Improving Sales Performance

Not every opportunity in your pipeline is a real opportunity.

In this episode of Improving Sales Performance, Matt Sunshine shares how top sales managers separate qualified deals from wishful thinking before inaccurate forecasts and stalled opportunities become costly surprises. Learn how to pressure test your pipeline, ask better coaching questions, and build forecasts based on evidence instead of optimism.

You'll learn how to:

• C...

Holding your team accountable doesn't have to create stress or fear.

In this episode of Improving Sales Performance, Matt Sunshine explores the difference between accountability and pressure, and why the best sales managers know how to create one without the other. Instead of relying on urgency or micromanagement, top-performing leaders build accountability through clear expectations, consistent coaching, collaborative conversations...

The best sales managers aren't defined by charisma or motivational speeches. They're defined by consistency.

In this episode of Improving Sales Performance, Matt Sunshine explores why a consistent coaching cadence is one of the biggest differentiators between average and top-performing sales managers. Rather than coaching only when problems arise, high-performing leaders build regular coaching rhythms that develop their people, stre...

Most sales managers know regular one-on-ones are important. But too often, those conversations turn into status updates, pipeline inspections, or rushed check-ins, leaving little room for meaningful development.

In this episode, Matt Sunshine breaks down five simple questions that can transform one-on-ones into stronger coaching conversations.

You’ll learn how to:

• Reinforce what is already working
• Uncover where salespeople ar...

In this Quick Take episode, we're drawing a hard line between two approaches that can look similar in the moment but produce very different results over time: coaching and micromanagement.

Matt breaks down how managers can develop new salespeople without creating dependence, including:

• Why micromanagement feels productive and why that feeling is exactly what makes it so dangerous to long-term performance
• The difference between wha...

In this Quick Take episode, we're redefining what it means to feel stuck and why the leaders most likely to experience it are often the strongest ones in the room.

Janelle Grove, VP Managing Director of the Growth Collective at The Center for Sales Strategy, takes the mic for this quick but powerful solo take.

Janelle breaks down three reasons high-performing leaders lose momentum, including:

• Why success itself creates isolation a...

In this Quick Take episode, we're breaking down what it really takes to set new salespeople up for success and why clarity, not just enthusiasm, is what drives early performance.

Matt shares six ways to set clear expectations for new salespeople without overwhelming them, including:

• Why leaders should start with outcomes, not activities. Because when new hires understand what success looks like, the checklist finally makes sense
• H...

In this episode, we're diving into the gap between insight and action and why even the smartest, most experienced sales leaders get stuck there.

Joining Matt is Janelle Grove, VP/Managing Director of the Growth Collective at The Center for Sales Strategy.

Janelle shares powerful insights, including:

• Why execution problems are rarely a strategy problem (and what's actually getting in the way)
• How leadership isolation silently kills ...

In this episode, we’re shining a spotlight on what it means to lead like a Talent Superhero and how prioritizing people fuels consistent performance. 

Joining Matt is Allison Delagrange, a 2X Talent Superhero and Senior Consultant at The Center for Sales Strategy. 

Allison shares incredible insights, including: 

• How to be a collaborative leader, not a condescending one (Hint, hint: Instead of criticizing weakn...

In this episode, we’re uncovering what high-performing sales organizations do in the first 90 days to turn new hires into confident, capable contributors. 

Matt is joined by Alina McComas, VP/Senior Consultant at The Center for Sales Strategy, who expands on the strategies she outlined in her article for the 2025 Talent Magazine. Alina shares what new hires really need to succeed and what leaders can do to support them fr...

In this episode, we’re taking a closer look at how executive coaching helps leaders evolve so their teams can truly thrive. 

And joining Matt is Donna Hall, SVP/General Manager at Robertson Lowstuter, whose piece in the 2025 Talent Magazine explores how executive coaching creates a ripple effect across teams and culture.

Whether you’re new to leadership or deep into your career, this conversation will help you rethin...

In this episode, we’re talking about what really causes sales performance to decline and what leaders can do to help their reps bounce back with clarity and confidence. 

Stephanie Downs, SVP/Senior Consultant at The Center for Sales Strategy, joins Matt to help break it all down. She expands on key ideas from her article in the 2025 Talent Magazine, where she shares a framework for diagnosing underperformance and reigniti...

In this episode, we’re exploring what smart sales leaders do before their top performers resign. 

And joining Matt is Beth Sunshine, SVP/Talent Services at The Center for Sales Strategy. 

Her contribution to the 2025 Talent Magazine highlights the importance of being ready long before turnover happens. And, here, she shares actionable ways to build that readiness into your talent strategy. 

Beth brings so much wis...

In this episode, we’re diving into how identifying and leveraging innate talent (rather than just experience) can help leaders build stronger, higher-performing sales teams. 

And helping Matt unpack it all is Trey Morris, VP/Senior Consultant/Director of Training Innovation at The Center for Sales Strategy. Trey’s article in the 2025 Talent Magazine explores how smart hiring decisions can transform team performance,...

In this Quick Take episode, we’re taking a few minutes to think about the day in the life of a salesperson before and after having AI tools at our fingertips.  

By the end of this short episode, you’ll have a solid bird’s-eye-view of how significantly AI has altered the daily routines and approaches of salespeople, making their strategies more efficient and effective.

LINKS:

Matt Sunshine

Sales Accelerator AI

Prac...

In this episode, we’re discussing the key differences between “closed” and “open” AI tools. We’ll also break down how Sales Accelerator AI, CSS’ own closed AI system, is designed to address the unique challenges salespeople regularly face. 

And helping Matt explore it all is Stephanie Downs, SVP/Senior Consultant at The Center for Sales Strategy.  

Stephanie offers so many awesome t...

In this episode, we’re discussing the benefits of having an AI Task Force at your company and how such a brain trust can be an invaluable resource to ensure that your organization stays ahead of the curve. 

Joining Matt to explore it all is Brent Tripp, Digital Marketing Coordinator & Podcast Producer here at CSS.  

Brent offers some solid points to think about, like: 

• Why it’s essential for everyone...

In this episode, we’re taking a look at how AI is supercharging CRMs and, specifically, exploring how HubSpot is transforming the way businesses manage customer relationships, sales processes, and marketing campaigns. 

Helping me break it all down are Maryanne McWhirter and Emily Hartzell, both VP/Senior Directors at LeadG2.  

Maryanne and Emily offer so many awesome points to think about, like: 

• How HubSpot i...

Previously this season, we explored how AI is transforming the world of sales coaching. Today, in this episode, we’re diving a bit deeper into that topic by chatting with two incredible guests from the AI coaching platform, Yoodli. 

Varun Puri, Co-Founder of Yoodli, and Ajay Jain, Head of Training and Enablement at Yoodli are here to break down exactly how their platform is revolutionizing the way sales professionals refi...