MySalesDay

Michael Hess
  • 5.0 (1)
  • BUSINESS
  • UPDATED WEEKLY

Sales is hard...brutally hard.   And it's messy.   My Sales Day is a podcast BY Sellers, FOR Sellers. I’m Michael Hess, Founder and Chief Seller Advocate of “My Sales Day”, and it's my job to make “the sales life” "less messy" for you...and of course,  to help you excel and perform at your peak abilities.  My goal is to make your time here educational, inspirational, and actionable.  And yeah, entertaining too…sales doesn’t have to be boring!  Selling is fun too, so let’s have some of that here as well. You'll get skill ideas, action items, and hugs.   Yes, hugs.   You need support and you don't often get it from inside your org, and you certainly don't get it from the street.   The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.   And if you need more of this positivity in your sales day, be sure to read  the MySalesDay email which you can get by subscribing at mysalesday.io (http://mysalesday.io). Hosted on Ausha. See ausha.co/privacy-policy for more information.

  1. Objection Handling That Wins Trust with Doug Weaver and Michael Hess

    5D AGO

    Objection Handling That Wins Trust with Doug Weaver and Michael Hess

    In this episode of the My Sales Day podcast, Michael Hess sits down with Doug Weaver to explore what happens when a long, successful chapter ends—and what the next one requires of modern sales leaders. Doug reflects on the emotional reality of moving on from Upstream Group after a multi-decade run, why creating a “proper ending” mattered, and what it feels like to step into a new venture as a solo act. From there, the conversation shifts into a lesson Doug learned early in his career that reshaped everything: stop focusing on your own performance and start focusing on what’s in it for them. In workshops, in sales calls, and in leadership—Doug argues the role is to be the host, not the entertainment. You’ll also hear a powerful anecdote about a salesperson asking for “a strategy to make customers feel like I care,” and Doug’s blunt, human response: care. Not as a tactic—but as a choice that changes outcomes. The second half opens a deep dive into objection handling—not as combat, but as service. Doug challenges the “comeback” mentality and offers a more effective objective: shorten the timeline to truth and expand the available information. The result is a practical, repeatable approach for sellers and sales managers who want more clarity, fewer stalled deals, and stronger buyer trust. Featuring: Doug WeaverHost: Michael Hess, My Sales Day Timestamps 00:12 Leaving success behind: how emotional was it to move on?00:59 Why the timing felt right and why Upstream Group was never “just Doug”02:44 The most important lesson from 28 years helping sellers and managers03:16 The turning point: performance vs. service—“be the host, not the entertainment”04:40 Creating participation: drawing out the quiet voices in the room05:16 Sustainability: why listening beats performing (two ears, one mouth)06:21 The “strategy to make customers feel like I care” story—and the humanity lesson08:02 The Weaver Collective: semi-retirement, coaching, and building the next generation09:56 Why frontline sales managers are under-supported (and why this matters now)10:43 Objection handling as the “whopper” skill—and why it’s never a one-and-done12:06 You don’t need perfection: the goal is to shrink objections, not eliminate them13:27 “We train humanity out of salespeople”—why objection handling isn’t conquest15:17 Doug’s framework: ask meaningful questions before offering answers16:07 The real objectives: shorten time-to-truth and expand available information18:05 Slow down on the off-ramp: understand why they’re saying it20:32 Anticipating objections before the call: role play, prep, and patterns24:13 Why sellers struggle: weak questions, lack of structure, and rushing to “answer”27:23 Objection resolution as service, not combat—and why practice builds confidence34:09 Moving objections upstream: don’t wait until “late stage” to surface resistance Hosted on Ausha. See ausha.co/privacy-policy for more information.

    1h 6m
  2. Ryan Picchini on Self Appraisal: Build Better Habits and Close More B2B Deals

