Can Sales Managers Be Friends with Their Reps? The Ultimate Sales Leadership Debate

Should leaders be friendly or firm? In this epic live debate from CoachEm’s inaugural Closing Arguments series, two powerhouse sales veterans, Mark Kosoglow (Co-founder & CEO at Operator, former Outreach leader) and Kevin "KG" Gaither (CEO of InsideSalesExpert.com, former ZipRecruiter exec), go head-to-head on one of the most controversial questions in sales leadership:

“Can, should, or would you be friends with your sales reps?”

Moderated by Matt Benelli, host of the Coach to Scale podcast, this unscripted, no-holds-barred session dives into real stories, polarizing philosophies, and battle-tested experiences on the fine line between empathy and authority.

What you'll learn:

When friendship enhances performance, and when it kills accountability

Why sales managers struggle with tough conversations

The hidden career risks of blurred boundaries

How modern leaders navigate connection, trust, and coaching culture

Get actionable takeaways for building high-performing sales teams while balancing trust, professionalism, and results.

This is not your average webinar. It’s honest. It’s engaging. It’s real sales talk for real sales leaders.

Sponsored by CoachEm: The world’s first AI coaching execution platform, built to scale sales success through data, coaching, and culture.

COMMENT below: Can you be friends with your reps? Where do YOU draw the line?

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