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How to Crush Sales in 2025 (Even If You Hate Cold Calls) With Drewbie Wilson

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In this value-packed episode of The Entrepreneurial You, Heneka Watkis-Porter sits down with Drewbie Wilson—sales coach, entrepreneur, and time-management strategist—to uncover the secrets behind sales success, mindset mastery, and purposeful use of time. Known for his transformative perspective on sales and discipline, Drewbie explains why high earners aren’t necessarily working harder, but thinking differently. He breaks down the invisible gap between average and extraordinary performance, centering on the irreplaceable trio: time, energy, and effort.

Together, Heneka and Drewbie dive deep into how shifting from a “sales-first” mentality to a “service-first” mindset can drive authentic conversations and foster long-term success in business.

From Scarcity to Strategy: Making Time Work for You

Drewbie reveals that the true game-changer in sales isn’t technique—it’s mindset. High achievers know how to leverage their time and aren’t afraid to invest money to free it up. Instead of hoarding resources and trying to do it all alone, top salespeople understand the power of delegation and structured growth. This, Drewbie says, is what separates low earners from the top 1% in the sales world.

Heneka agrees, noting that many entrepreneurs struggle with letting go of tasks that don’t serve their highest priorities. Drewbie’s advice? Focus on your zone of genius and be ruthless about time-wasting habits.

Sales as Service: How Shifting Your Focus Changes Everything

Rather than focusing solely on closing deals, Drewbie promotes a service-based mindset. He and Heneka discuss how this shift not only improves confidence but also leads to deeper client relationships. Heneka shares her personal evolution in the insurance world—initially resistant to the role’s intrusive questions, but eventually embracing them as tools for meaningful dialogue. Drewbie underscores that discomfort in sales often stems from a lack of alignment or understanding of the client’s true needs.

Ask Better Questions, Make Bigger Sales

Drewbie emphasises the art of asking hard questions to uncover a client’s pain points and motivations. Using a real-world example from Heneka’s upcoming leadership cruise, he outlines how sales strategy transforms when you truly know your customer. It’s not just about pitching a product—it’s about creating a solution that resonates with someone’s specific problem.

Cold vs Warm Leads: Intentional Outreach That Converts

In sales, not all leads are created equal. Drewbie lays out a simple yet effective system for categorising leads—cold versus warm—and how to engage each. Warm leads are familiar with your work and more receptive, while cold leads require context and rapport-building. He explains how consistent follow-up and curiosity-driven questioning can warm even the coldest leads over time.

The Power of Precision in the Sales Process

Sales success isn’t about manipulation—it’s about understanding. Drewbie breaks down the importance of listening, diagnosing a client’s problem, and presenting a step-by-step solution. When done correctly, the close becomes a natural conclusion rather than a pushy sell. He also addresses how tools like AI can enhance, not replace, genuine human connection in the sales process.

Time, Energy & Effort: The Ultimate Investment

Drewbie’s core message is simple yet powerful: your greatest assets are your time, energy, and effort. If used intentionally, these can generate exponential returns. He encourages listeners to rethink how they allocate their daily focus, making space for what truly drives growth and revenue.

What You’ll Learn in This Episode:

  • Why mindset is more important than skill in sales success
  • How to use service, not selling, as your core approach
  • Practical outreach strategies for warm and cold leads
  • The power of asking the right questions to uncover true client needs
  • How to invest your time and energy like top earners do
  • Why time management is the key to higher income and work-life balance

The episode wraps up with Heneka sharing details about the upcoming Leadership Cruise and encouraging listeners to connect with Drewbie, whose programs help entrepreneurs scale with intention and integrity. Whether you’re new to sales or looking to level up, this episode is packed with golden insights to help you build a purpose-driven sales strategy.

COMMUNITY CONNECTION:

Now it’s time for our Community Connection segment! We’d love to hear your thoughts on today’s episode or any questions you have for Drewbie or Heneka—email us at heneka@henekawatkisporter.com or WhatsApp us at 876-849-2571.

Also, don’t forget about the upcoming LeadHerShip Cruise, where leaders like YOU can network and grow aboard Royal Caribbean’s Liberty of the Seas! This four-day event combines empowerment with transformative learning against the stunning backdrop of the Bahamas. Contact us at heneka@henekawatkisporter.com or WhatsApp 876-849-2571 for more details!

CONTACT DREWBIE WILSON:

Website: https://www.drewbiewilson.com/
LinkedIn: https://www.linkedin.com/in/drewbiewilson/

TRENDING NOW:

Did you know that companies using AI in sales see a 50% increase in lead generation, but close rates drop drastically without human follow-up? In an era where data is abundant but action is scarce, Drewbie’s approach reminds us why personal connection still wins

If you enjoyed this episode of The Entrepreneurial You, subscribe on Spotify and Apple Podcasts, leave a rating, and share it with your friends. Visit henekawatkisporter.com to download a free eBook on how to conduct podcast interviews like a pro!

AFFIRM WITH ME:

I take bold action because my success starts when I show up my book.

Dive into the latest episode of The Entrepreneurial You podcast, where we uncover the transformative power of mentorship and coaching with our esteemed guest, a seasoned entrepreneur whose early setbacks paved the way for enduring success.

**Learning from Setbacks: The Mentorship Advantage**

– Early Struggles: Our guest reflects on the initial challenges faced when starting alone and the realization that solo efforts led to regression rather than progression.

– The Mentorship Turning Point: Discover the pivotal moment when our guest embraced the need for guidance and how this decision became a cornerstone strategy throughout their entrepreneurial journey.

– Navigating Transitions: Learn how seeking out mentors and coaches with each new venture or career shift can safeguard against significant pitfalls and foster triumphs.

– The Role of Mentorship in Success: Gain insights into how the right mentor or coach can accelerate your path to success and help you avoid the missteps that can hold you back.

Connect with today’s guest and find a mentor who can help steer your entrepreneurial ship towards success.

Closing Thoughts:
Thanks to our guest for sharing their journey and mentorship’s invaluable role in their achievements. To our listeners, remember that you don’t have to go it alone; mentors can be your compass to success.

Stay tuned for more episodes of The Entrepreneurial You and embrace the collective wisdom that can drive your business forward.

Affirmation:
I seek wisdom and guidance, harnessing the collective experience to fuel my entrepreneurial ascent.

For more information and resources from today’s episode, visit our website at henekawatkisporter.com. Engage with us on social media; we’re active on Heneka Watkis-Porter.

Remember: Stay engaged, stay entrepreneurial!

Picture of Author: Heneka Watkis-Porter
Author: Heneka Watkis-Porter

When I'm not podcasting, speaking, coaching or hosting first-class conferences (think Leadercast & She Leads co-founded with the Jamaica Stock Exchange), I'm passionate about helping women thrive and walk in their God-given purpose through Grace to Grow Mentorship and Training.

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