    FEB 3

    Ryan Picchini on Self Appraisal: Build Better Habits and Close More B2B Deals

    What separates good sellers from great ones usually isn’t hustle—it’s self-awareness. In this episode of the My Sales Day podcast, host Michael Hess sits down with Ryan Picchini (CRO at dotCMS) to unpack a skill most sellers avoid: analyzing your own selling behaviors. Ryan explains why self-evaluation is the lever that improves win rates, strengthens relationships, and helps sellers build a repeatable path to performance—not just a lucky quarter. You’ll hear practical ways to do self-appraisal even if your manager doesn’t coach, how to extract patterns from your calls and journals, and why top performers don’t stop “selling” when the deal enters late stage. Ryan also shares how leaders can coach tenured reps who think they’re “good enough,” and how a personal manifesto can drive the daily actions that produce long-term results. If you want to sell with more intention—and improve outcomes without burning yourself out—this conversation gives you frameworks you can use immediately. Featuring: Ryan Picchini, CRO at dotCMSHost: Michael Hess, My Sales Day Timestamps 00:17 Welcome back + why sellers avoid looking in the mirror01:20 “If you don’t know yourself, it’s hard to know your customer”02:01 Ryan’s new role as CRO at dotCMS and what changed03:02 Skill gaps leaders must face: demand gen, partnerships, rev ops, deal cycles04:10 Leadership as the multiplier: empowering the team vs doing it yourself05:45 The core idea: self-evaluation and the humility to grow10:17 Accepting feedback as a gift (and removing ego from improvement)12:40 What to do if you don’t have a coaching manager: retros, recordings, journaling15:04 A simple feedback framework sellers can use with their manager20:56 Coaching grizzled/top reps: how to position self-analysis to improve win rates28:21 Late-stage discipline: don’t replace action with “hoping and praying”31:06 Staying top of mind without “just checking in”33:20 Using your team to close: exec notes, CS/engineering support, strategic touches37:59 Personal manifestos: why action creates momentum (especially mid-January)40:04 Ryan’s story: early struggle, late payoff, and why consistency wins46:17 Final takeaway: self-evaluation is transformational for performance Hosted on Ausha. See ausha.co/privacy-policy for more information.

    49 min
  3. How to Prospect Like a Human. Susan Unger on Authentic B2B Selling That Wins Meetings

    JAN 28

    How to Prospect Like a Human. Susan Unger on Authentic B2B Selling That Wins Meetings

    Prospecting hasn’t gotten easier—but it has gotten more human. In this episode of the My Sales Day podcast, Michael Hess welcomes back Susan Unger, a career prospector who quite literally does this work for a living. Susan is a senior “door opener” at Kopp Consulting, where her sole focus is securing first meetings with C-level decision makers when no prior relationship exists. If anyone understands the emotional grind of cold outreach in today’s market, it’s Susan. Recorded in mid-January—peak prospecting season—this conversation tackles why so many sellers avoid prospecting, what’s changed post-COVID, and how being prepared actually gives you permission to be more spontaneous, human, and effective. Susan breaks down how phone, email, and voicemail work together to tell a story over time, why vulnerability disarms resistance, and how small shifts—like asking permission or slowing down your delivery—can dramatically improve results. You’ll also hear why improv classes can sharpen selling skills, how listening to your own recorded calls accelerates growth, and why attitude, energy, and consistency matter more than clever scripts. This is a practical, confidence-building episode for sellers who want to stop dreading prospecting and start owning it. Featuring: Susan UngerHost: Michael Hess, My Sales Day Timestamps 00:01 Welcome back + why this episode matters right now01:08 Why prospecting feels harder in today’s market02:32 Kopp Consulting explained: pure cold outreach and “door opening”03:14 Cold calling C-level execs with no prior relationship04:36 What changed after COVID—and why clients are more open now06:23 How Susan hands meetings off and secures the next meeting08:13 Why locking the follow-up meeting before ending the call matters09:26 Why sellers avoid prospecting (even when they know better)10:03 Preparation as the gateway to confidence and authenticity11:38 Being human on cold calls: vulnerability that works14:23 Breaking the ice and buying time with empathy16:03 You can think on your feet—practice makes it natural18:27 Why improv training improves sales conversations20:29 Authenticity, self-deprecation, and knowing your limits24:07 “Show up prepared, then allow your personality”27:24 Listening to your own calls: self-evaluation that pays off30:12 Asking permission on cold calls—and why it works33:31 Gamifying prospecting to beat resistance36:22 Burst prospecting and building daily momentum37:55 Why email + voicemail still create impressions39:22 How managers can coach prospecting through real examples42:20 Referral-based prospecting: the habit sellers forget45:39 Motivation, mindset, and confidence rituals that stick49:14 Quieting the inner voice and just starting50:11 Final takeaway: better habits, better selling Hosted on Ausha. See ausha.co/privacy-policy for more information.

