How to Win the Sales Roleplay Interview by Discovering Before You Pitch
Brandon Mitchell has hired 200+ sales reps. He designed this roleplay to simulate the hardest 15 minutes of a real sales cycle. "I'm going to play the CFO of a mid-size logistics company. You're selling our expense management platform. Show me how you run a discovery call." He leans back, arms crossed, and transforms into Pat Donovan, CFO: "Yeah, come in. You have five minutes — I have the quarterly review at 3. So what is this expense management thing about?" Five minutes. Arms crossed. Quarterly review as a clock. This is not a conversation — it's an obstacle course designed to separate reps who sell from reps who present. The ones who start with "Our platform offers AI-powered expense tracking..." are done before they begin. The ones who start with "Before I show you anything — what are you using now and what's not working?" get Brandon's attention and the job.
Why This Conversation Goes Wrong
You lead with your product features. "Our expense management platform offers AI-powered receipt scanning, real-time budget tracking, and integration with 47 accounting systems." You just gave a demo to a CFO who didn't ask for one. Brandon is timing you: if you pitch within 60 seconds, it's a red flag. He's looking for salespeople, not slide presenters.
You ignore the "5 minutes" framing. You launch into a 10-minute discovery session. But Pat Donovan said five minutes. Respecting the time constraint — "I know you're tight on time, so let me ask two quick questions" — shows you can sell under pressure. Ignoring it shows you don't listen.
You can't handle "we tried this before." "We tried ExpenseTrack last year. Six-month implementation, half the features were broken." Most reps either bash the competitor or freeze. Both fail. The winning response addresses the fear underneath: "That sounds painful. What specifically went wrong? I want to make sure we don't repeat it."
You talk about features instead of business outcomes. "Our platform has a 99.9% uptime SLA." Pat doesn't care about uptime. Pat cares about whether this tool can help cut operational costs by the 15% the board is demanding. Features are inputs. Outcomes are outputs. Sell the outputs.
The Discovery Before Pitch
Every VP of Sales who designs a roleplay interview is testing for one thing: does this rep discover before they pitch? The Discovery Before Pitch framework front-loads questions, builds on the prospect's answers, and connects your solution to their specific pain — not generic value props. The pitch earns the right to exist only after the prospect feels understood.
Acknowledge the time constraint and earn more
"Five minutes — I respect that. Before I take any of it talking about us, two quick questions: what are you using today for expense management, and what made you take this meeting?" Acknowledging the time pressure shows respect. Asking what brought them here reveals their motivation. If Pat says "My board wants cost reductions" — that's the entire sale mapped in one sentence.
Probe beneath the surface answer
"You mentioned three different tools. What's the cost of managing that fragmentation — in time, in headcount, in errors?" Don't accept the first answer. Dig into the impact. When Pat says "We spend $2M across three tools and it's a mess," you now have a dollar figure attached to the pain. That number will anchor your entire pitch.
Handle the burned-vendor objection with empathy first
"You tried ExpenseTrack and it went badly. I don't want to repeat that experience. What specifically failed — was it the implementation timeline, the functionality, or the support?" Don't defend your product against their past bad experience. Investigate it. Understanding what went wrong with the last vendor lets you position against those specific failures, not against an abstract competitor.
Connect your solution to their specific number
"You said $2M across three tools and a board mandate to cut 15%. If we could consolidate those three tools and cut that expense by a third — that's $650K toward your 15% target. Want me to show you exactly how?" The pitch is now math, not marketing. You connected their number to your value. Pat didn't hear a feature — Pat heard a solution to the problem the board is asking about.
Close for a concrete next step, not a commitment
"I'm not asking you to buy anything today. But based on what you've told me, a 30-minute proof-of-concept with your actual expense data would show you the real numbers. Who on your team would I need to include?" Asking for a low-risk next step — a PoC, not a contract — respects the CFO's buying process. Asking "who else" signals you understand enterprise sales are multi-threaded.
The moment that changes everything
Brandon isn't evaluating your pitch. He's evaluating whether you'd uncover the board pressure without being told.
The golden moment in Brandon's roleplay is when a candidate uncovers the board mandate to cut costs by 15% — a detail Pat Donovan never volunteers directly. The CFO says "We're under pressure to improve efficiency." The mediocre rep hears that and pivots to product features. The great rep hears it and asks: "What's driving that pressure? Is this coming from the board?" When Pat reluctantly confirms, the sale unlocks — because now you're not selling an expense tool. You're selling the CFO a way to meet a board mandate. Brandon has seen thousands of sales reps. The ones he hires ask that second-level question. The ones he passes on are the ones who hear "improve efficiency" and start pitching AI features.
What to Say (and What Not To)
Instead of
"Our platform offers AI-powered expense tracking with real-time analytics."
Try this
"Before I say anything about us — what are you using now, and what's not working?"
Instead of
"We're different from ExpenseTrack because..."
Try this
"That sounds painful. What specifically failed — the implementation, the features, or the support?"
Instead of
"Our solution can save you money."
Try this
"You said $2M across three tools. If we cut that by a third, that's $650K toward your 15% target."
Instead of
"Can we schedule a demo next week?"
Try this
"A 30-minute PoC with your actual data would show you real numbers. Who else should be in the room?"
Instead of
"We have great customer satisfaction scores."
Try this
"What would make you confident this wouldn't be another ExpenseTrack situation?"
The Bigger Picture
Gong.io analyzed 2.5 million sales calls and found that the top-performing reps spend 46% of the call in discovery and 22% in pitching. The bottom-performing reps spend 15% in discovery and 65% in pitching. The ratio is inverted. The reps who talk less about their product sell more of it. Brandon's roleplay is designed to surface this ratio within the first two minutes.
A 2024 LinkedIn Sales Solutions study found that the #1 trait enterprise buyers want from salespeople is "understanding my business before proposing a solution." Not product knowledge. Not charisma. Not persistence. Understanding. 72% of CFOs said they would take a second meeting with a salesperson who asked smart questions about their business, even if the product wasn't a perfect fit.
Here's why the roleplay interview is the most predictive hiring tool in sales: it tests instinct under pressure. A candidate can practice SPIN selling, memorize the Challenger Sale, and read every Sandler playbook. But when a hostile CFO says "You have five minutes" and crosses their arms, the prepared script evaporates. What remains is the candidate's genuine selling instinct — discover or pitch. Brandon can see it in the first 60 seconds.
Practice This Conversation
12 minutes · AI voice roleplay with Brandon Mitchell
Reading about this is step one. Practicing it changes everything. Sonitura lets you rehearse this exact conversation with Brandon Mitchell, a realistic AI vp of sales playing a skeptical cfo prospect who reacts to your words in real time. It takes 12 minutes. The next time you're facing a prospect with crossed arms and a ticking clock, you'll discover before you pitch — and that's how you close.
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