The Selling Podcast

Hosted by Mike Williams and Scott Schlofman

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312

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Aug 2026

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About the show

Feeling stuck in a sales slump? Pipeline looking thinner than a supermodel on a juice cleanse? Want to grow your business faster than a startup funded by a lottery winner? Then buckle up, buttercup, because "The Selling Podcast" is your new obsession! Join your seasoned (slightly graying but still very spry) sales pros, Mike and Scott, who collectively boast over 50 years of crushing quotas (and racking up enough airline and hotel points to live perpetually in a suite). They're not just here to drop wisdom; they're here to deliver a potent mix of "deep-ish thoughts and some truly mediocre advice" (their words, not ours... mostly) on everything from closing monster deals to navigating the wild ride of life. Every week, prepare for unfiltered stories, battle-tested philosophies, hard-earned insights, and enough random tangents to keep you laughing – and learning! They even drag in some special guests (who usually offer the really deep insights, just between us) to elevate the conversation even further. Whether you're a seasoned sales manager, a hungry rep grinding for commission, or just someone who wants to understand the human element of persuasion, Mike and Scott cut through the fluff with their signature blend of sharp sales strategies and hilarious banter . Stop wishing for more sales, start getting them! Hit subscribe, join the conversation, and let Mike and Scott help you sell better, live better, and most of all... enjoy all of it!

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60 recent

August 19, 202629 min

Why Sales Management Is Not Sales: The Final Sales Discovery Episode

This episode of The Selling Podcast concludes the five-part series on sales discovery by examining why sales management is not sales and what it truly takes to make the transition. Two Different Skill Sets and Philosophies Sales professionals and sales managers perform completely different roles; great sales reps do not automatically translate into great managers, much like elite athletes rarely make the most successful coaches. A salesperson focuses on selling products and developing accounts, whereas a sales manager focuses on developing high-performing people and multiplying the success of their team. Why Salespeople Want to Move into Management Many sales reps seek management tracks because they assume it will provide a simpler life, more money, and a ladder to climb since individual territories have limited upward mobility. Stephen Covey’s insight highlights the danger of spending a career climbing the wrong corporate ladder if management does not align with a person's true strengths and motivations. The Reality of Sales Management As a sales manager, your success is judged by everyone else's performance rather than your own, giving you only indirect control over the daily results. High-performing managers must resist the urge to jump in and close deals for their reps, focusing instead on mentorship, analytics, and shaping individual talent rather than creating miniature clones of themselves. Finding the Right Path If your motivation is to make money, control your time, and thrive as an individual contributor, you should stay in sales and focus on selling better and faster. If your deepest satisfaction comes from coaching, mentoring, and watching others succeed on stage, sales management is the proper path to pursue. SEO Tags sales management, sales career, sales discovery, selling podcast, sales coaching, sales leadership, individual contributor, sales mentor, career transition, sales training

August 12, 202631 min

How Do You Actually Leave Sales? The Truth About Career Transitions

This episode of The Selling Podcast dives into the often-overlooked conclusion of the sales career path by exploring how you actually leave sales and manage career transitions. The "Grass is Always Greener" Trap Sales reps frequently look at peers and assume their jobs are easier, faster, or better. This constant comparison is a natural human tendency driven by the search for a path of least resistance. Running Away vs. Running Towards When considering a move, it is critical to evaluate whether you are running away from a temporary slump or running towards a strategic, well-planned opportunity. Blaming the company entirely for performance issues is a common reaction, but true career growth requires separating emotional burnout from actual business viability. Leaving the Right Way Bridges should never be burned when exiting a role, as the business world is small and former rivals or colleagues can unexpectedly end up on the same team later. Maintaining professional connections and assuming positive intent ensures that your departure leaves a minimal wake and keeps future doors open. Treating Your Territory Like a Business Salespeople operate as entrepreneurs managing their own territories, requiring a lifecycle of starting, building, and executing a thoughtful exit strategy rather than quitting out of frustration. Ultimately, once you build a foundation in sales, you are always selling something, regardless of what career evolution comes next. SEO Tags sales career, leaving sales, sales transition, sales management, grass is greener, sales territory management, sales entrepreneurship, career change, sales networking, selling podcast

