MSL 303 - Unlock sales confidence: Six proven tips with a few AI prompts to turn rejection into revenue
In this episode, I dive deep into one of the toughest challenges every solopreneur faces: overcoming the fear of rejection when approaching sales conversations. I unpack the six mindset shifts and tactical steps that have truly helped me transform every "no" into valuable feedback and greater confidence. From normalizing anxiety and learning to detach personal meaning from rejection, to reframing each conversation as an opportunity for growth, I'm sharing both my wins and stumbles so you can build your own resilience in client outreach.
I also reveal how I use AI tools like call transcripts and chat analysis to get objective feedback and keep leveling up my process, and getting an objective viewpoint. As usual, you can expect honest stories, actionable tips, and my relationship-first philosophy that makes sales less about transactions and more about building trust. If you've ever felt discouraged by a "no" or hesitant to reach out, this episode is your playbook for pushing through, boosting your skills, and having fun building relationships and making sales.
Key takeaways:
Normalize the nerves: It’s normal to feel anxious about sales and take rejection personally as a solopreneur. Acknowledge those feelings so they don’t control your actions.
Reframe rejection: Every “no” is feedback, not failure. Use it as intel to get better in your next conversation, rather than seeing it as a personal setback.
Build resilience with practice: Confidence is a muscle that grows with action. The more you engage in sales conversations, the easier and more natural it becomes.
Serve, don’t just sell: Shift the focus from pitching to genuinely helping, learning about client needs, and building relationships instead of chasing quick wins.
Remember self-care: Supporting your mindset is non-negotiable. Take breaks, celebrate every outreach or conversation, and give yourself credit for consistent effort.
Detach from the outcome: Separate your self-worth from the results. Rejection is not a measure of value, just a step closer to the right opportunity.
How to use AI for sales practice and growth
Record and Transcribe Your Calls: Use Zoom, Fathom, or another recorder to capture sales and consultation conversations. Always get permission to record for personal development.
Analyze With AI: Drop your transcript into your favorite AI chat tool (ChatGPT, Perplexity, etc.). Prompt AI: "I just had this sales conversation. Can you review my transcript and highlight areas where I could invite more engagement, ask better questions, or move through objections with confidence?"
Iterative Prompting: Share relevant call context (prospect type, outcome, main challenge discussed) to get richer feedback. If the AI’s response feels off, add details in a follow-up prompt until the suggestions feel accurate and actionable.
Review and Apply Feedback: Use AI insights to identify improvement opportunities such as clearer discovery questions, faster budget qualifying, and building rapport through authentic conversation.
Practice Mindset Prompts: When reflecting, use journaling or AI to answer: "What did this conversation teach me?", "What strengths did I show?", "What one thing should I try on my next call?"
Experiment Across AI Tools: Try the same transcript and prompt in multiple AI platforms (e.g., ChatGPT, Claude, Perplexity) for diverse advice. Note patterns and consistent tips for practical growth.
Build an AI Sales Coach: Consider creating a “virtual sales coach” in ChatGPT, modeled after your preferred training voices (like Zig Ziglar), for regular, personalized practice and skill-building.
