AI Sales Roleplays with Michael Ocean

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Most salespeople dread roleplay training. It’s awkward, unrealistic, and rarely reflects the real challenges they face with prospects. In this episode, Mike Montague sits down with Michael Ocean, founder of Sell Me This Pen AI, to talk about a better way. Instead of building AI to replace sales reps, Michael built an AI-powered coaching assistant that helps them practice, improve, and perform without the pressure of a group setting or the pain of bad peer roleplays.

We dig into why enterprise and complex sales still demand a human-first approach, how AI can uncover blind spots and skill gaps, and what makes roleplay effective when it’s personalized and repeatable. You’ll hear how SMBs can use AI to scale coaching, not cold calls; why safe practice leads to real confidence; and the right balance between AI feedback and human management. If you lead a sales team or want to sharpen your skills without the cringe, this episode is your playbook.

Top Takeaways

1. AI should enhance, not replace, salespeople – Complex, high-trust sales conversations still require human judgment and relationship building.

2. Roleplays work best in a safe, personalized environment – AI lets reps practice without embarrassment or the limitations of a generic group scenario.

3. Practice improves performance, but most teams don’t get enough of it – AI makes it possible to scale individualized coaching without overwhelming managers.

4. AI can deliver unbiased, consistent feedback – Machine-led reviews focus on objective performance markers, not subjective impressions or mood.

5. Managers are still critical for context and motivation – Human leaders can interpret performance data, address personal factors, and inspire change.

6. Peer-to-peer roleplay often fails to reflect real buyer behavior – AI can simulate diverse personas and scenarios that mirror actual customer conversations.

7. Repetition builds confidence and skill mastery – With AI, reps can repeat scenarios as often as needed without wasting a colleague’s time.

8. AI reveals blind spots salespeople may not recognize – Pattern recognition and behavior tracking help uncover habits or weaknesses a human coach might miss.

9. Balance is key between automation and human connection – AI should handle repetitive training tasks so humans can focus on relationship-building and strategy.

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