🎙️Transcript: The Win Rate Podcast

The Win Rate Podcast with Andy Paul
"Answering the Accountability Question"
Andy Paul, Richard Harris, Mitchell Kasprzyk, Ralph Barsi
November 21, 2024

Summary

On this WinRate episode, host Andy leads a wide-ranging conversation with Ralph Barsi (Kahua), Richard Harris, and Mitchell asprzyk (Compile) about modern sales leadership: balancing process with improvisation, building accountability and agency, and using AI thoughtfully.

They critique fear-based cultures that over-index on activity metrics (e.g., firing high performers for “not following process”), and argue for curiosity, coaching, and outcome-centric measures like win rate and late-stage pipeline coverage. The panel also explores attention management, generational shifts in coaching, and how AI should augment creative, buyer-centric selling—especially around predicting and increasing the probability of a win.

7 Big Takeaways

1. Measure what matters: Track win rates, late-stage pipeline coverage, and buyer progress...not just meetings set or raw activity.
2. Coach to agency: Give reps ownership of plans; ask them how they’ll hit goals, then co-design and hold mutual accountability.
3. Balance process & jazz: Standardize fundamentals but encourage skilled improvisation; study top reps to codify what truly works.
4. Run post-mortems: When deals or initiatives miss, debrief for root causes; improve enablement, talk tracks, and internal alignment.
5. Fight attention fracking: Remove distractions (e.g., phones during calls), promote deep work, and favor handwritten capture when useful.
6. Use AI as a force multiplier: Analyze winning patterns, simulate tough conversations (procurement/security), and surface “next best actions” - don’t outsource thinking.
7. Think in probabilities: Before each step, ask, “Will this increase our chance of winning?” Choose actions with the highest expected impact.

Andy (Host):
Hi friends, welcome to another episode of the WinRate podcast. We were just joking that I should shave my head before we start, because I’m the only one here with hair. My illustrious panel: Ralph Barsi, Richard Harris, and Mitchell Kastersek. Everyone, take a second to introduce yourselves. Ralph, we’ll start with you.

Ralph Barsi:
Hello, everybody. Hair is overrated - so I agree Andy should shave his head. I’m Ralph Barsi, Vice President of Sales at Kahua. We’re in the construction management space, offering a project management platform for construction owners. I’ve been on the show before — honored to be back, and I love being here with Mitchell and Richard.

Andy:
Richard, you’re next.

Richard Harris:
Thank you. I’ll say the quiet part out loud: the three of us are a little jealous of Andy’s hair. I’m Richard Harris — sales trainer and go-to-market strategist. I teach reps how to earn the right to ask questions, which questions to ask, and when to ask them. I’ve known Andy and Ralph for years and always love being with them. Mitchell, great to connect and learn from you too.

Andy:
Mitch, over to you.

Mitchell Kasprzyk:
I’m Mitchell, VP of Sales at Compile. We’re a SaaS platform that helps organizations better manage and mitigate risk. And yes, I’m jealous of Andy’s hair. They say grass doesn’t grow on a busy street.

Andy:
New sponsor idea: Hair Club for Men? Brian Urlacher? Restore? Quick question for the panel: are you musical?

Richard:
I’m musically challenged. I dabble with guitar—not well. ADHD makes it hard to focus, but I love music and live shows.

Andy:
Listeners know Ralph is a rock drummer—still playing, right?

Ralph:
Many years. Love to play.

Andy:
And Mitchell is an opera singer.

Mitchell:
Not me—I’ll book the shows.

Andy:
Did you study singing, Mitchell?

Mitchell:
Yes. Looking back, I’m not doing it now, but I learned a lot. I performed in the U.S. and Europe.

Andy:
You toured?

Mitchell:
A bit. No groupies. But I met my wife—she’s a classical singer and still performs.

Andy:
Coolest performance?

Mitchell:
The Rainbow Room at Rockefeller Center in Manhattan—business conference gig with a pianist and program we put together.

Andy:
We’ll have an episode where you sing for us.

Mitchell:
I haven’t warmed up!

Andy:
Ralph, audience sizes for Segue?

Ralph:
Mostly 150–200; festivals helped. Band’s called Segue—S-E-G-U-E—not the scooter. We started in 1994; a couple of records are out on the platforms. Full heads of hair back then!

Andy:
Salespeople are interesting outside work. Richard once said, “Sales is like jazz.”

Richard:
Right—great musicians feel where it’s headed. In sales, people do it their own way; when aligned, it’s beautiful. Rock jams, opera—same magic.

Andy:
Isn’t the problem that leaders want scales and strict process instead of embracing improvisation?

Richard:
Exactly. When everyone follows a strong framework but still feels the flow, it works. But forcing rigid steps kills that.

