MySalesDay

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

49min | 02/03/2026

Description

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 for more information.

About MySalesDay

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.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

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.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

Description

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 for more information.

About MySalesDay

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.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

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.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

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