Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

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About this episode:

Ever had that feeling where your pipeline looks busy… but nothing’s actually moving? 
Yeah. Turns out, you’re not alone.

Sales leaders think stalled deals are a pipeline problem.

Sales reps are experiencing something very different.

In this episode, Ollie Whitfield sits down with Steve Myers, and John Richardson to unpack insights from analysing 5117 real sales coaching calls and what they reveal about why deals lose momentum.

The conversation exposes a gap between what salespeople ask for in coaching and what’s actually holding performance back. 

While most conversations focus on pipeline, deal progression, and “tips and tricks,” the real blockers often sit deeper—in decision process clarity, mindset, and how sales teams think about control in the deal. 

The episode explores why decision process dominates coaching conversations, why “closing” is often misunderstood, and how over-reliance on tactics masks underlying behavioural and mindset challenges. 

It also highlights the disconnect between prospecting responsibility and pipeline ownership, and how this impacts quota attainment and sales velocity.

This episode is essential listening for: VPs of Sales, Heads of Sales, Sales Managers and Revenue Leaders who are trying to improve sales coaching effectiveness, increase deal velocity, and build a stronger coaching culture that goes beyond surface-level tactics.

Brought to you by MySalesCoach.

Learn more about how we support leaders in building elite sales teams with our Sales Coaching Operating System:

www.mysalescoach.com

Simple comp plans are easy to explain. Bad comp plans are easy to regret.

This episode gets into the real damage sales leaders create when compensation becomes unclear, unfair, too clever, or easy to game.

Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

In this sales leadership lesson, Mike Pritchett of BuzzTrail and David Wilkins unpack what actually happens when comp plans drift away from the behaviours the business needs.

• Reps disengage fast when they cannot clearly see how they make money
• Changing comp after overachievement destroys trust and pushes good people out
• Complex plans create confusion, politics, and arguments over who deserves what
• Poorly designed incentives drive sandbagging, bad meetings, gaming, and low-value activity
• Too much disparity across reps creates distraction, resentment, and “why are they getting more than me?” conversations
• Team-based targets can hide poor performance and pull everyone toward mediocrity
• Commission-only setups sound attractive in startups, but make it harder to judge fit and build real team energy
• Small non-cash rewards can sometimes motivate better than taxed cash incentives
• Public recognition, competition, and simple scoreboards still matter because sales is hard and momentum matters

The core message is straightforward: compensation is not just about paying people. It shapes behaviour, trust, culture, focus, and performance. When leaders get it wrong, they do not just create payroll problems. They create distraction, resentment, short-term thinking, and a sales team that starts working the plan instead of working the market.

This episode is for VPs of Sales, Heads of Sales, SDR leaders, and founders trying to build comp plans that stay simple, reward the right actions, reduce internal friction, and help good reps perform without creating avoidable chaos.

• (00:00) - Start

Timestamps

00:00 Why simple comp plans outperform clever ones

08:35 The hidden damage of changing comp mid-year

16:42 Incentivising the wrong behaviour and how reps game the system

27:18 SDR and AE comp, quotas, territory fairness, and startup trade-offs

39:46 Why communal targets and uneven comp create resentment

48:58 Non-financial rewards, surprise incentives, and recognition that actually lands

Brought to you by MySalesCoach.

Learn more about how we support leaders in building elite and consistent sales teams:

www.mysalescoach.com

Everything feels like it’s moving—and nothing feels stable.

You’re expected to build a high-performing team while the ground keeps shifting beneath you.

Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

In this episode, Tom Boston and Emily Parker break down what it actually looks like to build and lead a sales team inside the chaos of SaaS—where strategy changes, expectations evolve, and pressure never lets up. 

This episode is for:

Sales leaders who are building or scaling teams in fast-moving environments, dealing with inconsistent performance, struggling with hiring decisions, or trying to maintain control and morale while everything around them changes.

