For sales leaders and teams ready to level up their conversations
The problem isn’t your pipeline. It’s how your team is showing up in salesconversations
A practical, high-impact workshop for sales leaders and teams who want to fix the conversation gaps that are quietly costing them deals.
Ready to bring this to your team? Let’s talk.
Not ready to book?
Problems we solve
Your sales team Is missing the moments that make buyers say yes
You’ve got the product. You’ve got the leads.
But in the moments that matter most — the moment to dig deeper, to guide instead of defend, to create clarity instead of confusion — your team misses.
It’s not a work ethic problem. It’s a conversation problem.
Most reps don’t even realize they’re skipping past critical buyer moments — the ones that turn curiosity into conviction, and conviction into closed deals.
These are the subtle moments where your sales team is losing deals.
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Closing rates are low — but it’s not a closing problem Most “closing issues” are actually caused by weak conversations earlier in the process.
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Conversations stall and lose momentum Your reps get thrown off by unexpected buyer reactions and don’t know how to recover or redirect.
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Calls lack structure and control Without clear agendas and upfront framing, buyers tune out or take over
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Objections trigger defensiveness, not discovery Reps rush to justify or discount instead of asking the next right question.
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Discovery stays shallow misses urgency, and fails to connect the problem to impact.
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There are no ‘lightbulb’ moments Buyers walk away unmoved — they didn’t see their problem in a new light, so they didn’t move forward.
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Reps freeze when things go off-script When buyers push back or change direction, reps lose their footing and calls fizzle.
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Coaching isn’t sticking Even with good advice, there’s no common language or framework to reinforce lasting behavior change
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Every rep sells differently — and inconsistently Without shared tools, messaging, and rhythm, performance is uneven and hard to scale.
Not sure if these are showing up in your team’s calls?
Take the Sales Breakthrough Assessment to uncover where your team’s conversations are strong — and where they’re quietly costing you deals.
The Breakthrough Sales Conversations Workshop
The foundation for transforming how your team communicates, sells, and wins.
The Sales Breakthrough Conversations Workshop is a practical, roleplay-driven session that equips your team with the four conversation tools used by top-performing sales teams.
This isn’t another sit-back-and-listen corporate training. It’s high-energy, highly interactive, and designed for immediate impact — in real conversations, with real buyers. Whether it’s an in-person or virtual experience, every workshop starts the same way: By setting the tone, raising the standard, and putting your team in the room with full attention. Within the first five minutes, they’ll know — this isn’t a keynote, a lecture, or death by PowerPoint. Everyone’s on the hook. That’s where real learning begins.
“We could’ve spent years trying to implement this ourselves — but without Chris, we never would’ve seen these results.”
Ed McKnight, OPES Partners
What we’ll work through together
The Pathfinder’s
Compass
A self-assessment that reveals each team member’s communication style and gaps
The Four Pillars of Breakthrough Conversations
– Learn what the top teams do differently — and how to apply it
Hands-on role plays and exercises
Built around your real deals, objections, and day-to-day team dynamics
What it’s like in the room:
Roleplay
Yes, your team will be on the spot. Because pressure builds capability.
Live coaching
Chris challenges, refines, and supports your reps in real-time
Immediate application
Nothing stays theoretical. What you learn gets practiced, shared, and put to work that day.
Want to see how this would work for your team?
Let’s have a quick conversation to see if this fits.
Not sure yet?
Take the Sales Breakthrough Assessment to uncover where your team is getting stuck
The transformation for your team
What Happens When Your Team Starts Leading Breakthrough Conversations
This isn’t a motivational event. It’s a turning point. Your team will walk away with practical tools they’ll use in their very next sales conversation — and every one after that.
By the end of the workshop, your team will:
These are the subtle moments where your sales team is losing deals.
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Stop pitching too early and start guiding buyers to real insight through layered discovery.
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Handle objections with curiosity turning resistance into opportunity
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Stay composed under pressure when calls go off-script, they won’t.
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Take control of the call structure setting the tone, framing the conversation, and keeping momentum.
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Create lightbulb moments — helping buyers see their problem (and your solution) in a whole new way.
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Adopt a shared language for feedback and coaching so improvements stick, long after the workshop ends.
This is how your team stops sounding like everyone else — and starts leading the kinds of conversations that close deals faster, build trust faster, and make selling feel less like a pitch… and more like progress.
“Our close rate went from 23% to 41.5% — and it’s still climbing.”
