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#14 – Don’t Be That Guy - MSP Sales Role-Play - Practice Wins (Ryan Alter)
If you’re not practicing, you’re guessing—and losing deals. In this “Don’t Be That Guy” session, Josh Peterson and former MSP owner Ryan Alter unpack practical, repeatable ways to role-play sales moments so your team reacts faster, handles objections with confidence, and books more meetings.
✅ Enjoyed this episode?
Like, subscribe, and share your biggest takeaway below.
https://beringmckinley.com/bering-mckinley-podcast-blog
Episode Description Ryan Alter (former MSP owner - co-host) and Josh Peterson break down how to build a sales practice culture that actually sticks—without awkwardness or wasted time. You’ll hear real scenarios from MSP life (gatekeepers, price pushback, “we love our current IT,” and post-call debriefs) and how to coach both junior reps and salty veterans.
👉 Why practice beats talent: moving from “trying not to lose” to “playing to win”
👉 Micro-drills that work: one objection, one outcome, 10 minutes, done
👉 Gatekeeper strategies that avoid the receptionist altogether (social proof, intros, and LinkedIn outreach)
👉 After-action reviews: the simple, non-judgment framework that improves every call
👉 Cross-team role-plays: dispatch, security tabletop, interviews—sales isn’t the only place to train
Natural keywords: MSP sales training, objection handling, gatekeeper strategies, cold calling scripts, discovery meeting recap, sales coaching.
Visit https://beringmckinley.com for more MSP resources.
🔗 Resources & Links
• Ryan Alter – Silverstream AV: https://www.silverstreamav.com
• Bering McKinley MSP Consulting: https://beringmckinley.com
⏱️ Chapters
00:00 – Why role-play (and why most teams avoid it)
00:45 – Meet co-host Ryan Alter & sales practice mindset
02:22 – Realistic scenarios - theory: how to frame the drill
04:29 – Athletes train 90% of the time—what about sales?
05:37 – The “ring-ring” drill and breaking awkwardness
07:58 – From “I’d say…” to actually saying it out loud
09:33 – Bold openings and memory-making moments
10:36 – After-action reviews that don’t turn into rambling
12:47 – Coach with questions, not “what I would’ve said”
17:53 – Prospecting focus: getting past the gatekeeper
20:32 – Warm paths to cold doors: intros and LinkedIn
23:34 – Junior rep practice: writing the outreach together
25:27 – The five objections you’ll hear on every call
27:43 – Yes, veterans must practice too
31:24 – Selling outcomes when you don’t know the tech
34:21 – Discovery openers that humanize the convo
38:02 – Train reactions like F1 pit crews—micro-drills
39:38 – Weekly cadence: one micro-moment at a time
41:32 – 1:1 vs group role-plays (and when to mix)
44:39 – Security tabletop & cross-dept simulations
49:23 – Add surprise players: the CTO walks in
50:47 – Book a session & where to watch replays
🔍 Primary Keywords
msp sales training, sales role playing, objection handling, gatekeeper strategies, after action review, cold calling scripts
🔍 Secondary Keywords
sales coaching framework, discovery meeting debrief, socratic selling, interview role play, security tabletop exercise, dispatch training
#️⃣ Hashtags
#beringmckinley #bmkvisionpodcast #msp #managedservices #salestraining #roleplay #objectionhandling #coldcalling #mspsales #gatekeeper #salescoaching #businessdevelopment #discoverycall #tabletopexercise #dispatch
View all episodes
By Josh PetersonIf you’re not practicing, you’re guessing—and losing deals. In this “Don’t Be That Guy” session, Josh Peterson and former MSP owner Ryan Alter unpack practical, repeatable ways to role-play sales moments so your team reacts faster, handles objections with confidence, and books more meetings.
✅ Enjoyed this episode?
Like, subscribe, and share your biggest takeaway below.
https://beringmckinley.com/bering-mckinley-podcast-blog
Episode Description Ryan Alter (former MSP owner - co-host) and Josh Peterson break down how to build a sales practice culture that actually sticks—without awkwardness or wasted time. You’ll hear real scenarios from MSP life (gatekeepers, price pushback, “we love our current IT,” and post-call debriefs) and how to coach both junior reps and salty veterans.
👉 Why practice beats talent: moving from “trying not to lose” to “playing to win”
👉 Micro-drills that work: one objection, one outcome, 10 minutes, done
👉 Gatekeeper strategies that avoid the receptionist altogether (social proof, intros, and LinkedIn outreach)
👉 After-action reviews: the simple, non-judgment framework that improves every call
👉 Cross-team role-plays: dispatch, security tabletop, interviews—sales isn’t the only place to train
Natural keywords: MSP sales training, objection handling, gatekeeper strategies, cold calling scripts, discovery meeting recap, sales coaching.
Visit https://beringmckinley.com for more MSP resources.
🔗 Resources & Links
• Ryan Alter – Silverstream AV: https://www.silverstreamav.com
• Bering McKinley MSP Consulting: https://beringmckinley.com
⏱️ Chapters
00:00 – Why role-play (and why most teams avoid it)
00:45 – Meet co-host Ryan Alter & sales practice mindset
02:22 – Realistic scenarios - theory: how to frame the drill
04:29 – Athletes train 90% of the time—what about sales?
05:37 – The “ring-ring” drill and breaking awkwardness
07:58 – From “I’d say…” to actually saying it out loud
09:33 – Bold openings and memory-making moments
10:36 – After-action reviews that don’t turn into rambling
12:47 – Coach with questions, not “what I would’ve said”
17:53 – Prospecting focus: getting past the gatekeeper
20:32 – Warm paths to cold doors: intros and LinkedIn
23:34 – Junior rep practice: writing the outreach together
25:27 – The five objections you’ll hear on every call
27:43 – Yes, veterans must practice too
31:24 – Selling outcomes when you don’t know the tech
34:21 – Discovery openers that humanize the convo
38:02 – Train reactions like F1 pit crews—micro-drills
39:38 – Weekly cadence: one micro-moment at a time
41:32 – 1:1 vs group role-plays (and when to mix)
44:39 – Security tabletop & cross-dept simulations
49:23 – Add surprise players: the CTO walks in
50:47 – Book a session & where to watch replays
🔍 Primary Keywords
msp sales training, sales role playing, objection handling, gatekeeper strategies, after action review, cold calling scripts
🔍 Secondary Keywords
sales coaching framework, discovery meeting debrief, socratic selling, interview role play, security tabletop exercise, dispatch training
#️⃣ Hashtags
#beringmckinley #bmkvisionpodcast #msp #managedservices #salestraining #roleplay #objectionhandling #coldcalling #mspsales #gatekeeper #salescoaching #businessdevelopment #discoverycall #tabletopexercise #dispatch