortable feelings?

I imagine it’s a similar feeling for some people when a prenup is suggested by a soon-to-be-spouse.

“Wait, you’re already planning for when we break up?”

While valid contracts (especially well-written ones) do cover what will happen if and when things turn sour, a good part of the contract covers what is supposed to happen when things go as planned.

The problem lies with how we look at contracts. We tend to associate contracts with things not working out.

But the whole purpose of a contract is to facilitate things working out in the best way that they can.

Contracts are one of the best communication tools you can have.

They are meant to build trust, not destroy it.

It’s a way to clearly lay out expectations – on both sides – so that you can ensure a successful business relationship.

To be clear, that doesn’t mean that everything has to be neutral. Even if one side has much less leverage, a contract’s main purpose is to outline clearly how that will play out in the relationship (e.g., they’ll take on more liability, require to pay more money, etc.).

The goal is to be very clear on the contract terms and what each side expects before moving forward.

To go back to the prenup point, well-written contracts will lay out a mechanism on how disputes will be handled.

It’s not a sign that things will go wrong; rather, you’re making sure that things will go as smoothly as possible.

It’s much better and easier to negotiate how a dispute will be handled when everyone is in honeymoon phase, excited and optimistic about working with each other.

If you leave this for if and when the dispute actually happens – when emotions are high and people are upset – you can bet that the outcome will cost you more time, money and heartaches.

Let’s go back to the moment when you’re wondering if you should send across a written contract. The important thing here is to change your mindset or perspective about contracts.

First things first, you need to change the way you view contracts. Change your perspective on contracts and realize that:

  1. The fact that you’re even suggesting a written contract conveys that you are taking this relationship seriously. How seriously? Enough to spend time, money or both to prepare a contract.

  2. Successful relationships are built on trust, and trust comes from transparency and clear expectations. There is no better way to communicate these things than through a contract.

Here are some suggested scripts to send along with your contract that communicate this new perspective:

I really enjoyed our discussion and look forward to working together! I want to make sure that we start on the right foot so we can ensure a successful working relationship.

Attached is a contract that I believe reflects what we talked about so far. It would be great if you could review and let me know if there are any inconsistencies with your understanding.

Here’s another example:

I am so excited to get this project off the ground. To help us continue the conversation, I’m attaching a draft contract that we can use as a guide on things we should talk about. I want this project to be a success and so it’d be helpful for me if we lay down clear expectations and goals.

To sum it up, remember that the contract itself is just piece of a paper. It’s what you put in it and how you deliver it that gives it meaning. And how you deliver it is a great opportunity to set the tone on how that contract will be received or negotiated.

Disclaimer: This article is for informational and educational purposes only, it is not legal advice.  It does not create an attorney-client relationship between you and Lawgood, its founders, or the author.  If you need legal advice, you should hire a lawyer. 


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Gina Pak

Gina is a co-founder and COO of Lawgood. She is an experienced business lawyer who loves to teach and empower entrepreneurs, especially when it comes to their business contracts. She graduated from Columbia Law School. You can find Gina on LinkedIn and Instagram.


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