August 5, 202635 min

Luck, Networking, and Grit: How to Land Your First Sales Role

This episode of The Selling Podcast continues the five-part series on sales discovery by tackling a practical, foundational question for newcomers and career switchers: How do you actually break into sales? Summer Sales as a Testing Ground The hosts explore the role of high-difficulty entry-level positions, such as summer door-to-door sales: Low Barrier to Entry : These roles often hire almost anyone, making them accessible for anyone looking to get a foot in the door. The Ultimate Grit Test : Pushing through grueling environments (like summer sales in Phoenix) acts as a real-world testing ground to discover whether you genuinely enjoy the profession before committing to it long-term. The Four Keys to Getting Into Sales Scott and Mike break down the core pillars required to land a quality sales role: Luck (and Focused Luck) : While timing and luck play a part, you create your own luck by placing yourself in the right environments (such as industry meetings or professional lobbies) and naturally starting conversations. Strategic Networking : True networking goes beyond mass-blasting on LinkedIn. It relies on curating genuine connections, reaching out through mutual contacts, and building authentic human relationships. Persistent Testing : Sales leaders and hiring managers often use delayed responses and interview hurdles as tests. Demonstrating resilience, follow-through, and hunger proves your work ethic. Training and Shadowing : Utilizing sales workshops, training dojos, and shadowing opportunities (like ride-alongs) allows you to evaluate the day-to-day realities of a job before jumping in. Finding a Meaningful Career Fit While low-barrier, "churn-and-burn" sales jobs are easy to find, securing a meaningful, long-term sales career requires careful evaluation. Using a checklist and conducting ride-alongs helps candidates vet company culture, daily responsibilities, and structural realities (such as compensation models) to ensure a true mutual fit. SEO Tags sales career, sales discovery, selling podcast, how to get into sales, sales networking, sales training, sales interview tips, sales shadowing, career shift to sales, sales fundamentals

July 29, 202633 min

Why Choose Sales? The Truth About the World's Best Profession

This episode of The Selling Podcast continues the five-part series on sales discovery by exploring a fundamental question: Why in the world would anyone choose sales as a career? Why People Fall Into Sales The hosts discuss how most people don't actively map out a linear career path to sales; rather, they naturally fall into it out of necessity or everyday human interaction. The Power of Human Nature : Even without heavy methodology, striking up a casual conversation and relating to people will inherently build trust and lead to sales over time. Desperation and Career Pivots : Many enter the field by accident or out of desperation when transitioning from entirely different industries (such as entertainment or technical fields) because every single company ultimately needs people to sell their products. Common Misconceptions: Reasons NOT to Get Into Sales Scott and Mike break down several misconceptions about what type of person succeeds in sales: Wanting to Manipulate People : If your goal is true manipulation for control, sales is the wrong profession. While short-term tricks might work, long-term success and peace of mind require a customer-centric approach. Believing You Must Be Extremely Outgoing : Being an extrovert with the "gift of gab" is not a requirement. In fact, talking too much hurts you because sales requires listening more than speaking; many top performers are introverts. Being Unable to Stand Being Alone : Sales can be an isolated business where you spend most of your time working independently. You must be self-driven, though reaching out to peers and the home office prevents you from becoming truly lonely. Why Choose Sales? (The Pros) Every Company Needs Sellers : Nothing happens in business until something gets sold. Because every industry needs sales professionals, you can pivot to an industry you genuinely care about. Helping Others Succeed : Great sales is not a zero-sum game. By providing tools and resources, you make your customers wildly successful, which in turn grows the entire business ecosystem. High Risk and High Reward : Sales carries significant professional and emotional risk (dealing with slumps, economic downturns, and variable income), but the financial upside and the dopamine rush of closing a hard-fought deal make it uniquely rewarding. SEO Tags sales career, sales discovery, selling podcast, why choose sales, sales profession, introverts in sales, sales risk and reward, sales mindset, business growth, sales fundamentals