    46 min
  4. Meeting Management for B2B Sellers with Lawrence Horne: Agendas, Storytelling, Trust

    JAN 20

    Meeting Management for B2B Sellers with Lawrence Horne: Agendas, Storytelling, Trust

    In today’s selling environment, you get fewer shots with buyers—and less time when you get them. That’s why meeting management (or better: conversation management) has become a modern sales superpower. In this episode of the MySalesDay podcast, Michael Hess sits down with Lawrence Horne—joining from the UK countryside—to break down what great sellers do before, during, and after a buyer conversation to earn trust, control momentum, and land the next step. Lawrence opens with a “Hall of Fame” early-career win: a creative, ambitious ad strategy that required persistence, internal alignment, and the confidence to do something that hadn’t been done before. From there, the conversation gets tactical: agenda-setting, discovery discipline, how to avoid hiding behind decks, and how to read buyer cues when you’re selling over video. If you’ve ever left a meeting thinking “we talked a lot but learned nothing,” or watched a seller speed-run a slide deck while missing obvious buyer signals, this episode gives you a cleaner framework: set a clear agenda, ask smarter questions early, earn the right to tell the story, and manage the room—especially when there are multiple stakeholders and unclear power dynamics. To close, Lawrence shares what he does to handle the turbulence of a sales year—the reset, the pressure cycles, and the mindset habits that keep performance steady when the numbers start yelling. Featuring: Lawrence HorneHost: Michael Hess, MySalesDay Podcast Timestamps 00:03 Welcome + Lawrence joins from the UK01:24 Today’s focus: meeting management and conversation control02:54 Hall of Fame sale: creativity, competitiveness, and ambition03:40 The big move: combining dealers into a higher-yield concept04:37 Crossing lanes? Clarifying internal boundaries and account ownership05:16 Persistence required: getting 15 stakeholders to agree06:24 Internal selling and organizational alignment behind the scenes08:45 Why clustering buyers/sellers increases demand and “yield”10:39 Why conversation management became the skill Lawrence chose11:55 Agenda discipline: knowing what the buyer wants to hear13:45 Why meetings are harder now: fewer buyers, fewer meetings, less time14:37 Selling over video: why precision matters more than ever15:05 Stop hiding behind decks: the danger of “get through the slides”18:59 The 25-minute meeting problem: balancing questions vs. pitching22:40 Pre-meeting agenda strategy: use the calendar invite to force clarity39:47 Selling to the top: managing mixed seniority and stakeholder dynamics42:53 The danger of misreading power in the room44:03 Handling turbulence: pressure cycles, health, mindset, and habits46:23 Culture matters: performance gets easier with great people47:16 The cost of being “the energy person” and why preparation reduces stress49:07 Closing: better habits equal better selling Hosted on Ausha. See ausha.co/privacy-policy for more information.

    51 min
  5. Practical AI Strategies for B2B Sellers and Sales Leaders with Jason Tsai

    JAN 13

    Practical AI Strategies for B2B Sellers and Sales Leaders with Jason Tsai

    AI has moved past the “is this real?” phase—and entered the “who’s actually adopting it well?” phase. In this episode of the My Sales Day podcast, Michael Hess sits down with Jason Tsai (joining from London) to break down what AI is actually doing inside modern sales orgs, where teams are still stuck, and how B2B sellers can use AI to sell more—not just produce more “work.” Jason shares the career path that led him from media planning to digital transformation roles, and ultimately into AI enablement at Pivotal, a growth studio that doesn’t stop at strategy decks—Pivotal embeds with teams to implement change and drive adoption. From there, the conversation gets practical: Why AI tools are mature, but adoption is uneven How sellers go beyond basic “write my email” prompts into scalable prospecting and enrichment How AI helps verticalize value propositions without breaking brand governance Where AI is useful for role-play, objection handling, and pressure-testing messaging The difference between using AI to produce “work slop” vs. using AI to sharpen performance Why the transformation is only half tools—and mostly human motivation, training, and habits If you’re a seller, manager, or sales leader trying to figure out what to do next—this is a grounded, non-hype roadmap for using AI to reclaim selling time and raise the bar on how you prepare, message, and execute. Featuring: Jason TsaiHost: Michael Hess, MySalesDay Podcast Timestamps 00:18 Welcome + first MySalesDay episode of 202600:40 Jason joins from London: “neither sunny nor dry”01:23 The mission: tangible AI action items for sellers and leaders02:10 Jason’s career arc: agency → publisher → Visa → ad tech → AI04:03 Falling down the AI rabbit hole + the “no time to learn AI” insight05:49 What Pivotal does: operator-led growth studio, implementation not slides06:02 Jason’s team: AI enablement, workflow mapping, “robots” that speed up real work08:32 Agenda: state of AI, skills impacted, adoption resistance11:04 Where AI is today: beyond experiments, now “uneven adoption”12:09 Sales AI example: Gong and what call data reveals13:35 The 30% problem: sellers spend too little time actually selling15:27 Leveling up prospecting: from ChatGPT searches to scale tools16:19 Scaling research + enrichment: Clay/Apollo-style workflows18:05 AI and value proposition: customization at the account/segment level21:37 Governance: using AI to grade/pressure-test messaging before it ships25:01 Negotiation prep: scripts, simulations, and objection handling practice30:28 In-meeting AI: awkward live, powerful for preparation and post-call learning48:13 Adoption resistance: tools are half the equation—humans are the rest49:30 How to drive adoption: make it role-specific + prove time savings51:24 Close: better habits equal better selling Hosted on Ausha. See ausha.co/privacy-policy for more information.

