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Building Trust and Relationships with Todd Wilkowski

Building Trust and Relationships with Todd Wilkowski

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 In this episode, Jake welcomes longtime friend and fractional general counsel Todd Wilkowski to the show.

Todd’s journey from commercial litigator to trusted problem solver in the business world reveals the power of relational sales and the importance of genuine connection over transactional hustle.

Todd dives deep into:
  • Why understanding who you are and your unique value prop fuels authentic prospecting.
  • The disconnect between traditional high-volume sales tactics and the modern need for meaningful relationships.
  • How lawyers, and anyone in professional services, can build trust and a “book of business” by focusing on strategic, proactive advice rather than reactive problem-solving.
  • The importance of being genuinely curious about your prospects, their story, and what truly drives them.
  • Why long-term relationship-building beats quick wins and why “relationships before transactions” is not just a saying but a business game-changer.
  • A cautionary story about the perils of approaching potential clients with a hard sell before establishing trust.
  • How fractional roles create an opportunity for smaller companies to benefit from specialized expertise without the overhead of full-time hires.
  • The value of playing the long game as a connector and trusted advisor.
Jake and Todd remind us that sales isn’t about dialing numbers or pushing products.

Instead, it’s about investing time into knowing your prospects, understanding their needs, and becoming a resource they look forward to connecting with.

Key Takeaways:
  • Believe in what you bring; don’t sell what you don’t believe in.
  • Be more interested than interesting—curiosity opens doors.
  • Trust takes time and can’t be rushed with immediate transactional asks.
  • Leverage your unique strengths and be authentic in your approach.
  • Relationships are the foundation of sustainable business growth.
If you’re tired of chasing cold leads and want to reboot your lead gen strategy with heart, this episode is for you.

This episode is brought to you by Orchestraight. You can get a free trial of Orchestraight, an NLP based Lead Gen tool, for 7 days, up at orchestraight.com.

Orchestraight. The straightest path to success.
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