July 22, 202633 min

What is Sales? 5 Part Series All About Sales

This episode of The Selling Podcast kicks off a five-part series on sales discovery by tackling a foundational question: What is sales, and how does it differ from persuasion, buying, or simply pitching an idea? Defining Sales vs. Persuasion The hosts debate the core nature of sales and where persuasion fits into the process: Scott's Definition : Sales is fundamentally about helping solve a problem using a solution you possess. He views selling as encompassing everything from commercial transactions to pitching an internal idea to colleagues in a business meeting. Mike's Definition : Sales is the facilitation of acquiring a good, service, or idea that an individual or organization genuinely requires. He draws a distinction between buying (customer-driven acquisition) and selling (interrupters, outsiders, or door-to-door reps introducing a need). The Role of Persuasion : While persuasion can sometimes lead to regret (such as talking a height-fearing spouse into a hot-air balloon ride), the hosts agree that helpful, ethical persuasion is a vital mechanism used to open the door for a true, mutually beneficial sales solution. The Four Pillars of Sales To execute a successful sale, a seller must establish four critical elements: Trust : Not just blind trust, but a deep enough understanding of the buyer's actual situation to know the offering is truly in their best interest. A Solution : Providing the best alternative available to solve the problem at that given moment. Communication : Clearly conveying why this solution fits the buyer's needs. Conviction : Having the absolute belief that what you are offering is the right path forward, steering clear of bad sales tactics. The Ultimate Test of a Sale While sales can involve pitching internal ideas or shifting perspectives, a true commercial sales transaction ultimately relies on a mutually agreeable exchange of value, goods, services, or currency where both parties walk away satisfied. sales definition, sales discovery, sales vs persuasion, sales strategy, selling podcast, sales profession, sales fundamentals, buyer vs seller, sales trust, business communication, sales mindset, sales training

July 15, 202630 min

Stop Being a Jerk: How to Perfect Your Sales Follow-Up Speed

This episode of The Selling Podcast features hosts Scott and Mike as they discuss the critical, often misunderstood art of follow-up timing and the importance of maintaining trust in client relationships. The Three Speeds of Follow-Up The hosts outline three distinct speeds of communication that help maintain momentum without crossing the line into desperation or pressure: Immediate Response (The First Speed) : When a prospective customer reaches out via email or a website, an immediate response is crucial. This initial touchpoint is not for selling; it is solely for acknowledging the inquiry and setting clear expectations for when they can expect a full answer. Progress Updates (The Second Speed) : These are essential when you cannot meet an initial deadline or are working on complex requests. They are vital for saving trust, as they show the client you are still working on their behalf and haven't forgotten them. Value-Based Follow-Up (The Third Speed) : This involves "dripping" relevant content—such as articles or ideas—to the client to add value. This keeps the conversation moving forward and opens doors for cross-selling and upselling. Building and Saving Trust According to the hosts, the key to successful follow-up is understanding that customers primarily seek certainty rather than constant contact. They categorize the state of the client-advisor relationship into three outcomes based on your actions: Building Trust : Delivering exactly what you promised by the time you promised it. Saving Trust : Proactively communicating when a delay is inevitable, thereby preventing the erosion of confidence. Losing Trust : Failing to communicate or missing deadlines without prior notice. The Follow-Up Formula To streamline your communication process, the hosts recommend following this five-step structure: Acknowledge : Confirm receipt of their message immediately. Set Expectations : Clearly state the next steps and when they will hear from you again. Provide Updates : Keep them informed of your progress along the way. Deliver Value : Share something useful, like a relevant article, to keep the engagement high. Ask for Action : Define what the next logical move is for both parties.

