The Truth About Strategic Thinking: Lessons from an International Dealmaker
Sometimes, the most powerful insights come from the simplest questions. For Jonathan Gardner, that question was: "Show me the numbers of all the VPs here that you can call who will pick up the phone or call you right back."
Crickets.
In a recent Breaking Beliefs episode, Jonathan shared his journey from a small-town dreamer to an international dealmaker working with giants like GM, Dell, and Starbucks. His story reveals an important truth about what it really means to be strategic—and it's not what most of us think.
From Small Town to Big Dreams
Growing up in a small town near Greenville, South Carolina, Jonathan wanted something different than the life he saw modeled. His father worked long hours in supply chain management, living to work rather than working to live. Young Jonathan vowed to create a different path.
Inspired by authors like Ayn Rand and driven by a desire to break free from his small-town constraints, Jonathan set his sights on becoming an "international dealmaker." As he puts it, he wanted to be "James Bond with a laptop and no guns."
This ambition led him through an international MBA, law school, and eventually to positions at major corporations like General Motors, Dell, and Starbucks. But along the way, he discovered that technical expertise alone wasn't enough.
The Strategic vs. Tactical Wake-Up Call
During his time at Dell, Jonathan received feedback that would change his entire approach to business. In a 360-degree review, twenty-one out of twenty-two people called him strategic. One person—his boss—called him tactical.
When Jonathan questioned this assessment, his boss delivered that pivotal question about VP phone numbers. The lesson? Jonathan was approaching relationships tactically, only reaching out when he needed something specific. This wasn't strategy; it was reactionary.
Real strategy, his boss taught him, involves building relationships before you need them. It's about creating connections that transcend immediate tasks or projects. This revelation forced Jonathan to confront an uncomfortable truth: despite his technical expertise and business acumen, he was missing a crucial element of strategic leadership.
Relationship-First Thinking
This insight led Jonathan to work with a coach for seven years, helping him rewire his approach to business relationships. He learned that true strategic thinking isn't just about:
Having technical expertise
Achieving perfect execution
Instead, it's about:
Building genuine connections
Understanding organizational dynamics
Creating networks of trust before they're needed
Approaching relationships with intention rather than necessity
The Result of Transformation
Today, Jonathan runs his own consultancy, helping mid-market companies land deals with Fortune 500 corporations. His understanding of both the technical and relational aspects of business allows him to bridge gaps that many others can't see.
His journey teaches us that being strategic isn't just about what you know—it's about who you know and, more importantly, how you build and maintain those relationships.
Key Takeaways:
Strategic thinking extends beyond technical expertise
Relationships should be built before they're needed
True strategy involves long-term relationship building, not just tactical execution
Sometimes our biggest professional growth comes from personal development
The way we approach relationships can be more important than our technical skills
Moving from Tactical to Strategic
Jonathan's story reminds us that transformation often requires us to challenge our assumptions about what makes us effective. Sometimes, the very habits we think are serving us—like only reaching out when we have a specific need—are actually holding us back.
The question isn't whether we have the technical skills to succeed. The question is: Are we building the relationships that will help that success happen?
What phone numbers are in your phone? More importantly, who would pick up if you called right now?