Picture this: A prospect calls and says, "We need a new CRM system. Can you help us implement Salesforce?" Your eyes light up—this sounds like a $50K project. You schedule a demo, craft a detailed proposal, and three weeks later get an email: "We've decided to go with someone else."
What went wrong? You took them at their word.
Here's what I learned after losing deals like this: when you dig deeper into that CRM request, you often discover that three different departments want three different systems, nobody has mapped their current sales process, and the CEO, sales manager, and IT director all have completely different definitions of success.
The best salespeople don't just take orders. They guide prospects through the right sequence of decisions, even when it means starting smaller than you'd like. Because sometimes the most profitable path forward begins with helping a prospect understand they're not ready for what they think they want.
Every business goal falls into one of three categories. Knowing which one you're dealing with is the difference between winning deals and winning clients.
Why most sales conversations start with the wrong question
When prospects reach out, they're usually asking, "Can you do X?" But what you should be thinking is: "What are they asking for, really?"
Every business goal fits into one of three buckets:
Insight goals: "What's really going on here?" These are assessments, audits, and discovery projects that uncover whether change is even necessary.
Planning goals: "How do we fix this?" Strategy development for a known problem. They know something needs to change, but they need a roadmap for how to make it happen.
Implementation goals: "Help us get it done." Hands-on execution support. They know what to do and have a plan—they just need help making it real.
Think of it like going to the doctor. Sometimes you know you have a headache and need aspirin (Implementation). Sometimes you feel terrible but need tests to figure out what's wrong (Insight). Sometimes you know you have diabetes but need help creating a treatment plan (Planning). I wrote an article about this way of thinking and wrote a whole chapter on it in my book.
Here's where it gets tricky for us as salespeople: most prospects don't actually know which type of goal they have.
When your expertise doesn't match their reality
Your company is probably excellent at Implementation: actually delivering solutions, training teams or installing systems. That's where the big money usually lives. But what happens when someone asks for an Implementation and you realize they haven't done the groundwork to make it successful?
Let me give you a real example. A healthcare startup reached out to me saying they needed help "scaling their sales team." Sounds like Implementation, right? They were ready to hire, had budget allocated, and wanted to move fast.
But when I started asking questions, I discovered they had no clear sales process, no defined ideal customer profile, and the founders disagreed on whether to focus on direct-pay patients or insurance billing. They didn't need Implementation. They needed Planning and maybe even some Insight work first.
Most salespeople face a dilemma here: take the money and watch the project fail, or walk away from a qualified prospect.
But there's a third option that's far more profitable.
The strategic power of starting small
Instead of proposing what they asked for (or walking away), I offered something different: a two-week Sales Strategy Assessment. For a fraction of their Implementation budget, we'd interview stakeholders, analyze their current approach, and create a clear roadmap for scaling.
This is what I call a gateway offering: a smaller, paid project that addresses their actual current need while positioning you for the larger engagement you really want.
I know what you're thinking: this sounds like I'm leaving money on the table. Actually, it's the opposite.
That healthcare startup? The assessment revealed they needed to solve their customer acquisition problem before scaling their team. We ended up doing a complete go-to-market strategy project worth three times the original Implementation deal. More importantly, it actually worked because we'd properly diagnosed the situation first.
Gateway offerings work because they solve the fundamental mismatch between what prospects think they need and what they actually need.
Four reasons gateway offerings win long-term
They build trust and demonstrate expertise. When you're willing to start smaller to ensure success, prospects see that you care more about their outcome than your commission. This isn't just good karma, it's smart business positioning that builds real trust.
They establish the real need. Instead of guessing what to implement, you gather the insights needed to craft a compelling proposal for the right solution. You're not shooting in the dark anymore.
They control the narrative. After your gateway project, you're not competing against other vendors who are proposing generic solutions. You're the one who discovered what they actually need and how to deliver it successfully.
They provide risk mitigation. Prospects get value even if they decide not to proceed with a larger project, making the initial decision much easier. Lower barriers to entry often lead to higher lifetime value.
I was working with a marketing agency that was hemorrhaging clients. The CEO wanted sales training for "better expectation setting." Instead, I proposed a Client Retention Assessment. We discovered that the real problem wasn't sales skills. It was a breakdown in handoff from sales to account management. Client retention improved from 68% to 91% within six months. If I'd just delivered the sales training they requested, none of this would have happened.
Making the pivot without losing momentum
Here's how to transition from their request to your gateway offering without losing the deal:
Start by acknowledging what they asked for: "I understand you're looking at CRM implementation, and we definitely have the expertise to help with that."
Then share what your diagnostic questions revealed: "Based on our conversation, I'm thinking there might be some foundational pieces to address first."
Finally, position the gateway as risk mitigation: "Before we implement anything, what if we made sure we're solving the right problem? I'd hate to see you invest in a system that doesn't address your core challenges."
The key phrase I use: "Let's start with a Discovery Workshop / Process Assessment / Strategic Planning Session to ensure whatever we implement delivers the results you're looking for."
Price your gateway work appropriately. It's not free consulting, but it should be accessible. Think 10-20% of your typical Implementation project fee. You're investing in the relationship and gathering intelligence for a much larger opportunity.
When your boss asks why you're not selling the big project
If you're part of a larger organization, you might need to get leadership on board with this approach. Here's the business case:
Gateway offerings increase both win rates and average deal sizes. When prospects trust you to diagnose before you prescribe, they become long-term clients worth far more than any single project.
Start small rather than asking for a complete service line overhaul. Propose a pilot program: "I'm seeing qualified prospects who need Planning before they're ready for our Implementation services. Can we test offering Strategy Sessions as a gateway? I estimate it could increase our win rate by 15% and our average deal size by 25%."
Track the results and prove the concept works. Most leadership teams will support approaches that demonstrably improve sales outcomes.
The long game
Not every prospect is ready for what you want to sell them. But the ones who need discovery work first often become your best clients. But only if you're willing to meet them where they are.
Gateway offerings turn "not yet" into "yes, let's start here." They transform you from just another vendor pitching solutions into a trusted advisor who ensures those solutions actually work.
The goal isn't to do smaller projects forever. It's to learn what should be done and earn the right to do the bigger projects successfully. Sometimes the most direct path to Implementation runs through Insight and Planning first.
Long-term clients are worth far more than any single project. Gateway offerings are how you build those relationships.
Want to learn more about diagnosing what your prospects really need? I share frameworks like this weekly in my newsletter, along with real case studies and practical scripts you can use immediately. The best salespeople are always learning new ways to serve their clients better — even when it means starting smaller than they'd originally planned.