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Convert 90% of your proposals using this approach

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One of the most frustrating parts of being a freelancer is putting a bunch of time into selling a client on your services only to get turned down. You spend an hour, or maybe several, on a proposal and then you either never hear from them again or you hear that they went with someone else.

I’m going to talk about how to move from the standard proposal win rate I hear about, (50%) to my win rate, over 90%.

Yes, you read that right. In most years, I win 90% of the proposals I send out. In the last 12 months I won 98% of the proposals I sent out, even in the face of stiff competition.

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This is how I do it.

Build trust first

One of the biggest mistakes that most freelancers and agencies make with their proposals is they rely on it to do the selling of the prospect. That’s how you get 10, 20, or even 30 page proposals.

You wax poetic about your team and your experience and the awards you’ve won. Your prospects don’t care about 90% of that. They have a problem they want solved and you wasted pages and pages telling them that you’re awesome.

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They wouldn’t be talking to you if you weren’t awesome, so let’s just take that as a given.

If you’re going to cut all that garbage out of your proposals, then you should be looking at 2 or 3 pages max. Focus only on the problem that the client has and what you can do to solve it.

If all that ‘selling’ junk is out, then you need to do most of your selling up front before they see the proposal. That means you have to get out from behind your computer screen and talk to the real person that is your prospect.

It means that in the phone call you don’t brag about how amazing you are. You don’t regal them with accounts of your ping-pong league. You ask them questions:

  • If they couldn’t do this project, what would they be doing instead?
  • Why aren’t they doing that instead?
  • Who is asking for the work to be done? Internal staff, clients, the board..?
  • How are they going to measure success of the project?
  • What is the budget allotted for the work?
  • What is the ideal timeline for the project?

Yes, there are likely some technical questions you need to ask, but those questions won’t sell the prospect on you. All the other business focused questions will.

It’s those questions that will give you the fodder for the short proposal that you are going to write.

In the process of asking these questions your prospect will come to understand that you are different than the typical freelancer.

You don’t simply talk like a nerd to them, you dig deep to get at what their real business needs are so that you can develop the right solution.

What a winning proposal should be

If your proposal isn’t supposed to be a big sales document, what should it be?

In short, it should only be a written copy of everything that you and your prospect have already talked about. There should be no surprises, including the budget.

They should look at it all and know that they’ve already given you a verbal ‘yes’ to every part they see.

If you’re supposed to cut out the company history and team biographies and only have a two to three page proposal, what should it contain?

Here are the six sections I use in all my proposals:

1. Current problem

The first thing you need is to describe to the prospect the problem they have. This is where all the questions you asked in the beginning come into play.

You are one of the only people that spent the time and asked valuable questions so you can describe it in their own words.

It should only take 2 short paragraphs to describe the problem if you’ve spent the time needed to dig in with the client and find it.

2. Objectives

This is not a 300 item list of all the things you’ll do for the client. This is where you tell them about the brighter future you are going to achieve when you work for them.

It takes all the selling work you’ve done up front to establish yourself as an authority and turns you into a strategic executor.

By the end of this section they should be dreaming about how your solutions will get them the business they wanted.

3. Gauging Success

When you start talking about how you’re going to measure success in a project, you turn yourself from a pie in the sky dreamer into someone that has a real handle on the business.

Be careful here; only state things that you can actually control.

If the overall goal is to make more sales, you can certainly bring in more leads, but if the client doesn’t train their sales staff well, they could botch all the extra leads and not get the increase in sales.

4. Options

Here are the options the client can choose from when they work with you. If there are 3 freelancers quoting on a project, and you provide 3 options while the other two freelancer’s provide the standard take it or leave it proposal, you have 3 options to their 2 options.

There are simply more ways the client can make the choice to work with you.

Additionally, by giving them three choices, it’s no longer that ‘take it or leave it’ proposal. Three options lets your prospect choose which level of engagement is right for them.

As you build out your options, don’t be afraid to make options two and three right at the top of the budget or just over. Many times I’ve had a client increase their budget by 50% to get the highest priced option because they wanted the value in it.

5. Timeline

The timeline is all about how long each option will take. If they choose option 1, it will take 4 – 6 weeks. Option 2 is 6 – 8 weeks, and so on.

Again, if option three is longer than their deadline, that’s fine. It may be that you can get the core of the project done inside the deadline and then they can get the extra value after the main launch.

6. Accountabilities

Finally, you need to make it clear who is responsible for which part of the project. Who will purchase the software needed to complete the work? What must the prospect provide you to get the project started?

Making these things clear up front, before they see any pricing, helps a prospect feel that they can negotiate any accountabilities until they’re comfortable with them.

If you can use these 6 sections in a proposal, and do the proper work up front in selling the client on you, you’ll start to win more proposals.

If you really want to lock in the maximum percentage of prospects that become clients, have them work on the first three sections of the proposal with you in Google Docs.

By getting them to contribute and change the proposal, you’re already getting them invested in working with you. They see their hand in the document as they read it and remember how committed you were to understanding what they wanted.

Once they’ve worked with you on the proposal, they are much more likely to trust you with their money.

Now, just because you use this format, doesn’t mean you will automatically start winning more proposals. It’s still on you to start doing more selling in advance before they ever have a chance to decide if they are going to work with you.

It’s up to you to learn to ask good questions.

It’s up to you to not only rely on email, and dive in to a call or meeting with a prospect.

If you can do that and use this collaborative proposal format, you will start to win more work. You will start to weed out the prospects that aren’t worth the effort.

You will start to get the business you dreamed of when you started.

Let me know your thoughts in the comment section.

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About Curtis McHale

Curtis is a business coach and speaker. He helps businesses build effective processes for vetting ideal clients and building the business they dreamed of.

Leave a Comment



  1. All the best! good day!
    Thanks for the text.

  2. Excellent advice! I really like how customer-focused this is. I look forward to implementing some of this into my creative business. Thank you!

  3. Thank you so much for this useful advice Curtis! Really love the clear structure with the 6 sections 🙂

  4. Just writing a proposal again and this comes just on time! Thank you, Curtis & Milloteam

  5. I don’t do many formal written proposals, but this is definitely a template I will save and refer back to when I need it. Thanks, Curtis!

  6. What a great post! Thank you so much – I find proposals to be the trickiest to nail, I’ve spent hours trying to figure out what to include, how to format it, when to actually discuss it with the prospect. One question I still have is whether you have the client sign the Proposal AND the contract, and if so, do you have them sign them both at the same time? I almost lost a client once because they were so taken aback with the contract I sent them, so in the end, since it was a smaller project, we didn’t even sign one…is there a specific situation when you need and don’t need contracts, or should you always have one?
    Thank you in advance!

  7. Chloe Brooks says:

    I love the advice about giving hem options! I’ve been working on developing my pricing structure and this is so helpful. Thanks, Curtis!

  8. This was very insightful. I usually have a small intro and strategy session with our potential clients before submitting a proposal where I ask questions to get to the heart of what they are trying to accomplish. However, we do send them a proposal that is pages and pages long with company bios, etc. I’m definitely thinking about implementing some of your suggestions, like them contributing in Google docs.

    • In my experience, you’d close more sales if you get them introduced to your team up front in the strategy session. The closer you can get them to actually shaking hands with your team, the more trust is built.

      More trust closes more sales.


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