From Sketch to Proposal: How and When Proposals Actually Begin

[AI-assisted for speed.]

Most people write proposals too soon.

They try to turn a good idea into a polished document before the alignment is real. They write as if the proposal is how the conversation starts. It’s not. If you’re writing alone, early, and ahead of the relationship, you’re writing into the void.

Proposals don’t start on the page. They start in shared space.

You Don’t Write Proposals—You Build Toward Them

A good proposal doesn’t pitch. It reflects.

It’s not a performance. It’s not a surprise. It’s the culmination of a collaborative process that began in dialogue—quietly, subtly, long before anything was typed.

In the early stages of conversation, you’re exploring. You’re listening for values, alignment, interest. And then something shifts. The other person starts using shaping language.

Shaping language is your sign that they’re beginning to imagine themselves inside the work. They’re not asking follow-ups anymore. They’re testing fit.

• “Have you tried this in New York?
• “What would it take to do this at scale?”
• “Do you know X group?”

These are not surface questions. They’re structural ones. They’re poking at the architecture. That’s the moment to stop talking and start sketching.

Start With the Sketch

If you’re together in person, sketch.

Pull out a piece of paper. Draw three circles—constituencies, pressure points, actors. Add arrows. Overlay constraints or collisions. Introduce the shape of the intervention. Say things like:

• “They’re all trying to solve this, but they keep getting stuck here…”
• “This approach creates new possibilities—but only if these things line up…”
• “Here’s a rough 1-2-3 that might structure the work. What’s missing?”

This is not a diagram. It’s not a logic model. It’s not even legible half the time. It’s just the first attempt to externalize the shape of the work.

What matters is the shift in posture. You’re no longer across the table. You’re side by side, looking at the same sheet of paper. They’re pointing, drawing, debating. They might pick up a pen.

You’re no longer explaining. You’re designing together.

And that shift is everything. The sketch becomes the shared surface. Not a document. Not an outline. Not a promise. Just the earliest logic of what you might build—together.

Then Move to the Concept Note

If you’re not in person, you start here. Or if you’ve already sketched together, this is how you continue. Either way, the concept note is where the work begins to take form in words.

But it’s not a draft. It’s not a pitch. And it’s definitely not a PDF.

A concept note is the most informal, lowest-friction articulation of what’s been discussed. Its purpose is not to inform or convince—it’s to extend the conversation. To offer a surface the other person can still shape.

It should:

• Use informal, conversational tone
• Favor bullet points over paragraphs
• Avoid logos, headers, footers, or design
• Be editable by default
• Contain whitespace and scannability
• Read like thinking-in-progress

Good phrases look like:

• “We could pull together a group like X, Y, Z…”
• “This is probably the crux of the challenge.”
• “If this lands, it unlocks the rest.”

The goal is to keep the energy alive. Don’t send it with “Let me know your thoughts”—that’s assigning homework. It turns your partner into a reviewer, and the document into a deliverable.

Instead, say: “Just tried to capture our thinking—curious if the third section reflects your take on the event structure.”

That kind of prompt doesn’t ask them to assess. It invites them to join. It gives them a way in.

How the Work Evolves

Once the concept note exists, the proposal begins to take shape around it. You don’t “start writing”—you continue refining.

• Bullets become paragraphs.
• Provisional 1-2-3s get tested and improved.
• Timelines and budgets begin to appear.
• The tone shifts from exploratory to declarative.
• The structure tightens.

And all of that happens inside a shared space.

You’ll see three types of engagement:

1. Immediate and enthusiastic — They jump in, add ideas, drop comments, and disappear. Great.
2. Quiet and watchful — They don’t edit, but they read, and chime in at key moments. Great.
3. Silent, but with permission — They never touch the doc, but they know they could have. So they meet the final proposal with recognition, not resistance. Also great.

The document is collaborative whether or not it’s co-authored. What matters is that it was open. That it could have been.

When It Becomes a Proposal

There’s no clear threshold where a concept note becomes a proposal. It just… does. It accrues formality, structure, and precision until you realize: this is it.

The 1-2-3 is stable. The outcomes are clear. The resource section is sound. The team is aligned. There’s nothing left to surprise them.

That’s when you stop editing. And that’s when you hit send.