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Prompt:
Roleplay as a {TITLE} at a {COMPANY_TYPE} company. You're skeptical but open. I'm going to pitch you {MY_PRODUCT}. Ask me tough questions, push back on my answers, and tell me when my responses are weak.
After 5 rounds of back-and-forth, break character and give me:
1. What I did well
2. What I should improve
3. Specific phrases that were strong
4. Specific phrases that were weak
5. An overall grade (A through F)
💡 Why this works: Reps who practice pitching daily outsell reps who wing it. AI gives unlimited practice reps.
🔄 Platform tip: Claude is better at maintaining a consistent character during roleplay. More natural pushback.
Prompt:
Roleplay as a {TITLE} who just picked up my cold call. You're busy and slightly annoyed. I sell {PRODUCT}. Respond naturally to my pitch attempts. Be a tough but realistic buyer.
Rules:
- If I use a generic opener, hang up (say 'click')
- If I earn 30 seconds, give me a chance
- Push back with real objections
- After the roleplay, coach me on what worked and what didn't
💡 Why this works: Cold calling is a muscle. Train it with realistic practice, not scripts on paper.
Prompt:
Help me do a weekly self-assessment. This week:
- Deals I advanced: {DEALS}
- Deals I lost/stalled: {STALLED}
- Best moment: {BEST}
- Worst moment: {WORST}
- Activities: {ACTIVITY_SUMMARY}
Assess me on:
1. Effort level (1-10)
2. Skill execution (1-10)
3. Pipeline management (1-10)
4. Time management (1-10)
5. Coachability — how well I'm improving (1-10)
Give me the ONE thing to focus on improving next week.
💡 Why this works: Self-awareness is the #1 trait of top sellers. Formalize your reflection.
Prompt:
Roleplay as a procurement director at {COMPANY_TYPE}. You're negotiating a {DEAL_SIZE} deal. Your goal: get at least 20% off my price of {PRICE}.
Use real procurement tactics:
- 'We have other options'
- 'Our budget only goes to X'
- 'Your competitor offered us better terms'
- Silence after I state my price
After 5 rounds, coach me: How did I do? Where did I give up value? Where was I strong?
💡 Why this works: Negotiation is perishable. Practice against a tough buyer before the real thing.
Prompt:
I just gave a demo. Here's the transcript/notes:
{PASTE_DEMO_NOTES}
Analyze:
1. Did I focus on their pain or my features?
2. Were my transitions smooth?
3. Did I check for understanding at the right moments?
4. Were there moments I talked too much?
5. Did I handle questions well?
6. Grade my demo (A-F) and give me 3 specific improvements
💡 Why this works: Most reps never get demo feedback. AI provides it after every call.
Prompt:
I'm a {ROLE_LEVEL: SDR/AE/Manager} who has been in sales for {YEARS} years. My strengths: {STRENGTHS}. My weaknesses: {WEAKNESSES}.
My numbers:
- Activity metrics: {ACTIVITIES}
- Conversion rates: {CONVERSIONS}
- Average deal size: {ADS}
- Sales cycle length: {CYCLE}
Identify:
1. The #1 skill gap holding me back
2. Specific resources to develop it (books, frameworks, courses)
3. A 30-day improvement plan with weekly milestones
4. How to measure progress
💡 Why this works: Working harder on the wrong skill is still losing. Find and fix the right gap.
Prompt:
Here are 3 emails I've sent recently:
{PASTE_EMAILS}
Analyze my email tone and style:
1. Am I too formal, too casual, or just right for {TARGET_AUDIENCE}?
2. Do I sound confident or desperate?
3. Are my emails about them or about me?
4. Am I using too many words?
5. Give me a 'before and after' rewrite of the weakest email
Be brutally honest. I want to get better.
💡 Why this works: Tone is invisible to the writer and obvious to the reader. Get an outside perspective.
Prompt:
I just read {BOOK_TITLE} by {AUTHOR}. The key concepts I remember:
{KEY_CONCEPTS}
Help me apply this to my sales role:
1. Summarize the 3 most actionable concepts
2. For each concept, give me a specific scenario where I'd use it
3. Create 2 prompts I can use to practice each concept
4. Design a 1-week challenge to implement one concept
I sell {PRODUCT} to {TARGET}.
💡 Why this works: Reading sales books is useless without implementation. Bridge the gap.
Prompt:
I just got rejected on a deal I really wanted. Here's what happened:
{WHAT_HAPPENED}
Help me process this productively:
1. What can I actually learn from this? (Be specific, not 'learn from every loss')
2. Was there a turning point where the deal could have gone differently?
3. Rate how much was in my control vs. out of my control
4. Give me one concrete action for my next similar deal
5. A motivational reframe that isn't cheesy
Don't coddle me. Help me get better.
💡 Why this works: Resilience isn't about ignoring losses. It's about extracting lessons from them.
Prompt:
My current elevator pitch:
"{CURRENT_PITCH}"
Refine it for a {TARGET_AUDIENCE} audience. Requirements:
- Under 30 seconds when spoken
- Opens with the problem, not my company name
- Includes a concrete result or proof point
- Ends with a hook that invites a follow-up question
- Sounds natural, not rehearsed
Give me 3 versions: formal (conference), casual (networking event), and cold call (phone).
💡 Why this works: Your elevator pitch is your most-used sales asset. Polish it until it shines.
Prompt:
I need to present {TOPIC} to {AUDIENCE_SIZE} people at {COMPANY}. Here's my outline:
{PASTE_OUTLINE}
Coach me:
1. Is my flow logical? Any gaps?
2. Where am I likely to lose their attention?
3. What's the strongest opening I could use?
4. Suggest 2 stories or analogies I could include
5. How should I handle Q&A?
6. Give me confidence tips for presenting to this audience type
💡 Why this works: Presentation coaching before big meetings can be the difference between winning and losing.
Prompt:
Give me an active listening exercise. You're a {TITLE} at a {COMPANY_TYPE} company describing a problem. Speak for 3-4 sentences about your challenge.
Then ask me to:
1. Paraphrase what you said in my own words
2. Identify the emotion behind your words
3. Ask one follow-up question that shows I was really listening
After I respond, grade my listening: did I capture the substance AND the subtext? What did I miss?
💡 Why this works: Active listening is the most underrated sales skill. You can practice it with AI.