July 8, 202630 min

Are You in the Right Restaurant? Finding Joy and Success in Sales

This episode of The Selling Podcast features hosts Scott and Mike as they discuss the critical mid-year ritual of analyzing your sales pipeline to set the foundation for next year’s success. The Mid-Year Pipeline Audit To ensure consistent growth, the hosts argue that you should always be planning at least two quarters ahead. They recommend a structured approach to auditing your current business: Analyze Success : Start by identifying what is actually working regarding your strategy, tactics, and product mix. Once identified, double down on those successful areas rather than trying to fix everything that isn't working. Evaluate Enjoyment : Reflect on which parts of your job bring you satisfaction and which do not. While you cannot avoid the "vegetables" (the necessary, less enjoyable parts of the job), you should identify if you are simply in the "wrong restaurant"—meaning you are working in a space that doesn't align with your strengths or preferences. Check Alignment : Determine if your desired direction aligns with the industry's trajectory and your company's business model. If your personal goals don't match the company's path, you will likely encounter friction. Mastering Momentum and Prospecting The conversation highlights that even when your current process is working, you must remain adaptable to avoid the "Blockbuster" effect—the danger of failing to pivot when the market shifts. The Power of Soft Introductions : Summer is identified as an ideal time for "soft prospecting." Because offices may be quieter or more relaxed, it is a prime opportunity to introduce yourself and gather information before the high-intensity fall season begins. Keep Your Foot on the Gas : While planning is essential, the hosts emphasize that you cannot "slack off." Sales is about building and maintaining a flywheel of momentum; constant input into the pipeline is required to keep that wheel turning in the right direction. SEO Tags sales pipeline, pipeline management, sales strategy, sales success, prospecting, mid-year review, sales performance, sales growth, the selling podcast, sales mindset, business planning, sales process, sales career, quota achievement

July 1, 202632 min

Why "Being Present" is the Secret Weapon of Top Sales Professionals

This episode of The Selling Podcast features guest Jerry Gregory, a high-performing healthcare sales professional and multi-time President’s Club winner, discussing the discipline required to maintain a customer-centric approach. Core Principles of Customer-Centric Sales Servant Leadership : Success is not about the individual salesperson, but about serving the client (physicians, administrators, and patients). By keeping the focus on helping accounts and patients achieve their goals, the financial rewards follow naturally. Understanding Stakeholder Needs : Every interaction must be tailored to the specific person in the room. Physicians : Focus on patient care, efficiency, and reducing "clicks" in the electronic medical record (EMR). Administrators : Focus on cost, revenue, and workflow optimization. The Power of Discovery : Sales professionals must move beyond the "status quo" by uncovering how their solution can provide tangible value. Mastering Time and Boundaries A significant portion of the conversation focused on the discipline required to manage a busy territory effectively: Strategic Time Blocking : To avoid being overwhelmed, Gregory utilizes strict time-blocking on his calendar. He checks emails only at three specific times throughout the day (e.g., 8:00 a.m., noon, and 5:00 p.m.). Managing Expectations : Clients are informed that emails will be answered within 24 hours, but that urgent matters should be handled via text or phone call for immediate attention. This protects the salesperson's ability to be fully "present" with the person currently in front of them. Perception vs. Reality : Service is often a matter of perception. By being attentive and reliable during visits—even if those visits happen every 7–10 days—a salesperson can be perceived as being "always there" to support the team. The Value Equation Gregory emphasizes that cost should not be the primary focus of a sales discussion, as it is a relative term. Instead, he advocates for focusing on the value behind the product . When discussing costs, he notes three primary levers: price, logistics, and quality . He explains that while a customer might desire all three, they must often choose two, and it is the salesperson's job to align the solution with what the customer values most.

