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This podcast is available on 8 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

No, this podcast does not typically feature guests.

My Sales Day

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by Michael Hess

36 episodes

Updated Weekly

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Podcast Overview

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.

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Publishing Since

8/13/2024

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🇺🇸 Charts #3

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Spotify 827

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Podcast Authority

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PoorBased on show quality, social media presence, reviews, charts, and more

Quality57

Social0

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Engagement0

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excellent

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40 minutes

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Recent Episodes

February 22, 2026

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 <a href="http://MySalesDay.io">MySalesDay.io</a> #MySalesDay #B2BSales #SalesPodcast #SalesMotivation Hosted on Ausha. See <a href="https://ausha.co/privacy-policy">ausha.co/privacy-policy</a> for more information.

February 16, 2026

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 Timestamps00:12 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 <a href="https://ausha.co/privacy-policy">ausha.co/privacy-policy</a> for more information.

February 3, 2026

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 Timestamps00:17 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 <a href="https://ausha.co/privacy-policy">ausha.co/privacy-policy</a> for more information.

36 total episodes available

Deep-dive analytics for My Sales Day

Frequently asked questions

Have a different question and can't find the answer you're looking for? Reach out to our support team by sending us an email and we'll get back to you as soon as we can.

What is My Sales Day?: 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.
How often does this podcast release new episodes?: This podcast updates weekly.
Where can I listen to this podcast?: This podcast is available on 8 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
Does this podcast accept guests?: No, this podcast does not typically feature guests.

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