How to Find & Fill Deal Gaps Early (Before It’s Too Late)

Most people think writing in sales is about documenting what you already know. But it’s not. It’s the process of discovering what you don’t yet know.

Shane Parrish from The Knowledge Project puts it this way:

Writing is the process by which you realize you do not understand what you are talking about. Importantly, writing is also the process by which you figure it out.

That’s good. “The process by which you figure it out.”

What you’ll quickly find is it’s not actually possible to sit down and write out a quality, executive-level message at a single point in your sales process. That first act of writing will simply be your discovery gaps becoming visible.

Instead, you’ll find writing out your message is the sales process.

It’s the ongoing loop of finding and then filling gaps at each stage. Because as you write down new inputs from your last meeting, you’re not just coloring in the blank spaces.

You’re changing the outcome of your deal along the way.

How to Keep Deals From Dying in 31 Different Ways

Remember those old Choose Your Own Adventure books?

If you were born after the early 90’s, they’re books where you’d read up until you hit a decision point. Then, you’d choose which way you’d go by flipping to different pages, based on a set of branching storylines. Each fork in the road held consequences for how your story played out — eventually landing you on one of a dozen possible endings.

Here’s a map of the book Journey Under the Sea, by R.A. Montgomery. It outlines the narrative with arrows for pages, circles for choices, and squares for endings:

This book is about finding the lost city of Atlantis, and get this: it has 42 possible endings. They fall into a few major categories like these, outlined by Atlas Obscura as:

Disappointment: you don’t quite get there, your ship is destroyed, your eyesight is damaged.

Hope: a mysterious submarine saves you, so you get a second chance, but only glimpse Atlantis in the sky

Danger: you might ride a whale, get eaten by a fish, get eaten by a shark, or die by a poisonous snake bite.

Atlantis: you find Atlantis, but you might destroy it before you get in. You might meet Atlanteans, who appear in different guises in different endings.

Then it goes on to say:

This book is particularly tough on readers. One analysis found that 75 percent of the endings are unfavorable or deadly. One of the most poignant endings is the one where you choose to pull back from your search, and someone else finds Atlantis, and you come to regret giving up your search.

Did you catch the parallel here?

1. Your discovery questions are forks in the road, and they change how your deals play out. Either leading to hope, disappointment — or someone else’s win.
2. Readers only get a happy ending 25% of the time. The other 75% are “unfavorable” or “deadly.” (Most sales teams’ win rates are even lower, around 20%.)
3. Here’s the big one, if you go back to the visual:
   You’ll never get the chance to ask certain questions — and therefore, discover certain answers, which would have illuminated a whole new set of questions to ask, and so on — without a thoughtful approach to your first discovery questions.

The point is that what you do in the early stages of your deal will completely change its trajectory.

So if you haven’t designed your sales process to continually reveal the right next question, you’ll get eaten by a shark. Or a hungry Atlantean. Or watch your deal die off for any one of 31 possible reasons.

A natural next question that leads us to, is, “Well how do we make sure we’re asking the ‘right next’ questions, to stay on the path to a win?”

Here’s how.

5 Steps to Find & Fill Deal Gaps

It’s a pretty straight forward process, really. You’ll:

1. Start the cycle with a good messaging framework.
2. Fill in what you can after your first conversation, based on your discovery.
3. Compare that early draft to what a completed, winning message looks like.
4. The gap between #2 and #3 reveals what you don’t know — while providing the roadmap for where to go in your next meeting.
5. Repeat.

Step 1: Here’s a simple framework you can use called The 1-Page Business Case:

Step 2: Fill in the framework, or let Fluint write your first draft for you.

Step 3: You can also use this business case scorecard to compare your draft to “what good looks like.”

Step 4: Based on the gaps you just saw, use this framework to craft the right next question to fill them. Which includes a simple grid like this:

Fluint runs this analysis and crafts these questions for you, like this:

You can also use the full discovery meeting planner, here:

As you move on to Step 5 and repeat, you’ll find little surprises you just can’t help asking about.

Which means your conversations start to become far more genuine, because you’re actually curious now. So you’ll ask something that’s more like:

“Since you mentioned your goal is X, I would have expected you to do Y, but you’re doing Z. What led you to try that approach?”

Instead of like a qualifying checklist, “So, what criteria are you using to make this decision?”

And that’s the last Choose Your Own Adventure parallel:

This isn’t just about how our deals play out as sellers.

It’s about putting our deals in writing, to guide the customer journey.

Crafting questions to guide their next decisions — and the internal buying conversations happening without us in the room — which changes the outcome of our deals, and their reality, one stage a time.