Most people think pitching is a moment, involving a call and a proposal. 

But it’s actually a process – one that unfolds over multiple conversations, papers, pauses, and decisions. Every engagement looks different on the surface, but they mostly follow the same rhythm. 

Not everyone you talk to will move through all of them.

It’s simply how professional services work.  

Once you understand pitching as a process instead of a performance, it becomes far less stressful. 

Let’s walk you through what you need to do to move an engagement from first conversation to a real decision. 

(And next week, we’ll cover what happens after the deal is signed.)

Before getting into the steps, let’s reset some expectations first: 

Not every conversation turns into a proposal. Not every proposal turns into a deal. 

And not every deal closes on a specific timeline. 

You could reach out to fifty people, have meaningful conversations with thirty, write proposals for eight, and end up closing three. 

That’s the math of consulting. 

Most consulting engagements move through eight steps: 

Prospects move through them at different speeds.

Picture a river that starts high at the water source in a mountain. 

As it converges into a larger reservoir, the stream goes through a lot. 

It can flow peacefully, run through rapids, or join other streams in a wider channel. 

The process isn’t a straight line – and it’s the same way with your prospects. 

Some parts require you to engage deeply, and others don’t. 

Some engagements go through with a breeze, while others pass some rough patches first. 

Some are even stuck in a puddle, until a blocker moves, and they start flowing back to the river again. 

At the first four steps of this process, you’ll start with a lot more than you’re going to close at the end. 

Some indie consultants come in hot — overselling their experience and treating a call like a mini proposal. 

But this stage isn’t about convincing anyone to buy.

It’s to establish enough credibility and clarity to justify a second conversation. 

Early conversations should help you learn more: 

Any answer you get from these questions becomes useful information. 

What worked best for me is to have a short, repeatable way to explain what you do and who you help — like a one-page bio template that highlights your expertise, experience, and case studies. 

But a simpler way to do it is an intellectual headshot. Introduced by Wes Wheless, it's a visual representation of what you do. 

We talk more about it in this interview:

At this stage, it’s all about building trust while going deep into what the problem is – NOT BY PITCHING, but by asking questions and listening carefully to the answers. 

Your focus here is on discovery, so make use of follow-up conversations and targeted questions.

You’re working to understand: 

At the same time, you’re paying attention to the working dynamic: 

These are crucial because you can’t work well with a client if you don’t know how they work.  

Also note that this step unfolds through multiple touchpoints, not a single call.

It’s also normal for some conversations to fall off at this point. 

From the second conversations you managed to secure, only a subset will reveal a problem that’s clear enough to define, important enough to prioritize, and funded enough to act on.

By the end of this step, you should be able to say: 

I understand the problem well enough to propose a specific approach. 

That’s the signal to move forward. 

You need a repeatable way to run discovery conversations to avoid improvising each time. 

A short set of go-to questions is usually enough to surface what’s real, what’s urgent, and what’s still unclear. 

I also suggest capturing notes during each conversation – the problem as you understand it, key constraints, and any open questions. 

Patterns show up quickly when you do this consistently. 

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At this stage, the goal is less about persuading and more about clarifying the problem – to yourself and then to the client. 

 The easiest way to do that is to structure proposal creation into two distinct steps. 

Some clients want a written document. Others want a deck to share internally. 

The simplest way to ask before you start writing. 

Writing proposals for multiple prospects is a lot of work – especially if you’re doing it from scratch. This is where having different proposal templates could greatly help you out.   

And these are different ways they could be done: 

We have these templates in The 2x2 Library – so make sure to sign up. 

This is the step that causes the most unnecessary anxiety: because once the proposal is sent, the ball is in their court.

All you can do is wait for a response or follow up every few days. 

Your proposal enters someone else’s internal chaos: meetings, inbox overload, shifting priorities, and internal alignment you may never see. 

Silence here usually means they’re busy, not a definite “no.” 

Many consultants hesitate to follow up because they don’t want to be seen as annoying – but it’s not pestering when done right.

When you follow up, it keeps you on top of mind and prevents your proposal from getting lost in the inbox.  

According to David A. Fields, you’ll need to send eight follow-up emails to you prospect after the last exchange. 

But I think that’s too many. 

Five emails are the sweeter spot: enough touches to stay top of mind, no inbox clogging. 

Like the proposals, clients also have different preferences on how proposals or follow-ups are sent. The important thing is to ask. 

But the rule of thumb is to send it by email to appear more professional and respectful. You can also give them quick heads up through text or their LinkedIn. 

As for following up, give the client multiple chances to respond honestly. This minimizes your chances of getting ghosted.

An effective follow-up follows a progression of intent: 

Some will re-engage halfway through the sequence. Some will never respond at all. 

It's simply how decisions move through organizations. 

And if there’s a ghosting prospect you want to bring back, here’s an article to guide you through the process. 

If you can move through these four early steps, then you’ve already solved the hardest part of consulting. 

The good news? The next part is where your expertise can actually shine. 

The rest isn’t about selling – it's more about execution and follow-through. 

Your success will depend on how you deliver client work, but we’ve got some guidelines to help you through it. 

Stay tuned for the next one.