Talking to Sales GOATs: Mike Weinberg

I am starting a new series. Inspired by the GOATs (Greatest of all time) of sports and sales, I realize how blessed I have been to meet and talk to some of the biggest luminaries in all of sales.

Because of this, I would be remiss not to reflect on what I've learned from them and share these learnings with the world.

Chapter 3: Simplifying Sales Leadership: Timeless Wisdom from Mike Weinberg

Some relationships in life alter your trajectory in profound ways, and my connection with Mike Weinberg is a shining example of this.

I'm blessed to live in St. Louis, where there is a plethora of sales talent, and like many, I have followed Mike for YEARS. It was unbelievable to me when I learned he knew who I was, and even more surreal when a breakfast meeting was arranged.

Mike Weinberg, whose books and blogs had been a guiding star for much of my sales career, sat across the table from me, as approachable and candid as his writing suggested. That breakfast turned into a series of impactful collaborations, culminating in my appearance on his podcast and his guest spot on mine. What follows is the story of a friendship built on mutual respect, sharp insights, and a shared passion for making sales great again.

The Breakfast That Sparked It All

It was August 13, 2021, and I found myself sitting across from Mike at a cozy breakfast spot in St. Louis. As I tried to keep my inner fanboy in check, we delved into a conversation that was as energizing as the coffee we sipped. Mike’s books, New Sales. Simplified. and Sales Management. Simplified., had been instrumental in shaping my sales philosophy, so I eagerly absorbed every word.

One of the most memorable moments of our conversation was Mike’s question: “What are your primary ‘Energy Draculas’?” He explained that these were the things that drained my energy and pulled me away from my primary mission. This simple yet profound concept struck a chord. I reflected on how senseless scrolling, endless notifications, and reactive tasks were diluting my productivity. Mike’s advice to “shine a light” on these Draculas and proactively eradicate them became a cornerstone of my daily routine.

Mike’s candor, wit, and no-nonsense approach left an indelible impression. As we parted ways, I felt reinvigorated and more determined than ever to focus on what mattered most in my career. Little did I know, this breakfast was just the beginning of a transformative journey.

On Mike’s Podcast: Lessons in Leadership

Months later, I had the honor of being a guest on Mike’s renowned podcast, The Sales Management Simplified Podcast. The experience was surreal, not only because I was sitting in the guest seat of a show I had long admired but also because of the depth of our conversation. Mike’s introduction still gives me goosebumps:

“Carson is an incredible human being. He is one of the most generous, giving, and caring people I know. A top sales producer turned extraordinary sales team leader, podcast host, and author. Honestly, I can’t believe it’s taken us this long to get you on the show.”

The discussion centered on navigating ambiguity in the tech industry and leading sales teams through challenging times. One key takeaway was the importance of staying at the pulse of your team’s morale and your customers’ evolving needs. Mike’s insight into the unique role leaders play in occupying “a ton of space in their people’s hearts and minds” resonated deeply.

We explored the concept of controlling the controllables. Mike prompted me to share my approach to maintaining balance in the face of uncertainty—focusing on what I could control: outreach quality, strategic execution, and building meaningful relationships. This principle, paired with Mike’s wisdom, reaffirmed my belief that leadership is about empowering others to shine.

Hosting Mike on Mastering Modern Selling

The tables turned when I had the privilege of hosting Mike on my podcast, Mastering Modern Selling. It felt poetic to bring the mentor who had influenced me so profoundly into my world. We focused on the enduring relevance of sales fundamentals amidst the rise of social selling and AI-driven tools. Mike being on Mastering Modern Selling with Brandon Lee , Tom Burton and me was a fulfillment of my birthday wish on November 1, 2023.

Mike’s perspective on balancing the “old and new” was both refreshing and actionable. He reiterated the importance of mastering the basics—targeting the right prospects, crafting compelling messaging, initiating meaningful conversations, and owning the calendar. Yet, he also acknowledged the evolving landscape, advocating for the thoughtful integration of tools like LinkedIn and AI without losing the human touch.

One of the highlights of our conversation was Mike’s framework for accountability: results, pipeline, and activity. He explained how effective leaders shine a light on these metrics, not to micromanage but to identify gaps and guide their teams toward success. His clarity and pragmatism turned a complex topic into a simple, repeatable formula for success.

Mike’s appearance on Mastering Modern Selling was more than just an interview—it was a masterclass in leadership, humility, and the art of selling. Our banter, built on mutual respect and shared experiences, made for an unforgettable episode.