Inside this sales leadership lesson:

• Feeling like you’ve “figured it out”… only for messaging, ICP, or strategy to change overnight
• Trying to lead with confidence when you’re figuring things out in real time yourself
• Translating top-down strategy into something your team actually understands and buys into
• Hiring people who look great on paper but can’t adapt when the environment shifts
• Managing high performers who resist structure and think results excuse behaviour
• Dealing with promotion pressure from reps who think they’re ready—but aren’t
• Keeping morale high when growth is messy, processes are broken, and support is limited
• Carrying extra roles (ops, enablement, HR) while still being accountable for performance
• Balancing autonomy with accountability without losing control of the team
• Building a team that complements each other—not just a group of similar performers

At its core, this episode is about the reality that SaaS growth is rarely clean. Leaders are expected to deliver results while navigating constant change, incomplete systems, and evolving expectations. The ones who succeed aren’t the ones with perfect plans—they’re the ones who can create clarity, build trust, and develop teams that adapt faster than the environment shifts.

• (00:00) - – Why building a sales team in SaaS still feels chaotic

04:30 – The real challenge: constant change + managing people through it

08:00 – Building a balanced team (and why hiring “more of the same” fails)

10:30 – Leading with clarity when the business keeps shifting

16:00 – Staying calm and building confidence through uncertainty

21:30 – Trust, autonomy, and setting boundaries with your team

25:00 – Hiring realities: coachability, resilience, and what actually matters

33:30 – Managing promotions, expectations, and team progression pressure

38:00 – What messy growth really looks like—and how to keep morale high

Brought to you by MySalesCoach.

Learn more about how we support leaders in building elite and consistent sales teams:

www.mysalescoach.com

Many sales managers focus on pipeline, activity, and numbers.

Top sales leaders focus on developing people.

Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

In this episode, Tom Boston sits down with Nia Woodhouse and Ollie Sharpe to explore the leadership behaviours, coaching habits, and decision-making that separate average sales management from truly high-performing sales leadership.

The conversation looks at how elite sales leaders structure coaching, build hiring processes, and create environments where reps consistently improve. Nia and Ollie explain why the best leaders separate performance management from skill development, ensuring that coaching sessions focus on mindset, skills, and long-term capability — not just forecast discussions.  

They also break down how top leaders set goals that are actually achievable by reverse engineering revenue targets into specific activity and performance milestones. Instead of chasing a big number without direction, great sales leaders help their teams build a clear roadmap that shows exactly how success will be achieved.  

The episode also explores hiring philosophy, emotional intelligence in leadership, and why the best leaders create trust by standing in front of their team when things go wrong — and standing behind them when they succeed.  

This episode is essential listening for VPs of Sales, Heads of Sales, Sales Managers, and Revenue Leaders who want to move beyond activity management and build teams that consistently perform, grow, and stay motivated.

• (00:00) - - How a leader’s habits shape the whole team

Timestamps

00:00 - How a leader’s habits shape the whole team

00:34 - Intro: what top sales leaders do differently

00:44 - What new sales leaders wish they knew before stepping up

03:22 - How top leaders hire: structure, skills, and culture add

09:15 - Interview red flags experienced leaders spot early

12:02 - Why pipeline reviews are not coaching

14:21 - How top leaders scale coaching with frameworks, not just advice

21:03 - Motivation, commitment, and what really drives performance

27:58 - Setting expectations without micromanaging

37:00 - What top sales leaders do best

Brought to you by MySalesCoach.

Learn more about how we support sales leaders in building and empowering elite teams:

www.mysalescoach.com

If deals keep stalling and the story is always “they’ve gone quiet,” the real issue usually showed up much earlier — and it often isn’t being said clearly in coaching.

PS.
Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

This session with Steve Myers and Richard Smith gets into the actual reasons deals don’t close, and how deal coaching can surface the truth without turning into a forecast grilling.

We break down how to diagnose what’s missing in the deal, validate what’s real vs assumed, and coach reps beyond surface-level reasons into compelling, evidence-backed buying drivers.

