How to Create Personal (Not Just Personalized) Sales Proposals

Content automation and streamlining proposals have been a hot topic recently — with good reason. As the number of proposals you respond to increases with potentially little increase in your team size, it can be enticing to fully automate proposals and deliver them with just a few clicks.

But, that time-saving automation can sometimes result in you getting out of sync with your customers and their needs.

To share best practices for creating genuinely personal proposals that aren’t just a conglomeration of personalization tokens pulled from Salesforce data, we couldn’t think of a better expert than Chief Customer Officer of legal operations software company Brightflag, Kevin Cohn. 

Kevin has 15+ years of experience in software sales and customer success and has recorded his findings, learnings, and experiences in a Medium blog over the last several years. We sat down with him to talk about what it means to create a personal, not just personalized, sales proposal. 

Before you even begin the proposal...

1. Build real rapport and trust in the sales cycle.

This might sound like extra work, but often putting in work at the beginning and starting on the right foot is the foundation for excellent proposals. And sales leaders may talk the talk, but as Kevin explains, they don’t always walk the walk, “Sales leaders constantly talk about the importance of rapport and trust, but the more I do this job, the more I realize how few people truly understand what it means. It's far more than banter and mirroring.”

“One of our newer reps has excelled at writing executive summaries that speak directly to the buyer's organizational culture. For example, he explained how our company values mirrored those of a particular Fortune 50 prospect in many ways. In another example, he led an initiative to create a collage of our employees standing in front of a QSR prospect’s restaurants.”‍

“Both examples were reminders that business-to-business is a misleading label; it's really person-to-person.”

2. Meet your prospects where they are.

“I'm a huge believer in using maturity journeys to center conversations. I'm of the somewhat unfashionable opinion that it's okay to talk about features, but you have to put them in the proper context.” 

And that context has everything to do with where your customer and the team they sit within is in their maturity. 

“We sell to first-time buyers, as well as more sophisticated enterprises looking to level up their legal operations. I've yet to meet a first-time buyer that cares about AI-powered forecasting — it's many stages beyond where they are in their maturity journey — but there's that pull to talk about the latest, greatest, and coolest features, particularly if they're differentiating, and you need to work hard to resist that.”

Knowing these intricacies, honing these personas, and having conversations that speak precisely to your prospect’s needs sets the stage for an exemplary proposal.

On that note...

Once you’re crafting the proposal…

3. Never skip the executive summary.

It can be a toss-up if a prospect asks for an executive summary when issuing a bid. Sometimes, they may just want the cold, hard facts and security details to score you against others. But, there’s only so much differentiating you can do in a Yes/No/Comments format. 

So, how do you reiterate and continue to prove your value to prospects?

As Kevin notes, “write an awesome executive summary, even if they don't ask for it and even if they tell you not to. In my experience, it's the only thing that everyone on the buying end actually reads.” 

He goes further on how to craft your executive summary in a blog post, “it needs to introduce the company, communicate an expert understanding of the buyer’s requirements, and explain why the buyer needs your unique capabilities.

“Labor over the executive summary. Every word should be carefully selected. Don’t use your company’s jargon, which the buyer may not understand. Share it with as many people as possible, especially people that aren’t involved in the deal at all; more likely than not, they’ll be the ones who provide you with the most valuable feedback.”

4. Answer the question before you explain the question.

This is an extremely simple but overlooked part of crafting proposals. As Kevin explains, “the most egregious example is responding to a yes/no question where the answer is yes, but the first word of the response is anything other than ‘yes.’”

In a blog Kevin wrote back in 2018, he introduced his “one sentence/paragraph/page” framework. It works like this:

• For any given question, you should be able to give a one-sentence answer, a one-paragraph answer, and a one-page answer. One-sentence answers are short (literally, one sentence); one-paragraph and one-page answers are longer and, as such, include more detail.
• When asked a question, assume you’ll only be given one opportunity—and about eight seconds—to answer it. For this reason, you should always give the one-sentence answer first.
• There’s nothing worse than getting the “this is way more information than I wanted” look (except perhaps the “you still haven’t given me the information I want” look), so stop there unless the person asks for more information, in which case you can give the one-paragraph answer and, if necessary, the one-page answer, in that order.

Speak to your customers, not just your value prop.

It can be easy to get into an automation rut and do the “easy” thing, but often, the best results come when we slow down, prioritize, and cater to our customers and prospects. 

Need more evidence that your content can’t just be fast but needs to be effective? Check out Why Sales Content Needs to Be Effective in 2021, Not Just Efficient.