The Key to Proposal Timelines

Posted on June 23rd, 2023 to Uncategorized

I’ve seen it time and time again — founders toil away, crafting a detailed sales proposal, only to be met with deafening silence after shipping it to the potential client.

As you wait to hear back, you can’t help but wonder where you went wrong.

We’ve all been there. 

But in the world of B2B sales, it’s not just about delivering a proposal and hoping for the best. Understanding the buying process and staying in sync with your client every step of the way is key —  from initial contact to signing on that dotted line. 

That’s why I recommend optimizing the engagement timeline in your sales proposal to start before the kick-off meeting.

This simple yet highly effective strategy sets clear expectations, keeps you connected to the client’s buying process, and ultimately increases your chances of sealing the deal.

In this blog post, you’ll learn how to take control of the sales process by integrating essential, pre-kick-off dates into the engagement timeline of your sales proposal. 

Let’s get started.

The Power of Asking the Right Questions

Before we jump into the nitty-gritty of including a comprehensive engagement timeline in your sales proposal, let’s talk about the power of asking the right questions. 

This step is crucial in crafting a winning proposal that aligns perfectly with your client’s needs and expectations. (You can read about this topic in this post – How to Finalize a Proposal With Your B2B Clients And Get the Yes).

Their Timeline

Start by digging into their timeline. How urgent is their need? Are there any key milestones or deadlines they have in mind? 

Understanding the timeline allows you to tailor your proposal accordingly, ensuring that you can meet their desired time frame and insert your pre-signing dates accordingly (more on that below0).


It’s no secret that financial considerations play a significant role in decision-making. By discussing the budget early on, you can align your proposal with their financial capabilities, offering a solution that fits comfortably within their resources. 

But it doesn’t stop there.


Discovering the decision-makers involved in the process is vital. Who holds the keys to the kingdom? Who has the final say? 

By identifying these individuals, you can tailor your proposal to resonate with their specific needs and address their concerns head-on.

Potential Obstacles

Lastly, don’t shy away from discussing potential obstacles. 

Are there any roadblocks or challenges that could hinder the smooth progression of the buying process? By openly addressing these hurdles, you can demonstrate your expertise and position yourself as a valuable collaborator who can help navigate and overcome these obstacles.

Remember, collaborative planning is key. By involving the client in the process, seeking their input, and co-creating the proposal, you establish a sense of partnership and mutual understanding.

This collaborative approach not only increases the chances of a successful proposal but also lays the foundation for a strong client relationship moving forward.

Now that we’ve emphasized the importance of asking relevant questions and gathering key information, it’s time to plot out the engagement timeline in your proposals. 

The Need For Pre-Engagement Timelines In A Sales Proposal

When I review proposals on behalf of my clients, I often see this common mistake: they jump straight into the onboarding or kickoff meeting, completely overlooking the important pre-contract work. 

This approach assumes buy-in before the contract is signed, which can lead to ghosting or unexpected delays or rejections.

I propose a different way forward: start your engagement timeline before the contract is even signed. 

By doing this, you set the stage for a seamless transition from proposal to contract, and you demonstrate your commitment to the client’s buying process.

To help illustrate this concept, I’ll share a simple example:

Let’s say you’re having a meeting with your prospective client on April 17.

By April 18, you commit to delivering a comprehensive proposal. Because you’ve asked the right questions and gained a deep understanding of their buying process, you know that the client plans to present your proposal to their board on April 25. 

Therefore, you schedule a call for April 26 to discuss final decisions and next steps. All of this happens before the contract is signed.

Do you see what’s happening here? 

By incorporating these pre-contract steps into your engagement timeline, you set clear expectations with the client. 

But the benefits don’t stop there. 

Starting the engagement timeline earlier also allows you to maintain a closer connection to the buying process. You can outline additional steps such as signing the contract, scheduling an onboarding or kickoff meeting, and planning for future milestones.

Are you wondering if including these details in your proposal could come across as pushy or presumptuous?

Let’s address that common concern next and how you can confidently shift your perspective.

Overcoming Resistance and Building Trust

I know that when I bring up the idea of including an extended engagement timeline in your proposals, you might have concerns about coming across as “too much,” or too forward.

Let me reassure you, not one of my clients has received pushback or raised eyebrows when they include the pre-engagement timelines in the proposal.

In fact, clients appreciate the clarity and strategic partnership that an engagement timeline provides because it shows that you genuinely care about their success and are all-in.

Additionally, an engagement timeline helps your clients manage their workload more effectively because they’re likely juggling numerous responsibilities. 

By providing a clear roadmap and taking the lead in outlining the steps, you set a clear path forward and take the burden off of planning and scheduling.

So, remember, including an engagement timeline isn’t about being pushy or presumptuous. 

It’s about being proactive and demonstrating your commitment to serving your clients in the best possible way. 

And there’s one more thing you can do to really set yourself up for success.

Bonus: Adding Value With Scheduled Strategy Sessions

Now, here’s a bonus tip that can take your client engagements to the next level: incorporating strategy sessions throughout the timeline for the engagement. 

These sessions provide an opportunity to step back from the day-to-day operations and have a higher-level conversation with your client. 

It’s a chance to assess what’s working, address any challenges or roadblocks, and align on future goals.

The benefits of strategy sessions are twofold. 

  1. Strategy meetings allow you to serve your client at a higher level.

 By offering dedicated time to discuss strategy and provide guidance, you showcase your expertise and reinforce your value as a trusted advisor. It’s an opportunity to demonstrate that you’re not just there to deliver a service but to actively contribute to their success.

  1. Strategy sessions become valuable touchpoints for identifying additional opportunities. 

By staying engaged and having regular check-ins, you can identify areas where your client may need further assistance or where there’s potential for cross-selling or extending the scope of your work.

So, don’t miss out on this added value. Pepper your engagement timeline with strategy sessions that elevate your client relationships and open doors for future growth and opportunities.

It’s a win-win situation that will set you apart as a service provider who goes above and beyond.

Now that we’ve covered the importance of addressing concerns and the value of strategy sessions, let’s move forward and delve into the practical steps of implementing an engagement timeline.

From Ghosting to Closing: Sales Proposal Success

In conclusion, incorporating an engagement timeline into your proposals is a powerful strategy that can transform your sales process. 

By asking the right questions, understanding the buying process, and setting clear expectations, you can overcome resistance, build trust, and establish yourself as a strategic partner to your clients. 

Don’t be afraid to include concrete timelines that start before the contract is signed, as it demonstrates your commitment and helps manage your clients’ workload effectively. 

And don’t forget the bonus of adding value through strategy sessions, where you can elevate your service and uncover new opportunities. So, take the leap, implement these tactics, and watch as your proposals transform into contracts – signed, sealed and delivered.

Don’t let sales challenges keep you from growing —  join me and a group of fellow founders and subject-matter experts for a free monthly mini-training, Q&A and networking session.

Register for the monthly Sales Roundtable here. 

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