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 DayTimestamps00:17 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 performanceHosted on Ausha. See ausha.co/privacy-policy for more information.