Navigating Leadership Through Uncertainty: Lessons from the Sales Trenches

As I sat down with Mike Weinberg for his renowned Sales Management Simplified podcast, I knew we’d touch on topics that matter deeply to sales leaders navigating these turbulent times. But what I didn’t anticipate was how much of our conversation would feel like a leadership therapy session—digging deep into the heart of what it takes to lead a team through ambiguity, pressure, and the unrelenting pace of modern sales. Mike, ever the straight-shooting host, started with an observation that hit home:

“Carson, your role isn’t just about hitting numbers. It’s about how much space you take up in your team’s hearts and minds. Especially in challenging times, leadership is everything.”

That set the stage for an honest conversation about what it’s really like to lead in an era where change is the only constant.

The Pulse of Leadership

Leading during uncertain times demands more than strategy; it requires emotional intelligence and unwavering clarity. The tech space, particularly in recent years, has faced seismic shifts—pandemics, layoffs, talks of recession, and market contractions. For leaders like myself, the challenge isn’t just about guiding a team to meet their targets; it’s about keeping them motivated and grounded.

“You’ve got to stay at the pulse of your team and your customer organizations,” I shared with Mike. “Sellers are problem eliminators. But we can’t solve problems effectively if we’re disconnected from what’s happening on the ground. That means being transparent, overcommunicating if necessary, and constantly aligning on priorities.”

Mike pressed me further: “Carson, how do you stay sane as a leader? With everything your team looks to you for, from hope to direction, how do you keep from getting whiplash?”

“Mike, I won’t lie—I’m tired,” I admitted. “And that’s okay to say. We’re human. But I also remind myself every day that 99% of humanity would kill to be in the position I’m in. That gratitude keeps me grounded. I also lean on my team and my peers. Leadership isn’t about being the smartest person in the room; it’s about knowing who to reach out to and how to elevate everyone around you.”

Building Community and Brand

“In tough times, you have a chance to build your brand,” I told Mike. “Your brand is what you’re known for, how your unique strengths make everyone around you better, and how you show up when things are hard. Now more than ever, it’s time to be that merchant of hope for your team and customers.”

Mike’s response was sharp: “When you say brand, Carson, is it about standing out from the crowd during tough times or something more?"

“Both,” I replied. “It’s about creating a reputation that’s bulletproof, even in bad years. It’s about being the leader whose team and customers trust them implicitly. For me, that means being authentic and consistent. You don’t have to hit every number to win. But if your team knows you’ve left it all on the field and your customers see you as a trusted advisor, that’s brand equity you can’t buy.”

Controlling What You Can Control

The concept of controlling what’s within our power was a recurring theme in our conversation. As Mike put it, “Carson, you talk about controlling what you can control. But for many sales leaders, that’s easier said than done. What does that really mean?”

I leaned into my love of analogies. “Sales is like poker or sports. There are variables you can’t control, but over the long haul, your preparation and consistency determine your success. You can’t control every outcome, but you can control your inputs: how well you research, how often you reach out, and how prepared you are for contingencies. It’s about putting yourself in a position where the odds shift in your favor.”

One of the stories I shared illustrated this perfectly. “The biggest deal of my career started with LinkedIn outreach. I messaged 526 director-level and above contacts in a single organization. That wasn’t about luck; it was about probability. I controlled the quality and quantity of my outreach and built a groundswell of influence within that company. Even when leadership changed seven times, our relationships were strong enough to keep us at the table.”

Mike was floored. “526 contacts? Carson, that’s unheard of. And the level of personalization you brought—highlighting sections of your CEO’s book for them—that’s next level.”

“That’s the point, Mike,” I said. “It’s not just about volume. It’s about intention. Every message was tailored. Every interaction added value. That’s how you stand out in a world where automation often drowns out authenticity.”

Social Selling as a Differentiator

Mike, ever the skeptic of “spammy social selling,” challenged me to explain my approach.

“Carson, most people think of social selling as an invite-and-pitch disaster. What makes your method different?”

“It’s all about genuine connection,” I responded. “Automation can’t replace authenticity. I don’t just blast messages; I engage. I hit the notification bell for top prospects, comment insightfully on their posts, and build relationships organically. One executive and I have never had a formal meeting, but we’ve exchanged book recommendations and ideas in LinkedIn threads. That’s the kind of groundwork that pays off.”

Landing the Step

As our conversation wound down, Mike asked for final advice for sales leaders.

“Land the step,” I said simply. “I learned this lesson climbing modest mountains in the Cascades. The summit looks daunting if you stare at it. But if you focus on the step right in front of you, you’ll get there. Sales and leadership are the same. Control the step you’re on. Build community. Serve your team and customers. The summit will take care of itself.”

Mike’s closing words summed it up best: “Carson, you are a gift to the sales profession. Your humility, wisdom, and authenticity are exactly what leaders need right now. Thank you for sharing so generously.”

Leadership isn’t about being perfect. It’s about showing up authentically, navigating uncertainty with grace, and bringing others along for the climb. In challenging times, we don’t just sell—we inspire, connect, and transform. And that, my friends, is how we win.

