Surviving Sales Leadership

The Questions You're Not Asking That Kill a Forecast in 5 Minutes

Most sales leaders have sat across from a rep who's fully convinced a deal is closing.  Champion engaged.  Proposal out.  Close date locked. And they're wrong. Richard Smith sits down with Chris Lingenfelter (VP Sales & CS, Level Up) and Nigel Arthur (former MD and SVP Sales, enterprise SaaS - now coach at MySalesCoach) to show exactly what separates pipeline from forecast - and how fast the difference becomes obvious when you ask the right questions. They cover why emotion is the single biggest killer of forecast accuracy, what entry/exit criteria your CRM stages are probably missing, and why a rep who "feels really good" about a deal is a red flag, not a green light. The session ends with a live deal review. Richard plays the rep. Nigel and Chris ask five questions.  The deal doesn't make the forecast. Find out which questions did it.

We Analysed 5117 Sales Coaching Calls - Here's Why Your Deals Are Stalling

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 [https://www.mysalescoach.com/the-modern-revenue-leaders-sales-coaching-manual?utm_source=podcast&utm_medium=organic&utm_campaign=] --- 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

The Comp Plan Mistakes That Push Good Reps Out

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 [https://www.mysalescoach.com/the-modern-revenue-leaders-sales-coaching-manual?utm_source=podcast&utm_medium=organic&utm_campaign=] 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

How To Build a High Performing Sales Team In The Chaos of SaaS

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 [https://www.mysalescoach.com/the-modern-revenue-leaders-sales-coaching-manual?utm_source=podcast&utm_medium=organic&utm_campaign=] 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 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

What Top Sales Leaders Do Differently

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 [https://www.mysalescoach.com/the-modern-revenue-leaders-sales-coaching-manual?utm_source=podcast&utm_medium=organic&utm_campaign=] 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 * (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 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