Asking For What You Want

“When you don’t ask for what you want, the answer is always going to be no.” – Alejandra Leibovich

Why Most People Don’t Get What They Want

Most people don’t get what they want because they don’t ask for it. It sounds absurdly simple, right? Yet entrepreneurs stay quiet about subpar service, tolerate poor employee performance, and accept less than they deserve. Why? Because they’re afraid of seeming rude, being judged, or making someone uncomfortable. In this episode, Alejandra Leibovich reveals how this silence costs more than rejection ever could.

When Uncomfortable Questions Change Everything

Every avoided conversation blocks better cash flow, stronger teams, and clearer communication. Alejandra exposes the real reasons we don’t ask: fear of judgment, shame about acknowledging gaps, and the need to be right that keeps us from risking discomfort. But this protection comes at a devastating cost: the complete stagnation in business and life.

Through powerful stories, Alejandra shows how asking what others won’t creates opportunities that didn’t exist before. You’ll discover why the most profitable questions are often the ones that feel awkward, inconvenient, or unnecessary.

Hot Seat: Clarifying the Challenge

Members dive into the practical application of asking uncomfortable questions. Listen as Alejandra guides them through the difference between being strategic and being rude, and shares examples of how persistence in asking can get surprising results. One member reveals how they rehearse conversations in their head instead of having them. This is exactly the pattern the challenge exercise is designed to break.

The Asking For What You Want Challenge

This week, ask three questions you normally wouldn’t ask due to fear or discomfort:

1. One question to a friend or family member that you wouldn’t normally ask
2. One question to a staff member or vendor about performance, service, or expectations you haven’t addressed
3. One question to a stranger to practice asking questions you normally avoid due to fear of criticism or a negative response

The key to this episode’s challenge is to watch the stories you tell yourself about deserving or not deserving what you want. Those stories are what’s preventing you from getting the results and profits you actually want. Remember: If you’re thinking “do I deserve this?” or “what will they think?” – that’s exactly when you need to ask. Growth requires taking shots even when the outcome is uncertain.

Related Episodes:

• Episode 5: Assumptions Limit You – Having difficult conversations with employees and clients instead of avoiding them
• Episode 7: What Are Your Priorities? – How avoided conversations create the small margins that cause business failure
• Episode 13: Speaking the Truth – Overcoming fear to have difficult conversations and the cost of withholding the truth

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