This is for you if you're a sales leader dealing with:

• “Close” deals that never close and pipelines full of hope instead of proof
• Reps who can’t clearly articulate why a prospect will actually buy
• Stalled opportunities where next steps were never properly locked in
• A coaching culture where people tell you what sounds good, not what’s true

In this episode, you’ll hear the deal-killers hiding in plain sight:

• Reps mistaking “they want X” for a real problem worth solving
• “I think…” language replacing evidence — and nobody challenging it properly
• Surface-level pain (“save time,” “be more efficient”) with no detail behind it
• Discovery that never gets to the full three levels of pain: symptom → business impact → how people feel about it
• No clear understanding of where budget comes from, how the decision gets made, or where veto power sits
• Leaders accepting the rep’s narrative without validating what’s actually happened
• Weak upfront contracting — so next steps aren’t agreed, meetings aren’t booked, and deals drift into silence
• Repeated stalls that look like a skills issue… but are really discomfort, need for approval, or fear of being too direct
• Keeping a deal alive when the best outcome is clarity to qualify out and redirect effort elsewhere

Most deals don’t fail at the end — they fail because the team never got the truth early enough. 

Great deal coaching creates the environment where the rep can say what’s missing, get specific about the gaps, and leave with clear actions — or the confidence to walk away.

Timestamps:

• 0:00 – 5:13 | Creating the conditions for truth: Removing agendas and power dynamics so the real issues surface
• 5:14 – 7:31 | Diagnosing what’s really going on: Buying journey context, decision process clarity, and validating the rep’s story
• 7:32 – 13:02 | The real reasons deals don’t close: Evidence vs belief, solution-language, and coaching to three levels of pain
• 13:03 – 18:10 | Repeat deal failure: Technical vs mindset problems, and why reps don’t use the skills they “know”
• 18:11 – 21:52 | Prep that prevents stalls: Meeting plans, upfront contracting, objectives, and keeping calls on track
• 21:53 – 24:05 | Outcomes that matter: Immediate next actions, strategic skill-building, confidence — and when to qualify out

If you’re a sales leader tired of chasing “almost” deals and want your coaching conversations to surface the truth faster — listen to this episode and start changing how your team diagnoses, not just how they close.

PS.
Want world class deal coaching for your team? We've got you.
Find out more here
https://www.mysalescoach.com/deal-coaching

Surviving Sales Leadership is brought to you by MySalesCoach.  

Learn more about how we support leaders in building elite and consistent sales teams:  

www.mysalescoach.com

Sales leaders believe they’re coaching more than ever.

Sales reps are saying the opposite.

Download The State of Sales Coaching in 2026 Report here

In this episode, Tom Boston sits with Kevin Beales (Founder & CEO at MySalesCoach) and Richard Smith (Head of Growth at MySalesCoach) to unpack the State of Sales Coaching in 2026 and the uncomfortable disconnect between sales leaders’ intentions and reps’ lived experience. Drawing on real data from sales leaders and sales reps, we explore why coaching feels broken, why AI hasn’t fixed it, and what actually drives quota attainment in today’s sales environment.

We cover why tenured reps want more coaching (not less), how pipeline reviews are being mistaken for coaching, why weekly coaching dramatically increases quota attainment, and why human coaching still outperforms AI-only approaches when it comes to mindset, behaviour, and long-term performance.

This episode is essential listening for VPs of Sales, Heads of Sales, Sales Managers, and Revenue Leaders who want to build a true coaching culture - not just survive this quarter.

Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

Brought to you by MySalesCoach. Learn more about how we support leaders in building elite and consistent sales teams:
www.mysalescoach.com

Sales leaders! Want to build strong teams without burning out in the process?

Introducing Surviving Sales Leadership, where each episode is a practical conversation with experienced sales leaders and elite sales coaches about what actually works.

Coaching reps, managing pipeline, forecasting, enablement, and navigating growth without everything feeling harder than it should.

No “just hold people accountable” nonsense. 
Real-world tactics and strategies that work in sales right now.

If you’re a sales manager, head of sales, sales director, or revenue leader who wants better results, better conversations with your team, and a little more confidence in the chaos, this show’s for you.

Subscribe and start surviving sales leadership today!