Checklist: Gap Selling
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"With Weflow, we’re now capturing all relevant activities and have full transparency into the performance of each sales rep. It’s a game changer."
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"Weflow gives us better visibility and predictability of our business."
"Weflow eliminated the need for our VP to ask, ‘Did you follow up with that deal?’. It tracks customer interactions automatically, creating a framework that drives accountability across the team."
"None of the other tools gave us a solution like Weflow. From the beginning, we had a really smooth process."
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"I had a first introductory call with Weflow. I think I was sold after 15 minutes. There’s no question that the people at Weflow understood the problems that we were trying to solve."
"I’ve worked with Gong before, but Weflow’s simplicity and real-time sync are game-changing."
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"We use Weflow to auto-capture activity data, run deal reviews, and analyze our pipeline to inform our forecast. Being able to spot deal risks early has improved win rates and pipeline health."
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What's Inside
Current-state diagnostics
- Discovery questions to map the prospect's existing reporting stack, technology in use, and the features they actually value
- Prompts on user count, workflows, location, and timing that reveal how the current solution gets used day to day
- Friction-surfacing questions covering shortcomings, process inefficiencies, and confidence in hitting next-quarter goals
Future-state definition
- Questions that force the prospect to articulate the specific changes they want and the reasons those changes matter
- Planning prompts that pin down how the prospect intends to execute the change and which steps they expect to take
- Value-tying questions that connect solved problems to freed-up time, resources, and reporting the team currently lacks
Gap qualification criteria
- Internal self-check prompts on business criticality, personal stakes, change catalysts, and the business drivers behind the deal
- Action-test questions covering what the prospect has already tried, team commitment, and blockers still in the way
- Urgency and success questions that lock down required timeline for results and how the prospect will measure outcomes
Daniel Schemmert
Daniel Schemmert is the Head of Growth at Weflow, where he's built the GTM engine from scratch. He spends valuable time talking to RevOps leaders about how they run pipeline, forecasting, and Salesforce. He's also the co-founder of RevOps Chat, the Slack community where 1,000+ RevOps practitioners share what's actually working inside their revenue orgs.
Go Deeper
GAP Selling Questions for Discovery: Current State, Future State, and Urgency
#54 Creating a highly effective sales & forecasting process
Sales Methodology Guide & Checklists
Frequently asked questions
What is Gap Selling and how is it different from a standard discovery call?
Gap Selling is a methodology built around diagnosing the distance between where a prospect is today (current state) and where they want to be (future state) — and then determining whether that gap is big enough to justify a purchase decision. Unlike a standard discovery call that often jumps straight to pitching features, Gap Selling keeps you in diagnostic mode until you've confirmed the problem is real, urgent, and worth solving.
Do I need to follow the current state, future state, and gap sections in order, or can I move between them?
The sequence matters more than people think. You need a clear picture of current state before future state questions land with any weight, and you can't accurately size the gap until you have both. That said, conversations aren't linear — if a prospect volunteers a future state detail early, capture it and loop back to fill in the current state context before moving on.
What information should I have about a prospect before running through these questions?
At minimum, know what solution they're currently using for the problem you solve, what their stated goal or initiative is, and whether there's been any recent trigger — a new hire, a missed target, a product change — that's driving urgency. Walking in cold with no context makes the current state questions feel like an interrogation rather than a conversation.
How do I know if the gap I've identified is actually large enough to move a deal forward?
The checklist gives you the right diagnostic questions — specifically "Why is achieving X goal so critical to the prospect's business?" and "Why does X goal matter so much on a personal level?" — and the answers will tell you. If the prospect can't articulate a concrete business consequence or personal stake, the gap probably isn't big enough to drive a decision, and you're better off knowing that early.
Which of these questions should I keep human-led versus scripting into a sales sequence or email cadence?
The current state questions — like "What are the biggest shortcomings with your current solution?" — can work in a pre-call survey or async format to save discovery time. The gap questions, especially "Are you committed to taking action?" and "What needs to happen to move forward?", need to stay live and conversational because the follow-up probing is where the real signal lives.
How often should I revisit these questions with an existing prospect as a deal progresses?
Revisit the gap section specifically at each major stage gate — after initial discovery, before a demo, and before you put a proposal in front of them. Business priorities shift, timelines move, and a gap that felt urgent in week one can shrink if something else takes over their attention. Checking in on "When do you need to see results?" and "How will you measure success?" keeps your deal grounded in their current reality, not the one they described three weeks ago.
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