Mike Rhea, CRO, ITS
Before
After
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Conversations stall and momentum disappears
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Calls feel scattered, and buyers take over
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Objections derail the conversation
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Discovery stays shallow
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Buyers leave unmoved
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“Our close rate sucks.”
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Coaching feels scattered
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Every rep is winging it
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Reps know how to redirect the energy and keep calls productive — even when things go off-script.
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Reps open every call with clarity, control, and confidence — setting the tone from the start.
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Objections become opportunities for deeper discovery — not moments of panic.
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Reps go three layers deep, uncovering urgency, impact, and emotion — not just symptoms.
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Prospects experience insight, clarity, and those all-important “aha” moments that move them forward.
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Closing improves — because conversations are stronger, cleaner, and more buyer-aligned from the start.
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Your team uses a shared framework and language — making coaching more effective and stickier.
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The team speaks the same language, uses the same tools, and performs consistently at a higher level.
Ready to see your team operate at a new level?
Let’s talk about bringing this to your company?
Is this workshop right for your team?
This isn’t for everyone — and that’s intentional. This is for teams who are ready to be challenged, to practice, and to shift how they sell at the conversation level
This workshop is built for:
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Sales leaders who are tired of one-size-fits-all training and want real behavior change
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Revenue teams who are great at the pitch but struggle to guide the buyer
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Sales orgs who want a repeatable framework to coach, review, and improve how reps communicate
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Founders and leaders who are still in sales themselves — and want to lead more effective calls
It’s not for teams who:
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Want passive training without real practice
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Are resistant to feedback or roleplay
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Don’t believe conversations are the root of their sales challenges
Think this might be a fit?
Want to see how this would work for your team?
Let’s have a quick conversation to see if this fits.
Not sure yet?
Take the Sales Breakthrough Assessment to uncover where your team is getting stuck
“Yes, and… changed the way we communicate — in sales and across our whole team.”
Ryan McBride, Field Effect
What sales leaders are saying
Don’t just take our word for it. Here’s how sales leaders and teams describe the impact of the Sales Breakthrough Conversations Workshop — in their own words.By the end of the workshop, your team will:
These are the subtle moments where your sales team is losing deals.
We used to coach by telling. Now our team asks the right questions — and it’s changed everything.
“Before working with Chris Duprey and The Question First Group, we, as business owners, had little insight into what was really happening within our sales team. There was no formal coaching—neither for us nor for them—and the coaching we had tried was mostly us telling the team what to do. It wasn’t changing behaviors.
Chris trained us in the Breakthrough Sales Conversations Methodology, and the impact has been transformational. We now watch our team’s calls, understand exactly what’s happening, and provide direct, meaningful feedback that drives real improvement. More importantly, Chris does this as part of his coaching, making our team more effective than ever.
The biggest shift has been in our advisors. They don’t just sell—they ask the right questions, uncover what clients truly want, and create lightbulb moments that inspire confidence in their financial future. We’ve gone from uncertainty about our sales process to being genuinely proud of the conversations our team is having.
The best part? The Breakthrough Sales Conversations Methodology is deceptively simple—but without Chris, we could have spent years trying to implement it and never achieved these results. Thanks to his coaching, our advisors are more skilled, our clients are better served, and our business is stronger.”**
– Ed McKnight, Economist & Business Owner, OPES Partners
This workshop gave us real tools we actually use — not just ideas to talk about.
“The Breakthrough Sales Conversation workshop was an incredible learning experience. Chris Duprey and The Question First Group led us through practical and actionable methodologies that transformed how we approach sales conversations.
Two key takeaways—leveraging ‘Yes, and…’ for smoother communication and the ‘Law of 3’ framework—helped us refine dialogue, improve precision, and bring authenticity to our sales interactions. This training not only sharpened our skills but also strengthened connections within our team. Highly recommend for any sales professional looking to strengthen their approach!”
– Ryan McBride, Sr. Partner Business Manager, Field Effect
From Sales Struggles to an 80% Increase in Close Rate: How The Question First Group Transformed Our Sales Team
“Working with The Question First Group has been an incredible experience. As the Chief Revenue Officer at Intelligent Technical Solutions, I’ve worked with many sales training companies, but this has been, without a doubt, the best.”
When we first engaged with The Question First Group, we started with a workshop that brought our entire sales team together. That session was eye-opening. We uncovered major gaps in our sales process—our reps were making assumptions, jumping to solutions too quickly, and engaging in pricing discussions too early. Most importantly, we realized we weren’t conducting deep enough discovery.
