Innovative Sales Leadership Approaches

For my first 16 years in tech sales, I averaged 240K/year W2 income. In my last 4 years, I averaged 720K/year. In order to triple my income, I had to change my sales approach entirely. Here's what I changed: I started using a new approach that I now call Yo-yo selling: 🪀 Yo-yo selling emphasizes starting at the executive level, conducting thorough discovery within the organization, and then returning to the executive with a tailored business case. Like holding a yo-yo, you are constantly in communication with the Executive Sponsor and updating them as you collect information and conduct deep discovery lower down in their organization. You are literally going up and down the organization, but always taking everything back to the Executive Sponsor to surface your findings along the way. Here's a breakdown of the framework: 🎯 𝐈𝐚𝐧 𝐊𝐨𝐧𝐢𝐚𝐤’𝐬 “𝐘𝐨-𝐘𝐨 𝐒𝐞𝐥𝐥𝐢𝐧𝐠” 𝐅𝐫𝐚𝐦𝐞𝐰𝐨𝐫𝐤 This strategy involves a three-step process: 1. Start at the Top (Executive Engagement) Initiate contact with a senior executive to understand their most pressing challenges, the reasons behind the need for change, and the consequences of inaction. If your solution aligns with their needs, secure their sponsorship for further discovery within their organization. To secure the Executive Meetings, it's essential to create a tailored POV (point of view) on where you think you may be able to help them based on your initial research of their highest level goals and priorities. Chat GPT has made this research a LOT faster now. 2. Conduct In-Depth Discovery (Middle Management) Engage with department heads and key stakeholders to uncover the day-to-day challenges they face. Focus on understanding their processes, pain points, and the implications of current inefficiencies. Gather direct quotes and insights to build a comprehensive view of the organization's needs. 3. Return to the Executive (Present Findings) Compile the insights gathered into an executive summary and business case. Present this to the executive sponsor, highlighting how your solution addresses the identified challenges. Tailor your demonstration to focus solely on relevant aspects that solve their specific problems. 🚀 Why It Works 1. Accelerates Sales Cycles: Engaging executives early ensures alignment and expedites decision-making. 2. Builds Credibility: Demonstrates a deep understanding of the organization's challenges and showcases a tailored solution. 3. Facilitates Internal Buy-In: By involving various stakeholders, you ensure that the solution meets the needs of all parties, increasing the likelihood of adoption. I'm pleased to share that that Yo-yo selling was recently awarded as a Top 15 Sales Tactic of All Time by 30 Minutes to President's Club, and I received a cool plaque for entering the 30MPC Hall of Fame. Since I have no chance of entering the Hall of Fame for my baseball or golf game, this is a nice consolation prize 😁

How many times have you heard someone say, ‘We’ve always done it this way,’ or ‘No, we can’t do that because…’? As sellers, it can be frustrating! 😖And while, these statements might feel logical, they could be the fastest way to lose a deal—or miss out on the creative idea that could help you win one. As sales professionals, we’re not just selling products; we’re solving problems, driving initiatives, and designing solutions tailored to our customers’ objectives. But here’s the challenge: our competitors are often selling the same things. So, how do we stand out? The answer lies in how we approach selling—not just what we sell. And that’s where I’ve been inspired by a concept from Duncan Wardle’s book The Imagination Emporium: the power of “Yes, And….” When we default to “No, because…,” we shut down ideas before they’ve had a chance to grow. We stay stuck in the same “river of thinking,” unable to innovate or offer anything truly unique. This mindset can feel safe—it’s rooted in what’s worked before—but it also keeps us from creating the differentiated solutions our customers are looking for. The magic happens when we shift to “Yes, And….” ✔️ It sparks creativity. Most of our conscious brain is consumed with day-to-day tasks—emails, meetings, and presentations. But innovation happens in the subconscious, where unexpected connections and ideas emerge. “Yes, And…” helps unlock that creativity. ✔️ It builds momentum. When we agree to build on ideas instead of dismissing them, we create bigger, bolder, and more innovative solutions. ✔️ It fosters collaboration. Sales success doesn’t happen in silos. Bringing together diverse perspectives helps ideas grow into solutions that truly stand out. ✔️ It differentiates us. Customers don’t just want products; they want partners who think differently and design unique solutions to their challenges. “Yes, And…” empowers us to deliver on that promise. Here’s how you can put this into practice: ✔️ In your next sales meeting with your account team, commit to saying “Yes, And…” to build on others’ ideas. ✔️ Hold off judgment—let ideas grow before evaluating them. ✔️ Celebrate small wins and steps toward creativity. What are your thoughts on “Yes, And…” in sales? How do you encourage innovation on your team? #sales; #deals; #innovation

I used to describe my leadership style as “iron fist, velvet glove.” I thought it sounded tough but fair. Turns out… I was just being kind of a jerk. I was promoted into sales leadership at 23. No training. No roadmap. Just pressure to get results. I defaulted into both what came naturally to me and what I saw other sales leaders modeling: direct feedback, rigid expectations, and micromanagement. The results came. The trust didn’t. What I learned the hard way is: Respect isn’t a byproduct of results. It’s a byproduct of being the kind of leader your reps actually want to follow. It wasn’t until I learned how to show my reps how much I cared instead of expecting them to trust that I cared, that I started earning the right to challenge directly. That shift from “brutal honesty” to “compassionate candor” (ala Kim Scott) changed everything. If you want to build a high-performance sales culture, start here: Say it with words. Show it with your actions. Make sure your team knows you give a damn. Earn the right to give feedback by investing in real relationships. 👉 Here are 5 ways you can show it with your actions: 1. Be visible, not just accessible. 2. Show up to celebrate wins and not just to critique misses. 3. Lead 1:1s with curiosity. Ask questions that surface their goals, blockers, and motivators. 4. Challenge behavior, not people. Give feedback based on behavior and outcomes, not personal traits. 5. Be dependable. Consistency builds psychological safety faster than pizza parties ever will. High standards don’t have to come at the cost of psychological safety. 📌 Have you ever had to rethink your leadership style? ✨ Enjoyed this post? It's a preview of what you'll find in my debut book, Profit Generating Pipeline: A Proven Formula to Earn Trust and Drive Revenue. Snag your copy today: www.salesledgtm.com/book

One of the biggest misses I have seen in Sales Leadership is not empowering your front line managers. They are the bridge between you and your sales reps. They're crucial for your strategy to trickle down and take effect. Here is my framework for success: Invest in Continuous Training. Not just product training, but leadership & soft skills development. I remember the time when I was thrown into a leadership role with little training....I vowed never to let that happen in my teams. Provide Actionable Data. Data-driven decisions are gold. But raw data or anecdotal comments? Not so much. Ensure your managers have clear, actionable insights. I've seen a manager's face light up when they move from spreadsheets to a visual deal board in Gong! Mentorship & Feedback is a two-way street. Encourage them to seek feedback & provide them with regular insights from your end. I once had a mentor who would give me real-time feedback, sometimes even mid-meeting. Brutal? Yes. Effective? Absolutely. Active Listening - I can't stress this enough. Some of the best strategies I've adopted came from listening to a manager's on-ground experience. They're your ears on the ground, after all. Setting Clear Objectives. Keep the targets realistic. Align them with the company vision. When managers I worked with understood the 'why' behind their targets, they were twice as motivated to achieve them. Foster a Culture of Passion & Innovation: Celebrate the wins, but also the innovative attempts. Sometimes it's about the journey. How are you supercharging your front line managers? What experiences shaped your strategy? #LeadershipMatters #SalesStrategy #Empowerment #TechSales