Surviving Sales Leadership

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.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 proofReps who can’t clearly articulate why a prospect will actually buyStalled opportunities where next steps were never properly locked inA coaching culture where people tell you what sounds good, not what’s trueIn 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 properlySurface-level pain (“save time,” “be more efficient”) with no detail behind itDiscovery that never gets to the full three levels of pain: symptom → business impact → how people feel about itNo clear understanding of where budget comes from, how the decision gets made, or where veto power sitsLeaders accepting the rep’s narrative without validating what’s actually happenedWeak upfront contracting — so next steps aren’t agreed, meetings aren’t booked, and deals drift into silenceRepeated stalls that look like a skills issue… but are really discomfort, need for approval, or fear of being too directKeeping a deal alive when the best outcome is clarity to qualify out and redirect effort elsewhereMost 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 surface5:14 – 7:31 | Diagnosing what’s really going on: Buying journey context, decision process clarity, and validating the rep’s story7:32 – 13:02 | The real reasons deals don’t close: Evidence vs belief, solution-language, and coaching to three levels of pain13:03 – 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 track21:53 – 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 herehttps://www.mysalescoach.com/deal-coachingSurviving 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.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.Download the report here:https://www.mysalescoach.com/the-state-of-sales-coaching-in-2026-reportBrought 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!