Andy:
Here’s a story: a senior enterprise seller (club last year, 140% YTD) was fired for “not setting enough meetings.” Second such case in 30 days. My post blew up—some said it couldn’t happen; my inbox filled with similar stories. Leaders used process to override judgment and results. Ralph, could you ever do that?

Ralph:
No. It doesn’t seem rational. Maybe there’s missing context—attitude, behavior—but based on what you shared, I’m puzzled.

Mitchell:
We should measure the right activities that drive outcomes. Setting meetings matters, but if someone’s hitting goals, that’s a signal. Insecure leaders fear being questioned when a high performer succeeds outside the template.

Richard:
Where’s the accountability for everyone? Leaders must hold themselves accountable first. If someone can crush numbers with fewer meetings, learn from them—record, study, coach the rest. And if culture is off, perhaps it’s a blessing to move on.

Ralph:
Agreed. Metrics I care about: pipeline coverage to quota—especially late-stage coverage given cycle length. Also culture: surface concerns early; don’t surprise people with the door.

Mitchell:
Lack of curiosity hurts. A curious leader asks, “Why is this person excelling, and how do we scale it?” Fear-based leadership clings to compliance.

Richard:
Many leaders confuse blame with accountability. Healthy accountability is mutual.

Richard (to Ralph & Mitchell):
How do you hold yourselves accountable in healthy ways?

Mitchell:
Have one-on-ones that set shared goals: “Here’s the company goal; here’s my slice and how I’m pursuing it. What will you own by year-end?” Ask them how they will hit targets—let them own the plan; coach after they propose it. Agency creates buy-in.

Andy:
Agency matters—research shows more autonomy improves outcomes (even longevity). Marines train to make decisions under pressure—same principle.

Ralph:
I invert the org chart: I serve the team, remove obstacles, and listen first. Then I add context and options: “Here’s the mission. A, B, C, D can work. If you’ve got a better path, share it. If not, start with B.” That lowers defenses and invites ownership.

Andy:
Great lesson: my CEO once let a rep run an approach I thought was wrong—he said “Good luck.” It failed, the rep learned, and we codified the lesson. Leaders must resist the urge to be the hero.

Richard:
Generational lens: Gen X “figured it out” with little coaching; Millennials/Gen Z want more coaching—which Gen X once called micromanagement. Truth: we’re jealous of the coaching tools available now.

Andy:
Attention fracking (engineered distraction) is real. Some schools now require phones locked away; handwriting improves recall.

Richard:
We need deep work: remove phones from desks during call blocks. My son’s class handwrites in-class work—it’s helping.

Andy:
“Figure it out” mindset: stop complaining that nobody answers. In the past we had no direct dials or email; we innovated anyway. Do something different—even if not scalable.

Mitchell:
In VC-backed SaaS, frantic pressure creates fear, which reduces psychological safety. That pushes activity for activity’s sake—and worse selling.

Richard:
AI helps, but only as good as the thinking behind it. Prompt quality matters; don’t outsource judgment.

Andy:
Prompt engineering might not be a long-term career—models will improve. Tools differ; try more than one and think for yourself.

Richard:
AI saves some time but frees creative energy. Still, people mindlessly copy how “everyone else” uses tools.

Ralph:
“More” isn’t better—better is better. Invest in your craft; be a student. If you let AI think for you, you won’t grow.

Mitchell:
Use AI to add value beyond product talk. Role-play harder conversations—procurement, security—so reps are ready where deals stall.

Richard:
Also record internal deal conversations (RevOps, CS, IT) and feed insights into CRM/forecasting. We already record external calls—internal alignment matters too.

Ralph:
We record more internally now; next step is piping insights into CRM for stage/health signals.

Andy:
Beware AI learning from poor baselines. If your win rate is ~20%, your models may encode mediocre behavior. Commit to performance improvement first.

Richard:
Think sports analytics: “expected goals.” In sales, ask: what action now most increases our probability of winning? Choose the higher-probability step.

Andy:
Many sellers don’t consciously ask, “Will this step raise my win odds?” Build that habit.

Mitchell:
Also think in deposits/withdrawals (Covey). Win trust early—look for the “oh wow” inflection moments; use AI to help find and replicate them.

Ralph:
A ServiceNow exec once told me: “Don’t report the weather—predict it.” Use data to prescribe next best actions at each stage.

Richard:
We should be close to AI recommending coaching based on fastest-moving deals. That’s useful—provided the data quality’s high.

Andy (wrapping):
We’ve gone long—thanks all. I’ll wear a bald cap next time to fit in. Let’s aim for four beards on the next episode.

All:
(Laughter, goodbyes, thanks.)