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You just got off a call that felt really good. The conversation flowed, they were asking the right questions, and you could tell they were genuinely interested in what you do.

Then right at the end, they say it: "Can you send me a proposal?"

→ What do you do?

Most founders hear that and feel a little rush of excitement. Like the deal is basically done and all that's left is the paperwork.

They hang up, open their laptop, and spend the next two hours building out a document with pricing, timelines, and deliverables. They hit send and wait.

Then nothing happens.

A week goes by and they follow up. The prospect says they're still reviewing it. Two more weeks pass. More silence.

Does this sound familiar?

Here's what I want you to understand.

"Send me a proposal" is not the finish line. It's a yellow light, and if you treat it like a green one, you're going to waste a lot of time wondering why deals keep stalling out.

So what do you actually do when someone asks for a proposal?

Here's the five-step process I coach my clients through.

Before you say "absolutely, I'll get that over to you," ask yourself whether you actually know enough to send something meaningful.

A proposal is only useful if you understand:

→ If you're fuzzy on any of those things, sending something is basically like throwing a dart blindfolded and is a waste of your time.

Pro Tip: Ask, "Before I put it together, I want to make sure it's tailored to what you actually need. Can we grab 20 minutes to walk through costs and make sure we are aligned on pricing in order to achieve your outcome goals?"

Proposals and Contracts often get intertwined and have interchangeable language. They mean different things to different people.

When someone asks for a proposal…

→ They might mean they're ready to move forward and just need something to make it official.

→ They might mean they like what they're hearing and want something to take back to their team.

→ They might mean they want to see the different pricing options.

Those are completely different situations that require completely different responses.

Before you build anything, find out which one you're dealing with.

You're not interrogating them. You're doing your job so you can avoid miscommunications later on.

This is the step I see people skip most often, and it costs them deals every single time. Without a target start date, there's no urgency.

A proposal sitting in someone's inbox with no associated timeline can wait forever.

As you're wrapping up, ask them directly when they would ideally want to get started if everything went well on their end.

Then, work backward from that date.

If they want to kick off in July and it's May, when do you need a signed contract by to commit them to the schedule, put resources behind it, etc?

That needs to be a part of the discussion. (IKYMI: Create Urgency Without Sounding Salesy)

A date is what turns a nice conversation into an actual plan. And a plan is what moves partnerships forward. The more committed they are to a date, the better chance you have that the deal will actually happen.

Nobody talks about this step enough, and it kills deals that seem like they have momentum. Right when you think it's done, you find out it has to go through legal review, or a committee needs to weigh in, or their fiscal year doesn't start until October.

→ That July start date just became a November start date, and you're back to waiting on someone else's process.

Ask the question early: "Once you're ready to move forward, how does the contracting process typically work on your end? Is it something you can sign off on directly, or does it need to go through procurement or legal?"

You're not creating doubt by asking this.

You're clearing up the gray areas.

If legal review takes three weeks, that's actually good information. If they don’t know, that’s also good information and you can work with them to get the answers.

Asking this early helps you plan for it instead of getting blindsided right before the finish line.

A lot of people treat pricing like it's something to tiptoe around, so they don’t bring it up until they’ve had multiple calls or they bury it at the back of the proposal.

Be the one who initiates the pricing conversation, and do it confidently.

When you get on that proposal call, share your screen, show them the numbers, and walk through it in plain language.

No over-complicating it. No apologizing for it.

Two things happen when you own the pricing conversation.

Keep it simple, keep it clear, then ask directly: "Does the investment make sense given what you're trying to accomplish?"

That one question will tell you everything you need to know about where they actually are.

A quick note on the proposal itself.

Keep it clean. An investment table, a statement of work that ties back to it line by line, order details, and a signature section. That document should also function as the contract. When they're ready to move forward, there's nothing else to send. You've already covered everything together on the call.

Use this Free Proposal Template and the “How To” Guide to use it effectively.

If you’re sending over pricing without a call to discuss, stop immediately.

If you’re sending over a proposal because they want more information, stop immediately.

If you’re sending over anything and you don’t actually know why, stop immediately.

Take a step back.

Ask the “uncomfortable” questions.

You must confirm where you’re at in the process and eliminate any ambiguity as fast as possible.

It is going to save you hours of your time and give you back a bit of your sanity.

One Final Important Note:

You do not have to nail all five steps in a single conversation. If the only thing you accomplish when someone asks for a proposal is getting a live pricing call on the calendar before you send anything, you are already ahead of most people. The questions about start dates, decision makers, and procurement can all happen there.

The goal, right now, is to eliminate sending a document into the void and hoping for the best.

Don't wait for a real call to practice this. The worst time to figure out what you're going to say is when you're actually on the phone with someone.

Pull up your LLM, find a mirror, or grab a colleague and practice your response to "can you send me a proposal?" out loud.

It doesn’t matter if it’s rough or you’re stumbling. The point is that when it happens for real, you're not scrambling.

"Send me a proposal" doesn't have to be a coin flip. Slow down, ask the right questions, and run a clear process every time.

You control the outcome from here.

What's a deal in your pipeline right now where you got a proposal request but skipped one of these steps? Reply and let me know. I read every response.

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