But the real game-changer wasn’t just a one-time workshop—it was the ongoing coaching. Unlike other programs that offer a multi-day bootcamp with no follow-through, The Question First Group embedded continuous learning into our culture. Every other week, our team works with an instructor, receiving real-time coaching, structured lessons, and even homework to reinforce their skills. This consistent engagement is what has truly transformed our sales approach.
The results speak for themselves:
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Close rate increased by 80% from 23% to 41.5%, and still climbing.
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Better sales conversations We now set clear agendas, handle objections proactively, and guide buyers through the discovery process.
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Fewer stalled deals and ghosted prospects Our team maintains control throughout the sales cycle, ensuring clear next steps after every call.
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Stronger leadership As a leader, I’ve shifted from giving my sales reps answers to coaching them toward self-discovery—empowering them to be independent and scalable as we grow.
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A more confident sales team While there was a learning curve, our reps are now closing more deals with fewer people—creating efficiency and momentum.
If you’re considering working with The Question First Group, my advice is simple: do it. The return on investment has been massive—not just in revenue, but in the personal and professional growth of my team.
I’ve worked with many sales training companies, but none compare. This isn’t just another training program—it’s a system that embeds world-class sales skills into your organization. I’m borderline obsessed with it, and if you give it an honest shot, I’m confident it will transform your team too.
– Mike Rhea, Chief Revenue Officer, Intelligent Technical Solutions
Ready to see results like these with your team?
Whether your team needs better discovery, stronger objection handling, or just more confidence in the room — it starts with better conversations. Let’s talk about bringing this workshop to your org.
Want to see how this would work for your team?
Let’s have a quick conversation to see if this fits.
Not sure yet?
Take the Sales Breakthrough Assessment to uncover where your team is getting stuck
Flexible Workshop Options Built for Your Team
Every team is different — and so is every workshop. Whether you’re looking for a fast, high-impact reset or a deeper transformation across your team, there’s a format built to fit. Workshops are available in-person or virtually, and customized to your team’s real-world challenges.
1-Day Workshop
Get everyone aligned, activated, and equipped with the core principles.
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High-energy, high-impact reset
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Introduction to the four tools
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Hands-on practice + real coaching
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Perfect for team kickoffs, off-sites, or leadership alignment
Best for teams who want immediate traction and a shared foundation.
2-Day Workshop
Deepen the skills, reinforce learning, and build internal ownership.
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Delivered in 2–3 live virtual sessions
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Interactive, camera-on, call-based environment
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Can include custom call reviews and asynchronous coaching
Best for teams ready to go beyond awareness and build lasting capability.
Virtual Workshop
Designed for remote teams who want the same level of transformation - without travel.
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Delivered in 2–3 live virtual sessions
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Interactive, camera-on, call-based environment
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Can include custom call reviews and asynchronous coaching
Best for distributed teams or those looking to pilot the experience before going deeper.
Want to see how this would work for your team?
Let’s have a quick conversation to see if this fits.
Not sure yet?
Take the Sales Breakthrough Assessment to uncover where your team is getting stuck
*Pricing varies based on team size, location, and customizations — but every engagement starts with a quick discovery call to align on fit and outcomes.
Meet Your Coach
Chris Duprey doesn’t just teach sales teams to communicate better — he helps them lead breakthrough conversations.
Chris Duprey is a former Army officer turned business leader, coach, and partner at The Question First Group. His mission is simple: to help sales teams and leaders have conversations that build trust, uncover truth, and move deals forward.
Chris began his leadership journey in the 82nd Airborne Division, where a pivotal lesson from a mentor taught him the power of listening and being fully present — even under pressure. As a company commander, he developed his soldiers into capable leaders, a discipline he carried into the business world after transitioning out of the military.
Since then, he’s led high-performing teams, earned his graduate degree at Quinnipiac University, and been mentored by world-class communicators like Marcus Sheridan and Adam Barlow. Chris combines battlefield-level clarity with deep emotional intelligence — helping sales professionals transform how they show up in the room, on the call, and with their clients.
Through his work at The Question First Group, Chris trains sales teams across industries to master the four principles of Breakthrough Conversations — not just to close more, but to lead better.
Outside of work, Chris is a musician, a devoted dad, and someone who believes that self-awareness, clear communication, and a little pressure-tested practice can make anyone more effective in the moments that matter most.
Want to explore what this could look like for your team?
Book a call directly with Chris and find out if the workshop is the right fit.