June 24, 202631 min

Building and Maintaining Momentum: The Rocket Fuel of Sales Success

Just like a rocket consumes the majority of its fuel in the first minute of flight to break gravity, building momentum in sales requires significant, upfront energy. Once established, however, that momentum acts like a flywheel, making every subsequent action—from prospecting to closing—easier and more efficient. Three Strategies to Sustain Sales Momentum 1. Get Out of Your Head: Overanalyzing rejection and worrying about the "what ifs" is a primary momentum killer. To stay out of your own way, focus exclusively on objective, controllable activities —such as the number of calls made, emails sent, or discovery meetings booked—rather than obsessing over the immediate outcome of a single interaction. 2. Never Neglect Your Pipeline: A common trap is pausing pipeline-building activities when you are experiencing a "win streak" because you are too busy finalizing paperwork. This is a recipe for a future lull. Professional sales reps recognize that they must "tend both ends of the stick"—celebrating current successes while simultaneously planting the seeds for future business to ensure sustainability. 3. Adopt a "Goldfish Mindset": Whether you suffer a bad day or a crushing loss, avoid letting negative experiences compound. Instead of ruminating on what went wrong, ask: What happened? What did I learn? What am I going to do next? By maintaining a short memory and focusing on the next task, you prevent a single bad day from turning into a bad month or quarter. Key Takeaways for Sales Professionals Normalize the Highs and Lows: Sales is a long game. Do not let one "best day ever" lead to overconfidence, nor let one bad experience derail your entire week. Stay consistent with your daily routines. The Best Time to Dig a Well is Before You’re Thirsty: Never wait until your pipeline is empty to start prospecting. Consistent effort in building your future opportunities ensures that when one deal closes, another is ready to take its place. Maintain Balanced Confidence: To succeed in sales, you need enough self-confidence to bounce back from rejection without becoming arrogant. This internal drive is what keeps you moving forward, even after setbacks. SEO Tags sales momentum, sales pipeline, sales success, sales mindset, prospecting, sales strategy, sales routine, overcoming rejection, sales growth, the selling podcast, sales performance, lead generation, sales professional, sales psychology

June 17, 202628 min

Mastering the Art of the Referral: Turn Success into Your Next Opportunity

Are you struggling to fill your pipeline? Many sales professionals are hesitant to ask for referrals because they fear it comes across as self-serving or uncomfortable. In this episode of The Selling Podcast , Scott and Mike break down the three most effective strategies to turn satisfied customers into your best advocates, proving that asking for referrals doesn't have to be forced—it just requires the right timing and approach. The Three Keys to Asking for Referrals 1. Capitalize on the "Success Moment": Timing is everything. The best time to ask for a referral is during the "euphoria" phase—that moment when your customer is experiencing a successful outcome and is genuinely excited about the solution you provided. Don't wait for a follow-up call; seize the moment when the client is already praising your work. 2. Ask for Specific Individuals: Avoid being vague. Instead of asking if a company knows of other organizations that could use your services, ask for the names of specific individuals. This makes it easier to draw a personal connection and target someone who may have moved to a different department or organization. 3. Facilitate a "Soft Introduction": Lower the risk for your client by requesting a low-pressure connection, such as a LinkedIn introduction, an email copy, or even a casual lunch. When asking for this, encourage the client to share the emotion they felt—how they felt before you solved their problem versus how they feel now . Pro-Tips for Seamless Referrals The "Soft Open": Set the stage early. Within the first ten minutes of a conversation, gently mention that you help others in similar situations. This prepares the client for the eventual request once they achieve their own "success moment". Lead with Emotion: People connect with stories, not just stats. When a client refers you, it is far more powerful when they share their emotional journey: "I was frustrated, but now I feel free". Teach your clients to frame their recommendations with that same passion and feeling. Be Sincere: Authenticity is your best tool. Your clients know you are in business to make money, but if you focus on genuinely sharing the success and solving problems for others, the referral becomes a natural, helpful extension of the relationship. SEO Tags sales podcast, referral marketing, sales pipeline, sales tips, lead generation, customer success, sales strategy, relationship building, consultative sales, business growth, The Selling Podcast, professional development