PitchPen AI Trainer

Win Deals inDiscovery

Great discovery calls are the foundation of every closed deal. Master the questions that uncover budget, authority, need, and timeline.

Why Most Discovery Calls Fail

Surface-Level Questions

Reps ask "What's your budget?" instead of understanding the business impact and building a case for investment.

Interrogation Mode

Rapid-fire questions feel like an interrogation. No rapport, no trust, no second meeting.

Missing Red Flags

Reps miss buying signals and warning signs. They chase bad fits and lose good opportunities.

No Clear Next Steps

Calls end with "I'll send you some info" instead of clear commitment and timeline.

The Cost of Bad Discovery:

Poor qualification wastes months chasing deals that were never going to close, while winnable opportunities slip away unnoticed.

67%

of lost sales from poor qualification

Source: DemandZen

50%

of time wasted on unqualified prospects

Source: Geear

3.1x

higher win rate with proper ICP alignment

Source: OroCommerce

The PitchPen Discovery Framework

1. Current State Discovery

Start with natural small talk to build rapport, then understand their world today. What's working, what's not, and why they're looking for change.

Questions You'll Master:

  • Walk me through your current process...
  • What's the impact when this doesn't work?
  • How long has this been a challenge?
  • What have you tried to fix it?

Skills You'll Build:

  • Active listening
  • Following up naturally
  • Quantifying pain
  • Building rapport

2. Desired Future State

Paint a picture of success. Understand their goals and what winning looks like for them.

Questions You'll Master:

  • If you could wave a magic wand...
  • What would success look like in 12 months?
  • How would this impact your team?
  • What's the value of solving this?

Skills You'll Build:

  • Vision alignment
  • ROI building
  • Stakeholder mapping
  • Creating urgency

3. Decision Process

Understand how they buy, who's involved, and what could derail the deal.

Questions You'll Master:

  • Who else needs to be involved?
  • What's your evaluation process?
  • What could prevent this from happening?
  • When do you need this solved by?

Skills You'll Build:

  • Qualifying authority
  • Timeline discovery
  • Risk identification
  • Next step commitment

Practice with Real Buyer Personas

The Skeptical Executive

Short on time, seen it all before. Learn to quickly build credibility and get to the heart of their challenges.

You'll practice:

  • • Getting past surface objections
  • • Demonstrating industry knowledge
  • • Earning a follow-up meeting

The Technical Evaluator

Wants deep details but isn't the decision maker. Navigate technical questions while uncovering business drivers.

You'll practice:

  • • Balancing technical and business
  • • Identifying the real buyer
  • • Building a champion

The Eager Champion

Loves your solution but lacks authority. Learn to leverage enthusiasm while qualifying real buying power.

You'll practice:

  • • Coaching your champion
  • • Getting to power
  • • Building a business case together

The Budget Holder

Has money but needs to see clear ROI. Master the art of value discovery and business case building.

You'll practice:

  • • Quantifying business impact
  • • Uncovering hidden costs
  • • Building ROI together

Discovery Excellence = Sales Success

2.3x

Higher Win Rate

with proper discovery

47%

Shorter Sales Cycle

better qualification

31%

Larger Deal Size

uncovering more value

89%

Forecast Accuracy

proper qualification

After 30 Days of PitchPen Discovery Practice:

Ask better questions naturally
Build trust in minutes, not meetings
Qualify out bad fits early
Uncover hidden decision makers
Create urgency authentically
Secure clear next steps

Master Discovery Before Your Next Call

Stop wasting time on unqualified opportunities

3 free calls • 5 minutes each • No credit card required