Why Your Proposal Emails Are Killing Deals

Today’s Skill: Running Proposal Reviews

Here’s a sales mistake I see all the time:

A founder has a great discovery call, spends hours crafting a beautiful proposal, then sends it off over email and waits. And waits. And then either gets ghosted or a polite, “Sorry, not for us” response.

In fact, it just happened to my friend Chris. (You can read the full Linkedin post here)

Emailing a proposal without walking through it live is a big no-no. I get why you do it, though. I used to do the same thing.

We are scared to talk about money. It feels a bit icky. So, we avoid it by lobbing over the proposal thinking that will pad the landing. However, it only creates unnecessary friction.

Literally and figuratively, you are leaving money on the table.

Why Reviewing Proposals Live Matters

You Control The Narrative

Without you there, they interpret numbers however they want. A $25k proposal can look like a cost instead of an investment. Live, you anchor it to their outcomes. You confirm their needs.

You can articulate the importance of certain items that were added and why you structured the roll-out the way you did.

You Hear Objections In Real Time

If they skim a PDF and don’t get it, you may never hear why. On a call, you can hear the pushback and reframe it immediately. Objections can actually be buying signals.

Let’s talk through those instead of creating an email barrier between you and the prospect.

You Keep Momentum

Emails invite delays. A live review lets you book the next step before you hang up. It let’s you talk through how they are feeling and where you go from here.

You aren’t guessing when and where you’ll hear from them next. You’re discussing that live with them.

You Tailor In The Moment

When you walk them through it, you can emphasize key points that ties pricing directly back to their goals, not a generic package. Plus, if your proposal is complex, you have a better chance of speaking to the key areas and highlighting exact costs to avoid confusion.

BTW, if you need to simplify your proposal, read this!)

What To Do Instead of “Sending It Over”

1. Set Expectations Early

Let them know: “When we get to pricing, I’ll walk you through it live so we make sure we didn’t miss anything and nothing gets lost in translation.”

2. Book The Review Before You Write It

At the end of a call: “Great, I’ll put together options based on what we discussed. Let’s book 20-30 minutes Tuesday or Thursday to walk through it together.”

3. Keep It Simple

Use their language. Anchor pricing to the outcomes they said matter most. Present 1–2 clear options. A proposal doesn’t have to be the contract. It can literally be a one-page overview of what they are purchasing.

Don’t overcomplicate it. If it looks complex, so do your products/services.

4. Hear Their Concerns

The proposal review should be a two-way conversation. Make consistent pit stops after key sections and ask directly how they are feeling. Here’s a few questions you can use.

“How does the total project cost align with the budget you had in mind?”

“As you look at these options, what feels most aligned and where do you see potential concerns?”

“If we moved forward with [Insert Option], does this feel like the right structure and timing for your team?”

5. Test Commitment Live

Close the review with: “How does this all feel from your end? Are you ready to kick off the partnership or are there any final concerns we should discuss first.”

Listen intently and walk with them in whichever direction they move you. This is about them choosing the path, not you “closing them” on one.

→ There may not be an answer at the end of this call but there should be a clear path forward. If you have to send the proposal through email now it will be much clearer, especially if they will be sharing with others.

It goes proposal call, then proposal email (if necessary). In that order.

Trying to flip this order around can cause massive disruptions in your sales process.

The Bottom Line

This has nothing to do with the actual proposal. It has everything to do with having a direct business conversation and figuring out what needs to happen to move forward.

Email is passive and impersonal. Phone calls are not.

The proposal call should be a negotiation, not necessarily on costs, but on confirming everything that is included in the partnership. Things may need to be added or taken away. Scope may be altered. It’s better to discuss that live than back and forth through email.

Or worse, never having the conversation at all.

Don’t be scared to ask for time to go over the proposal. If they are serious about doing business with you and solving this problem, it’ll be worth their time.

Your Action Item

On your next deal, refuse to just “send it over.” Book a review call to discuss it live.

Come prepared with a detailed proposal that aligns with the goals you’ve discussed.

Walk through it slowly and confirm alignment along the way,

You’ll be surprised how engaging the conversation becomes and how much faster you get to an answer, one way or another.