
30 Hard Hitting Questions for Entrepreneurs to ReSet for Success
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Absolutely — a brutally honest self-audit can be a game-changer for entrepreneurs.
Here's a list of 30 hard-hitting questions to help any self-employed entrepreneur confront the real issues and reset for success.
🔍 30 Hard Questions Every Entrepreneur Should Ask Themselves
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What time do I start work each day — and is it consistent?
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How many proactive calls or messages to prospects did I make this week?
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How many meetings did I have with decision-makers in the past 7 days?
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Are my short- and long-term goals written down, clear, and measurable?
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Do I review my goals daily, weekly, and monthly?
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How many hours of actual focused, high-impact work do I do each day?
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Am I spending more time consuming or creating?
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How do I structure my day — do I follow a clear routine or just ‘react’?
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How often am I distracted by low-value tasks or social media?
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Do I regularly track KPIs and metrics that drive my business forward?
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Am I crystal clear on my ideal client avatar?
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Is my offer clearly solving a painful problem or fulfilling a strong desire?
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Do I truly believe in the value and transformation I provide — and can I articulate it with conviction?
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How often am I sharing stories and case studies that prove my value?
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Am I consistently asking for referrals, testimonials, and introductions?
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Am I positioning myself as an expert using content, authority, and thought leadership?
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What’s my personal brand saying about me online right now?
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How much am I investing in my own learning, coaching, or mentoring?
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Am I working on my business or just in my business?
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When was the last time I innovated, created a new offer, or tested a new strategy?
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How much of my time is being wasted on things I could outsource or automate?
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Am I truly holding myself accountable — or just making excuses?
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How many hours of quality sleep am I getting consistently?
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What is my daily/weekly physical exercise routine like?
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Am I feeding my brain and body with the fuel it needs — or just surviving on caffeine, sugar, and stress?
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What habits are dragging me down or keeping me stuck?
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Do I feel joy, purpose, and alignment with what I do — or just pressure and survival?
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Who do I surround myself with — growth-minded people or energy vampires?
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If my current habits continue for the next 12 months, where will I be?
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If I were coaching myself — what would I tell myself to do differently, starting tomorrow?
Get your copy of the Hard Hitting Worksheet here - click here
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