Episode 165-Upgrade Your Career with Tim Madden
In this episode of The Prospecting Show, Dr Connor Robertson sits down with Tim Madden, the founder of Executive Career Upgrades. Madden has helped thousands of professionals and executives take control of their careers, move into better positions, and build confidence in their leadership. The conversation explores practical frameworks for career transformation, mindset mastery, and the importance of treating your career like a business.
Dr Robertson opens by saying, “Your career is the single largest investment of your time and energy—yet most people never build a strategy around it.” Tim nods. “Exactly,” he replies. “People invest more thought in their next vacation than in their next career move.”
From Corporate Frustration to Career Freedom
Tim Madden’s story begins in the corporate world. After a decade in executive recruiting, he recognized a pattern: highly qualified professionals were stuck because they didn’t know how to communicate their value. “I saw talented people missing promotions, underpaid for years, or afraid to make a change because they lacked a plan,” he explains.
That realization led to the creation of Executive Career Upgrades—a program designed to help mid-career and senior-level professionals reposition themselves for high-impact roles. “It’s not about luck,” Tim says. “It’s about learning how to market yourself.”
Dr Robertson adds, “That’s such an important distinction. Success in any field isn’t just about competence; it’s about communication and confidence.”
Why Most People Stay Stuck
Tim outlines the three reasons professionals stay in unfulfilling roles: fear, comfort, and confusion.
- Fear – the fear of rejection, instability, or failure.
- Comfort – being “busy enough” to justify inaction.
- Confusion – not knowing what’s next or how to get there.
“Most people think they need clarity before action,” Tim says, “but clarity comes from action.”
Dr Robertson agrees. “That’s the same principle in entrepreneurship—you don’t discover your next step by waiting; you discover it by doing.”
The CEO Mindset for Career Growth
Tim believes every professional must become the CEO of their own career. “You are the product, the marketer, and the brand,” he says. “If you don’t manage your reputation and trajectory, someone else will.”
He recommends professionals audit their “career P&L”:
- Revenue: compensation and growth.
- Expenses: stress, burnout, lack of purpose.
- Assets: skills, network, achievements.
- Liabilities: fear, outdated habits, limiting beliefs.
“When you treat your career like a business, decisions become clearer,” he says.
Dr Robertson responds, “That mirrors what we teach founders—measure your inputs and outputs, and you’ll see where to optimize.”
Building a Personal Brand That Attracts Opportunities
One of the strongest takeaways from the episode is Tim’s emphasis on personal branding. “The job market is noisy,” he says. “Your online presence must tell a consistent story about who you are and the results you create.”
He recommends professionals optimize three key digital touchpoints:
- LinkedIn: Craft a results-driven headline and about section. Use measurable outcomes to show value.
- Content: Post weekly insights about your industry to establish thought leadership.
- Visibility: Engage meaningfully with decision-makers—comment, share, and send context-based messages.
Dr Robertson adds, “That’s the same way we build brand equity in business. Reputation compounds faster than marketing spend.”
Tim nods. “Exactly. You can’t control opportunities, but you can control visibility.”
The Power of Networking the Right Way
Tim challenges the idea of traditional networking. “Most people network when they need something,” he says. “Real networking is about giving before asking.”
He teaches professionals to adopt a “value-first” mindset. “Before sending a message, ask yourself, ‘How can I make this person’s day better?’ That approach changes everything.”
Dr Robertson shares a similar insight from acquisitions. “Relationships are assets,” he says. “When you give value consistently, doors open naturally.”
Tim adds, “The moment you stop thinking of networking as transactional, you start building leverage.”
The Role of Mindset in Career Advancement
Both Dr Robertson and Tim agree that mindset is the hidden driver of career growth.
“Skills get you in the door,” Tim says. “Mindset keeps you in the room.”
He defines mindset as “the stories you tell yourself about what’s possible.” Professionals who advance quickly are those who replace self-doubt with self-direction.
Dr Robertson notes, “That same mental model applies to entrepreneurship—belief drives behavior.”
Tim adds, “When you shift your identity from employee to value creator, your career accelerates.”
How to Position Yourself for Executive Roles
Tim shares a practical blueprint for professionals seeking high-level opportunities:
- Clarify your target. Define the exact role, title, and industry you want.
- Build a magnetic message. Create a narrative that connects your past results to future value.
- Leverage LinkedIn strategically. Use advanced searches and content to connect with hiring leaders.
- Master the interview. Prepare stories that demonstrate impact, not activity.
- Negotiate with confidence. Know your market value and anchor the conversation around ROI.
Dr Robertson summarizes, “It’s the same as building deal flow in acquisitions—clarity, positioning, and persistence.”
Why Career Growth Is a Continuous Process
Tim stresses that career growth isn’t a one-time upgrade—it’s a lifelong process. “Every level requires a new version of you,” he says. “What got you here won’t get you there.”
He encourages professionals to build a habit of quarterly self-reviews. “Ask yourself: What did I learn? What results did I create? What new value can I offer?”
Dr Robertson adds, “That’s exactly how successful founders operate—they iterate continuously.”
Balancing Ambition and Fulfillment
A recurring theme in this episode is balance. Tim explains that chasing promotions without purpose leads to burnout. “If success costs your health or relationships, it’s not success—it’s sacrifice,” he says.
He teaches clients to align career moves with values. “When your work aligns with who you are, energy replaces effort.”
Dr Robertson agrees. “Fulfillment isn’t the opposite of ambition—it’s the fuel for it.”
Overcoming Career Plateaus
Tim shares that career plateaus are often psychological, not external. “People blame the market, but the real block is internal,” he says.
He recommends reframing stagnation as a signal for reinvention. “When you hit a plateau, it’s your cue to re-evaluate, not retreat.”
Dr Robertson adds, “That’s the same with acquisitions—stagnation means systems or vision need upgrading.”
The Future of Work and Career Strategy
Tim and Dr Robertson discuss how the modern workplace is shifting toward flexibility, autonomy, and results-driven leadership. “Titles are less important now,” Tim explains. “Value creation is what companies pay for.”
He predicts that future leaders will prioritize skills portability—the ability to adapt across industries. “You’re no longer defined by one job title,” he says. “You’re defined by your transferable results.”
Dr Robertson adds, “That adaptability is what makes professionals recession-proof.”
The Importance of Mentorship
Tim emphasizes the impact of mentorship. “You can’t see your blind spots alone,” he says. “The right mentor collapses time by giving you perspective.”
Dr Robertson adds, “That’s why podcasts like The Prospecting Show exist—to give people access to the conversations that accelerate their journey.”
Practical Action Plan
Tim closes the episode with a step-by-step plan for professionals ready to upgrade their careers:
- Audit your current situation. Identify what’s working and what isn’t.
- Define your target role. Be specific about the next step.
- Rebuild your brand. Optimize your resume, LinkedIn, and messaging.
- Expand your network. Engage intentionally every day.
- Execute daily habits. Apply for roles, publish insights, and follow up consistently.
Dr Robertson wraps up the episode by saying, “Success is a process, not a position. Your career grows in proportion to your consistency.”
Tim smiles. “Exactly. And consistency compounds faster than any promotion.”
Key Takeaways
- Treat your career like a business—you’re the CEO.
- Build systems for visibility and reputation.
- Networking is about giving, not asking.
- Your mindset determines your mobility.
- Clarity + Execution = Career Acceleration.
- Fulfillment sustains long-term success.
- Reinvention is a lifelong skill.
Listen and Learn More
Listen to the full episode here: Upgrade Your Career with Tim Madden