TL;DR: 5 Lessons from a Sales Call Gone Wrong
If you're in any kind of advisory or consultative role, here’s what this post will teach you about earning trust and delivering value fast:
- Set clear expectations upfront - What will we accomplish in the next 20 minutes?
- Give value before you ask for anything - Share one concrete insight or play immediately
- Ask permission to critique - Don't assume people want your feedback right away
- Show your work - Bring your framework to life with examples.
- Propose no-risk next steps - Make it easy to say yes to learning more
Ever been invited to a “strategy call” that was supposed to be a problem-solving session, but halfway through you realize you’re being sold to?
That happened to me recently.
We’d been referred to a consultant to help improve Proposify’s trial-to-paid conversion. The meeting was pitched as a working session, a chance to “dig in and come up with some plays.” Perfect. I brought our product and design leads, ready to brainstorm, take notes, and leave with 2–3 experiments to run next week.
But instead of the strategy session I expected, it turned into unstructured talk, unsolicited critique, and then... a sales pitch.
And here’s the thing: even if it had been a sales call, it still wouldn’t have worked. Because what was missing wasn’t polish or charm, it was purpose. There was no value delivered before the ask.
By minute 17, I had to cut it short: “This just feels like a sales call.”
Let me break down what went sideways, because there's a masterclass hidden in this train wreck.
The 5-Minute Breakdown: What Went Wrong (and What You Can Learn)
- The anatomy of a sales call gone wrong
- Why first impressions matter more than you think
- 5 principles that separate consultants from vendors
- What this means for your own sales approach
The Setup
Here’s the context: We were looking for insight into our trial-to-paid conversion problem at Proposify. A mutual connection had recommended this PLG (product-led growth) consultant, saying he helps SaaS companies improve activation and conversion.
The calendar invite even said we’d “dig in and come up with some plays.” That set the expectation of a collaborative workshop. Instead, what we walked into felt like a qualification call and that mismatch is where things started to derail.
Where It All Went Wrong
1. No Upfront Outline
The call opened with casual intros but no clear direction. No agenda, no confirmation of goals, no time boundaries.
What should have happened: "We've got 20 minutes. My goal is to give you two plays that typically lift trial conversion 10-30%, we'll pressure-test them against your situation, and if they're useful we can discuss what working together might look like. Sound good?"
2. Critique Without Permission
Five minutes in, before we’d even defined what success looked like, the consultant launches into: "Do you want the good news or the bad news about your product?"
Then he proceeds to tear apart our onboarding flow without asking if we wanted feedback or understanding the context (like the bug we'd literally discovered 20 minutes before the call).
What should have happened: "I signed up to experience your flow firsthand. Mind if I share a few observations from fresh eyes, and we can discuss if they're representative?"
3. Questions Without Value
The next 10 minutes were all discovery: "What's your PLG vs SLG split?" "How are you tracking toward your revenue goal?" "What's your data infrastructure look like?"
All valid questions, but he was extracting information without giving anything back. It felt transactional, not collaborative.
4. The Framework Pitch
Finally, around minute 15, before offering a single actionable idea, he launches into his service offering: "What we do is build self-service models through our three-part framework: foundation, funnel building, and scaling..."
No connection to our specific problems. No examples. No concrete value delivered first.
How the call should have gone:
If the consultant could have earned trust and set up natural next steps:
Immediate Value
"Based on what you shared and my signup experience, here are a couple of quick plays we typically see work. I’ll walk you through them so you can test one this week.”
Collaborative Diagnosis
“Let’s map your funnel together using our quick worksheet. I’ll benchmark it against our data and send back the biggest leaks and a simple experiment plan.”
No-Risk Next Step
"I'll send both plays in writing by end of day. If the direction resonates, we'll run a one-week activation sprint with your team. If it doesn't move the needle, we part friends."
The Bigger Lesson
This isn't about one bad call. It’s about credibility.
In any kind of advisory sale, you have to earn the right to sell. That happens when you give value before you ask for anything.
It’s the difference between vendors vs consultants.
Vendors extract information to qualify you for their solution.
Consultants share insights to help you solve problems.
Vendors lead with frameworks and processes.
Consultants prove relevance first, then show how they’ll help.
Vendors ask for your time and consideration.
Consultants offer no-risk ways to prove value.
The difference isn’t what they sell, it’s when and how they sell it.
The irony? This consultant probably knows his stuff. But his approach made me question whether he understood our business well enough to help.
First impressions aren’t about polish. They’re about proving you can create value from the very first conversation.
If you're in sales or consulting, this might be a good time to record your next few discovery calls and listen back. You might be surprised by what you hear.
Watch: How Sales Reps Get Discovery Wrong
Stop pitching too early. Sales discovery fails when it’s rushed, robotic, and all surface-level. Discovery isn’t about qualifying — it’s about creating clarity. Great reps make prospects feel understood before they ever pitch a solution.