    53 min
  6. Complex Sales: Why Nuance Is the Spice of SaaS

    08/19/2025

    Complex Sales: Why Nuance Is the Spice of SaaS

    In this episode, Grant le Riche, VP of Client Strategy at Eighty Twenty joins me to dive into the mindset required to master the complex sales process. Grant shares how his career evolved from highly transactional sales to a more strategic, consultative approach. We talk about the importance of preparing for every interaction, even when you think it's just a formality, and how he recovered a deal after his boss "junked up" a meeting. Grant also reveals his secrets to building authentic champions and why self-appraisal is a critical skill for any professional seller. Join us as we discuss: [2:29] Working with siloed departments and the nuances of complex SaaS sales  [13:45] Why every informal meeting isn’t and champion development [24:23] If AI is the canary in the coal mine for critical thinking in sales [37:02] Proactively addressing and shrinking your buyer’s objections For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    43 min

  7. 07/22/2025

    Qualifying Your Buyers: Sharpen Your Invisible Sword to Win More Sales

    Qualifying clients is the invisible sword every seller must wield, but too few do so effectively. Penry Price, Founding and Managing Partner at Charcoal Advisors, joins me to explore why qualifying is foundational to successful selling, despite often being underutilized. Penry leans on his experiences at Google, LinkedIn, and other major media entities to highlight how a disciplined approach to qualifying protects precious selling time, uncovers genuine client needs, and ensures that efforts align with opportunities most likely to close. Listen to learn how properly qualifying clients can transform your pipeline, sharpen your strategic focus, and dramatically improve your sales outcomes. Join us as we discuss: [1:40] Managing external factors through preparation and persistence [15:51] Navigating big expectations and why a little paranoia is a good thing [21:19] How qualifying your clients is your ultimate timesaver [25:03] Flipping the sense of urgency on its head and the art of brand storytelling For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    51 min

  8. 07/08/2025

    Don't Just Pitch: A Masterclass in Point of View Selling

    Charlie Thomas, Founder of Charlie Thomas Coaching & Consulting, doesn’t focus on pitching harder. Instead, he leans on point of view selling to think bigger. Charlie joins me to share how bold ideas and strategic alignment can transform not just deals, but careers. He recounts the day he closed a multimillion-dollar partnership with Dr. Pepper Snapple by inventing a value-driven offsite on the fly, and how that single act helped multiple clients climb to CMO. From there, he breaks down the mechanics of POV selling, the role of strategic discovery, and why cultivating alignment is key to speed, health, and trust in every sales relationship. Join us as we discuss: [2:29] How an authentic point of view creates action and builds trust [17:33] Why speed and health make up the golden rule of performance — alignment [25:40] The importance of strategic initiatives and a sense of urgency For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    38 min
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About

Sales is hard...brutally hard.   And it's messy.   My Sales Day is a podcast BY Sellers, FOR Sellers. I’m Michael Hess, Founder and Chief Seller Advocate of “My Sales Day”, and it's my job to make “the sales life” "less messy" for you...and of course,  to help you excel and perform at your peak abilities.  My goal is to make your time here educational, inspirational, and actionable.  And yeah, entertaining too…sales doesn’t have to be boring!  Selling is fun too, so let’s have some of that here as well. You'll get skill ideas, action items, and hugs.   Yes, hugs.   You need support and you don't often get it from inside your org, and you certainly don't get it from the street.   The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.   And if you need more of this positivity in your sales day, be sure to read  the MySalesDay email which you can get by subscribing at mysalesday.io (http://mysalesday.io). Hosted on Ausha. See ausha.co/privacy-policy for more information.

Information

  • Creator
    Michael Hess
  • Years Active
    2024 - 2026
  • Episodes
    34
  • Rating
    Clean
  • Copyright
    © Michael Hess
  • Show Website
    MySalesDay