They’re laughing now...really laughing. You asked about something small, something easy to answer, and it unlocked a story. The conversation isn’t stiff or polite anymore. It flows from one story or example to another. You’re not talking much at all, just listening and nodding when they pause—probing just enough to keep them sharing. And in that moment, they’re not wondering what you do or how much you cost. They’re too busy feeling understood. And you seem interesting and maybe more importantly, safe.
That’s what a great first date feels like.
But sales discovery calls... ahhhh, no, they feel nothing like that.
Because too many agencies walk into that first meeting ready to impress rather than to connect. They lead with credentials. Talk about their process. Drop case studies like breadcrumbs. But while they’re busy proving they’re a good fit, they forget the one thing that actually creates fit: connection.
The Skill That Turns a Discovery Call Into a Trust Magnet
The most effective discovery calls I’ve ever run had one thing in common: I spoke far less than the prospect.
Not because I didn’t have value to add. But because I knew the fastest way to create a connection wasn’t to explain what I could do. It was to understand what they really needed. To do that, I needed to explore what they’d tried, what had worked, and what they were afraid wouldn’t work again. You don't uncover that by talking. You uncover it by asking unique questions and then listening intently to the answers.
Most agency owners underestimate just how rare that kind of attention really is.
But during a pitch process, your prospect isn’t used to being heard without interruption. They’re used to being sold to. They're used to answering the same formulaic, shallow questions that lead predictably to pre-packaged solutions. So when you ask a better question, one that signals genuine curiosity or offers an intriguing angle, they feel the difference immediately. And when you don’t follow it immediately with a pitch, but instead another question, that's when the real magic happens.
They lean in. They allow themselves to relax and reflect. They start showing you not just what they need, but begin feeding you the intel you need to deliver it better than anyone else in the world.
And that’s the moment you become unforgettable.
Because while every other agency is trying to impress them, you’re making them feel heard... understood... invested.
And people remember how you made them feel far longer than they remember what you said.
What Question Is Your Prospect Really Asking?
Here is what that prospect is actually asking when they ask about industry experience. They are asking whether you will treat them the way the last three agencies treated them, by assuming that category knowledge equals company knowledge. They are asking whether you see them as a type or as a specific business with a specific problem that happens to exist in a particular industry.
When you immediately respond with case studies and category expertise, you just answered "yes, I am going to make assumptions about you based on pattern matching."
And that answer, even though you did not mean it that way, just cost you the trust you needed to win the work. You thought you were building credibility. Instead, you lost the sale.
Learning to hear the real questions behind the surface questions is the difference between a 15 percent close rate and a 50 percent close rate.
What Changes When You Hear The Real Question?
I saw this firsthand many years ago when a liquor brand called. The Brand Manager said their social media campaigns were not working. They needed to fix the issue sooner rather than later. They were talking to a few other firms but wanted to hear how we could help them.
[NOTE: When I started Converse Digital back in 2010, we were a social media agency managing customer-facing social media profiles on behalf of brands, mainly in the liquor and travel spaces. Today, we help agencies build business development engines inside their firms and teach them how to develop a Perfect Pitch™]
I could have talked about launching and managing hugely successful social media programs for Firefly Sweet Tea Vodka and Fireball Whiskey, or shared our Mardi Gras case study showing how we successfully rebranded Mardi Gras from "Girls Gone Wild" to "Family Friendly Fun" using only social media. Or I could have talked about our innovative social + retail program for a whisky brand in Texas, leveraging inexpensive, geo-targeted social media and wet tastings to drive sales.
That is what they expected. That is the approach the three agencies before us had taken.
Instead, I started by asking why they were following their current playbook. What specifically was not working? And more importantly, why did THEY think it was not working?
Twenty minutes into answering my questions, the Brand Manager finished telling me everything she could think of about everything they'd done thus far. And I asked one last question... the one that ultimately won us the account.
I said we'd be happy to submit a proposal to launch a new social media campaign. But, before I did, would she be open to a proposal to rebrand via that social media campaign?
After what seemed like an eternity of silence, she said, "Every other agency spent its call teaching us about social media. You are the first agency to challenge us to reconsider our entire strategy. I'll need to talk to my boss about it... But I'd be willing to entertain the idea."
