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

Jeff Zito: 30-60-90 Plans and Account Planning for B2B Sellers

Jeff Zito just accepted a new role as Regional Vice President at Cadent and he joins Michael Hess on the MySalesDay Podcast to break down the exact frameworks that help B2B sellers ramp faster and sell more strategically. This episode tackles two topics that can change your year: building a practical 30 60 90 plan when you start a new role and running a simple account planning process that keeps you proactive instead of stuck “selling out of your inbox.” Jeff shares how he approached his own 30 60 90 request, why early credibility matters, and how to set realistic expectations around activity, meetings, and momentum. Then the conversation shifts into account planning, including account segmentation, retention risk, and relationship mapping so one contact is not a single point of failure. If you are a B2B sales professional or sales manager, this is a playbook episode on speed to market, building pipeline early, and creating repeatable habits that compound over time. Time stamps 00:26 Jeff Zito announces his new role as Regional Vice President at Cadent 01:39 Why 30 60 90 plans matter and how they connect to account planning 03:54 Jeff’s reaction to being asked for a 30 60 90 and how he built it 06:00 The foundations of a strong 30 60 90 plan: learn, diagnose, execute 08:44 What “closing” really means in the first 90 days and the value of mini wins 10:49 Setting expectations with your manager and how to sniff out unrealistic plans 11:58 First 30 days priorities: master territory, audit pipeline, prospect immediately 13:27 How to coach hesitant sellers and create early “layups” for confidence 15:17 What must happen in your first 90 days to set up a strong year 17:25 Prep work and organization as the hidden advantage in ramping fast 20:41 When new hires should be tested on objections, competitors, and messaging 22:01 The effort standard in modern sales and why the first week matters 27:01 Shadowing, role playing, and peer learning to accelerate readiness 30:15 Holding activity levels accountable and leading by example as a manager 35:39 Account planning as the shift from reactive to strategic selling 37:26 Segmenting accounts and focusing time where revenue is most likely 38:45 Protect, retain, grow: managing risk and finding white space 45:05 Relationship mapping to reduce risk and build multiple champions 47:52 The best plans are owned by the rep and built with follow through Watch the full interview on the MySalesDay YouTube channel Subscribe to the daily sales newsletter at MySalesDay.io [http://MySalesDay.io] #MySalesDay #B2BSales #SalesPodcast #SalesMotivation Hosted on Ausha. See ausha.co/privacy-policy [https://ausha.co/privacy-policy] for more information.

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 Weaver Host: 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 managers 03:16 The turning point: performance vs. service—“be the host, not the entertainment” 04:40 Creating participation: drawing out the quiet voices in the room 05:16 Sustainability: why listening beats performing (two ears, one mouth) 06:21 The “strategy to make customers feel like I care” story—and the humanity lesson 08:02 The Weaver Collective: semi-retirement, coaching, and building the next generation 09:56 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-done 12:06 You don’t need perfection: the goal is to shrink objections, not eliminate them 13:27 “We train humanity out of salespeople”—why objection handling isn’t conquest 15:17 Doug’s framework: ask meaningful questions before offering answers 16:07 The real objectives: shorten time-to-truth and expand available information 18:05 Slow down on the off-ramp: understand why they’re saying it 20:32 Anticipating objections before the call: role play, prep, and patterns 24:13 Why sellers struggle: weak questions, lack of structure, and rushing to “answer” 27:23 Objection resolution as service, not combat—and why practice builds confidence 34:09 Moving objections upstream: don’t wait until “late stage” to surface resistance Hosted on Ausha. See ausha.co/privacy-policy [https://ausha.co/privacy-policy] for more information.

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 dotCMS Host: Michael Hess, My Sales Day Timestamps 00:17 Welcome back + why sellers avoid looking in the mirror 01:20 “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 changed 03:02 Skill gaps leaders must face: demand gen, partnerships, rev ops, deal cycles 04:10 Leadership as the multiplier: empowering the team vs doing it yourself 05:45 The core idea: self-evaluation and the humility to grow 10:17 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, journaling 15:04 A simple feedback framework sellers can use with their manager 20:56 Coaching grizzled/top reps: how to position self-analysis to improve win rates 28:21 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 touches 37:59 Personal manifestos: why action creates momentum (especially mid-January) 40:04 Ryan’s story: early struggle, late payoff, and why consistency wins 46:17 Final takeaway: self-evaluation is transformational for performance Hosted on Ausha. See ausha.co/privacy-policy [https://ausha.co/privacy-policy] for more information.

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 Unger Host: Michael Hess, My Sales Day Timestamps 00:01 Welcome back + why this episode matters right now 01:08 Why prospecting feels harder in today’s market 02:32 Kopp Consulting explained: pure cold outreach and “door opening” 03:14 Cold calling C-level execs with no prior relationship 04:36 What changed after COVID—and why clients are more open now 06:23 How Susan hands meetings off and secures the next meeting 08:13 Why locking the follow-up meeting before ending the call matters 09:26 Why sellers avoid prospecting (even when they know better) 10:03 Preparation as the gateway to confidence and authenticity 11:38 Being human on cold calls: vulnerability that works 14:23 Breaking the ice and buying time with empathy 16:03 You can think on your feet—practice makes it natural 18:27 Why improv training improves sales conversations 20:29 Authenticity, self-deprecation, and knowing your limits 24:07 “Show up prepared, then allow your personality” 27:24 Listening to your own calls: self-evaluation that pays off 30:12 Asking permission on cold calls—and why it works 33:31 Gamifying prospecting to beat resistance 36:22 Burst prospecting and building daily momentum 37:55 Why email + voicemail still create impressions 39:22 How managers can coach prospecting through real examples 42:20 Referral-based prospecting: the habit sellers forget 45:39 Motivation, mindset, and confidence rituals that stick 49:14 Quieting the inner voice and just starting 50:11 Final takeaway: better habits, better selling Hosted on Ausha. See ausha.co/privacy-policy [https://ausha.co/privacy-policy] for more information.

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 Horne Host: Michael Hess, MySalesDay Podcast Timestamps 00:03 Welcome + Lawrence joins from the UK 01:24 Today’s focus: meeting management and conversation control 02:54 Hall of Fame sale: creativity, competitiveness, and ambition 03:40 The big move: combining dealers into a higher-yield concept 04:37 Crossing lanes? Clarifying internal boundaries and account ownership 05:16 Persistence required: getting 15 stakeholders to agree 06:24 Internal selling and organizational alignment behind the scenes 08:45 Why clustering buyers/sellers increases demand and “yield” 10:39 Why conversation management became the skill Lawrence chose 11:55 Agenda discipline: knowing what the buyer wants to hear 13:45 Why meetings are harder now: fewer buyers, fewer meetings, less time 14:37 Selling over video: why precision matters more than ever 15:05 Stop hiding behind decks: the danger of “get through the slides” 18:59 The 25-minute meeting problem: balancing questions vs. pitching 22:40 Pre-meeting agenda strategy: use the calendar invite to force clarity 39:47 Selling to the top: managing mixed seniority and stakeholder dynamics 42:53 The danger of misreading power in the room 44:03 Handling turbulence: pressure cycles, health, mindset, and habits 46:23 Culture matters: performance gets easier with great people 47:16 The cost of being “the energy person” and why preparation reduces stress 49:07 Closing: better habits equal better selling Hosted on Ausha. See ausha.co/privacy-policy [https://ausha.co/privacy-policy] for more information.