How to Ace Your Proposals by Going Multiple Layers Deep

A proposal is more than just a document; it’s a representation of your ability to understand the needs of your client and deliver value. It must dive multiple layers deep— demonstrating consideration of the total value of your deal and all stakeholder considerations.

In this post, we’ll explore how to ace your proposals by diving into the five Ws: Who, What, When, Where, and Why. By understanding these essential elements and asking the right questions at the right time, you’ll craft proposals that resonate with your audience and set you up for success.

Asking the Right Questions, to the Right People, at the Right Time

Before we dive into the five Ws, it's essential to understand the importance of asking the right questions. To ace your proposals, you need to first focus on what the client or partner truly needs. The initial step is internal: ask yourself what objectives your proposal should meet, what pain points your client is dealing with, and how your product or service will solve them.

But here’s the trick: don’t stop there. The next layer is equally important—asking the right questions to the right people at the right time. For example, if you’re negotiating with a potential new hire, you wouldn’t just ask them about their experience; you’d reach out to their references to ask about work ethic, reliability, and collaboration. Gathering firsthand information from the right sources will lead to a more comprehensive proposal that hits all the right notes.

Now, let’s break down the five Ws to ensure your proposal is as deep and comprehensive as possible.

1. Who: Understanding Your Audience

Knowing who you are addressing is one of the first and most critical layers in building a successful proposal. Are you pitching to an executive team that values ROI, or to a department head focused on efficiency and timelines? Understanding your audience will allow you to tailor your language, tone, and focus.

For example, if you’re writing a proposal for a potential client, the emphasis should be on why your company is the best option and how you meet their unique needs. If you’re negotiating internally for resources, focus on the specific requirements and how your proposal aligns with organizational goals.

2. What: Defining the Scope of Your Proposal

Next, you need to get clear on what you are proposing. This seems straightforward, but many proposals fail because the scope is either too vague or too narrow. Going multiple layers deep means asking:

• What problem are you solving for your client or counterpart?
• What are the deliverables, and how will they add value?
• What is the long-term impact of your proposal?

In a negotiation, this is where you identify whether you are creating value or extracting value. Be specific about what you are offering, and make sure it’s clear to both parties. After all, confused minds don’t buy—or accept—proposals.

3. When: Timing is Everything

When it comes to proposals, timing is a significant factor. Knowing when your audience needs the deliverables helps ensure that your timeline is not only realistic but also aligned with their expectations. Time can also be used as a lever of power in negotiations. If you control the timeline—either by meeting it faster or knowing when to apply pressure—you can gain an advantage in the discussion.

Consider this: If the client needs something immediately and you’re able to deliver ahead of schedule, you’ve instantly increased the value of your proposal. On the flip side, if their needs are further out, you have more time to prepare a detailed, polished presentation.

4. Where: Understanding the Geographical and Contextual Factors

Where your audience will use or implement your proposal can sometimes be overlooked but is an important layer to consider. Are there geographical considerations that need to be addressed? For example, if your solution involves physical delivery or on-site work, will the location impact timelines, costs, or logistics?

Even if geography isn’t a factor, context can still be important. If your proposal is for a digital product or service, where and how it will be accessed matters. Make sure your proposal accounts for the client’s usage scenarios, as this shows that you’ve thought about how your solution will work in the real world.

5. Why: Justifying the Need

Finally, the why is arguably the most important part of your proposal. Why does your client need what you’re offering? Why is your proposal the best solution for their problem? If you can’t answer these questions clearly, your proposal will likely fall flat.

In your proposal, articulate the need for your solution in a way that’s easy to understand. Demonstrate the value it brings, whether it’s solving a pain point, improving efficiency, or delivering long-term benefits. Without a compelling “why,” the decision-makers won’t have the motivation to move forward with your offer.

Digging Deeper: Layered Questions for a Stronger Proposal

To truly ace your proposals by going multiple layers deep, ask yourself these layered questions for each of the five Ws:

• Who else should you be speaking to for deeper insights?
• What additional value can you offer that goes beyond the obvious?
• When is the best time to present the proposal to maximize its impact?
• Where will the proposal be used, and are there any logistical challenges to consider?
• Why should the client choose you over your competitors, and how can you make this clear?

By digging deeper into each of these questions, you’ll create a proposal that is not only comprehensive but also resonates on multiple levels with your audience.

The Art of Going Multiple Layers Deep

Crafting a winning proposal is about more than just addressing the surface-level needs of your client. It’s about going multiple layers deep—asking the right questions, gathering meaningful insights, and understanding the nuances of your audience's needs. By focusing on the five Ws—Who, What, When, Where, and Why—you can ensure that your proposals are thorough, compelling, and more likely to succeed.

The next time you sit down to draft a proposal, remember to dig deep. Don’t just focus on the immediate asks—think about the broader picture. With a strategic approach and a focus on value, you’ll not only ace your proposals but also build stronger, more effective partnerships.