And her answer told me everything I needed to know. The other agencies had just answered a question she did not ask. She asked whether they understood her specific challenge. They answered with generalizations about social media for liquor brands. The gap between those two things is where trust died and where we won the business.
Yes, it took one more phone call and a written proposal to win the account. But we were the ONLY agency asked for a proposal. And that's the power of asking before selling.
Why Do We Keep Answering The Wrong Question?
We answer the wrong question because we prepare for pitches by anticipating what we think prospects will ask. We build decks around our process. We select case studies that demonstrate category expertise. We prepare to talk about us, not them.
I see it over and over again. When a prospect asks about an agency's experience, they talk about their process, show case studies, or, my personal favorite, share the dreaded client logo slide.
Instead of seeing the question as a hope for diagnosis, the agency immediately starts writing the prescription without understanding the prospect's unique symptoms.
The Three Questions That Reveal How to Win Any Pitch
There are a few questions that I have used on hundreds of calls over the last two decades. You don't have to use these exactly as I've phrased them. Instead, consider this an inspirational exercise. Use it to create your own questions based on your unique situation. In no particular order...
"What do brands usually get wrong when they find themselves in your situation?" I love this question because it's highly unusual in a sales discovery call. Agencies won't ask it because it requires the questioner to display humility by admitting they don't have all the answers. It gives the prospect permission to project what they fear they are getting wrong without stating it out loud. It also positions the search for answers as a collaboration of equals versus "agency as saviour" swooping in with the perfect solution to save the day.
If you're feeling courageous and want to go for broke... "Who gets fired if we can't solve this problem?" Again, you'll probably be the only agency to ask it. But more importantly, it conveys something I think is incredibly important because prospects hire beliefs, not services. When you ask this, you're telling the prospect that you understand they're taking a risk, and maybe a huge one, by hiring you and buying into your recommendations. More importantly, you'll get an immediate sense of the project's importance to the company as a whole. Use this insight to manage the risk/reward aspect of your proposal or pitch.
And my personal favorite final question, "What haven't we been smart enough to ask you but should definitely know?" Again, you're displaying humility. Clients don't hire you to have all the answers. They hire you to ask the right questions. This one demonstrates that you understand there may be hidden core issues that must be addressed in the winning proposal. And if none of your competitors asked this, chances are you're now working off information only you have access to.
A True Professional Who Knows What You Don't
I like Tom's style! He is straight to the point and backs up his counsel with proof points and analysis. We held a 20+ executive senior staff training with Tom and the feedback from our senior staff has been phenomenal. Our executives have adopted a number of his techniques and have taken his advice on helpful software programs and apps that have made them more effective at selling and prospecting. Tom is still assisting some of our people with ongoing training. You will not regret working with Tom! He is a true professional who knows what you don't and that is invaluable.
Todd Fromer / President
How To Crush Your Next Sales Discovery Call
Be the Sun, not the Wind.
There is an Aesop fable in which the North Wind and the Sun quarreled about which of them was the stronger. According to the fable, while they were disputing with much heat and bluster, a Traveler passed along the road wrapped in a cloak.
"Let us agree," said the Sun, "that he is the stronger who can strip that Traveler of his cloak."
At once, the North Wind began to blow harder and harder. But the traveler just pulled his coat tighter. Then the Sun came out and warmed things up. At first, the traveler loosened his jacket until he grew so heated that he took it off himself and lay under the shade of a tree.
The morale of Aesop's story is simple: Gentle and kind persuasion succeeds where force and bluster fail.
Use smart, unique, questioning, and active listening to draw the prospect closer and feel more comfortable sharing their real needs, desires, and fears with you. Then create a proposal or pitch that makes them feel confident they're not only in the right room, but talking to the right agency to succeed where others have failed.
The Moment That Tells You It’s Working
You'll know the approach is working when you start to hear your prospect say things like:
- “No one’s asked us that before.” That means you’ve stepped out of the comparison pile.
- They start using “we” instead of “you.” That’s joint-project language.
- They stop asking about process and start asking about outcomes. That’s buying behavior.
When you start hearing these phrases, you know you've not only built rapport but you've likely shortened the sales cycle and improved your odds of winning.
Ready to Stop Having Awkward Sales Discovery Calls?
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This post was originally published on Painless Prospecting, the weekly sales and marketing blog created by the fine folks at Converse Digital. If you want to learn how to create, engage in, and convert conversations into new clients and customers, give them a call.