A Masterclass in Modern Selling: Lessons from Mike Weinberg

This episode was more than a conversation—it was a deep dive into the art and science of sales leadership, personal growth, and staying grounded in a fast-changing industry. We tackled topics ranging from social selling to leadership transformation, and Mike brought his trademark candor and insight to every moment.

Celebrating Authenticity and Leadership

The episode opened with a special birthday surprise for me—a cameo from Leah Thompson, none other than Lorraine McFly from Back to the Future. While the surprise left me speechless, Mike quickly brought us back to focus, sharing this profound truth:

“Carson, leadership isn’t about how much you achieve alone. It’s about what you enable in others. Especially in today’s sales environment, leadership is about humility and empowerment.”

This sentiment set the tone for the episode as we explored what it takes to thrive in sales leadership.

The Transition from Salesperson to Sales Leader

Mike’s insights into the shift from top-producing salesperson to sales manager struck a chord:

“The only thing that a salesperson and a sales manager have in common is the word ‘sales.’ As a manager, you’re no longer the hero. You’re winning through your people. That requires selflessness, patience, and a total mindset shift.”

I couldn’t agree more. I’ve often reflected on how my early promotions into management revealed hard truths about leadership. Mike and I both admitted to learning the hard way that leading isn’t about doing—it’s about developing others to do their best work.

“Leadership sets the tone,” I added. “Good leadership empowers managers to lead with clarity and conviction, not as micromanagers but as enablers of success.”

Navigating the Challenges of Modern Sales Management

Mike’s discussion of the challenges sales managers face was particularly striking. He noted how many managers are buried in administrative tasks and fail to prioritize coaching their teams:

“The sales manager’s role is to develop their people. Yet most are stuck in spreadsheets and firefighting. We’ve lost the art of field coaching—spending time with reps, prepping for meetings, and debriefing after them.”

I shared my own experience, emphasizing the joy of seeing team members grow:

“One of my proudest moments was when a team member who used to rely on me for every meeting eventually became completely self-sufficient. Leadership isn’t about being needed; it’s about building confidence and capability in others.”

Social Selling: From Charlatan Tactics to Authentic Connections

Mike’s critique of early social selling trends sparked a lively discussion. He recalled:

“In the early days, social selling was pitched as a replacement for traditional methods. Charlatans promised that posting and automating outreach would replace relationship-building. It was a disaster.”

I agreed wholeheartedly, adding:

“Social selling is a tool, not a replacement for sales fundamentals. It’s about genuine connection. I’ve used LinkedIn to engage with prospects by hitting the notification bell on their posts, commenting insightfully, and building relationships over time. Authenticity wins every time.”

Mike praised this approach:

“Carson, what you’ve done with LinkedIn is next level. You’ve shown how social selling can supplement—not replace—classic sales strategies. That’s what makes it work.”

Lessons on Accountability and Culture

Mike shared a simple yet powerful framework for sales managers to ensure accountability:

1. Start with results: “Review where your team stands. Are they hitting their numbers? If not, why?”
2. Examine the pipeline: “The pipeline is the lifeblood of the business. What’s being created and advanced?”
3. Dive into activities only if needed: “Activity reviews should be a last resort. If results and pipeline are strong, the activities will speak for themselves.”

This method resonated with me. “Accountability is about shining a light on reality,” I said. “When leaders focus on results and pipeline first, they give reps the autonomy to succeed while still holding them accountable.”

Transforming Failure into Fearlessness

Toward the end of the episode, we discussed the role of failure in growth. Mike shared a vulnerable story about struggling in his first year as a sales manager:

“I failed because I tried to do it all myself. It wasn’t until I learned to delegate, trust my team, and focus on coaching that I started to succeed.”

I echoed this sentiment, sharing a lesson from my own career:

“Failure is inevitable, but it’s also a gift. It’s taught me resilience and the importance of focusing on what I can control. My biggest successes came from learning how to embrace failure as a stepping stone.”

Closing Thoughts: A Challenge to Leaders

As we wrapped up, Mike issued a challenge to sales leaders:

“Your job is to create an environment where your people can thrive. Focus on culture, accountability, and development. If you do that, everything else will follow.”

I couldn’t agree more. Leadership is about showing up authentically, navigating challenges with grace, and empowering others to succeed. This episode wasn’t just a conversation; it was a blueprint for modern sales leadership.

To Mike’s point, when leaders prioritize their teams and focus on creating value, they don’t just hit numbers—they transform lives. That’s the heart of what makes sales leadership so rewarding.

To catch the full episode, visit Mastering Modern Selling

Learning from the GOATs like Mike Weinberg has been a tremendous blessing, reaffirming that true leadership is about empowering others, staying authentic, and turning every challenge into an opportunity for growth.

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